Welcome to Leading by Design!

A blueprint for career strategies in product design leadership

⏰ Today In 5 Minutes or Less

A deep dive into how the team at Artefact  transformed agency friction into a global resource management tool, proving that the best products solve your own "Big Friction."

Case Study: 10,000ft

This week, I’m exploring the career of Rob Girling, co-founder of the iconic consultancy Artefact and the co-creator of the resource management tool 10,000ft. For those looking to dive deeper into our whole conversation, you can find the complete interview in my book, Leading by Design.

Rob’s journey is a masterclass in moving from a "service" mindset to a "strategic product" space. 10,000ft was born not from a desire for market disruption, but from the raw pain of managing a growing team of 30 designers on a spreadsheet that was starting to break. It was designed to solve the "clunky spreadsheet" problem for creative agencies and distributed tech teams who need a high-level perspective on organizational health.

10,000ft was acquired by Smartsheet in 2019. Separately, Smartsheet was acquired by Blackstone and Vista Equity Partners for $8.4 billion deal.

Snapshot of the User Interface Design from 10,000ft

1. “Build What You Know” Principle

Between 2006 and 2011, Rob and the Artefact team, led by co-creator Martijn van Tilburg and business partner Gavin Kelly, were swept up in a wave of design optimism. Gavin, an Artefact co-founder, served as the "third leg" of the 10,000ft stool, providing the essential strategic balance the project needed.

Despite their design pedigree, the team spent years chasing "snazzy" concepts and "magic" prototypes that failed to gain traction. The missing ingredient? A lived-in, deep understanding of the problem space.

The breakthrough happened when they looked inward at their own friction. As Rob explains:

The Insight: Your most valuable product opportunity is rarely a "Blue Sky" idea; it is likely the problem you face every single day. For the 10,000ft team, it was the breakdown of resource management.

Action for Leaders: Stop hunting for "The Big Idea" and start auditing "The Big Friction." What is the one recurring task that your team complains about every Friday? That friction isn't just a nuisance; maybe it’s your product.

2. Spotting the "Spreadsheet Breaking Point"

A spreadsheet that works perfectly for 10 people; It’s "clunky" but functional for 20; at 30 people, it becomes a liability. When you reach a "breaking point," you have two choices:

• The Service Choice: Hire an operations person to manage the mess.

• The Product Choice: Design a system that automates the mess.

Rob, Martijn, Gavin, and team chose the latter. They realized that if their agency needed a high-altitude view of project workflows, every other creative organization on the planet probably did too. They were right! I used 10,000ft to manage the workflow and visibility into our impact as a business driver as Chief Design Officer for [24]7.AI.

3. From "Optimistic Prototyping" to "Technical Empathy"

One of the most profound insights for the team was the gap between a vision and a viable business. The team realized that while designers excel at the "Front-End", they lacked visibility into the "Back-End" (the support infrastructure and the sales cycle).

Rob describes this shift as a move from arrogant design to technical empathy:

4. Designing the Culture as a Product

One of the most compelling takeaways from the 10,000ft story is that the software was a direct manifestation of Artefact’s internal culture. Rob and Gavin built Artefact as a "flat" organization that rejected traditional micromanagement. Consequently, 10,000ft was designed with a "high-altitude" view where every team member could see the entire landscape of the company’s work.

The Leadership Lesson: Software is "Coded Culture." When you build a tool, you are essentially coding your culture.

• If you design for transparency, you are advocating for a high-trust culture.

• If you design for "locked" permissions, you are reinforcing a culture of gatekeeping.

Leading by Design: The Insider's Handbook for Tech Leadership

🚀 The Short of It Is

If you are an aspiring design leader looking to build successful internal products, here is the essential playbook for how to do this:

1. Audit Your Own Friction: Look for the "Big Friction", that recurring, painful task your team handles via a breaking spreadsheet.

2. Build What You Know: Success comes from a lived-in understanding. Even as UX designers (like Martijn and Rob), your strongest tool is your own frustration.

3. Find Your "Third Leg": Don't go it alone. Just as Gavin Kelly and Rob provided the necessary foundational support for Martijn and the team, find partners who balance your design vision with business and strategic rigor.

4. Practice Technical Empathy: Move beyond "snazzy" prototypes. Respect the complexities of engineering and scaling.

5. The "Functional Hack" Strategy: Don't wait for perfection. Build the simplest version that solves the core problem and get it into users' hands immediately.

The full interview with Rob Girling, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Lynn Bacigalupo

Welcome to Leading by Design!

A blueprint for career strategies in product design leadership.

⏰ Today in 5 Minutes or Less

By reading this, you will identify the four mindset shifts necessary to move from designing interfaces to directing product strategy and market viability.

From UX Lead to Product Manager: The Strategic Pivot

The transition from UX Lead to Product Management (PM) is one of the most natural, yet culturally jarring, shifts a design leader can make. While you already possess the empathy and research rigor required for success, moving into a PM role requires shifting your focus from the "Guardian of the User" to the "Guardian of the Business."

How do you turn UX expertise into a seat at the leadership table? Lynn Bacigalupo, Global Product Manager at Icomera, has the roadmap. In this feature, she breaks down her transition from design strategy to overseeing cutting-edge AI transit solutions. For the complete masterclass on her leadership philosophy, check out the full interview in “Leading by Design: The Insiders’ Playbook to Tech Leadership”.

Inside the Roadmap: How Lynn Bacigalupo Translates UX Strategy into High-Impact PM

Transitioning into PM isn't about leaving design behind; it’s about applying design to the business model itself. While UX Designers and Product Managers work in the same trenches, their North Stars differ.

As Lynn notes, "In both UX and product management, the focus is on understanding the user's needs... but the cultural shift has been noticeable." To successfully transition, you must move from the "How" (the interface, the flow, the interaction) to the "Why" and "What" (the market fit, the ROI, and the roadmap).

UX vs. PM: Strategic Priorities

Step 1: Broaden Your Time Horizon

One of the most significant adjustments Lynn highlights is the shift in perspective regarding time. "When I was working hands-on, my focus was on the immediate deadline," she explains. "As a leader, my thinking often extends to a five-year timeframe."

As a UX Lead, you likely think in sprints or release cycles. As a PM, you must believe in market cycles. In Lynn’s world of rail transit, infrastructure lasts decades, but tech evolves in months. A PM must navigate this "friction," ensuring that a product launched today won't be obsolete by the time the hardware is fully deployed.

Step 2: From UX Research to Market Intelligence

Her background in research strategy smoothed Lynn’s transition. However, PM research goes beyond usability. It involves understanding industry-wide shifts.

For example, Lynn leverages industry studies to identify where AI can improve rail operations. She isn't just asking if a button is clickable; she's asking if Video-based AI is the most cost-effective way for transit agencies to report passenger counts to the government.

To move into PM, you will measure efficiency and viability alongside usability.

• UX View: "Can the user complete this task?"

• PM View: "Does completing this task reduce operational costs for the client?"

Sally and Lynn, The UN Plaza, San Francisco, December 2025

Step 3: Master the "Internal" Customer Journey

A pivotal moment in Lynn’s PM career involved improving internal network operations tools. She realized that if the internal teams couldn't support the product, the external customer experience would eventually fail.

She approached this with a "consultant mindset", gathering stakeholders, identifying pain points, and presenting solutions. This is a UX strategy applied to Organizational Design. To be an excellent PM, you treat your developers, sales teams, and support staff as users. Lynn’s Advice for Collaboration:

Step 4: Embracing "Hybrid" Methodologies

As a UX Lead, you might be a devotee of Agile or Lean. As a PM, you have to be a pragmatist. Lynn notes that while Icomera uses lean startup methods, the realities of complex hardware and long backlogs often require a hybrid approach.

"Launching involves much more than simply releasing the product," Lynn cautions. You have to consider:

• Can the project engineers implement it?

• Does the service team know how to support it?

• Is there robust monitoring in place?

A PM ensures the entire ecosystem is ready, not just the code.

Step 5: Leading with Values

Perhaps the most profound insight Lynn shares is how her leadership was shaped by working with a development team in Ukraine. This experience reinforced Value-Based Leadership.

In the transition from individual contributor to PM, it is easy to become obsessed with "output." Lynn argues for a focus on "people as individuals." This empathy, a core UX trait, is actually a superpower in Product Management. It allows you to build the trust needed to navigate the "unstructured" ways in which many organizations actually make decisions.

Leading by Design: The Insider's Handbook for Tech Leadership

How to Start Your Transition from UX to PM Today

If you are currently a UX Lead looking to move into Product, here are three actionable steps based on Lynn’s experience:

1. Volunteer for a "Non-Design" Problem: Like Lynn’s internal tools project, find a bottleneck in your company’s operations and lead the discovery phase to fix it.

2. Learn the Language of Stakeholders: Start attending meetings with Sales, Marketing, and Finance. Understand what metrics they care about (Revenue, Churn, ROI) and map your design wins to those goals.

3. Frame the "Why": In your next handoff, don't just explain the user flow. Explain the market necessity. Why is the business investing $100k in developer hours for this specific feature right now?

The Short of It Is 🚀 

The transition from UX to PM isn't about losing your design soul; it's about giving your design skills a larger playground.

The full interview with  Lynn Bacigalupo, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Ajay Thakur

Welcome to Leading by Design!

A blueprint for career strategies in product design leadership

⏰ Today in 5 Minutes or Less

How do you balance high-level design with engineering reality? This week, Ajay Thakur (Chief Information Officer at Movius and former Head of Cognitive Computing and Staff Engineer at Uber) shares a deep dive into bridging the gap between aesthetic vision and technical feasibility.

The Evolution of the Technical Product Designer

As design leaders, we often focus on "user delight" and "user journey." However, in the high-stakes world of global scale, think Uber-level complexity, delight, and a golden path journey without feasibility will stall.

If you’ve ever had a vision stalled because "the API doesn't support it" or "the bandwidth costs are too high," you’ve hit the technical wall. To lead modern product design teams effectively, moving beyond the "design specification handoff" culture is essential.

Empowering creative teams to learn about the technical levers that determine whether a product succeeds or fails in production is a step toward increasing the department’s return on investment (ROI) for the business it serves.

In a featured interview from my book, Leading by Design, Ajay offers an invaluable perspective on the synergy between our disciplines, arguing that the next generation of product designers looks beyond the interface to understand the "machinery" that brings their visions to life.

The Designer’s New Toolkit: Technical Empathy

Ajay’s philosophy is rooted in technical empathy. At Uber, where real-time data is the heartbeat of the app, he views designers as vital partners when they possess a deep understanding of the system's constraints.

For Ajay, the "magic" of a customer experience is actually the result of rigorous negotiation between design ambition and engineering reality. When designers understand the "Why" behind a technical "No," they can pivot to a "How" that actually works.

3 Key Ideas to Mastering Technical Design

Using Ajay’s insights, here are three ways you can lead your team toward technical fluency:

1. Map the "Data Journey" Before the User Journey

Ajay emphasizes data availability. In real-time apps, if data is slow or inaccessible, your design fails.

• The Approach: Don't just design the "happy path." Ask your engineers: "What is the fallback state if this API call takes longer than two seconds?" or "Do we actually have access to this user data in real-time?" Designing for data latency is just as important as creating the user interface (UI).

