[upbeat music] Hello and welcome back to another episode on the Chief of Staff podcast. I'm Scott Amenta, the founder of the Chief of Staff Network and your host on today's episode.
There's a version of the chief of staff that stays high level, coordinates across teams, and never quite owns anything. And then there's the version Judy Abad plays.
She's moved fluidly between senior functional leadership roles and chief of staff more than once.
She was one of Facebook's first chiefs of staff right after the IPO, built and led product marketing at Slack, launched business products at WhatsApp, and now serves as chief of staff at Freshworks.
She's seen both sides of the table and has a clear point of view on what it actually takes to operate at the highest levels in either seat.
We get into what separates the two roles, how she thinks about picking careers deliberately, and why she believes most confidence is just projection. Here's my conversation with Judy. Judy, welcome to the podcast.
Nice to have you here. Thanks, Scott, for having me, and I'm really happy to be here. How are you feeling today? Good.
It is Monday morning here in San Francisco, California, so just trying to get through a long list of to-dos. And it is Monday evening for me, and I still have a long list of to-dos, so we're both on even pages. Yeah.
It never ends, right? Never ends. I'm really excited to have you here today. You have a very storied career that I'm excited to dive into with you.
Maybe just give us, the audience, a quick like thirty-second to one-minute preview of what your career looks like. This is probably the hardest question I'll ask. Yeah.
I wish I had a, like, pre-scripted answer, but I'll be brief. I started my career in tech and have never really looked back. I joined Facebook really early around employee five hundred. I was in sales there.
I became a chief of staff. Moved over to the Instagram team, where I helped launch our first ad products.
And then I went over to Slack, where I ran product marketing and was early there as well, so it was around employee one hundred. So I've been kind of through that hyper-growth path at a couple of different places.
After Slack, I went back to WhatsApp, and I helped launch business products there. Then I joined TripActions, which is now Navan, and did a whole host of things at startups before landing where I am today at Freshworks.
These are some of the biggest household names in tech, both B to B and B to C. You've led marketing and product now at WhatsApp, Slack, Instagram.
These are, like, real domain leadership that calls for deep expertise in those areas. You've also been chief of staff at multiple companies.
And what I'm so interested about talking with you today is what do those two kind of factors look like? What does functional leadership look like versus being a leader at the highest levels as a chief of staff as well?
Talk to us a little bit, like, at the senior level, what actually separates how you operate in those two kinds of roles? Where does the work feel different?
Well, first, I am really excited to be here talking to you because I am so passionate about the chief of staff role, and I really love the community you've built. I love the content you guys put out to help people.
I mean, I really wish I had this when I was early in my career 'cause I'm still learning as well, but I get it now, and I get to hopefully give back a little, and so I'm really excited to be here for that reason.
I would say there's a couple things that are really different about the roles.
One is when you're leading a team, you own a product or a monetization line, and you're really deeply accountable to the metrics or outcomes you're trying to achieve in that specific area.
You make a lot of decisions based on imperfect knowledge, and you become a domain expert in sort of that one part of the company's performance.
For me, for example, it was business monetization at WhatsApp, which was one of a few of our top priorities at the time.
We also were very focused on user growth, payments, and ongoing integration efforts across Facebook, Instagram, and WhatsApp.
As a chief of staff, you have way more breadth across that entire portfolio of company priorities, but you really don't have as much ownership over each metric.
So I think as a chief of staff, you really have to be able to see the end-to-end outcomes.
You have to prioritize, synthesize all types of information so that you can help advise teams on how to move forward and when to escalate things to your boss.
I think when you're in a functional role in leading a team, you really are trying to do the opposite, which is, how do I take care of as many things as I can myself and not escalate?
But as a chief of staff, you really have to have kind of that EQ, IQ of, hey, this team is really stuck, and if you can get involved and help them make a decision, you will unblock and help accelerate the overall effort, you know, meaningfully.
I think of myself now really as both a force multiplier and an absorber, so really making sure that my boss knows what's happening, and I can help connect the work across departments that would otherwise operate in silos.
But at the same time, absorbing a lot of that organizational complexity for him so that he knows what the decision and the outcome is, but he doesn't necessarily have to know how messy it was for the team to get there.
There's a lot of, uh, qualitative aspects to being a chief of staff. I think some of the best chief of staffs will operate this way, and they feel deep accountability to anything they work on.
For me, if I touch something, it's going to be better. The process will be better. The end result will be better.
