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[upbeat music] Hey, friend. It's Scott Amenta here, the founder of the Chief of Staff Network. I'll be your host on today's episode.

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We help chiefs of staff through the three Cs: cohorts, curriculum, and community via Slack, cohort-based programs, live events, conferences, and more.

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You can learn more about our membership, events, and courses at chiefofstaff.network. We've got a great episode ahead of us with the former chief of staff at Redesign Health and now executive coach, Juhi Kabra.

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In this episode, you'll learn about how Juhi navigated her career path from Blackstone to Palantir to Redesign Health, where she served as chief of staff to the CEO for five years before transitioning to her latest endeavor as an exec coach, investor, and facilitator.

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Juhi has joined the Chief of Staff Network as one of the lead facilitators of Chief of Staff Launchpad, a new program designed specifically for aspiring chiefs of staff looking to land positions or new chiefs of staff wanting to set a strong foundation for the journey ahead.

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We also discussed her learnings on navigating and aligning the exec team, what chiefs of staff should focus on in their first ninety days of the role, and when to recognize that it might be time to move on from the position.

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Here we go. Juhi, welcome to the podcast. Hi, Scott. Thanks for having me. So you've had probably one of the most extraordinary careers, at least I've seen on LinkedIn in a long time.

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You've held roles at companies like Goldman Sachs, Blackstone, Palantir, Redesign Health. I mean, these are all household names at this point. Tell us a little bit about your background.

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Like, what led you to your chief of staff role eventually at Redesign? It's a great question. People often look at my background and don't really understand the path there.

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I would say I have always been someone who's chased people more than sort of like function, company name, or role. So yeah, I was an operator and investor for sort of fifteen plus years- Mm-hmm...

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prior to becoming an exec coach now, and I was the chief of staff at Redesign Health for a little over five years, and also head of the office of the CEO.

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And I would say in terms of what led me there, at the end of my time at Palantir, I found myself doing a little bit of everything and really enjoying the projects, thinking about people, and really considering the human dynamic, especially as we scaled massively, and I wanted to take all of that learning and help build a business from the ground up.

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I was really attracted to the vision and mission that Brent Shaheen, the CEO of Redesign, had, and at the time that I joined, it was a handful of people and a deck for the most part, you know, with a little bit of infrastructure.

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Mm-hmm. So it was really exciting to have the opportunity to go build the business with him. In terms of chief of staff as a title, he and I grabbed coffee a few days before I officially signed.

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It ended up becoming a three-hour coffee during which he told me about all of the important things that needed to be done that he either didn't have capacity for or wasn't in his sort of zone of genius, and those were gonna be the things that I was gonna work on.

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And we didn't really know what title made sense. This was frankly before chief of staff was such an in vogue role or title, and we decided- Yeah... chief of staff felt like a good catch-all.

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And so that's how I ended up in the chief of staff role when I first joined. And like any good chief of staff role, it evolved a lot over my time there.

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You were, compared to what we see today, definitely early in the position. At what stage was Redesign at that point when you were starting to have those conversations?

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So I spoke to Brent for almost a year prior to joining. Mm-hmm.

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Really wanted to get to know each other, which I think is, you know, one of the tips I'll always tell aspiring chiefs of staff, understanding what your relationship with your principal is going to be and who that person really is is incredibly important.

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Redesign was founded in twenty eighteen. I joined in twenty nineteen. It was a handful of people. Redesign is a venture studio building health tech and healthcare companies. Mm-hmm.

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At the time that I joined, I think two concepts had been ideated, funded, and launched. Yeah.

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By the time I transitioned out about five years later, we'd launched sixty-plus companies in the health tech space, and we'd grown from, you know, a handful of people to a couple hundred in my time there.

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You've worked with plenty of executive teams. What do you think makes a great chief of staff indispensable? Technical skills are sort of baseline, right?

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Being analytical, and I think the type of technical skills that you need honestly depend on what type of executive you're a chief of staff to.

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Are you chief of staff to a product leader, an engineering leader, a people leader, a CEO, et cetera? But I think what really makes a chief of staff truly indispensable are what a lot of people will call soft skills.