2. Design for "Minimal-Regret" (The Agile Mindset)

Ajay favors the Agile Manifesto for its speed and "minimal-regret" delivery. He argues that "less is more" often leads to better outcomes and stability.

• The Approach: Challenge your team to identify the "heaviest" part of their design. If a feature requires a custom API or excessive network bandwidth, ask whether there is a way to achieve the same user goal using existing components or proven frameworks. This reduces friction and speeds up velocity.

3. Transition from Mockups to "Technical Logic."

Ajay highlights the importance of interaction flowcharts and documenting the "Why" behind choices. With the rise of AI, the gap between design and code is shrinking.

• The Approach: Encourage your designers to think in logic, not just layouts. As AI-powered interfaces begin to anticipate user needs, designers will be defining the rules and predictions the UI should make. A designer who can write a working prototype or prompt an AI to generate functional code is no longer just a "design" partner; they are a technical design lead.

Leading by Design: The Insider's Handbook for Tech Leadership

The Future: Designer-Developer Synergy

When AI can turn a single engineer into a team of hundreds, designers don't become less relevant; their technical literacy becomes the differentiator. By bridging the gap between design and code, we move toward a future where designers aren't just drawing interfaces, but directing AI-driven logic and producing functional prototypes.

But what, if anything, is holding you back? Samira Rahimi, Head of Platform Experiences Design at Uber, hits the nail on the head in her article “The Parts of Your Job AI Should Absolutely Steal.” She asks: “What stops designers—tools, or fear?”

If you’re leading a design team today, the hard part isn’t the tools; it’s the mindset. For years, designers were taught that the "machinery" wasn't their job. That legacy is the real blocker. To move forward, we have to normalize technical experimentation, making it low-risk and, eventually, a core part of the creative process.

Your Challenge: Confront the "Technical Wall"

Overcoming the fear starts with a conversation. Ajay Thakur identified his top three constraints as API limitations, bandwidth, and data availability.

What are yours?

Does your team have a framework for discussing these technical levers, or do you hit a "wall" every time you move from Figma to production? Leave a comment and let me know how you are encouraging your team to move beyond pixels and into the code.

The full interview with Ajay Thakur, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Anshuman Kumar

Welcome to Leading by Design!

A blueprint for career strategies in product and design leadership.

⏰ Today in 5 Minutes or Less

Learn how Anshuman Kumar, former SVP of Design at Asana, drove $10M in annual recurring revenue by gamifying product optimization and owning the P&L.

The Evolution of Design Executive Anshuman Kumar

For many designers, the transition from practitioner to manager feels like a natural progression of craft. But for Anshuman Kumar, former SVP and Head of Design at Asana, the leap from manager to executive required a fundamental shift in perspective. It wasn't just about leading a team of 100+ designers; it was about shifting the "output" of design from pixels to business decisions to maximize design leadership and business ROI. As Anshuman shares in my book Leading by Design, becoming an executive meant moving beyond the screen to influence the company's financial trajectory.

In his career journey from Yahoo to Google and to the helm of Asana’s design org, Anshuman mastered a skill many design leaders struggle with: speaking the language of the business. This shift is essential for bridging the gap between UX and the bottom line.

One of the most profound realizations he had was the change in "time horizon." While a manager might focus on the following product cycle, an executive must look much further ahead; at Google, he lived six months in the future, but at Asana, his horizon moved to three years, allowing him to drive product optimization and gamification strategies that resulted in a staggering $10M revenue impact.

This shift meant moving away from the "unannounced Figma visit," which he learned can accidentally intimidate some designers, and moving toward multi-million-dollar budget accountability and long-term organizational health.

📖 Case Study

Gamifying the P&L to Drive $10 Million in ARR

The most striking example of his business-first leadership occurred when Asana set Annual Recurring Revenue (ARR) as a North Star for R&D. Anshuman saw this as an opportunity to prove his design team's worth in a language the board of directors would understand.

1. Identifying "Revenue-Sensitive" Surfaces 💰

Drawing on his early career experience at Yahoo, where changing a font size on an ad product could immediately impact the bottom line, Anshuman knew that certain "surfaces" (user interfaces) were more sensitive than others. He focused his team on payments, new user adoption, and retention.

2. Doing 30% of the Work for Others 👷🏾👷🏾

Instead of waiting for permission, his team audited critical surfaces and identified every UX bug that could be hindering conversion. They identified problems and provided solutions. From the documented list of solutions, he invited the stakeholders to choose what to optimize.

3. Gamification and the Leaderboard 🎲

To drive momentum, they created a leaderboard to track experiments conducted by cross-functional teams. This turned a technical backlog into a competitive game, motivating teams to fix "P2" (moderate-to-high-priority bugs affecting core functions or user experience) and "P3" (low-priority minor bugs, cosmetic glitches, or single-user problems) that had been ignored for months. 

4. The Result: A $10 Million Success 🤑

When Anshuman approached the Chief Product Officer, he didn't talk about "user delight" or "aesthetic consistency." He said, "We’re going to make $12 million in one year." By the end of the year, the design-led optimization initiative had driven $10 million in ARR (annual recurring revenue). More importantly, it sparked a cultural shift in which the entire R&D team realized that the quality of the product user experience is a direct driver of business growth.

Lessons for Aspiring Design Executives

Anshuman’s success offers a blueprint for design leaders looking to claim a seat at the executive table:

• Own the P&L: Don't wait for someone to hand you financial responsibility. Set ambitious targets, tie your design goals to revenue or retention, and be willing to be measured by those numbers.

• Avoid False Trade-offs: An executive’s job is to find the "third way" when business needs and design vision seem to conflict.

Leading by Design: The Insider's Handbook for Tech Leadership

The Short of It Is 🚀

A design leader's journey at the highest level isn't about protecting the "sanctity" of the craft from the "coldness" of business. It’s about using the design process to solve the business’s most complex problems. When you can walk into a room and tie a UX improvement to a $10 million revenue bump, you aren't only a designer, but a business leader who happens to use design as your primary tool.

The full interview with Anshuman Kumar, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

But before we dive in …

^{Today’s newsletter is sponsored by Beehiiv} 

Introducing Julie Baher

The Executive Who Champions Passion as a Strategic Asset

Today I want to introduce you to someone who has built a remarkable career on the principle that passion is a strategic asset. Julie Baher is a Digital Health Executive and veteran of the UX community. Her journey from designer to executive illustrates how connecting your authentic self to your professional pursuits isn't just about job satisfaction, it's about achieving maximum impact and earning a real voice at the strategic table. To understand her perspective, you need to know a bit about her background

That connection to medicine and science, seamlessly woven together with her technical and design skills, became the powerful strategic foundation for her ultimate executive role. Julie has written about this in her LinkedIn article, Finding Your Passion at Work and in an interview in my book Leading by Design. Let’s dive into her insights.

The Foundation: Combining Disparate Interests

Julie's career was built on a series of purposeful convergences. The first lesson for design leaders is to stop viewing your skills as linear. Julie’s journey into User Experience (UX) was fueled by a lifelong fascination with combining seemingly disparate fields. She realized her passion lay in the “intersection of art and problem-solving,” specifically, the desire to combine her “love of math and creativity.”

This fascination quickly translated into a professional philosophy: “Once I discovered graphic design, I thought, 'Why isn't this taught in schools?' It's applied art, not fine art. You're not trying to be a Rembrandt but creating practical, useful things. And I'm a practical person.”

This insight, that design is fundamentally about creating practical, functional solutions is the core value that anchored her career. It allowed her to focus on its problem-solving application.

Jule with Sally, December 2025, Santa Fe, New Mexico

The Strategic Act of Value Alignment

Julie emphasizes the importance of "finding companies where her values align with the organization's mission." She has consistently selected organizations—from Adobe to Citrix to Myriad and now GeneDx, where she could genuinely connect her interests to the mission:

• Helping Creatives: At Adobe, she connected with her love of darkroom photography and desktop publishing to help creative professionals.

• Supporting IT: At Citrix, her background in building computers and IT allowed her to connect with IT customers.

• Improving Human Health: This is where the long-shelved passion for science finally became central. At Illumina, Myriad and now GeneDx she could integrate her biology background, interest in medicine, and software design skills to help scientists, doctors, and patients through genetic insights.

This deep alignment is what enabled her to “excel as an executive leader.” She isn’t just performing a job; she is fulfilling a deeply personal mission.

For design leaders, the transition to the executive level often means a battle for respect and recognition. Julie notes the common pitfall in some tech environments: UX is often marginalized, brought in late, and viewed as providing mere “window dressing”. However, her value-aligned career in the life sciences provided the perfect counter-narrative, proving that passion directly leads to influence.

The 'Big Tent' Advantage

In tech, the product story often revolves around an engineer and a product manager. Julie found that the life sciences industry naturally operates with a “big tent” approach.

This environment, where her passion for science gave her instant credibility, allowed her to achieve her ultimate goal: positioning herself as a valuable strategic contributor. She realized that to fully embody the role of a Vice President, she needed to shift her mindset “away from simply being the UX leader” and toward broader strategy. Her foundational passion gave her the conviction to “be more assertive about my role” and avoid being undervalued.

Systemic Problem-Solving

Her deep interest in understanding the system is another critical facet of her passion. As a child, she loved Richard Scarry’s book, What Do People Do All Day? This childhood curiosity grew into a professional strength: "I like knowing how things work and seeing the systems at play." And this this translated into a unique ability to tackle enormous, complex scopes. For example as VP Digital Health for Product Management and User Experience Design for Myriad:

• Integrated Leadership: She led the product management team in addition to UX. This dual role gave her the necessary “authority to comment on development work and other areas” and ensure UX is involved in the entire product stack, aligning design priorities with the overall business vision.

• Design Thinking for Systems: Her team used visual mapping, workflow analysis, and journey mapping to understand the entire “Jenga tower” of the ecosystem—including customer service, billing, and medical professionals—before making changes.

The Takeaway

Julie Baher's journey powerfully illustrates this truth: Passion is not a luxury in executive leadership; it is your core strategic asset.

Think about it: genuine enthusiasm provides the kind of clarity and conviction that mere experience cannot.

• It gives you the clarity to choose the right companies—those missions and cultures that deeply resonate with your purpose.

• It builds the credibility necessary to be a truly strategic contributor, allowing you to speak with authority that transcends departmental silos.

• Most importantly, it arms you with the conviction needed to assert the value of design against entrenched organizational practices and short-sighted thinking.

Your Multifaceted Advantage

Your unique combination of interests whether you blend graphic design and mathematics, or biology and software engineering is not a distraction to be minimized. It is the strategic narrative that will define your executive success. It's the unique lens through which you see problems and solutions that no one else can match.

Don't settle for environments that merely tolerate your skills. Seek the organizations that actively reward your multifaceted interests and allow you to align your deepest personal values with their mission.

When you embrace this intersection of passion and skill you move beyond being a highly effective team leader to becoming a visionary strategic executive who truly shapes the future of the business.

What Drives You?

What is the unique, driving passion, the combination of skills and interests that motivates you to do the work you do today, and how are you leveraging it to move your company's mission forward?