But I think the chief of staff role still to this day can be kind of nebulous, and it really depends on the kind of person you have in the role versus when you're leading a marketing team or leading a product team.
Like, the job description is specific enough that you know what you're looking for and you know the type of skills you should bring.
Whereas like a chief of staff, there's this ambiguity to it, which really depends on kind of where the company is in its point in time and how the executive likes to work.
We'll talk a little bit about how that ambiguity is one of the forces that gives the chief of staff its power. At least that's my belief.
Going back to some of your comments around the kind of broad exposure that this role has, the breadth that it has kind of across the business. These are phrases that we hear pretty consistently on this podcast.
Talk to us a little bit about how you bridge that gap, moving between a senior chief of staff role where you have that broad exposure and then moving into a more functional leadership position.Where now the domain expertise is more important, you're really focused over, like, a specific division or wing of the business.
Does it feel like you're taking a step back in some ways by losing that broad exposure? And psychologically, how has that been for you as you've kind of oscillated between these two types of positions?
I get this question a lot, even in real life. I mean, you know, when I'm interviewing for jobs, sometimes l- people will be like, "Why do you want to be a chief of staff?"
And I think we can get into kind of motivations and sort of my framework for picking careers later.
But I think fundamentally for me, I've kind of gone between the two, mostly because I want to be at a company that I believe has a lot of opportunity, and then figure out how do I best help that company execute.
And for me, sometimes that's in a functional role.
But also, sometimes I think that's just as a chief of staff, where you wanna have kind of this higher level of expertise around what the company is doing well and what it isn't.
I actually think one of my greatest strengths as a chief of staff is being able to see that end-to-end outcome and always thinking like the end user, and that really comes from spending my first decade plus at companies launching products and growing revenue where we cared really deeply about people.
First at Meta and Instagram, of course, and then at Slack, and then at WhatsApp. I actually think there's a way to learn this.
I would say, like, people who go to business school kind of develop a little bit of this thinking, but there's also a framework that I love, which is called Jobs to Be Done, and that's really just putting yourself in the end user.
What is it that they're trying to achieve, and how do you help them get there? And that's kind of all of the work, the product, the messaging, all of that.
Today, a lot of my work is internally focused, but I'm always thinking about who is gonna be most impacted by the result of what we're trying to do.
And I almost work backwards from saying, "This is what we're trying to achieve. Now, what are the steps and the teams that need to be involved, and at what pace and timeline, in order to go and achieve that thing?"
So maybe it's a sales ops team that's gonna be impacted because we're changing the way we forecast, or maybe it's we wanna make a change to our billing, and so we need to think about operations, pricing and packaging, and the customer-facing teams where the end outcome is really, you know, how will we impact our end customer?
But there's all these moving pieces that need to work in sync and be in lockstep in order to have that end outcome we're trying to achieve.
And a lot of what I do now as a chief of staff is just making sure that the teams that are gonna be impacted or the teams that have work to do and accountability here have the right context to make those decisions in their areas of expertise and allow for a really smooth and fast execution.
What I'm hearing as well is that you've pretty consistently relied on your functional expertise, like the skills that you developed in product, in marketing, in sales, potentially, as part of your chief of staff role, and that has kinda set the context for how you've approached your chief of staff kinda leadership position as well.
You know, knowing how these parts of the business operate and, you know, having more fluidity and, and understanding of what those teams might be going through and how they should be working together.
Going back to your phrase, force multiplier, but also absorber, right?
You're there to help absorb not just problems from your principal, but across the entire organization and make sense of those and how they need to work together.
A lot of chiefs of staff that are looking to be kind of like real strategic partners at the C-suite level have a hard time actually getting there.
Many chiefs of staff might be sitting somewhere between that director and vice president level but have never truly stepped into the C-suite. What do you think it actually takes to get there?
Like, how does that path run through functional depth? Do you have to move into a functional leadership role to then become that more senior chief of staff? Is that a necessity?
It's a great question, and I'd actually be curious what you think because you see so many chief of staffs, and you interview so many different ones. I have the broad exposure in this question, yeah.
I turn that around you. You have the expertise and the broad exposure here. I think for me, it really depends. I would never say absolutely yes or absolutely no.
I think as a chief of staff, an advice I give a lot of people who are taking on their first chief of staff role is you wanna build credibility by owning something end to end, and you wanna get into the weeds of what you're doing, and you do not wanna stay high level.