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I don't like that term, but things like trust, judgment is one of the biggest ones, and then of course, you know, emotional intelligence as a superpower.

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I also think being confident is actually really important, and the reason for that is confidence allows you, in my experience, to then demonstrate humility.

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People who have a lot of humility, I think it comes from a place of being actually quite confident, and I think that's a critical skill in a chief of staff role, being able to sort of chameleon how you show up really confidently externally, but with a lot of humility internally often.

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And the other reason confidence is so important is the breadth of the role.

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You are constantly, in many chief of staff roles, being thrown into tasks or initiatives that you have never done before or you're being dropped in to parachute as the head of blank function, you know, head of marketing, head of product, when there's a leadership transition or there's a gap on the leadership team.

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And so I think having the confidence to say, "Hey, I haven't done this before, but I will figure it out," and the humility to know that you've got to ask people for help when you need it, I think a lot of that comes from confidence.

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So I would say trust, judgment, strong EQ, and confidence are really what set a, I think, indispensable chief of staff apart. I agree, and I know you said you don't like the term soft skills.

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I tend to agree with that as well.

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We've been calling them power skills, which comes from an article I read a long time ago, and I'll, I'll drop a link below the podcast to thatBut yeah, I mean, you're dropped into so many different situations that the level of exposure is kind of unparalleled compared to other roles, regardless of where you are in your career as well, right?

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Some chiefs of staff are just very early in their career and still working with executive teams and kinda seeing all the challenges and problems that a company is exposed to and being asked to weigh in and provide guidance to much more senior people.

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You need to have a lot of confidence to kind of react well and kind of present yourself well in those situations. So the power skills are where it's at. Absolutely. Increasingly so these days.

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So Julie, we're here to talk a little bit about Launchpad. You're helping to lead some of the sessions in Chief of Staff Launchpad.

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We're, we're super excited to be rolling this out with you, and you know, the first thing that you're gonna be talking about is navigating and aligning the executive team.

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So why do you think that this kind of navigation-- why is it so difficult to align an executive team? I think there are a lot of components that make this complex, right?

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First, you're in a role where you're trying to influence without authority. At the end of the day, most chiefs of staff are not the manager for other executives.

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You might have a team, you might not, but either way, you're certainly not managing officially the other executives.

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And so it requires a lot of what I call, you know, many people call influence without authority, and that's just a hard thing to do.

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In terms of why is it actually hard to get the exec team on the same page sometimes, of course, everyone wants to be on the same page, right? There's no poor intentions.

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I think what I've observed happen is startups are moving so quickly, and individual executives are building their teams, and they have monstrous goals. Everyone is trying to accomplish so much.

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And as teams grow and mandates get more complex, it's very easy to forget or lose sight of what is often called first team mentality. I think this was a concept that Frank Slootman mentioned in his book, Amp It Up.

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He was the CEO at Snowflake for a while, and I'm sure it's mentioned in, you know, a lot of other places too.

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But first team mentality being the concept that the executive team is your first team, and if you are the CPO, chief product officer, and you have a bunch of product leaders under you, that is obviously your team too, but your first team is the exec team.

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And it's hard to lose sight of that because everyone needs resources. Everyone will feel like their projects are the highest priority, and that's where I think a lot of the misalignment can happen.

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Those are a couple of the reasons it can be hard. The other thing that I think happens is sometimes it feels like you're aligned at the high level.

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Like, you talk in the room, you're like, "Yep, everyone's on the same page. We've got the same strategy." And then every leader goes back and tells their team their interpretation of what was discussed in the room.

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And if you hear all of those, you'd think they were all in different meetings. And so one of the things that I've learned the hard way is that, you know, this alignment at the high level is not enough.

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What is the communication like? What is the talk track?

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How are we actually going to break this down for the rest of the org such that everyone's on the same page, and we're not all going back and telling our teams different things, even if we had the best of intentions?

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So those are a couple of the reasons I think it's so hard and why it's so important. It's a really important point. This game of telephone is where great ideas go to die in execution, right?