The full interview with Julie Baher, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

You received this email because you subscribed to or bought one of our products.

Thank you! 

© 2026 Sally Grisedale, Clear Channel Coaching.

Photo by Andy Kelly on Unsplash

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

Today, in 5 Minutes or Less ⏱️

You will learn two essential AI strategies that top design leaders use to secure their team's value, drive business efficiency, and navigate the current wave of tech layoffs.

Did You Know 🔎 

Intense contraction and strategic realignment in the tech industry in the US have led to significant ongoing layoffs in the tech sector, according to the official count.

• 2024 = 95,667 layoffs

• 2025 = 206,102 layoffs

• 2026 = Continued volatility. 58% of US business leaders  anticipate more layoffs driven by a permanent shift in staffing needs. AI is the Force Multiplier: 37% of companies expect to replace roles with AI by the end of 2026. 

According to an HBR report, half of a skill's value is lost within 2.5 years. This demands a new skill set to remain relevant, making continuous strategic evolution a prerequisite for survival during periods of organizational upheaval.

The data underscores that if you work in tech as a design leader, your priority for the next year is radical reinvention of how you define, communicate, and execute your work to maximize your value in an AI-driven, data-driven, speed-to-market-obsessed environment.

The Steps You Can Take to Navigate Org. Change with AI

The holiday season, starting around Thanksgiving, is when executive teams finalize next year's budgets, headcount, and often, the inevitable cost-cutting layoffs. This "scorched earth" corporate thinking—designed to hit short-term quarterly targets by shifting salaries from laid-off staff to top performers—is a reality I've seen play out at Apple, Yahoo, and Meta.

To insulate your team and make an undeniable business case for their continued existence, here are two core AI strategies you can adopt to keep your design function intact.

Integrate AI to Enhance Design Efficiency and Scale

To demonstrate efficiency in your organization, integrate AI tools to accelerate, improve, and scale design output. For example:

• Automate Tedious Tasks: Implement AI tools (like generative AI for rough drafts or predictive tools) to automate repetitive, low-value tasks (e.g., basic layout variations, repetitive image resizing, or generating design spec documentation). This frees up designers to focus on complex problem-solving and strategic thinking.

• Create AI-Powered Design Systems: Use AI to make the design system smarter. This could involve using AI to automatically audit accessibility compliance, predict optimal component usage based on context, or quickly generate localized variations of UI elements, ensuring consistency and reducing manual effort across the entire product suite.

• Accelerate Prototyping and Testing: Leverage AI to quickly generate diverse prototypes and simulate user behavior at scale, significantly reducing the time spent on manual A/B testing setup and analysis, leading to faster iteration cycles.

Drive Strategic Value by Leveraging AI for User Insight and Personalization

The second, more critical step is to leverage AI to unlock new avenues of business value and strategic impact. This involves shifting the design focus from merely building interfaces to designing intelligent, highly personalized, and data-driven experiences.

• Design for Intelligent Experiences: Focus on how AI can create new, valuable product features that are useful, transparent, and trustworthy. For example, designing the inputs, outputs, and feedback loops for AI features such as personalization engines, intelligent recommendations, and automated workflows. 

• Translate AI Insights into Actionable Design: Make data-backed decisions that directly improve key business metrics like conversion, retention, and time-to-task completion, and do this using AI to synthesize user data (e.g., behavior patterns, sentiment analysis, task success rates) into clear, actionable design insights.

• Establish Ethical and Responsible AI Design Guardrails: To protect long-term business value and user trust, you must help the company define policies on data privacy, mitigate algorithmic bias, and ensure transparency into how AI influences the user experience. If you lack visibility into this work, ask for it. If your company hasn't started addressing these issues, take charge and lead it. Owning the Service-Level Agreements (SLAs) for ethical AI and experience quality is how you acquire influence and power within the company.

The Short Of It 💥 

Ultimately, protecting your team from vulnerability to layoffs this holiday season requires you to recast and actively promote your essential value proposition. This means achieving immediate fluency in the strategic deployment of AI. This is achieved through two critical, integrated actions:

1. Integrate AI to Enhance Design Efficiency and Scale: Use AI tools to accelerate and expand your creative output.

2. Drive Strategic Value by Leveraging AI for User Insight and Personalization: Apply AI to data to deliver highly personalized experiences that yield significant business impact.

That's it for this week!

PS: Would you like to receive more leadership strategies? Here are three ways you can do that.

• Schedule a free coaching strategy call

• Buy, gift, and review my book 

• Subscribe to this Newsletter

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

Today, in 5 Minutes or Less ⏰

You’ll learn the mindset shift that turns creative focus into leadership success, how to overcome impostor syndrome by focusing on judgment rather than expertise, and the strategy for creating an experience-delivery system (EDS) that guarantees executive buy-in.

Executive Insight with Phil Clevenger 🔍

At the time of our interview, Phil Clevenger was the Vice President of Product Experience at DocuSign, leading a team of over 150 professionals. His deep experience includes 17 years at Adobe, where he designed the first versions of Adobe Lightroom, and a pivotal early career mentored by the renowned designer Kai Krause, who taught him the enduring lessons he uses to shape digital experiences today. The full interview with Phil is included in my book, Leading by Design, in the chapter "How to Get the Top Job."

The Individual Contributor (IC)-to-Leader Shift

“As you transition from Individual Contributor (IC) to a managerial role, you face a profound challenge: shifting from a "24-hour cycle of worry and stress" focused on your own deliverables to a leader responsible for political standing as well as securing and directing resources. One salient mindset shift is to be consistently cultivating your "oxygen supply" -  the executive sponsorship that validates design as a business asset, rather than a cost center.

Phil’s Executive's Thesis

Phil's thesis is that leadership is a tremendous liberation from being a "prisoner of me" (the self-oriented designer) to being focused on service and scale. The reward of an executive role is having "far more impact on a broader scale than I ever did as an individual contributor" by elevating others and using design judgment and resources to solve large-scale business problems.

1. The Strategic Translation: Linking Design to Revenue

Phil Clevenger's strategy starts with a clear mandate: understand the business's financial goals, then build a design strategy to meet them.

Example Problem: Adobe's SaaS products were largely vertical and often not well integrated for a variety of reasons. The business needed to break them into flexible, composable UX microservices to increase revenue and gain a competitive advantage—allowing for custom sales bundles and bespoke customer environments.

The Design Solution: Phil and his team created what they called an "Experience Delivery System." This system, a large step beyond a conventional design system, was a set of standards and infrastructure meta-components necessary to deliver a unified, frictionless experience across all existing services and to embrace new or incoming services. Design built the foundation that enabled the new financial strategy.

Phil and Sally. Nov 19 2025, San Francisco

2. Translating the Business Goal into a Design Imperative

Phil recognized that simply breaking apart the back-end code would create a Frankenstein's monster on the front end if design didn't intervene. His design objective was twofold:

• Improve CX (Customer Experience): Ensure the experience matches the specific needs of each customer (addressing the "bespoke environment" goal).

• Reduce Friction: Drastically reduce the learning curve for users by creating a frictionless, consistently understandable user experience, regardless of which services they are utilizing.

3. The Solution: The Experience Delivery System (EDS)

The EDS was the strategic design initiative Phil championed to solve the technical and customer-facing problems simultaneously. It went beyond the scope of a typical Design System:

4. Gaining Buy-in: Prioritizing the Invisible Work

Phil's insight lay in how he advocated for this major undertaking. Instead of simply asking for budget to "build a design system" (which sounds like an internal expense to finance), he framed the EDS as the critical enabler for the C-suite's explicit revenue goal:

• The Argument: "We cannot achieve the goal of flexible, integrated services and increased competitive advantage unless the customer experience is equally seamless. The Experience Delivery System (EDS)  is not a design tool; it is the necessary foundation for delivering the bespoke, frictionless experience that will drive user adoption and retention across our new product architecture."

• The Priority: He ensured the EDS was a top-tier priority on the design strategy sheet, directly linking its objectives and milestones to the overarching Adobe business objective. Phil ensured the design team "knew and needed to do" this work to accomplish the stated business goals, securing the mandate without waiting for the business to explicitly request the infrastructure.

By connecting the EDS to the quantifiable goals of increasing revenue and strengthening competitive advantage (via better CX and faster development), Phil transformed a foundational design project into an indispensable business strategy project.

Use Phil's Tips Yourself: 4 Tactical Steps for Design Leaders 🪜

1. Focus on Service to Find Success

When worried about losing your creative spark, shift your focus from self-orientation to kindness and empathy for your team's growth, which Phil found to be a massive source of personal energy and inspiration. 

2. Lead with Judgment over Expertise

When leading non-design teams (e.g., Research, Content Strategy), overcome impostor syndrome by remembering that successful leaders, like politicians, rely on informed judgment and the specialized knowledge of their staff, not personal expertise.

3. Cultivate Your "Oxygen Supply”

Recognize that executive sponsorship is crucial. If key leaders retire or move on, the environment can shift, forcing you to "spend time educating them, proving yourself all over again”. Always be building and maintaining connections across your organization.

4. Determine Resourcing Scientifically

“Avoid the "Wicked Witch's throne room" trap of fixed ratios. Instead, focus on the ratio of designers to feature-level Product Managers, starting with a 1:1 assumption and adjusting based on transparent project scope and needs.

5. Apply the Right Metrics & Measurement

How the leader connects design work to business KPIs; Phil assesses the design team not on constant shipping speed, or whether designs get shipped at all, but on two equally important factors: 

1) The quality of their work and 

2) Their ability to build positive relationships. 

“The ultimate measurement of a kick-ass team is the positive impact seen in the business, which is evident when engineering or product management partners voluntarily reach out with gratitude and appreciation for the design contribution and collaboration."

Phil’s Leadership Lesson ✍🏽

The essential mindset shift for an executive leader is to "free yourself of some of the fears" you had earlier in your career. Stop worrying about being right or being the best. Instead, "lean back a little bit, take it all in, listen hard, use your best judgment, delegate well, empower others, and move to the next thing." This non-personal approach allows you to focus on the work as a role, not a personal drama, and enables greater impact while reducing stress.

Phil Clevenger’s experience teaches us that the highest form of design is leading people and strategy. His insights are a roadmap for turning your fear into freedom and your function into a true business driver. 

Dive deeper into Phil Clevenger's full interview in my book, "Leading by Design: The Insiders Playbook for Tech Leadership.”  Order your copy today! 

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy, gift, and review my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

Today, in 5 Minutes or Less 

This article offers product design leaders strategies to navigate the common "role ambiguity" and friction that arises when Design, Product, and Engineering teams—each measured by distinct metrics (experience, revenue, speed)—must collaborate on great products. Drawing from an interview with Colin Grigson, Design Director at Remitly, readers gain an actionable blueprint for overcoming clashes and building influence.

Conflict: The Real Cost of Velocity 🥊

According to research published in the Harvard Business Review on collaboration challenges, product development teams frequently suffer from "role ambiguity." This happens when different disciplines—like Design, Product, and Engineering—fight over the ownership of the user experience, which inevitably leads to political infighting instead of a unified user focus. This friction is severely exacerbated by their distinct, often competing, metrics: Product is typically measured on delivery and revenue, Engineering on speed and stability, and Design on experience and usability.