Like, the job itself necessitates that you're pretty high level because you're overseeing so many different things as your exec is, and you don't truly, truly own one functional thing.
But it doesn't mean that you can't dig deep with some of the folks on your team and figure out what their day-to-day l- is like, what they're motivated by, what their goals are, and actually work with them on it so that people believe and trust in your ability to get things done and your competency.
I do that in whatever job I'm in, so whether that's helping to write a PRD, writing email copy, putting decks together, helping to plan really important tool implementations that we're doing, change management, whatever it is.
Like, actually getting in the weeds and saying, "Hey, let me take over this piece of the work, and you can give me feedback on whether or not you think it, like, meets the bar for what you would want someone on your team to help you do."
There is no shortage of work at companies that are growing fast. They almost never have enough people to do the work that needs to be done.
And so I think it's really about almost inserting yourself in a really authoritative way to say, "Hey, like, this is a priority for my exec. I'm gonna jump in and help on this."
And not staying high level where there's a tendency to do that when you're a chief of staff, either because, A, you don't think you have the time or, B, you don't think it's your place.
And I'm always like, as a chief of staff, you own everything, and you kind of own nothing, but you really are overseeing everything. So you need to jump in and help figure out where there are problems and solve those.
Like, run towards the hardest things in the organization. That's, I think, one thing around just how do you build that credibility and how do you kind of get to be a more senior and truly kinda C-suite leader.
And I think the flip side of that is that I just think you really wanna look at kind of the slope of the individual.
You wanna understand if they have a high future potential because they're growing fast, they're learning a lot, and they're performing really well. And I think that these people can exist anywhere.
They don't have to have functional leadership experience.The most important thing really is can you learn quickly? Do you have high EQ? Do you have an intense curiosity and a strong sense of ownership?
I think it's easy, a- an easy proxy that's correlatory but not necessarily causal is to say, okay, well, this person has led a function at this company, and they know what great looks like, and therefore, I believe they know how to build best in class.
And I've seen that lead to amazing hires, but I also think I've seen that lead to pretty mediocre hires, where once they leave that company, they're out of their depth.
They don't actually know how to do the work that they say they know how to do.
So I really think it's really about how do you evaluate people and where are you looking for that skill and where do you think that functional depth matters or not?
I actually agree with a lot of what you said, and we've talked a little bit about this on this podcast before.
Two of the proxies that people tend to look at as, like, I'm moving up in the career ladder, you know, tend to be P&L ownership, and am I managing a team?
And how big is that team, and who's reporting into other managers within that team? And I think those are, like, probably the most traditional ways of measuring progress, right, on the kinda career spectrum.
I don't think that they necessarily have stood the test of time. Organizations are getting flatter.
Chiefs of staff are becoming more prevalent, in part because of those reasons, and someone that has this very broad exposure and, like, can help these teams see around the corner for challenges that might be arising in other parts of the company, especially larger companies, is a really critical role.
I fully agree with you though.
For a chief of staff that has so many things thrown at them, whether they're choosing so or not, what's most important is that they ultimately decide to take ownership over the things that matter most.
I would caveat that by saying the chief of staff also has the responsibility in helping his or her principal be the deciding voice to say no to more of those things than they say yes to.
And in saying no, that is the opportunity to choose when to say yes, and then to go kind of, like, full on into that new project. That doesn't mean that you need to abandon your chief of staff responsibilities.
It does mean, though, that you're gonna be spending more of your time in, like, one part of the organization, and that is not necessarily a path into, like, another functional leadership role, but it is certainly a path in the rest of the leadership team and the rest of the company for that matter, seeing you as a leader of this thing that is driving part of the business, and that by itself helps you to move into, like, these more senior levels of the position.
That is my take. And I think we've seen some examples of that on this podcast and certainly people that I've spoken to, where you do not have to be a functional leader to be a C-suite executive.
[laughs] Just because you have been a CMO before is not indicative of the fact that you will be a great CMO somewhere else either.
And so I think chiefs of staff do have it in them to become C-suite execs, and it may not be as clear of a path as has been outlined and demonstrated by the numerous other stories we see of functional leaders moving up the ranks and then holding multiple C-suite positions over the rest of their career.
I think we need more of those narratives, right? And that is part of the goal of having you here a- and other amazing operators is to help frame that story for our listeners. Absolutely.
I would say, like, one of the things that's really exciting about being a chief of staff, and an opportunity that I think does come up if you are a strong performing chief of staff, is the ability to fill in leadership gaps and build some of that functional expertise as you're going.