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The executive team can leave that room feeling fully aligned, on the same page, and yet when they have to make sense of it to downstream managers and kinda the rest of the ground-up organization, it takes a turn in trying to put those ideas back into context where it's relevant for those individual teammates.

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You know, I think the chief of staff, like, we always use this phrase, dot connector, and dot connecting is not just happening at the highest levels, it's happening all across the organization.

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And so, yeah, I think it's a really salient point. And I think a lot of that also stems from executive team alignment needs to first start from is the chief of staff and CEO aligned?

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And that relationship, we talk a lot about, you know, how important that relationship is to build, and I feel like even though we talk so much about it, it still is the thing that is often forgotten in why chiefs of staff or how chiefs of staff actually become successful in the role.

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Can you talk a little bit about what you've observed kind of in your experience? What does a strong relationship between a CEO and a COS look like?

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In my opinion, this is actually the single most important factor that will determine your chief of staff experience.

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Obviously, the company and what the company does and all these other things matter and the overall team, but the relationship you have with your principal, with the CEO, in my opinion, number one factor in how you will enjoy and how you will experience this role.

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So it's a really important question that you're asking. I think when I look at strong chief of staff and CEO relationship is there's a few things. Some are obvious.

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I think there needs to be deep, deep trust and psychological safety.

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And I think the reason that this is important is a really, really effective chief of staff will often be the one holding a mirror to the CEO, will often be the one frankly sharing hard truths or hard feedback that others might not have felt comfortable sharing.

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They're often the eyes and ears, and part of the role, in my opinion, is to be a foil, to be that person that can debate with the CEO in a really productive, constructive, effective way, knowing that sort of one plus one will lead to five.

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But the only way that there's safety and space in doing that is if there's trust and psychological safety, and both parties truly understand and believe at their core that both people have the best of intentions.

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So if I'm sharing something hard with you, I'm doing it from a place of wanting to ensure that you're set up for success and the company's set up for success.The other big thing in terms of relationships is having a lot of clarity on the role.

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One mistake I've seen a lot of people make on both sides, both the person going into the chief of staff role as well as the sort of CEO or principal seeking the chief of staff, is not being aligned on what sort of chief of staff you're looking for.

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You mentioned this, Scott.

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There are chiefs of staff who are very early in their career, a couple of years out of college, and then there are chiefs of staff who are fifteen, twenty years sort of executive level chiefs of staff.

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And I think understanding at the simplest level, the way I often describe it is are you going to be an extension of the executive or are you going to be a complement?

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And are you kind of dividing and conquering or are you taking that executive's agenda and supporting them in executing on it and pushing their sort of vision forward?

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And I think just understanding like what level chief of staff are you starting out at and what is the intent and what is the opportunity to grow is really important.

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So getting a lot of clarity on the role and the way in which you're intended to interact, and happy to expand on that if that doesn't make sense. No, that makes a lot of sense.

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And I'm gonna give a quick shout-out to the Chief of Staff Network Leveling Framework. Actually follows exactly what you just described.

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Unfortunately, it did not exist when you and I were chiefs of staff, but would've been really helpful. And so we've taken a lot of those learnings and applied it to that framework.

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[laughs] I've actually shared that framework with so many people who have approached me about chief of staff opportunities that they're exploring.

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I will say, "Hey, literally print this out and take it and talk to the principal or CEO that you're going to work with, and make sure you're on the same page about basically what level they're looking for and you're at, and the growth path from there."

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It's important because it also provides kind of the stepping stone opportunities for how that relationship will evolve and, you know, whether you're taking kind of projects directly off of your principal's plate or if you're operating kind of more on your own within the organization at times, that can make a world of difference in kind of navigating the position either into future levels or in and out of the position as well to other kind of roles at the company.

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Absolutely. I'm gonna shift gears here because you are teaching another class in Launchpad more focused on kinda careers and job search.

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So tell us, like if you were a new chief of staff in your first ninety days, what would you be doing to build kind of trust and momentum in the role? There's a few things that I think about in my first ninety days.

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One is I just love a good old listening tour. I find it is incredibly effective.