Given that all these functions are collectively accountable for delivering great products and services, the central challenge for a product design leader becomes: How do you effectively navigate the inevitable conflict and align these disparate priorities?

Below is part of an interview I conducted with Colin Grigson in 2024 for my book, “Leading by Design: The Insider’s Playbook for Tech Leadership". In his extraordinarily candid conversation about this most challenging of issues, cross-functional collaboration in product development.

Executive Insight with Colin Grigson🔥

Colin Grigson is the Design Director at Remitly, a company revolutionizing international money transfers, where he guides the user experience for millions of customers across 170 countries. Colin's impressive career spans major tech giants, including leading product design teams at diverse companies like RingCentral, Redfin, Apptio, and Expedia, with formative design roles at PayPal, Doxo, Amazon, and Dell. His journey offers a unique lens into the strategies and mindset required not only to secure, but critically, to keep the top job in design. Colin graciously shared his perspective on this crucial question:

How do you build trust and collaboration with cross-functional teams, especially when priorities or perspectives clash? 

Here is what he had to say.

“I think trust really starts with being authentic. People can tell when you’re being real, whether they can name it or not; they just feel it. You don’t want to come off as robotic or overly polished, but you also don’t want to be so casual that it feels sloppy. It’s about finding that middle ground where you’re professional but still human.

For me, that means being honest and a little vulnerable. I’ll share what’s actually going on, whether it be the wins or the frustrations. I don’t play politics, and I try not to sugarcoat things. I’d rather be upfront and have a real conversation about how we can move forward together. People seem to respond well to that.

There was a time when three engineering leads couldn’t agree on how we were going to move our design system forward. Everyone agreed we needed it, but no one wanted to take the lead on it. Finally, I pushed on them and said, ‘I need y’all to figure this out. It’s not my place to decide how, but we’ve got to move this forward.’ I’ve learned that being direct, but kind, goes a long way.

Building trust also means giving people space to make their own calls, even if it means they might fail. If you never let folks experiment, nothing new happens. I try to give the same respect to product and engineering that I want for design. My team takes ownership of our work, we present it, we take the hits, and we learn from it. And I think when people see you doing that, it earns credibility.

At the end of the day, we’re all on the same team. Design, product, engineering, and we each have our piece of the puzzle. But if we’re honest with each other and take responsibility for our part, collaboration stops feeling like a tug-of-war.”

Too often, designers hide behind product management. We should be more assertive and vocal about our ideas. As you mentioned, it is crucial to support other functions and build vulnerability. We need to stand behind our work and be willing to learn from our mistakes.

Engineering can be a tricky field. I often start by fostering a strong relationship with my cross-functional peers. Most engineers I've encountered genuinely care about building quality products. They may not always share our aesthetic preferences, but they understand the value of good design and user experience. By consistently delivering high-quality work and demonstrating its impact, we can gain the trust and support of product teams.

When approaching engineers, it's important to consider their perspective. They often prioritize scalability and efficiency. We can foster a more productive and collaborative relationship by framing our discussions regarding how our work can improve their ability to build and maintain systems.

Engineers have different love languages, right? So, how do you show up for them in a way that works for them? Often, designers come in and start changing patterns, and engineers ask, “Why are we changing this? We do it this way everywhere else!” because they're pulling in components, shared assets, and all that. The designers have to come up with answers to these questions, and the engineers might think they're a bit weak. This creates tension because, eventually, someone has to build it, often ending up in this weird in-between place.

And that’s why I think involving engineers early in the review process is crucial. They need to be included from the start. One of the biggest challenges engineers face, which takes time to address, is their dual mindset. On one hand, they’re constantly asked to deliver solutions within tight constraints. “How long will this take?” “What are the limitations?” These are the questions they’re accustomed to answering. However, it's important to encourage them to think beyond these constraints and explore the possibilities.

But for a lot of design work, you're doing the opposite. You're acknowledging the constraints but not letting them dictate the solution. You're asking, "What's the right thing to do?" Then, the constraints help you make the necessary compromises to achieve that goal.

However, when it comes to technology, we should always be pushing the boundaries and evolving. We shouldn't constantly pull back on constraints. So, the challenge is getting engineers, who often operate within specific constraints, to think more creatively and contribute as "yes and" partners. This shift in mindset can make them invaluable to the process.

When you shift into that creative problem-solving mindset, things happen, right? People start thinking, "We have this limitation, but if we connect it to this other thing, we could do it in half the time." Getting them into that mindset is key and takes time and effort, starting with the product and bringing everyone together to focus on it.”

🛝 Step To Transform Your Relationships

Based on Colin's deep experience, here are the non-negotiable actions you can take away to transform your cross-functional (XFN) relationships:

1. Be Authentically Vulnerable: Don't be afraid to be a person first. Share real struggles (both work-related and personal) to encourage others to drop the corporate armor. This informality creates the psychological safety required for real conversations about what's best for the company.

2. Embrace Radical Ownership and Take the Hits: Never let a PM present controversial design work. If the user experience is criticized, you, as the design representative, must stand up, take the hits, and own the outcome. By insulating the PM/Engineer from the heat, you build political capital and gain the "leeway" to experiment and fail later.

3. Frame Design in Their "Love Language": When speaking with engineers, stop talking about aesthetics and start discussing scalability and efficiency. Frame your design system proposals and component changes around how they improve the engineers' ability to build and maintain systems. This shows respect for their priorities.

4. Enforce Early and Deep Engineering Involvement: Don't wait until the final review to involve Engineering. Include them from the start to get them into a "yes, and" problem-solving mindset, rather than defaulting to a "no, because of constraints" mindset. Challenge them to think creatively about how to overcome technical limitations, not be ruled by them.

5. Be Direct with Kindness: When organizational "passing the buck" happens (like the design system example), do step in and be direct. Establish the "what" (e.g., "You all figure it out; we need a design system lead") while respecting the "how" by trusting your cross-functional peers to own the solution. Honesty, even when direct, is appreciated more than political games.

🔌 The Power of Vulnerable Authority

The most powerful form of leadership in a cross-functional environment is vulnerable authority. You don't build trust by being perfect or by hiding behind process. You build it by being authentic and willing to be held accountable.

By respecting the value other functions bring, by proactively taking ownership of the bad outcomes, and by giving your peers and your team the room to make decisions and even fail, you earn the authority to lead. This radical shift in accountability is the single most effective currency for securing and retaining the design function's influence at the highest levels of a tech organization.

💡Ready to Master Cross-functional Leadership Influence?

The journey to strong cross-functional leadership is paved with honest, often difficult conversations. Colin Grigson’s insights offer a powerful blueprint for navigating this tension with authenticity and courage.

Dive deeper into Colin’s full interview and proven strategies for mastering design influence in my book, "Leading by Design: The Insider's Playbook for Tech Leadership." Order your copy today! 

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy, gift, and review my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

UnsplashPhoto by Christina @ wocintechchat.com on Unsplash

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏱️ Today, in 5 Minutes or Less 

You’ll learn the three strategic pillars of alliance building: how to elevate your visibility, the exact strategic questions to forge trust with your cross-functional partners, and why alliances are indispensable to your executive safety net.

 🔎 Alliances as Insurance Against Political Risk

Failing to cultivate proactive alliances is the number one reason high-potential leaders are sidelined. In leadership roles, your reputation is often shaped not solely by your actions, but by how others interpret and communicate them to organizational leaders. If people are unaware of your value to the business, their ignorance becomes a barrier to your progress—effectively keeping you from asking for, and getting, what you want.

A study by the Corporate Executive Board found that executives who actively build a broad, strong network of internal allies are 2.5 times more likely to report career satisfaction and feel they have a "safety net" to navigate political resistance and organizational change.

Using Strategic Inquiry Questions at Work

Building a strong alliance begins with strategic inquiry—structured, short, open-ended questions that move beyond small talk to uncover your partner's true priorities, pain points, and definition of success. These questions, which often start with "What" and "How," are the keys to building trust and securing influence. If you’ve ever witnessed a user experience researcher conducting an interview, this is how they will be asking their questions. Short less than 12 words, and asked with genuine curiosity.

1. Build Rapport First: Focus on Their World 🧭

Start your meetings by showing genuine interest in their strategic goals. This builds the foundational relationship before you make any asks.

2. Address Potential Problems Openly: Partner, Don't Blame 🛠️

When a project hits a roadblock, use inquiry to understand their perspective on the root cause and align on a path forward. This positions you as an ally.

3. Share Wins Strategically: Document and Scale Success 📈

When a project succeeds, use the opportunity to document and scale that success together. This reinforces the value of your partnership and increases your collective visibility.

The Short of It Is

In tech leadership alliances aren't a luxury; they are your safety net and your springboard to achieving your career goals. To ask for what you want and keep your job, you must actively forge supportive, trustworthy relationships with your cross-functional peers. Do this by making your team's work visible and by using strategic inquiry to understand their world.

Cultivate trust through transparency, accountability, and consistent delivery. By consistently translating your principles into the language of business—data, logic, and predictable growth—you solidify your reputation as a dependable and trustworthy leader, expanding your influence and impact without needing to resort to demanding or political behavior. To learn more about this topic, please buy my book “Leading by Design: The Insider’s Playbook for Tech Leadership”

What is the one strategic question you'll commit to asking your most critical cross-functional partner this week?

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Photo by Markus Winkler on Unsplash

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏱️ Today, in 5 Minutes or Less 

You'll learn the two essential steps tech leaders take to immediately demonstrate value, shift from a reactive to a predictive design strategy, and align design KPIs directly with financial business outcomes.

 🔎 The Design Cost Center Problem

As you climb the design leadership ladder, your role shifts dramatically: you move from being responsible for making things to being responsible for making decisions.

A common challenge is that many senior leaders get stuck when the C-suite views their function as a "cost center"—a group that makes things look good, but whose value isn't explicitly tied to the business's core goals: revenue, retention, and growth. New executives can get bogged down in process and politics instead of demonstrating measurable business impact, which often leads to high leadership turnover.

In fact, a study by the Corporate Executive Board found that 46% of newly hired executives are rated as disappointments within 18 months. A primary reason is their inability to effectively connect their function's work (like design) to the tangible business results the organization values. They fail to link design metrics (e.g., usability scores) directly to financial metrics (e.g., conversion rate or Customer Lifetime Value), thus failing to prove their financial worth.

Stepping into a new Chief Design Officer or equivalent role requires a data-backed narrative that proves design is a strategic growth driver, not a cost center. To avoid the common pitfalls of leadership transition, here are the two things you can do to actively prove your worth and establish your influence from day one.

1. Quantifying Your Impact

Tech doesn't wait. Your first strategic move is to swiftly pinpoint the business metrics that truly matter and align your design Key Performance Indicators (KPIs) to measurable results. As a design executive, you must identify the precise business outcomes your efforts will impact.

This means focusing on direct, measurable outcomes that your company tracks and that you can improve with your function:

• 💰 Financial Performance Are you driving financial performance by optimizing conversion funnels or increasing Average Order Value?