It's almost, like, not, like, necessarily a you have to trade off being a functional expert or a chief of staff. You can almost build both, and I totally don't think it happens at every company.
But certainly at startups what I've seen and what I've personally experienced is when there is sort of a new need for a leader to come in, I've stepped in.
I've seen other chief of staff step in and kind of run the function until they can figure out who should lead.
So at a company I was at, we went from series B to series C, and at that time we decided we should split out sales and customer success and move customer success into its own dedicated leadership function.
So I spent four to five months running that customer success team, helping them build out their playbooks, implementing customer success specific tools, meeting with customers, understanding the business and how they drive themselves, helping to think through sort of a new set of metrics that we would really wanna look at depending on how we segment the business and the product lines we had, and then really spending a lot of my time building that bench and finding the right leader for the function.
A couple months later, our head of marketing left, and so I stepped in until we found a new marketing leader as well.
But I think you can put yourself in a position to get opportunities like that if you really prove yourself to be a deeply competent chief of staff.
When you're evaluating kind of new opportunities, say, uh, your recent role at Freshworks, what has made you choose between interviewing for a functional leadership position versus a chief of staff role?
Or did that process happen naturally as you were having conversations with the company, and you felt, «I'm better suited for this chief of staff role because I love this principal.
I think we're gonna work really well together. I can be that force multiplier for him or her»?
Or have you been more, like, directed, I guess, in the sense of, oh, I'm gonna look for CMO positions for this next bout of my career? I think it's so deeply personal.
I would never pretend to know what everyone should do or how people's careers should look like, but I'm happy to share how I think about it. One is I'm a big Taylor Swift fan, so this is relevant, I promise.
Taylor has this thing.
You know, she did the whole Eras Tour, like the most highest grossing tour of all time, but I remember in a documentary with her once, she talked a lot about how you have to continue to evolve in your career, and you have to continue to sort of be really deliberate at the stage and point in time you're at, be unafraid to try different things and do different things.
So for her, that was like going from country to pop to sort of, um, like that folksy guitar acoustic stuff and kind of where she is now.And I actually think for regular people like us working at jobs, it's sort of similar.
I mean, you really wanna meet yourself in the moment in time that you're at. And I think that a lot of these decisions are two-way doors, and people tend to take it very seriously.
Like, when I'm finding my next job, I better find this thing that I love and I'm deeply passionate about, and it better be the thing I wanna do forever. And I just don't think that that's fundamentally true.
Every decision around a career is essentially reversible. I mean, I don't think you should be quitting jobs every month, but you could.
You could walk away from anything that isn't serving you anymore, and you can go and reinvent yourself and do something different.
I'm a really, really big fan of that, like, meme where it's like, you can just do things, and I say that to my husband all the time, and especially, like, with our kid, when we're, like, stuck trying to figure something out.
I'm like, "We can just do things. We can make this up as we go, you know?
Just figure it out and we'll fly blind for a little bit, but we're smart, capable, competent people, and we'll eventually get to the place we're trying to go, even if we meander a little bit."
And all of that, I think, is to say is that in different points in my career, I've wanted to do different things. I've been really early and an executive at a startup. It was one of the first AI startups.
We had an incredible trajectory at launch, and then we just couldn't find our footing. But that, to me, was an experience where I think a lot of people would be like, oh, wow, that was a failure. It was a failed startup.
But for me, it scratched an itch that I had, which is I really wanted to build zero to one. I wanted to see if that was a place and time where I would enjoy the work, and if I'm honest, I didn't love it.
There are just so many different types of problems you encounter when you're truly building zero to one than when you're building one to a hundred or a hundred to a million. And so I know that I didn't like it.
It gave me a ton of credibility in the founders that I talked to and that I invest in, and it gave me a really much sharper lens to actually evaluate founders. So it made me a better investor.
So there's always, I think, a lesson, and the ever optimist in me is always seeing the positive in experiences that other people might look at and say, "Okay, well, that didn't work out the way you wanted it to."
In my career right now, I am really looking for companies that I think have a lot of potential.
I'm looking for places where I believe in the product, and it has product market fit already, and also just giving me the opportunity to impact something at scale. So big where it has product market fit, but not too big.
And then the other thing that I think I have really, really oriented towards, especially as I've gotten longer in a career, is just working with people that I think are really great.