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I mean, I think if the company is 150 people or less or, I don't know, maybe 100 people or less, I'll just go out on a limb and say you should talk to every single person if you can.

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Not all at once, not all in the first week, but over the course of the first, let's say, six weeks, twenty, thirty-minute coffee chats with every single person.

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And the thing I love to do is come up with the same three or four questions I'm going to ask every person at the beginning and then kind of free for all anything else they wanna share.

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And the amount of data that you can get from those conversations is invaluable, and you have a free pass to do so when you first start. So take advantage of being a newbie to have those conversations.

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And listening tour, the name is really important. It's listening.

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So I will try to spend thirty seconds on my introduction or send them something in advance that they can read and try to spend as much time listening as possible.

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And these days, with the power of ChatGPT, if you or, you know, any other tool that you use, if you put all those notes into something, you will be able to get a really succinct and really excellent summary of what's going on at the company, the good, the bad, the ugly.

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So that's just number one thing I always recommend, especially in the chief of staff role. The second thing is you are in a position where you're allowed to ask a lot of questions, so take advantage of that.

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You can always ask questions, but I think when you're new to a company and you're in a chief of staff role, you're allowed to ask questions that might not land well three or four months later, either because people expect you to know what you're doing or people might sort of question the intention of the question.

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But in the beginning, you can ask anything. I think if you find something that is being done in a unique or weird way, I'll just use the word weird, that's sort of silly language, try to understand why.

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One mistake I find is people see something being done differently than maybe the way it was done at their old company or different from sort of like what the book says, and they try to leap in and fix it before really understanding what's the history, what's the context, why does this company do things differently.

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So that's three. I would say I like to understand what's the unofficial org chart. There's always an unofficial org chart. Who are really the influencers? Who do you talk to if you need to get something done?

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I could go on and on, but that is a really critical part of sort of the first few months of observation. And then the last thing, these are all things that feel kind of passive, like listening, right?

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And that's intentional or observing. I'd say the one thing to do is literally make a list of every leader in the organization and figure out one thing you can do for them in those first three months.

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It could be as simple as raising your hand to say, "Hey, I'll take notes and send follow-ups after this meeting." It doesn't have to be a big gesture.

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But start to demonstrate the value that you can bring in small ways as you start to formulate what are the bigger picture things that you wanna work on over the coming weeks and months.

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I think one of the biggest mistakes is sort of jumping into a huge initiative without a bunch of context and without a bunch of allies in the organization, and that can go really poorly.

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And I always say if every executive doesn't view you as a huge ally of theirs, even if you're reporting to the CEO, if every other executive doesn't think of you as sort of a linchpin and someone they are so, so happy to have on the team, you're not doing the job right.

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So find a way to kind of build those alliances, those partnerships. Spend time getting to know them. You'll need each other. Absolutely. What an amazing list.

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I mean, as a checklist for getting started as a chief of staff, those were all extremely noteworthy. So yeah, thank you for sharing that. Maybe we flip to the end of the chief of staff journey, right?

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So we, we just covered the beginning first ninety days. What's a lesson that you took away kinda later on in your chief of staff journey?

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How did you know that it was time to move on?So I'd say a lesson I learned kind of late in my journey is how to say no and. I think I used to just say yes to everything.

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And look, I think that can be really effective in your first several months as chief of staff.

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I think you're gonna be drinking from a fire hose no matter what, and I think all of the contacts, getting exposure to all of the projects, again, the good, the bad, the ugly, I think it's actually really helpful.

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Over time, it can turn into a crutch where everyone's just coming to you, and you can become overwhelmed and ultimately become a bottleneck, and that's not good for anybody. You're juggling way too many plates.

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Way too many things. So for me, it took a long time. I wish I'd learned earlier how to say no and.

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If someone came to me and asked me to essentially do something that just wasn't aligned with my biggest priorities, even if it was important for the company, learning how to say, "Hey, no, I can't do that, but here's what I can do.

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I can send you this template I've used. I can introduce you to this person that can help. I worked with so and so last time."

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What can you do for that person to support them without fully doing the thing so that they still feel like you're a great ally and resource?

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So that would be a lesson I learned definitely late in my chief of staff career, but once I put it into place, it was really effective.

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And then in terms of knowing when it's time to move on, that's a really hard question.

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For me, the evolution went from being a chief of staff with no sort of direct reports and just partnering with the CEO to ultimately building what we call the office of the CEO, which I think is becoming an increasingly common transition, which meant I had sort of a deputy chief of staff reporting to me.

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I also managed our executive EA, et cetera. And so that transition felt really, really fun. And I got to experience new challenges like managing people and having a wider mandate.

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I'd say for me, I mean, I don't know, this is a little bit of a qualitative, not quantitative answer, but for me, it's all about my energy.

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And so I would say every six months or so in general, I like to do something called an energy audit where I'll just literally download the last two or three weeks of my calendar, categorize everything I've been doing into a few buckets, and then identify are these like really high energy creating experiences or are they draining?

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And when I start to find that I'm falling more and more into draining, I check, like, "Hey, am I doing the things that are aligned to my job?" If it's been a weird couple of weeks, okay, fine.

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But if I'm doing stuff that is my job and I'm starting to feel really drained, kind of to me usually says that it's time to either evolve the role or move on, not because the work isn't important, it's very important, but because in some way I've probably almost mastered it or I'm not learning as much, and it could probably benefit from a fresh set of eyes, whatever it is.

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And so it's time to either delegate, evolve the role and/or at times, you know, fully move on to your next role.

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I think as you said before, it takes a lot of confidence to also recognize that it's time to move on potentially, right?

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Too many people may be apt to kind of hang on to it, even if it's not giving them that energy, or say, "Hey, there's gonna be some shift in the company six months from now, so I'll hang on until then."

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And, you know, then six months later, it's the same calendar situation, right? And, and even less energy. It takes a lot of introspection, I think, to realize there's a next step here for me.

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Now, how do I have that conversation with my principal? How do I either shift internally or start looking externally?

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Chief of staff can open up lots of doors, but it is also-- it can be a difficult position to describe kind of what things, you know, were measurable impacts in the company while you spent your tenure in the role.

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Let's end with kind of one takeaway that you hope every participant walks away from Launch Pad. That is a hard one because I imagine there's going to be so much tools, community, frameworks. There's gonna be a lot.

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But I would say, I think the chief of staff role, if you wanna be an operator of any sort, is just the biggest professional hack out there in terms of accelerating your career, which is why I love that we're calling this program Launch Pad.

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The thing I would say that I want people to take away that maybe isn't obvious, like in the curriculum or through the classes, is the community.

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I think the one thing about a chief of staff role, and frankly, any leadership role, is that it can feel lonely.

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The chief of staff role, especially a lot of companies maybe only have one chief of staff or only a handful, and it's a very unique chameleon role that a lot of people don't always understand.

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And so I would say in my own experience, it was lonely. I wish I'd known more about Chief of Staff Network when I was a chief of staff or earlier in my chief of staff experience. But I would say lean into the community.

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So if you hear someone speaking in the class that you feel like you've got good vibes with, send them a private message either through Slack or through the chat feature on Zoom or get their contact info, find them on LinkedIn, grab a virtual, or if possible, even better, IRL coffee with them.

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Those relationships, like my network of other chiefs of staff as I grew and evolved in this role, was just invaluable.

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And obviously, you know, a hack there is just to join the Chief of Staff Network, and then you have access to a bunch of folks. But I would say take advantage of the people who are on this journey with you.

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That would be the one sort of takeaway I'd say outside of, like, the obvious, like, take advantage of the tools and the frameworks and, and the resources that are brought to bear through the program.

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Nothing beats the value of community.

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And, you know, for a role that can feel so lonely, it's very important to have a few other people that can relate to your position, whether that's just complaining about your principal or actually doing, you know, real tactical work.

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There's a place for both. Exactly. Julie, thanks so much for joining us today. We're super excited for the program. I'm gonna share all the links to your website, your executive coaching resources and services.

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We're super excited for you to be partnering with Chief of Staff Network on this and excited to see where it goes. Thanks, Scott.

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