• 📈 User Growth and Engagement Are you fueling growth through increased user acquisition and sign-ups or boosting the daily/monthly active user ratio?

• 🤗 Customer Retention and Satisfaction Are you solidifying user loyalty by elevating Customer Satisfaction (CSAT) or reducing the churn rate?

Knowing what the business goals are and how design will achieve them becomes your narrative for quantifying your team’s impact.

2. Pick a North Star Project Goal

Once you know the key business metric, it’s time to pick an unambiguous, measurable goal that becomes your team's North Star. We're talking about a concrete, time-bound benchmark, such as "boosting new user task completion rates by twenty percent within the next quarter.”

For example, Anshuman Kumar, former SVP and Head of Design at Asana, adopted Annual Recurring Revenue (ARR) as his team's North Star. Here's how he created and executed a plan to ensure his design team's efforts were directly tied to business results:

1. Auditing High-Value Surfaces: The team didn't review every screen; they concentrated their audit on user experience (UX) surfaces that were critical to revenue, adoption, and payments.

   • Ask yourself: For every critical UX bug or point of customer friction we identify, what is it costing the business by not addressing it?

2. Reframing UX Bugs as Revenue Opportunities: They cataloged every critical UX friction point and presented it not as "design debt," but as ready-to-go revenue experiments with documented solutions. This instantly turned design improvements into a business priority.

   • Ask yourself: What parts of our product experience actively prevent our customers from getting thing done quickly and effortlessly?

3. The Priority Framework: The design team curated a list of high-impact opportunities and proactively presented it to cross-functional partners. They effectively shifted the conversation from being a blocker to a partner providing a curated menu of guaranteed, high-return experiments.

   • Ask yourself: Who is the most influential cross-functional partner whose success is directly linked to ours, and how can I initiate a 'value trade' - where we help them achieve their top priorities in exchange for their support of our North Star goal?

To maintain focus and drive excitement, Anshuman implemented two tactical steps:

1. A Leaderboard was Built: A public leaderboard was established to gamify the process, tracking the number of experiments run and their resulting impact on ARR.

2. Focus on False Trade-Offs: Resolving situations where business goals (ARR) and design goals (better experience) seemed to conflict, finding solutions that satisfied both metrics simultaneously.

The result of Anshuman’s North star design strategy was a dramatic proof point: They generated $10 million in ARR that year. This success fundamentally changed the company culture, proving that the quality of the user experience is as vital as the features themselves.

The Short of It Is

To prove your value in a leadership role, you must immediately connect design effort to quantifiable business outcomes. Start by identifying the core financial metric your team can influence, then define a specific, measurable North Star goal. This focused, data-driven approach is the fastest way to solidify your position as a strategic executive.

If you’d like to learn more real life stories from current executive leaders in tech, including the interview with Anshuman Kumar please buy my book “Leading by Design: The Insider’s Playbook for Tech Leadership”.

That's it for this week!

"Wait, I wrote this? Let me check the fine print. Yep, my name's there. Wild."

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Photo by Ian Schneider on Unsplash

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

⏱️ Today, in 5 Minutes or Less 

As an aspiring creative leader, you've likely dreamt of the Chief Design Officer title. It’s the ultimate validation of your craft, talent, and leadership. But let’s pull back the curtain on this rarefied air.

What happens when your career success is no longer measured by pixel-perfect UI or user delight, but by seven-figure budgets, quarterly financial results, and boardroom influence?

The journey from a design manager  to an executive design leader is a radical metamorphosis. As a former Chief Design Officer, it  takes you away from the practice of your craft and away from managing directly to a place that relies on projecting your value and having an impact through influence.

 🔎 Did You Know

The Executive Reality: Lonely, Intense, and Life-Changing

Being an executive is often lonely. You trade time with your teams for countless meetings with leaders who speak the language of finance, operations, and market share, expecting you to speak it too. You pore over spreadsheets, endlessly recruit, present to "scary dudes," and are in a constant state of context-switching. If you let it, your time is no longer your own.

Yet, this is a rare, privileged position where the financial rewards can offer life-changing generational wealth. When your compensation breaches the seven-figure threshold, the stakes—and the pressures—become immense. You're in the "shark tank," where complacency is a death sentence, and your perceived value is a battleground.

The question is: Are you ready to trade your designer's heart for an executive's mindset?

🧠 The Mindset Shift: Designer vs. Executive

Creative behavior and portfolio skills alone may not be enough to sustain long-term success at this level. The executive arena demands an additional investment in financial education and the ability to communicate the value of your organization’s output to the business bottom line.

Business leaders focus on the verbal, analytical, and orderly (left-brain thinking), measuring worth by collecting hard skills in financial strategy and quantitative analysis. As a designer, you live in the broader world of creation and process flow (right-brain thinking).

To thrive, you must seamlessly merge these two worlds. Here is a look at the fundamental shift in focus required to make that leap:

🕵🏼 The Research Backs It Up

This distinction between design management and executive leadership isn't just theory—it's backed by research into successful C-suite transitions:

Shift from Functional Expertise to Strategic Acumen: 

A study published in the Academy of Management Executive emphasizes that the transition to executive roles requires leaders to shift from a focus on deep functional knowledge (like design) to a greater emphasis on strategic vision, resource allocation, and organizational architecture. The skills that made you a great design manager (mastery of craft) become secondary to your ability to communicate financial and strategic value to the CEO.

The Need for "Organizational Savvy"

Research by Marshall Goldsmith highlights the "What Got You Here Won't Get You There" principle. Moving to the executive level demands Organizational Savvy—the political intelligence, interpersonal influence, and financial literacy necessary to operate effectively at the top. This replaces the emphasis on individual or team output, which defines a successful design manager.viding the experience and visibility required to fast-track your journey to the top.

Landing the top design leadership role is an achievement, but sustaining it requires a proactive, multifaceted approach.

Opening the first edition of my new book Leading by Design

In my recently published book, Leading by Design: The Insider's Playbook for Tech Leadership, I delve deep into the essential strategies for surviving and thriving in this executive design seat. We explore how to demonstrate your impact rapidly, build unshakeable relationships, and amplify your sphere of influence.

Are you ready to design your career transition from manager to executive with intention?

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Book a free coaching session for 30 min. strategy call

• Buy yourself a copy of my book

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

👏 In This Week's Newsletter 

That moment, when I learned my early design work on mobile software in India for Apple had inspired a colleague to pursue a career in UX, became the spark that defined the purpose of my book. After spending 29 years navigating the journey from Apple's labs to leadership roles at Yahoo and Meta, I realized there was a huge, uncharted void: a lack of guidance for those ready to leap from design management to the C-suite.

That's why I wrote Leading by Design to fill that gap, giving the next generation of aspiring design executives a practical playbook I wish I'd had.

🌟 The Ripple Effect of Design Work 

In March of 1997, I was a guest speaker at Carnegie Mellon University (CMU), where I presented my work on mobile software for midwives in rural India. It was an honor, but I assumed that was the end of the matter.

Eight years later, while having dinner with Yahoo colleagues in Beijing following a conference we’d co-sponsored, one person mentioned having attended that CMU symposium. They explained that seeing our work—specifically how we used a user-centered design process to develop mobile software for healthcare nurses—had directly inspired their career in User Experience Design (UXD).

That powerful realization, that our work creates deep, lasting career impacts, is what shifted my perspective and fueled my purpose to do more.

🚀 Navigating my Way to the Executive Table

In the intervening years, I went from the future-focused labs at Apple to a sudden reset after Steve Jobs’ return, a visa cliffhanger, and personal loss.

I soon found myself at Excite!, then on the rocket ship that was Yahoo, where I joined as the first design manager. I helped build a team that supercharged media services, driving serious revenue and climbing market ranks. This intense period propelled me from an individual contributor to a Senior Director, navigating layoffs, visa battles, and the ever-evolving tech landscape.

Growing up in rural England in the 1980s, the idea of leading UX teams in Silicon Valley was utterly foreign. I nearly said no when Apple called on the eve of my graduation to join their Advanced Technology Group. But destiny intervened, launching me on a 29-year journey through Apple, Yahoo, Meta, and various startups, culminating in my international executive coaching practice for creative leaders.

🛠️ Your Practical Playbook for Executive Influence

That experience in the Beijing restaurant revealed the undeniable need to guide the next generation of creative leaders who are driven by the belief that good design is good business.

Guidance for individual and design manager roles is plentiful, but the path to executive design leadership is largely uncharted. I wrote this book to fill that void. Having reached the executive level myself, I realized that sustaining the role requires an unwritten set of skills that move you beyond tactical thinking.

My goal is to equip ambitious, aspiring creative leaders with the confidence, influence, and practical strategies needed to not only secure the top job but to truly excel in it.

What You'll Master from Reading the Book

• Business Acumen: Many design leaders struggle to explain the business impact of their work. This chapter eliminates that struggle by revealing how the C-suite truly perceives design and which key business metrics matter most. Learn to leverage these common tech metrics to your advantage, allowing you to speak truth to power and articulate the clear Return on Investment (ROI) your team drives for the bottom line. You can download this chapter for free using the QR code at the end of chapter 6. 

• Strategic Positioning: Learning to strategically position yourself and build strong, essential relationships with cross-functional partners.

• Political Savvy: Practical strategies for building alliances, neutralizing saboteurs, inspiring fence-sitters, and channeling the energy of provocateurs.

• Expert Insight: The book is enriched by the journeys of seven exceptional executive thought leaders (from companies like Artefact, DocuSign, Uber, Myriad Genetics, Icomera, Remitly, and Asana) who generously shared their ascent to executive leadership.

📢 What Tech Executives Are Saying

⭐⭐⭐⭐⭐

Game-changer for Tech Design Professionals Gunning for Executive Spots

Reviewed by MV, in the USA on Sept. 29, 2025

"Leading by Design is a game-changer for tech design professionals gunning for executive spots... she focuses on nailing interviews, measuring impact, and crafting a killer personal brand. Love the data-baked strategies that bridge creative skills with C-suite savvy." 

"A reflective and insightful guide for aspiring technology leaders... Rather than presenting rigid rules, it offers a flexible 'playbook' rich with practical advice... Highly recommended." 

⭐⭐⭐⭐⭐

A Reflective and Insightful Guide for Aspiring Technology Leaders

Reviewed by Richard Mellor in the UK on 19 September 2025

“I connected with so much of it, prompting me to reflect on key moments and lessons from my own career path. If you aspire to become a tech leader and wish to make a meaningful impact by demonstrating empathy, adaptability, and prioritising people, this book is highly recommended.”

⭐⭐⭐⭐⭐

A Masterclass in Leadership - Highly Recommended

Reviewed by Joe Miller, in the USA, on September 23, 2025

“Her authentic storytelling and framework, supported by inspiring interviews with notable leaders, deliver both guidance and motivation. Reading this book felt like a masterclass in effective leadership. It’s a must-have for anyone serious about growing as a leader—I’ll be recommending it widely.”

✅ Call to Action: Take the Next Step in Your Career

1. Get Your Copy: Purchase "Leading by Design: The Insider’s Playbook for Tech Leadership" on Amazon today and begin your transformation into a confident, impactful executive.