And it doesn't mean I have to like all of them, but I have to respect them, and I have to feel like they are working towards something together.
And it's because everybody really wants to do what's best by the company, and people care about their careers, they care about building teams, whatever it may be, sure.
But, like, at the end of the day, do I feel like we're all here because we wanna do right by the company and do right by our end users?
I think especially whether you're a functional leader or a chief of staff, you want to have a great boss.
You wanna make sure that the boss you work for is someone you think is gonna be invested in giving you those opportunities that will help you grow and is really just a person that you wanna work with and see win.
I think a lot of what I tell people now, and I would say that this is actually different maybe from, like, fifteen years ago in my career, I think today I'm at a place where I don't wanna win with people who are jerks.
I would much rather work at a place that's really, really great and try to get us to win than feel like the impact that I have is really huge and positive, but is contributing towards something that I just don't fundamentally believe in or people that I don't really wanna see win.
Yeah. It's awesome advice. I know it was not meant to be a playbook, but it's certainly a lot of interesting takeaways in what you just said.
The through line is that you've been very deliberate about each of these choices throughout your career, whether it's joining a very early-stage startup and kind of taking, one might argue, a different set of risks, right?
Every company is risky in its own way, to your investing career, to obviously kind of all of your history at Facebook and WhatsApp and now Freshworks.
Looking back at your chief of staff role specifically at each one of those companies, how have they differed?
So earlier in your career when you were chief of staff to kind of where you are today at Freshworks, what has that progression looked like for you? You've obviously done lots of other things in between all of that.
Maybe that has played a role, and we've talked a little bit about that at the beginning of the episode. But talk to us a little bit about kind of the two or three instances now that you've been a chief of staff.
So at Facebook, originally, the chief of staff role was really meant for a high-performing young person to come into the role for two years and then eventually move into another part of the company and lead a team.
That was really how Cheryl saw the role, and then my boss, David, as well. At the time, I was only ever the second person to hold that chief of staff role for the CRO at Facebook.
And so it was really kind of like, let's get really young but really smart and talented people who are gonna hustle and figure this out as they go along.
And I would say that role has completely evolved now, where there's lots of chief of staffs at Facebook, where there's lots of career chief of staffs, people who have a ton of experience, more like a chief of staff you'd see in government.
In that role, I was really learning everything as I went. There was not a single thing that I did in that role that I had ever seen or done before.
And so it's really about how do you kind of start to build your own frameworks?
How do you test the way that you work, and how do you really build out your own experience and define the role for yourself based on sort of what are the natural strengths or things that you gravitate toward?
I've always been an intensely curious person. My toddler and I get along great right now because we're always asking each other why. It's really fun to talk to him.
But I've always been that person who pulls at a thread until I'm absolutely positive I'm at the very end of it, and then I figure out, how do I go and fix this, or how do I go and make sure that the team is progressing and moving towards the end goal we're trying to get to?
I would say probably the biggest difference in the roles since is I've gained a lot more confidence in what I'm capable of, and thatJust comes with experience, I think.
It comes with being able to say, "I've done this before. I know what this should look like."
And that's probably an argument for even functional expertise in some ways, but certainly in having more depth and more time in the role as a chief of staff.
You start to see kind of patterns emerge in what execs want you to prioritize, in the kinds of problems that arise at companies, no matter what their end business looks like or who their end customer is.
And you figure out, you know, how do you take what you've done before, and how do you tailor it for the context and the background of the current company you're at?
And then you just have a lot more, I think, authority and autonomy in going out and actually solving the problem. How would you define the changes in this, like, seat at the table?
Thinking back to your time at Facebook to where you sit within Freshworks today, what is your influence level?
What are the types of conversations that you're having with either the executive team or the broader management teams?
And how much has that influence changed as you've kind of matured and gained new skills along the way and are perceived, right, as a different leader within the company?
I think a lot of this actually is almost, like, personally led in the sense of when I first started as a chief of staff, I was so junior in a room of, you know, VPs and C-level executives.
There were times when I was just afraid to speak my mind.
I would sit there and think, "Okay, well, if I ask this question, I'm probably the only person who doesn't know this, and so, like, why don't I just try to figure this out later on my own and not ask the question in front of a bunch of execs where I'd be wasting their time?"
And then on occasion, where I did pressure test and where I did ask questions, it turned out to be things that everybody was wondering and no one had said aloud.
And I noticed this with my boss as well, where he would always ask the questions that felt dumb, and then you'd see people be like, "I never stopped to consider that." And you'd kind of see how their face changes.