2. Download a Free Chapter: For a deeper look at what drives the C-Suite, download your FREE Chapter 6 on Metrics for Design Leaders right now! [Link to Free Chapter 6 Download Here]

3. Share Your Insight: If you've already read the book, please consider writing a review on Amazon. Your feedback is crucial for helping aspiring leaders find their playbook! 🙏

That’s it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like to see me cover in the future? Just shoot me a DM or an email.

With ❤️ from Sally

Today, in 5 Minutes or Less ⏱️

In this newsletter, you’ll discover why negotiating a job offer is a test of your leadership, how to research and value your worth, and the essential steps to take when a formal offer is on the table.

Proof of Your Power 🔋  

A study from the Harvard Business School found that candidates who negotiated their offers increased their total compensation by an average of 7.4%, and an additional study by the same school found that those who asked for more money were perceived as more competent. Having a negotiation game demonstrates your capacity to lead with conviction.

A Better Way to Think About Negotiation 🤝🏽

I want to share a personal story that taught me a powerful lesson about negotiating job offers. Early in my career, I was offered a dream job at a well-known tech company. I was so excited about the product, the brand, and the team that I accepted the first offer they gave me, even though the base salary was a significant cut from my previous role. My mindset was that I was "not in it for the money"; I was in it for the opportunity to lead others researching and designing customer centered exciting new products and services.

The offer I accepted, despite its lower salary, included a substantial grant of stock options. At the time, I didn't fully grasp their value. I just saw it as part of the package. Years later, that equity proved to be far more valuable than the initial salary. It was a happy accident that I ended up in a great financial position despite my reluctance to negotiate. 

As creatives, we're often drawn to projects that feed our passion, not our wallets. While I got lucky this time, it could have easily gone the other way.

Negotiating a job offer isn't a betrayal of your values. It's a way to show you can lead with conviction and ensure you and your team are valued for the work you do.

Your Game Plan for a Top Job Offer ♟️♟️

Define Your Non-Negotiables: Before you start negotiating define the absolute minimum you're willing to accept. To figure this out, understand your expenses or "run rate" and then add a buffer for your desired lifestyle and savings goals. This buffer, whether it's 10% or 20% more, gives you room to negotiate without compromising on your core needs and ensures you won't accept a deal that undervalues you.

Know Your Worth: Research salary ranges for comparable roles at similar companies using sites like Glassdoor, Levels.fyi, and Salary.com. Leverage your network to get insights on compensation structures. Understand a startup company might offer lower salary but higher equity, while an established company may offer the opposite. 

Embrace the "Total Compensation Package": A job offer is more than just a base salary. It might include short-term incentives (STIs) like a sign on bonus, and long-term incentives (LTIs) like stock options and RSUs. Don’t be put off if the salary is not what you hoped, explore the total compensation and see what is negotiable, for example an additional number of vacation days, upgrades for class of travel, quality of hotel. If you are having to move or apply for a visa what level of support for things like relocation costs, tax filing, mortgage support, visas for yourself and your family. Then there are other perks including free or discounted food, team entertainment, vehicle allowances, severance packages, concierge facility, further education, coaching budgets etc. A portion of your earnings potential often lies in these incentives, so don’t be afraid to ask. 

Want to improve your communication and negotiation skills? Even if it's not in your job description, I'd suggest checking out these two articles. They completely changed my perspective when I transitioned from a mature tech company to a startup. After reading them, I felt empowered to accurately position my value, and the negotiation process left me feeling truly satisfied and welcomed by my new team

• How Not to Bomb Your Offer Negotiation By Haseeb Qureshi, Managing Partner at Dragonfly Capital 

• 15 Rules for Negotiating a Job Offer  by Deepak Malhotra Professor of Business Administration at Harvard Business School

Know When to Walk Away: If an offer doesn't meet your needs and expectations, be prepared to decline it. It's better to walk away from a bad deal than to accept a role that undervalues you.

The Short Of It 💥 

Negotiating a job offer isn't about being greedy; it's a critical test of your leadership and your ability to advocate for yourself. By reframing the conversation around total compensation and doing your research, you empower yourself to make strategic choices that align with your long-term goals. Don't settle. View the offer as the starting point of a conversation and be prepared to advocate for your worth and your teams once you are on board.

What's the most valuable lesson you've learned from a past negotiation? 

Is there a specific part of your career goals you'd like to work on? I’d be happy to discuss it with you, just send me a direct message or an email to sally@clearchannelcoaching.com.

That's it for this week!

With ❤️ from Sally

Here are a few ways I can help:

• If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Design (subjective) vs. Data (objective)  

If you're a product designer, you're used to focusing on the craft of what you create. But sometimes, it can be a challenge to translate your work into the metric-based language that's valued by colleagues in business-driven roles.

Turning your work into a data-backed narrative takes time, and it's especially tough when you're working ahead of a product launch and don't have all the information you need. If you've ever struggled to get your voice heard by people who are focused on data and the bottom line, these frameworks are two ways to structure your work and present results in a language they'll understand.

Whether you're presenting to the board, giving product updates, or interviewing for a job, your ability to translate your work into business outcomes is critical for three key reasons:

1. It Builds Credibility: Business leaders speak in metrics. Data helps you prove that you understand the big picture. By grounding your design decisions in evidence, you earn the trust and respect, allowing you to advocate for design as a strategic, analytical discipline.

2. It Aligns and Motivates Your Teams: Data provides a common language you can use to frame problems and measure success, giving your designers clear, measurable goals. This shows them the direct, tangible impact of their work.

3. It advocates for the User Strategically: Data-driven stories are your most powerful tool for advocating for user needs. You can tell a compelling narrative that connects user problems (backed by quantitative and qualitative data) to a clear business opportunity. This elevates design from a tactical role to a strategic partner in key business decisions.

How to Quantify Your Impact 💥

Two of the most effective methods are the SOAR and STAR frameworks. Although similar, each serves a distinct purpose. These frameworks provide a clear, easy-to-follow structure that turns raw data into a compelling story. Instead of merely presenting numbers and charts, they guide you in framing data around a specific event, making the information more relatable and memorable.

SOAR Method 🚀

The SOAR method (Situation, Obstacle, Action, Result) is a powerful technique for highlighting your problem-solving and critical thinking skills. It's especially effective when you need to showcase how you've successfully overcome significant challenges.

• Situation: You start by providing the context and setting the scene. For example, "We wanted to launch a new product feature to attract a younger demographic."

• Obstacle: You explicitly identify the obstacle or challenge that made the situation difficult. This highlights your ability to foresee and navigate problems. For example, "However, our existing user data showed that our current customer base was primarily older, and we had no information on the preferences of the younger target market."

• Action: Describes the specific, data-driven actions you took to overcome the obstacle, showing your resourcefulness and analytical skills. For example, "I conducted a comprehensive market analysis using social media sentiment data and competitor benchmarks. I then launched a small-scale survey of a sample of younger users to gather qualitative and quantitative feedback, which provided the insights we needed."

• Result: Concludes with the measurable outcomes and lessons learned. The results should directly tie back to how you successfully navigated the obstacle. For example, "The data-driven insights allowed us to tailor the feature specifically for the target audience. The feature launch was a success, leading to a 30% increase in new user sign-ups from the younger demographic and a positive return on our marketing investment."

STAR Method ⭐

The STAR method (Situation, Task, Action, Result) is a structured approach used in behavioral interviews to provide detailed examples of past experiences. It helps you articulate how you've handled specific situations, completed tasks, and achieved results, making your answers clear and compelling.

• Situation: Begin by setting the scene. Describe the context or a specific challenge the organization faced. This is where you introduce the problem that the data will help solve. For example, "Our Q2 customer churn rate increased by 15%."

• Task: Clearly state the objective or goal. What did you need to accomplish? This is the specific mission related to the situation. For example, "My task was to identify the root cause of the increased churn and propose a solution."

• Action: Detail the steps you took to address the problem, emphasizing your use of data. This is the core of the narrative, where you highlight your analytical process. For example, "I analyzed customer feedback data, support ticket logs, and user engagement metrics. The data revealed a clear pattern: customers who didn't use our new feature within the first 30 days were 2x more likely to churn."

• Result: Conclude with the tangible outcomes of your actions. This is where you quantify the impact of your data-driven solution. For example, "As a result, we created an automated onboarding campaign for new users, which led to a 10% decrease in the churn rate for that cohort and a $50,000 increase in quarterly recurring revenue."

The Benefits💥 

These frameworks can help you:

• Provide context and move beyond just showing data points to explaining the "why" behind them.

• Highlight impact by forcing you to connect your actions to concrete, quantifiable results, demonstrating the value of your work.

• Make it memorable by structuring your information as a story, making it easier for your audience to understand and act upon your insights.

If this is a challenge you face, you may be interested in my book, Leading by Design: The Insider's Playbook for Tech Leadership, which comes out on September 23, 2025. I've dedicated Chapter 6 to showing you how to take common business metrics and translate user-centered design principles into attention-grabbing business results with impact. It will be available as a free download with purchase.

If you struggle with leveling up your communication for business outcomes, I’d be happy to help. Just send me an email to sally@clearchannelcoaching.com.

That's it for this week!

With ❤️ from Sally

Here are a few ways I can help:

• If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

• Book a free coaching session for 30 min. strategy call

• Contact me with feedback and suggestions for future topics  

Today, in 5 Minutes or Less ⏱️

Ready to land that top design job? This week's newsletter shares  how to move beyond your portfolio and master an  executive interview. How to prepare with intention, research with purpose, and showcase  strategic thinking that will make you the  leader they can’t afford to lose.

Did You Know 🔎 

The average length of an executive job search is 6 to 9 months, a timeline often extended by the meticulous preparation required to secure a top role. This fact alone highlights the critical need to elevate your interview game; your time is valuable, so every interaction needs to count.

Proof in the Data 📈

According to a recent study from Korn Ferry, the most desired trait in a C-suite candidate is strategic thinking, with companies prioritizing candidates who can articulate a clear vision and connect it to business outcomes. This means your interview isn't just about past achievements but about your ability to shape the future.

Data from LinkedIn's Global Talent Trends report highlights that 75% of hiring managers believe personal brand and preparation are more important than ever for senior roles. This means your proactive research, tailored questions, and genuine curiosity about the role and company culture can be the deciding factor in a competitive field.

A Case Study 👩🏽‍💻

The journey to an executive or senior leadership role isn't is about demonstrating who you are. Many candidates fail by focusing solely on their portfolio and past projects, past employer brand recognition, missing the chance to showcase their executive presence. True leadership is revealed not just in what you've done, but in how you think, how you prepare, and how you articulate your vision for the future.

Imagine a top-tier designer and leader named Ava. She's a finalist for a Chief Design Officer role at a major e-commerce company. In her initial interviews, she focused on her portfolio and past successes. While her work was impressive, she felt she was missing a deeper connection with the hiring managers.

Before her final presentation, Ava took a new approach. She spent two days meticulously testing the company's product, from the mobile app to the website, making detailed notes on the user experience. She also researched each interviewer, discovering they had recently launched a new product line.