It reminds me of a story where when I was at Stanford, I took a class with the former Secretary of Defense under Bill Clinton, and he would tell us stories about his time as Secretary of Defense, and he accomplished a ton of incredible things as Secretary of Defense.
And so I would go to office hours and just ask him a ton of questions about what that experience was like because, at the time, I had this feeling that I wanted to work in government, so I just wanted to learn from him.
But I asked him what it was like to work with Bill Clinton once.
And he said, "The thing that made Bill really remarkable was that you could be an expert in, like, Russian-US relations, and you could have studied that and been working in that field for forty years, and you could come to him with a two-page brief on how to advance, you know, this talk and this negotiation, and he would be able to read that, have way less depth of expertise than you, but know exactly the right questions to ask you to pressure test what you were thinking and why you came to the recommendation that you came to."
And I think knowing that and sort of being really cognizant of wanting to develop that skill for myself and then truly seeing that at Facebook, I think Cheryl and my boss, David, are master class operators.
And being able to even be in a room with them and watch them execute, let alone help them make decisions and be the person that at least my boss turned to for advice, was a really, really incredible learning experience.
I mean, I always talk about how, like, instead of business school, I did a couple years as a chief of staff at Facebook right after we IPO'd and basically learned probably on the ground, you know, more than what they did there.
And Cheryl used to always say, like, "Why go to business school when you're building the case studies that they're gonna study at business school?"
So I always felt like that experience just taught me so much, and it was a lot of trial by fire.
And now, when I'm in the room and just slowly as you kind of have more shots on goal and you take more at bats, you learn how to be that person for yourself, and you learn how to ask those questions.
And look, sometimes they are dumb questions, but most of the times you're voicing aloud the concerns that other people had, and you're actually meaningfully helping the work progress because you're identifying the gaps or the silos, and you're helping to connect that so that people can actually go and a better result comes from it.
I love it. I think you hit the nail on the head. It's all about personal confidence.
And, you know, I think for a role where every chief of staff has the same title, and the title can, in a lot of ways, be misleading, we would talk about the ambiguity in the role, right, for all the projects that you might be working on, for all of the depth and breadth that you have kind of across the business.
But the real ambiguity is also in the title itself, and this is not a very ambiguous title when it comes to the political and military world, right? The title is well established. It's pretty well defined.
And the perception of it is, I would argue, relatively the same kind of across those industries.
When you get into private sector, and tech especially is a culprit of adopting titles and roles and making things up as we go along, the external perceptions of this role can also be a challenge for any sitting chief of staff or someone like you that has actually moved in and out of this position over their career.
So in some ways, this role, and in some minds especially, and we can correct those people today, the role is still kind of junior adjacent.
It may even be perceived as, uh, more administrative than it is strategic, so more parallel to, like, a senior EA.
When you're, like, genuinely a senior executive or sitting in a chief of staff seat with decades of real functional leadership and experiences under your belt, how do you navigate that perception?
When you interviewed at Freshworks for your chief of staff role, was it clear that this was, you know, at the more senior end of that spectrum based on the job description?
Or was it something that you felt you've had to redefine?Each time you go into one of these conversations, and is that still happening? [chuckles] No, it's a really fair question.
I actually think this is something that when people are looking for a chief of staff role, they should filter out for immediately.
So, I think a lot of times job descriptions will give you a sort of sense of how they believe the chief of staff operates, but certainly during the interview process, like, I would be asking really pointed questions around the types of projects you think you'd work on, how many other chief of staffs there are, who does the chief of staff report into?
I mean, I've looked at roles where they actually report into strategy and operations and not to their actual... and dotted line into sort of the C-level exec, and that to me makes no sense.
I think for some people, sure, that will work, but at the way that I operate and the level I operate, it doesn't make sense for me to report into somebody else and dotted line into the exec that I'm going to support.
So that to me is, like, just a question of being really good at evaluating and finding the kind of role that you're interested in.
The other piece of it is I really think, like, having a strong first 90-day loosely plan is really, really important. And to me, I just jump into things right away. Like, nobody has to tell me where the problems are.
I'm gonna talk to everybody, and I'm going to figure that out, and I'll do that by aligning myself closely with what my boss's priorities are, identifying the wedge of, hey, here's where it's broken, so I'm gonna spend my time here, and that will ultimately get you to achieving the priority that you want.
I think some of it is a little bit of an attitude, which is just, I'm gonna jump into everything, and I'm going to make it better.
And if you don't see that in the first three weeks where I'm on this project, then we can talk about it and figure out where I should do better, but I'm not gonna ask for permission.
I'd rather apologize if I've overstepped my boundaries later.
And what I have found in almost every chief of staff role that I've been in is that people welcome this kind of help when it's done at, like, a highly skilled level and when it's also done, you know, with EQ and understanding kind of the interpersonal dynamics and complexities that can make this work really hard.
And I really think it's just about making sure that as a chief of staff, you're always cognizant of how you can do that, how you can have a positive impact, and how you can help meaningfully accelerate the work that other people are trying to do.
Because the truth is, at any level in a company, people are going to be grateful for help when it comes from someone that really can actually move the ball.
I love that you take the, uh, the old adage of don't ask for permission, ask for forgiveness in the tech industry and just applied it directly to your own career path.
By the way, early on in my career as a chief of staff, I actually got feedback in one of my performance cycles from someone who was like, "Judy has a tendency to want to do everything on her own, and she needs to stop and think about where do these resources already exist or who are the people she can talk to in order to help feed input into the, like, plan of action she's taking."
And I thought that was actually really great feedback because I am somebody who I think is very, like, headstrong, and I'm gonna own this. I'm gonna figure it out, and I can do it.
And getting that feedback early in my career has really helped me also say part of doing it is being able to bring people along with you and making sure that others feel deeply accountable for the work that they have to do, and not you taking on the work for them because you don't think that they're gonna be able to do it.
This was very early on, like, before I had ever even managed a team. I think when you have experience managing people, you kind of inherently understand that you can't do everything by yourself.
It's a great example though, because that kind of feedback earlier in your career can be instrumental in the way that you approach new challenges, new opportunities, right?
New people that you're working with for the rest of your career. I had a similar experience when I was a chief of staff. I had a coach. Well, not my coach specifically.
She came in to help mentor and coach, like, the rest of the executive team. I was lucky to get a little bit of extra time with her.
She really helped to steer me in a way and think about my role very differently than the way that I was approaching it, right? And I was relatively early in my career.
And like you said, I started to lean in a little bit more heavily on the executive team meetings and be a little bit more vocal on the things that I thought were important and step into the projects that I thought would matter for the business that, you know, I might end up leading or spending more of my time on.
It was absolutely the right thing to do. It was not a thing that I would've necessarily done myself.
You know, I wasn't necessarily getting the feedback from kind of my, uh, direct principal at the time, and that's okay, right?
Sometimes you need an external person that has enough clarity, enough insight or context to offer that feedback, and then, uh, it's up to you to take it and run with it.
I think that's a good suggestion for every chief of staff or non-chief of staff even listening to this episode, is if you have that mentor in your life, use them as much as possible.
And if you don't, spend the time going to find that person because whether they're working for you or not, again, like, that kind of feedback is really instrumental, especially earlier in your career.
Were there other moments as you were kind of exploring chief of staff roles or, or moving up in the ladder that stood out to you as, like, instrumental game changers in the way that you saw yourself or the way that you were working?
Yeah. Actually, I give this example a lot because I found it to be so personally motivating.
When I was at Slack and I was running product marketing there, we were about to launch our enterprise product, and so we came out of a particularly tough meeting where I just felt like we weren't prepared.
We didn't really have a solid plan for what the product should look like and therefore what the launch should be, therefore what metrics we should track and what we really thought was gonna make this outcome successful.
And I was pretty frustrated, and I was really frustrated with myself because I took a lot of ownership and blame for the meeting not going well.
And Stuart pulled me aside and he said, "No one knows what they're doing here. This is brand new for all of us, and you know this better than anyone else because you're living and breathing it every day."
And he was like, "So just own it and don't be afraid to say what you think is important and just-Steer the ship where you think it should go, and if it's not right, we'll have those debates and we'll have those conversation.
But no one knows what they're doing. And I take that advice with me everywhere I go.
I actually think if we all deep down could admit to ourselves that we don't really know what we're doing, it's actually a really healthy place to then be able to say, "Okay, well, no one really knows what they're doing, but I'm the person who spends all day thinking about this," or, "I'm one of few people in the company who have the most knowledge about this."
It gives me personally a lot more confidence to then say, "Well, put the ball in my hands. I'm gonna drive the decision here, and we're gonna figure this out as we go along. Like, we'll make mistakes.