In her presentation, she didn't just show her past work; she integrated her observations from her product testing. She proposed a few thoughtful, high-level ideas for improving the new product line's user flow. Her preparation paid off. She demonstrated a deep understanding of the company's challenges and showed a level of strategic insight that went beyond a typical interview. She was hired, with the CEO later saying, "Ava didn't just tell us what she had done; she showed us what she could do for us, specifically."

The Playbook: Elevate Your Interview Game 🎲

Here are the steps Ava took to land the top job:

Go Beyond the Product. Become an Insider: Don't just look at the product from the outside; become a temporary user. Sign up, navigate the onboarding, and use the service as a customer would. This direct experience will uncover your most insightful questions and reveal a deep understanding of their business, a level of preparation few candidates will reach.

Research Your Interviewers. Be a Detective: Your interviewers aren't just names on a calendar; they're the people you'll work with to build the future. Research their backgrounds, their work, and their public profiles. This isn't about flattery; it's a sign of professional respect and a strategic way to find common ground. Knowing their priorities and past successes will help you tailor your responses and show that you've already started thinking about how to partner with them.

Master Your Presentation. Speak with Passion: Your presentation is your moment to showcase your leadership presence. Rehearse it until you're so comfortable you can speak your truth no matter what. A great technique is the "record and review" method: record yourself, then watch the video three times. First, listen only (sound on, video off) to assess your vocal quality. Second, watch only (sound off) to see your body language. Third, transcribe what you said to identify and eliminate filler words. The goal isn't just to be perfect; it's to be so comfortable with your content that your genuine excitement and conviction shine through. That passion is contagious and will leave a lasting impression on your audience.

Reveal Your Growth Mindset. Share Your Scars: Senior leadership is a journey of continuous learning. Instead of presenting a flawless record, show your ability to self-reflect. Discussing a lesson you learned from a project that didn't go as planned isn't a sign of weakness—it's a demonstration of strength. It proves that you're an introspective leader who can analyze outcomes and grow from them, a critical trait for any executive

The Short Of It 💥 

Landing a top design role is about much more than a strong portfolio. It's an exercise in strategic preparation and self-awareness. To stand out, you need to:

• Become a temporary insider by testing the company's products and services.

• Be a detective by researching your interviewers and their backgrounds.

• Become a master communicator by practicing and refining your message.

• Reveal your growth mindset by sharing lessons you've learned along your journey.

This approach transforms the interview into a strategic conversation. You're not just a candidate; you're a leader ready to contribute from day one.

Is there a specific part of your interview prep you'd like to work on? I’d be happy to discuss it with you, just send me a direct message or an email to sally@clearchannelcoaching.com.

That's it for this week!

With ❤️ from Sally

Here are a few ways I can help:

• If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Photo by Ricardo Viana on Unsplash

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

Today, in 5 Minutes or Less ⏱️

You'll learn the spoken and unspoken expectations of a top creative leadership role in tech, the personal sacrifices that often come with the job, and the steps to navigate it all with intentionality.

Did You Know 🔎 

The most shocking expectation for a top leader isn't the workload; it's the surprising pressure to maintain an "eternal youth" facade. Many leaders find themselves taking extraordinary measures, from cosmetic procedures to rigorous diets and exercise, just to "look the part" and appear to be winning at their job. This can blur the line between professional success and personal identity in an unexpected and unsettling way.

The Numbers Don't Lie 🔢

A 2023 study by Gartner on C-level executives found that nearly 60% of tech leaders reported feeling constantly "on," with their work-life boundaries completely eroded. Furthermore, research from the American Psychological Association indicates that 75% of executives experience high levels of stress, directly linking it to the pressure of a demanding schedule and the need to be a constant high-performer. This data highlights the reality that while some expectations are clearly defined, the personal toll of managing them is often overlooked.

The Human Impact 🚀

This pressure isn't just about long hours; it's about the erosion of personal joy. The things that once brought unadulterated pleasure can begin to feel frivolous. Leaders often find their lives becoming transactional, opting to pay others to handle tasks they once loved doing themself. This shift can lead to a profound sense of isolation and a disconnect from what truly makes them happy, as the job consumes their identity and personal time.

Charting a New Path 👣

You can have it all (not always at the same time), but you don't have to do it all.

As a leader, you know the feeling of being pulled in every direction. Your work consumes your calendar and your brain space, leaving little room for anything else. The constant travel, late-night emails, and weekend work can feel like the price of success.

But what if you could lead effectively and reclaim your personal life? It's not only possible, it's essential for long-term impact and fulfillment. It starts with being intentional; defining your purpose and values beyond your job title.

Consider Sarah, a design director in tech who felt her life was being consumed by her job. She was always on call and traveling on weekends, feeling like she was losing touch with her family, community, and hobbies. Realizing this wasn't sustainable, she took a weekend to herself to get clear on what she valued most and what she wanted more of, and less of, in her life.

She realized her purpose wasn't just to be a "design director." She also wanted to be a supportive partner, creatively inspired and a more impactful leader. With this newfound clarity, she consciously rearranged her schedule and resources to support those values.

Be Creatively Inspired: To regain her sense of creativity, she began scheduling a monthly "artist's date." This as a solo expedition to do something that enchants and interests you. The ritual helped her reconnect with her creative spirit which made her feel alive again. Julia Cameron's book The Artist's Date Book was the source.

Be a More Supportive Partner: Sarah realized she needed to be more present for her family. She started by scheduling dedicated family time on her calendar each morning—time that couldn't be overwritten. She also reclaimed more weekends by changing her travel habits. Instead of flying to company headquarters on Sunday evenings for Monday meetings, she began traveling on weekdays instead. For international trips, she stopped padding her travel with weekends to "get over jet lag," a practice she found was rarely effective. She shortened her trips, confining her travel to weekdays whenever possible. This meant less time spent awake at 3 a.m. in a hotel room in Bangalore watching reruns of National Geographic.

Be a More Impactful Leader: Sarah realized that if her calendar was always full of other people's agendas, she had no room for her own. She had to make time in order to align her strengths and experience with the business goal to build a world class UX design team for hte company. This clarity meant she now became very good and two things. Delegating and building sustainable teams.

1. Delegating: Sara created a monthly inventory of all her meetings and asked herself for each one, "Is attending this meeting the best use of my time?" If the answer was no, she considered who might want to take it on and how it would help them grow their career. This strategy is known as defensive calendaring, and you can find a Google Sheets template online to help you get started.

2. Building Sustainable Teams: Sarah's time was consumed by endless recruiting and hiring meetings, a process largely driven by recruiters focused on hitting short-term targets. She realized that to be a more impactful leader, she needed to shift from a reactive approach to a long-term hiring strategy that would truly serve the business.

   She started by closely analyzing her team's structure, specifically the ratio of junior, mid-level, and senior designers. She considered whether she had the right number of senior leaders to serve as her second-in-command and if her team had the necessary leadership bench strength to handle the work in her absence. Sarah aimed to spend more time collaborating with other executives on design strategy across the company and needed to trust her team could carry on the work without her.

   Sarah envisioned what a better team ratio would look like three years down the line for both the business and her team. She developed a comprehensive plan with clear career paths to cultivate a pipeline of future leaders. She also recognized that some of her current senior leaders had limited opportunities for growth within the existing structure and would need to transition out of the team within that three-year timeframe. Sarah improved what she could within her team and collaborated with the recruiting department, sharing her new vision to ensure a more aligned and strategic approach to building her team's future.

The Short Of It 💥 

Taking a step back to define what truly matters to you now, as a creative leader, not a manager or an individual contributor, can transform your life and impact as a leader. By aligning your work with your personal values, you can create a career that is both impactful and sustainable. You must protect your personal well-being, invest in your team's autonomy, and remember that true leadership is as much about your own sustainability as it is about your company's success.

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like me to cover in the future? Just send me a direct message or an email.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

Today, in 5 Minutes or Less ⏱️

You'll learn how to clarify your leadership motivations, identify your unique strengths, and use them to articulate your career achievements in a powerful way.

Did You Know 🔎 

According to a Harvard Business Review study 95% of people think they're self-aware, but only 10–15% truly are. This gap highlights the critical importance of self-reflection in leadership, as what you believe about your own strengths may not align with reality. The Harvard Business Review published an article citing research that found self-aware leaders receive more promotions, get more positive performance reviews, and are more effective at managing teams.

Building Resilience Through Self-Reflection

For creative leaders in tech, self-reflection isn't a soft skill—it's the engine of your resilience. It's the deliberate practice of stepping back to analyze your experiences, decisions, and emotions. By truly understanding the "why" behind your leadership—your core motivations, values, and strengths—you build the confidence to navigate the inevitable challenges of your career. 

This introspection is what allows you to lead with genuine authenticity and inspire  trust from your teams. In a field that demands constant innovation, knowing your unique value and being able to communicate it effectively is the difference between leading and simply managing. As a Gallup study of 1.2 million employees found, teams with managers who leaned into their strengths saw a 12.5% increase in productivity and a 15% reduction in turnover—a clear signal that your inner work directly impacts your team's success.

The Path to Becoming an Even Better Leader

/The journey to becoming a better leader through self-reflection involves several key steps. Here are a few I have found most useful:

Assess Your "Why” ⁉️

The first step toward becoming a truly authentic leader is a deep dive into your own motivation. Ask yourself: What is my "why"? Is your energy fueled by building human connection and fostering community (Social Person)? By the excitement of brainstorming and innovation (Ideas Person)? By the satisfaction of creating clarity and efficiency (Systems Person)? Or by the joy of empowering your team to reach their full potential (Supportive Energy Person)? Understanding the answer to this question is the foundation for a more purposeful and impactful leadership journey.

Identify Your Strengths 💪🏽

Ready to stop guessing and start leading with confidence? The key is to know where you naturally excel. I recommend the Gallup Strengths Based Leadership Assessment to identify your unique talents within the four leadership pillars of Executing, Influencing, Relationship Building, and Strategic Thinking. Once you know where your greatest strengths lie, you can leverage them to drive better results and build stronger teams

Connect Strengths to Achievements 🏆

Your value isn't just in what you've done, but in how you did it. When you talk about your achievements, shift from a simple list to a powerful narrative using a framework like the SOAR method (Situation, Obstacle, Action, Result). This allows you to highlight the specific strengths that define your leadership. For instance, rather than just stating you delivered a project on time, you can articulate how your communication skills navigated stakeholder conflicts (Obstacle) or how your strategic thinking led to a critical pivot (Action) that resulted in a better-than-expected outcome (Result). This method transforms a simple accomplishment into a clear and compelling story of your personal impact.

The Short Of It 💥 

To position yourself for the top job, you must first know yourself. By understanding what motivates you and what your core strengths are, you can effectively articulate your value to others. The SOAR method is a practical way to connect your natural abilities with your professional achievements, creating a powerful, unique narrative that proves you have what it takes to lead.

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like me to cover in the future? Just send me a direct message or an email.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

⏱️ Today, in 5 Minutes or Less 

In this newsletter, you will learn about the five key paths to position yourself for the top job in your field.

 🔎 Did You Know 

Ever wondered why some people seem to just fall into amazing jobs while you're spending hours on LinkedIn Easy Apply? It's not magic; it's networking, but probably not in the way you think. While it's easy to get caught up in the grind of crafting the perfect portfolio and resume, the real secret to landing a top-tier role often lies in who you know.