No one's gonna be perfect, but we're gonna try together to get to this, like, asymptote of perfection as a team.
And that requires all of us to voice the things that we are experts in and throw it out there until we can figure out the right path." And I don't know, it was just really inspiring for me.
I think I was, like, 29 at the time, so it was one of those things where I think about it all the time. A lot of confidence is just something that you project, and you are figuring it out as you go along. Yeah.
Everybody's making it up. Some people just make it up a little bit better, and they know what to do with it. [laughs] Yeah, exactly. Last question on this topic.
For someone a little earlier in their career who's trying to figure out, do I stay in this chief of staff seat? So many chief of staff seats are set up to be rotational, right?
And that's, I don't know, it's not necessarily, like, the right way of doing it. It is a way of doing it.
But for chiefs of staff that are kind of sitting in that either very structured rotational seat or just, you know, it's implanted in their mind that after 24 months I should be doing something else, what is your suggestion in terms of how they should think about kind of growing further into the chief of staff role?
And we've talked a lot about the psychology of it's really on you to kind of lean in and take opportunities where they present themselves versus moving into a functional leadership role.
I mean, neither is the right choice. The best choice is going to be different, I think, depending on the context.
But I'm just curious if you have any other advice, like, based on your own path, things that have stood out. So much of it is, one, recognizing, again, that these decisions are totally reversible.
Sometimes you have an idea of how you want your career to go, and for whatever reason, it doesn't go that way.
And just knowing that you can change your mind and reverse course, and maybe you don't, like, start as senior as you want to somewhere else, but, like, it is what it is. You can figure it out.
You can go and redo any decision really that you want.
And I think it's one of those things where it's a really, really healthy thing to constantly be challenging yourself and figuring out what it is that you want in life versus feeling stuck down a path because you don't think there is any other path available to you.
My personal advice really is to always be having that conversation with your principal.
I think if you love the company you're at and you want to stay there, if you are the kind of person who is always willing to do what's best for the company, you are gonna increase your surface area to be lucky and to find that right role for you.
And I think it does vary a little bit.
At a startup, there's always just so much more that you can grow into and do, for better and for worse sometimes because it's more chaotic, versus a large company, of course, where it's a little bit more structured.
So you're not gonna go from, like, being chief of staff to the CFO to running product on something. But actually, at startups, I have seen people going from chief of staff to then running large product teams.
It kind of depends, I think, on where you're at, what exactly that number of possibilities looks like.
But being really smart about saying, "I want to work on really strategic problems that are high priority to the company, and I'll do that where it is most important," I think will never lead you to a bad decision, provided you want to stay at that company.
And sometimes that might be extending your job in the chief of staff role and working with your principal to do that.
Or it might be going and running a team where maybe you're three layers below your principal, but you actually have that responsibility, that ownership, and you're beginning to build that functional expertise.
I think one other thing that I just tend to do in my own life but is really important is to think very long term about your career.
Like, if you're lucky and if you want to, your career is gonna be decades, and so you really want to act now but plan in decades.
And what I mean by that is, what is gonna make you happy when you think about being mid-career or when you're about to retire? What are the things that you're gonna want to say, "I'm glad I accomplished those things"?
And then act now to go find those opportunities for yourself.
I really believe, like, the function of your professional life is to find a structure that allows you to do the things that come so naturally to you, that other people look at you and they say, "Wow, how did you think of that?
How did you do that?" And you're almost building that narrative backwards about why you're good at it. And if you do that well, it can compound, and it can turn into joy over decades.
And this really requires knowing when to walk away as much as it does knowing when to invest. Scott, I think it's like what you said.
You have to know what your goals are, and you have to know what your non-goals are, and then you focus on your goals. And I think careers are kind of similar.
Like, you just have to be okay sometimes walking away when you think you've got a losing hand and then doubling down when you think you have a winning hand. Nothing else to say. Mic dropped.
I'm leaving this conversation motivated, inspired, and looking at the broader outlook of my career. Judy, thanks so much for the time. I really appreciate it. Thank you for having me, Scott. This was awesome.
Thanks again to Judy for joining us on this episode. If one thing jumped out to me the most, it's that the chiefs of staff who get taken seriously don't wait to be invited.
They run towards the hardest problems, they own them, and they figure it out as they go. Judy's whole career is really proof of that.
If this conversation resonated with you, you can find Judy on LinkedIn at the links down below in the description.
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