Data from Jobvite shows that referred candidates are 4 to 15 times more likely to be hired than those who apply cold. And for senior-level positions, that number is likely even higher. Why? Because a referral is a form of social proof. When someone at a company vouches for you, it gives hiring managers confidence. It also signals that you're a good cultural fit and that your expectations for the role are well-aligned, which dramatically reduces the risk of you bailing early.

So, how do you tap into getting referred to a top job?

👔 Cultivate Your "Loose Ties"

Don’t wait until you need a job to start networking, rather, adopt a strategy of intentional loose-tie outreach. The place to start your outreach is with people on the periphery, rather than people close to you.  According to sociologist Mark Granovetter in The Strength of Weak Ties, loose ties expose you to entirely new worlds. To cultivate loose ties, schedule a recurring time each month to check in with a few former colleagues or industry contacts with the intention to build a reciprocal relationship.

It was through a loose tie that I was connected with a recruiter at Sequoia Capital. A month later, I was hired to set up an international Design Team - this was exactly the role I was seeking at that time. 

Want to start cultivating your own network but feel overwhelmed by the thought of traditional networking events? I highly recommend Karen Wickre's book, Taking the Work out of Networking. She offers great advice on how to build what she calls a "brain trust" by sustaining the "loose touch habits” a couple of many she recommends are mentioned above.

🚚 Move from a Mature to a Growth Company 

While working at mature companies like Apple, Meta and Yahoo provided me with invaluable career experience, my path to an executive position and Chief Design Officer truly accelerated when I moved to a smaller, faster-paced growth stage startup. At a tech giant there is an abundance of top-tier talent which can create intense competition, making it challenging to get the hands-on leadership opportunities you need to grow. Startups and growth stage series A and B companies are often defined by their lean structures and rapid growth, offering a unique chance to quickly take on a wider range of responsibilities and gain direct exposure to executive-level decision-making. This kind of environment is a powerful catalyst, providing the experience and visibility required to fast-track your journey to the top.

🏛️ Start Your Own Company  

The phrase "everyone has a startup in them" perfectly captures the spirit of Silicon Valley. Rob Girling's journey is a masterclass in how to start your own company. 

After working at design giants like IDEO, Sony, Microsoft, and Apple, he decided to build something of his own. He co-founded Artefact, a Seattle-based design consultancy. He and the team built an application designed out of Artefact's own internal needs to get a "big picture" view of their projects and teams. They created a resource management application called 10,000ft. The application was acquired by Smartsheet in 2017. That acquisition ultimately became part of an $8.4 billion deal in 2024 by Blackstone and Vista Equity Partners. 

In my upcoming book, Leading by Design: The Insider's Playbook for Tech Leadership (due out in September 2025), I interview Rob, whose story offers a powerful lesson for aspiring creative leaders on how to turn a great idea into a thriving business.

🍴 Carve Out Your Specialist Niche

For many, the top job has always meant becoming a manager, but there's an alternative that allows you to lead without managing people: the Principal Designer, also known as Distinguished Designer, Fellow, Chief Design Architect, Staff Designer, or Lead Designer. This executive-level individual contributor (IC) role is for you if you want to drive strategy and vision while staying deeply connected to the craft of design and you lead through influence and deep expertise.

So, What Makes a Principal an Executive?

Principals operate at an executive level, focusing on the big picture to solve a company's most complex and ambiguous challenges. They often lead "tiger teams", groups assembled from across the organization to tackle problems that can't be solved through traditional methods. For example, after the Russian interference in the 2016 U.S. election, I witnessed firsthand how a Principal-led team at Meta created a new industry standard for ad transparency. They designed products for Facebook to protect legitimate political discussion and address a critical, high-stakes problem.

🥂 Get Promoted From Within

Seek Out "Stretch" Opportunities

Look for projects that go beyond your current job description. Volunteer to lead a new initiative or take on a task that challenges you. By expanding your influence, you demonstrate that you're ready for more responsibility and can contribute to the company's success in ways that aren't tied to your current role.

For example, offer to present your team's work to senior leadership. This gives you visibility with key decision-makers and showcases both your team's accomplishments and your part in them. By connecting your work to broader business goals, you prove you're thinking strategically and have the capacity to influence others, essential functions of any leadership role.

Make Your Manager a Partner

Your manager should be your biggest advocate. Be upfront with them about your career goals and express your interest in a senior position. Ask for direct feedback on the skills you need to sharpen and how you can get more exposure to high-impact projects. When you make your manager a partner in your growth, you can strategically work toward a promotion with their support.

💥 The Short Of It

Landing a top job in leadership isn't just about crafting a perfect portfolio; it's about being strategic. Whether you're networking through "loose ties," moving to a startup company for accelerated experience, starting your own company to build your vision, carving out a specialist niche as a Principal Designer, or getting promoted from within by seeking out stretch opportunities and making your manager a partner, each path requires you to proactively demonstrate your leadership potential. The key is to stop waiting for opportunities to come to you and start creating them yourself.

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like me to cover in the future? Just send me a direct message or an email.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Claim your free copy of the Personal Planning Workbook "Sally's Soul Searching Research Guide” and discover how to unlock purpose and direction in the areas of your life that are in your control.

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

Today, in 5 Minutes or Less 🕰️

In this issue, we'll explore the typical career paths for aspiring design leaders in tech, demystify the firm foundation you need to start your journey to the top job.

Did You Know 😊

The "10-year rule" for mastering a skill is a well-known concept, but in the tech industry, the timeline for design leadership is a pressure cooker. While your counterparts in traditional sectors may spend decades slowly climbing the corporate ladder, you need to prove your strategic value and business acumen at lightning speed. It's not uncommon for design leaders to secure an executive or senior leadership role within their first 10-13 years of their career. This compressed clock means every year counts, and every decision is a critical step toward the top. To position yourself for a top leadership role, you need to be intentional and strategic at each stage.

Years 1-5: Foundational Excellence: This is your time to become a master of your craft. Hone your skills in a core discipline, build a strong portfolio, and gain a deep understanding of the technology and business you're designing for.

Years 5-10: Expand Your Influence: Shift your focus from individual contribution to team and project/product leadership. Seek opportunities to manage projects and teams, contribute to product strategy, and build strong cross-functional relationships. Learn to connect your work to the bottom line. Job titles and focus might evolve like this:

Individual Contributor: Your focus is on execution of design tasks, the quality of individual output and personal craft and skill development.

Design Manager: You focus on team impact and output, individual growth, developing team members, project oversight.

Design Director: You focus on departmental strategy, cross-functional alignment, operational excellence, scaling functional  impact.

VP/C-level Design Leader: You focus on company-wide design strategy, organizational impact, business growth, future-proofing design, and executive advocacy.

✍ Case Study: Moi!

🍏 The Foundation: Deep Craft at Apple

I started my career straight out of college as an Interaction Designer in Apple's Advanced Technology Group (ATG). I spent three years honing my craft, learning from some of the best minds in the industry. My first management moment came when I was asked to lead an interdisciplinary team researching omnidirectional display technologies. It was my first taste of management—not by choice, but by necessity—and it set the stage for everything that followed.

💻 The Hustle: Agency Life and Startup Scraps 

After five years Apple closed ATG and I joined the design agency Studio Archetype as an Interaction Design Director. Then I moved to Excite@Home as a Principal Interaction Designer. This was over a two year time span where I learned to adapt to different environments, navigate immigration challenges, cope with my father passing away, buy my first house… you get the picture. It taught me resilience, tenacity and adaptability and so much more that would prove invaluable as I grew up personally and professionally.

🚀 The Leap: Scaling a Team at Yahoo 

Seven years into my career, I was given a huge opportunity: to become Yahoo's first Design Manager. Over the next five years, my role and responsibilities grew exponentially. I helped build and scale projects and teams, and connected design outcomes directly to business results. I left Yahoo as a Senior Director, taking a much-needed career break. After 12 years of being an immigrant ‘alien of extraordinary ability’ where my right to be in the U.S. was tied to my visa, I had finally secured my green card and applied for U.S. citizenship

🧘‍♀️ The Detour: A Break to Build Something New 

My career then took a fascinating six-year detour. I leveraged the principles of user-centered design thinking in a completely different context: running my own Feng Shui consulting company. I immersed myself in Chinese metaphysics, a discipline that taught me new ways to look at systems, patterns, and human experience from the outside in. I know what you might be thinking, why not something practical or monetizable, like an MBA? Go figure!

💡The C-Suite: Back to Tech with a Fresh Perspective 

My unconventional career path came full circle when I returned to the tech world to build a UX design team for the startup, [24]7.ai. The skills I'd developed during my break—systems thinking, pattern recognition, and a fresh perspective on human-centered design—were crucial. They empowered me to build a cross-functional, international design teams from the ground up.

Over the next five years, I rose to become the company’s Chief Design Officer. After that, I spent a year as a Director of Product Design at Meta before starting my own coaching company. This new chapter allowed me to shift my focus to the human experience from the inside out, and I now dedicate my time to supporting the next generation of creative leaders in tech as they navigate their own unique leadership journeys.

🤑 How to Apply This 

My story isn't a playbook, but a reminder that a leader's career isn't always a linear climb. The moments that seem like detours, the layoffs, the side hustles, the career breaks are often where the most profound growth and unique skills are forged. It's these diverse, often difficult, heart wrenching experiences that truly set great leaders apart. A journey into leadership, I found, requires a lot of introspection and learning. Two learnings I came to see were essential to leadership are nurturing allies and being an active listener. Here’s why:

🕸️ Build and Nurture Allies and Supporters

Your leadership is ultimately measured by the trust others place in you. The most powerful proof of your influence is not what you say about yourself, but what others say on your behalf to those in power when you are not in the room. Your network is more than a list of contacts; it's a living ecosystem of support. Engage with people, learn about them and find your tribe.

👂 Practice Active Listening

In a heated debate with engineering and product teams about a critical feature, it's easy to get defensive and immediately jump to protecting your team's work. An active listening approach offers a powerful alternative.

Active listening is about understanding perspectives, asking clarifying questions, and reflecting on what's been said. Instead of reacting defensively, you could pause and ask, "What are the core concerns from engineering about the timeline, and from product about the user value?"

Their responses will help you identify common ground and propose a solution that respects everyone's constraints and priorities. This strategy not only builds consensus rather than creating conflict, but it also establishes a foundation of trust.

💥 The Short Of It 

The path to the executive suite is less about a linear climb and more about a strategic expansion of your skills, influence, and network. The key is to see every experience, conventional or not, as a story of continuous growth, and the time to start writing your next chapter is now.

On that note, I have to be honest this newsletter took a longer break than I intended. The reason? I've been writing my first book! I'm so excited to finally share that I've completed "Leading by Design: The Insider’s Playbook for Tech Leadership," which is coming out this September. I poured everything I know into this project and can't wait to share more details with you in the coming weeks.

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like me to cover in the future? Just send me a direct message or an email.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Claim your free copy of the Personal Planning Workbook "Sally's Soul Searching Research Guide” and discover how to unlock purpose and direction in the areas of your life that are in your control.

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics