starting any new job is kind of a lot there are processes to learn personalities to navigate and complicated problems to wrap your head around but starting a new job in an executive role is a completely different ballgame you have all of those usual new job learning curves but you're adapting to them
in an environment where the stakes are higher the expectations are probably unrealistic and there are a lot of eyes on you.
My guest today is Yui Zhao, an executive coach and the founder of The Uncommon Executive.
Having served many years in executive roles at companies of many different sizes, from fang to scale -ups, Yui now works with new and established executives to navigate a level of achievement that many of us aspire to but where few set foot.
We discussed some of the myths around executive life, how to adapt to a totally new dynamic, and toward the end of the conversation, she even outlines some crucial steps to take that you won't find on your 90 -day success plan.
Let's jump in. Welcome back to the Product Manager Podcast.
I'm here today with Yui Zhao.
Yui, thank you so much for coming and joining us today.
Glad to be here. Can you tell us a little bit about your background and how you got to where you are today?
Sure, sure. So, I started my career in consulting at McKinsey out of college and eventually landed in technology through co -founding a wine e -commerce startup and then being the first PM at Thumbtack, which was a local services marketplace.
Went from there after five years to Instagram where I led the featuring and profile teams, did a couple of shifts within Meta more broadly, and then eventually took on a role as the CPO and then CTO of a digital health startup, Series C that was focused on telehealth for pets.
and from there, I really actually took all of that experience and wanted to do something a bit different and transitioned into full -time coaching and teaching and writing.
So not something that I sort of would have anticipated in the start of my career, but very happy with where I've landed.
Yeah, it sounds like an awesome career trajectory, and I'm so excited that you have that experience to share with us today because we're going to be focusing on the transition into a first executive product role, which is, you know, it's a role that very few of us are privileged to enter, but it's a very
different transition from any other that we might have made.
So you've mentioned before that one of the biggest shifts is moving from a team first perspective to a company first kind of thinking when you move into an executive role.
Can you tell me a little bit about that, like walk me through that mindset shift and what it looks like in practice?
So, you know, many of us, as we come up through the ladders in the organization, we often think of our team as the function that we're in, right?
So for product folks, it's the other PMs.
And then generally speaking, for PMs, it's PM engineering design, maybe data, maybe research, right?
But you're kind of within that technology bubble and you think of that as your first team, right?
And the main difference when you get into the executive levels is your first team becomes the other C -suite leader.
So the other VPs within the organization.
And so it is first a mindset shift, because I think for most people, when you have a problem, when you have a question, when you have something you want to get done, you go to the engineers, you go on your team, you know, within your group, or you go to other PMs, or you go to your manager, but it's
within your general function and area, right?
Versus in an executive role, the first people you actually need to go to are like the VP of sales, or the chief marketing officer or the chief legal officer.
And that can be very counterintuitive for someone stepping into that role the first time, because it's a very natural tendency to be like, OK, let me focus on making sure product is doing great.
Right. Let me make sure that we're collaborating well with engineering and design.
And those are still things that are important.
But the unique role that only you can do becomes how do you actually get every function to work together on cross -functional company -wide projects.
And making that like your first priority rather than your team can be a very counterintuitive shift for a lot of folks.
Yeah, I can imagine.
So let's talk a little bit about that executive team dynamic.
I'm sure it's a little bit different from, like you said, some of the things that are more in your specific area.
How should new product executives approach building relationships with peers in like sales, legal, all these other functions that they might not have had many exposure opportunities to before?
It's a great question.
And I would actually say that it starts before you get to the executive level.
And what you'll find is that often people who have exposure to these different functions, who've either done like a tour of duty or come from varied experiences, actually have an advantage and a higher likelihood of getting into the executive roles because it is actually so important to understand,
how do I work with sales?
How do I work with legal?
When do I bring in policy and the CFO?
And how do I talk about financials and quarterly earnings?
And so I think it actually starts long before stepping into the role to really understand what are the different pieces of the business and what are the different functions and how do they fit together and how are they motivated and how do they work?
But stepping into that role as an executive, The first thing to understand is really the dynamics of the team and why you were brought in.
I say this a lot because I think sometimes people bring a lot of history and experience with them into a new role and they have this idea of like, this is how things should work or this is how I imagine things work.
And this is a role of product within that.
Now, I think the most important thing when you walk in is being like, okay, how do I quickly prove or disapprove my hypothesis?
about how things really work in this new environment.
And so whether it's spending time with the board, the CEO, the founders, or with the rest of the executive team, I find that the most important questions are like, what are your priorities?
What do you expect the product person to be doing?
And what are the challenges that you wish we had solved a year ago?
You know, that you are hoping either someone in this position solves or in general, as a company, we solve together.
So it's really about figuring out like, what is your job?
I mean, sounds a little silly to say that.
But really, like, what are you trying to get done?
And why were you brought in?
And in some scenarios, that could be very clear, like through the interview process and the company and everyone's aligned on like, these are the two burning fires, I need you to help us put it out.
And the other scenarios, and actually, in my case, at Fuzzy, it was kind of ambiguous.
And if you ask different people, they had different answers from obviously their vantage point as a part of the job was actually, okay, what is the thing that we as a group think needs to get done and why and how do I make sure we actually bring alignment to that?
So really just like figuring out what are the top priorities to go solve with the rest of the company rather than what are the top priorities within product.
Huge mindset shift.
So when we're talking about collaborating with other executives and trying to figure out what your job is.
A big part of that would be feedback and being able to establish really solid lines of communication.
So what strategies have you found effective for creating, first of all, psychological safety in which, you know, this is a high stakes role and there's a lot of unknowns, especially when you're first in this executive space.
So how do you create psychological safety with other executives and maintain a really genuine two -way communication trajectory with your team?
I think both with your peers as well as with your team, being aware of the power differential people don't like to talk about power but I like to talk about power but there's power differential within various functions and within the organization and the bigger that power differential the less likely
you're going to get the truth that's just the way people work right when they're talking to someone who they perceive as having a lot more power than them they're going to tell you mostly good things they're going to kind of hide a bit not like stuff away, but kind of, you know, hide a bit of like the truth
about what's really happening on the ground because either out of fear or out of, Oh no, this is not something that I want her to deal with because, you know, I think that, you know, she has many other higher things happening.
And so that's one thing to keep in mind.
And so as an executive, when I sort of connect with my peers, I always try to figure out like, how can I build a trust -based relationship where we have the same incentives?
Because the biggest blocker to really honest relationships, in my opinion, is when you have different motivations and when you perceive that you have different goals that you're trying to achieve.
So maybe sales is trying to hit their quarterly goals and product is trying to build like some infrastructure thing for like the longterm, right?
And so it's a very simple, classic example, but there's a perceived mismatch in like, what are you trying to get done?
What am I trying to get done?
And I find that one of the first things to draw out is, like, what are our shared goals?
What are our shared incentives?
What do we want to achieve together?
And align on that first?
And then going back to what we're just talking about, this, like, company first mentality, that's usually where the alignment is.
It's like, well, you both want this company to be successful.
You both want this company to grow.
Like, you may be thinking different timeframes, but, you know, there's a shared vision there.
And so that's really the starting point.
And then I think it's important with teams to really sort of be very explicit and repeatedly be very explicit about the fact that you want honest feedback.
And really when that person comes and is not sure if they should have brought this thing up or it's a career limiting move, right, like that you really actually encourage them in how they feel comfortable, whether it's publicly, whether it's privately, that like, hey, I'm really glad you brought this up.
Right. Like, I know it was kind of scary.
I know you were not sure, but I'm really glad you brought it up.
And then if they're comfortable with it, like making an example of like this person brought this up and it was really great.
And if other folks have ideas or suggestions or challenges like this, I'd love to hear more of it.
And just actually saying that probably 10 times more than you think you should until it really becomes a part of, oh, OK, like this is how Yui likes to operate.
She just kind of wants to know.
And, you know, to your point, creating that safety of like, I'm glad you told me, I'm glad that we're talking about it because this is a very important thing to bring up.
OK, I love that point.
I think that that's applicable to roles of any kind as such a critical skill to build is that getting comfortable with constructive criticism.
It's hard bridge to cross, but it's such a game changer.
And I think on that note, like sometimes I think people are afraid to give constructive feedback because they view it as a personal thing.
You need to do something like viewing needs to do better at this, right?
Like that becomes a very personal thing.
And I think that type of framing can be tricky and like difficult to get across correctly versus the company has this issue.
Our teams have this issue.
Even I have this issue, like make it your thing.
Like I have this challenge where, you know, it takes me a long time to do X, right?
Those are much quote unquote safer options for framing because you're not attacking the other person, right, necessarily or putting them on a defensive.
you're just saying i have this problem or i see this problem or you know in general i see teams have this problem but it's not about them it's not especially if it's a new executive coming in like it's not like they did something wrong it's just here's a problem that i see that i think it would be impactful
to go solve yeah you did an episode i think it was the last year about emotional intelligence through product leadership a big takeaway from that was depersonalizing feedback and really focusing on what was the action the outcome and kind of removing it from you know because everybody is, you know,
there's a good faith there and assuming positive intent that really goes a long way.
And when you're kind of aligning with that mindset of like, we're just doing what's best for the outcomes that we want and not because, you know, it's because you think you have a personal failing or anything like that.
Let's switch gears a little bit and talk a little bit about the perception of executive life, because I think this is a big blocker for some folks who are, you know, interested in that kind of career progression, but maybe you're a little bit uncertain about how that'll affect their day to day or what they
might have to deprioritize in order to succeed at that level.
So what are some common myths around the role that might be holding some really talented, born leaders back from pursuing executive positions?
Well, I think the first one is that executives work 24 seven, and you could not have a personal life outside of your work life.
That's a very common one that often when I talk to folks about, why do you not want to consider continuing to move up?
That's a big one, men and women, right?
Where they're like, no, I don't want to spend my entire waking hours working.
But then related to that, oh, it's just super stressful, right?
Like there's a lot of super challenging decisions all the time and, you know, I don't want that level of stress.
And I do think that there are definitely roles out there at the executive level or at any level really, where it's all consuming and it's high levels of stress.
And for anyone who's worked at large companies, for example, when I was at Meta, There were, you know, specific company priorities and teams that matched that priorities where we would actually meet with Zuck on a monthly.
And sometimes during COVID -19, we met weekly.
That's super stressful.
That is you work around the clock because you just had a meeting.
Now you have another meeting with, you know, Zuck.
And so, but there's other teams within Meta where it's very stable.
You know, if you had a similar strategy for the last two years, everyone's been there for like 10 years.
Everyone kind of knows what's going to happen tomorrow.
and actually, you know, next week and the next quarter.
And so it is much more stable.
Same with company stages.
There are stages of the company, right?
Where if you're really trying to find product market fit, if you're really trying to like get that next round of funding, it's gonna be a lot more stressful.
There's gonna be a lot more decisions that need to get made versus if you're more in a time of execution, if you're more in a time of like, hey, this is the strategy, let's just go make it happen, you're going to have a higher amount of control over your schedule and your calendar.
And so it's the same in executive roles, right?
And I think also at most levels, it's like there's going to be a spectrum.
And to the extent that having a life outside of work is an important priority, there are sort of CPO roles and CTO roles and even CEO roles where it is more of a nine to five and you don't work weekends.
That said, I think there is always an element of like emergencies, right, where you're kind of that first point of contact if something goes wrong.
But again, you can kind of look at industry dynamics.
You can say like, there's certain industries where there's a lot of emergencies and sort of last minute things that happen outside your control.
And there are certain industries that are just more calm.
And, you know, most things are within your control.
So again, really looking at the dynamics of the environment, because there are roles out there where you can have that level of seniority and authority and type of sort of decision making without everything feeling like the environment's changing all the time.
I keep having to get pinged in the middle of the night and all of that.
Okay. Well, it's good to know that that's not a universal, that that stereotype isn't universally true, but I'm really glad that you brought up kind of the nuances in company size and maturity and how that can kind of impact the role because as we know, whether it's VP or head of product or CPO, or really
a lot of higher level product roles can look really different depending on the company size and maturity and even just the leadership dynamics that exist within that team already before you've come on.
So when you're working with your own clients who are coming into an executive role, how do you help them adapt their approach based on some of these contextual factors?
This is why I enjoy coaching so much.
They're all individual, unique snowflakes and individual, unique situations because you have the person and their history, their experience, their strengths, what their beliefs are about the world and their values.
And then you have the environment, which is your point, like the size of the company, the stage, the makeup of the rest of the team.
And you put those two together and there's usually not another pair that's exactly the same.
right? There may be similarities that you can start extrapolating, but there's a very unique fit of person with environment that they're in.
And so when it comes to coaching, I focus as much about understanding and anticipating and figuring out how you're perceiving the environment as much as what you have to change.
And I think sometimes people are surprised by that.
Like a lot of folks come in and say like, okay, here's what I need to learn.
I need to better communicate.
I need to do these things.
I need to like gain these skills.
I'm like, great, maybe, you know, if you want to learn them, you should learn them.
But let's also look at your environment.
Let's look at how you're set up.
Let's look at what stages of your company is.
And let's look at who's around you, who's on your team, what are their strengths?
And let's see how you're actually interacting with your environment and what you're putting out there and what you're getting back.
And sometimes it's actually about putting a different thing out there that you kind of already know how to do and then getting different responses back to really change your thinking about what's possible and what the potential narrative or outcome might be of what it is that you're doing.
Oh, interesting. Okay.
I love that approach.
I'm very curious about the dynamic of working with the board and investors.
I don't know if you've seen severance.
I'm sure that there's some people who are listening who've seen severance, but there's kind of the presence of the board as sort of this thing that's looming that no one beyond the executive level really has much contact with.
It sounds very amorphous and sort of scary until you're really in a role where you're making direct contact with.
And, you know, I know that they're human beings.
It's not like people who are investors.
The alien planet. We've made contact with them.
I would love if we could talk a little bit about what that's really like coming into a situation where you're dealing one on one with board members or investors.
What are some of the key things that first -time executives should really know about managing these relationships effectively?
There's a running joke that you always have a manager, right?
Some people think like when you get to the executive level, you can do whatever you want.
And then they realize there's the board and you can't do exactly what you want.
And then you become a public company.
And then there's even more expectation around how the company performs and all that.
So there's always a manager.
There's always someone else out there.
And I think what's unique about the board dynamic is that it's not a single manager, make things more fun.
It's a board of directors, right?
So they come from different backgrounds, they bring different experiences and that's their value, but they'll have different perspectives and they care about different things.
But together, they really have one, I'll call it one stick that they can use, which is removing the CEO.
if you think about it at the end of the day like what a board can do they can approve and or deny acquisitions whether it's someone purchasing you or you purchasing a certain company or they can fire the CEO.
That's it. Those are the two leverage and it sounds a little silly whoever's on boards here like you know give me a moment here but like that's really at the end of the day what boards can do and so their real leverage most of the time we're not talking about acquisitions is the CEO and the CEO wanting
to stay in their job.
There's an ultimatum, basically.
So if you think about it from that perspective, the board is not really that scary in a way.
And the CEO controls everyone else's job.
So to the extent you want to stay in your job, like that's how it floats down, right?
But as like the CPO or CTO or someone who's reporting to the CEO or whoever is on the board, you're helping them be successful.
And that's really the framing around it.
It's like you're on the same team and at the end of the day, you're all on the same team because you all want the company to be successful.
And that's the board's goal is like, make sure the company is growing and you don't do anything illegal, like the governance piece, right?
And so to some extent, everyone wants the same thing, but it comes down to the specific dynamics of, okay, maybe the CEO based on their incentives and compensation, like they're more incentivized for a short term.
And maybe they should actually be incentivized more for the long term.
So usually there is the more specific dynamics within people and within functions.
And that is where as an executive, you're spending most of your time.
So at a high level, you're agreed.
But when it comes down to like, where do resources go?
Where do dollars go?
Where are we going to invest?
That is where the board can be really helpful or not helpful and making sure that the company goes in a particular direction and so often it comes down to how well one the board trusts the general board of directors trust the ceo right because if they really trust the ceo then it makes things easy it's
like whatever the ceo says like it's generally speaking the decision that sticks sometimes there's misalignment between the board and the ceo so then the question for you as an executive is like okay what do you do in that scenario?
Do you use the board to help you convince the CEO to do something?
Or do you agree with the CEO and you want to go convince the board to change their minds?
And so that becomes a much more complex puzzle.
And then there's all your peers and, you know, what do they think and what do they want to do?
And that's really what like, quote unquote, managing the board looks like is managing the dynamic of like, what do you think is right?
What does the CEO think is right?
What does the board think is right?
How are they the same or different?
And then how do you all kind of get together and actually land on a direction for a long enough period of time for it to play out?
Easier said than done.
This is where a lot of the chaos gets introduced.
I can see why people would need an executive coach.
So, yeah. And speaking of that, so we're talking a lot about some of these initial relationships that are really important to establish and get off on a strong foot.
How about in a broader context, what kind of patterns have you observed in terms of where new executives typically struggle the most in their first 90 days, either tactically or otherwise, or strategically?
How do you help them navigate some of those early challenges?
So I think that there is, and we've touched upon pieces of this, there are so many different aspects of the role.
There's the company first, which we talked about, which is like your peers, your first team getting to know like all the different functions and their leaders, their experiences their motivation then there's a board getting to know how well the CEO and the relationship with the board and who the board
members are and how they're interacting and then there's your actual team which is everyone that reports to you as well as their key cross -functional peers so in product you get the joy of like you get product but you also get engineering and design and data and research and all the other functions so you're
trying to do a lot of things at the same time And you don't really get the luxury of time because usually when you're coming into a role, there's already like a list of 20 decisions that people wanted to get made that's waiting for you.
And they're not easy decisions because the easy ones already got made.
They're all super tricky, like there's no correct answer, gray area questions.
And there's a list of 20 of them where they're like, hey, Yui, can you solve this and this and this in the first 30 days?
And you're like, I don't even know the name of this thing yet, right?
And so you're really, I think people call it drinking from a fire hose, but I think when you ramp up as an executive, it's particularly true.
And I think that's why sometimes you actually see executives make not so great calls early on.
It's because they get forced into this dynamic of like, I don't really know the company yet.
I mean, I have my experience and my history and I'm going to try to pattern match.
Like, oh, I've seen this before.
Like, roughly, this is the direction we should go in.
But if that pattern match is inaccurate in some way, then you'll actually see executives make not so great calls in the beginning, but get better at it over time.
And so what I generally help people with is this like, when should you make a call?
When should you not make a call?
How do you actually pressure test your intuition and pattern matching as quickly as possible?
Like what are some key signals of like, hey, this thing that you think holds true, like doesn't hold true in this particular scenario?
Like, how do you get like really like your spidey sense to be like, maybe I should rethink that?
And then how do you really prioritize?
And we actually send, for a lot of executives that are in the onboarding phase, we spend a lot of time being like, what are all the things you need to do?
And what are really the things that you really need to do?
And sort of anticipating, honestly, which balls to drop and which ones to really get right?
Because that can be just more difficult in the first, let's say, 90 days because you don't yet have the full context.
You don't know the people fully well and you're in this like learning, but also very quickly than having to decide things that no one else was able to decide very quickly.
This is interesting because I think I've seen this play out before because it's very typical that companies don't hire executives on a snap decision.
It's usually a long hiring process.
They're really looking for the right fit.
And in that time, these kinds of decisions build up pressure and there's a lot of urgency around trying to solve them rapidly once the new executive has been hired or brought on board.
So in that case, as a new executive, you're coming into a situation where there's a great deal of pressure to solve these problems, like you say.
And yeah, like all of these contacts that you just mentioned are all kind of very much real.
You've got a limited scope of knowledge and a great deal of pressure to make decisions quickly.
So what are some of the strategies that new executives can do to kind of onboard themselves and get familiar with the landscape that they're dealing with as efficiently as possible, and also manage expectations for making sure that everyone is on board with the timeline that's necessary to make a right
decision? Yeah, it's a great question.
Writing is usually faster than talking.
So as much content in written form as possible.
I mean, I read faster than somebody can tell me information, right?
And so send me decks, send me previous reviews, send me stuff in writing, because I will process that faster from a context perspective.
Two is like very quickly figuring out like whose judgment in the organization today do you trust?
And this is a very subjective thing, but I think it is very important for executives to actually figure out who the people in the organization are that may already have the answer.
They just don't have the authority because they're not the CPO or whatever, right?
right but often i find that the answer is somewhere and somebody is very frustrated that that's not yet the solution and it's about a kind of like especially within your function like being like that director that vp like that engineering lead they have a really good sense and even if they might not even
have the answer you might be like can you help me push this forward like can you help me drive this and really getting those people empowered to be like hey i need you to go do these things.
And then usually it's a little bit of asking the right questions with peers and other functions in terms of figuring out like, again, what are their priorities?
What are their challenges?
What are they motivated by?
One of the first things I generally make sure people understand is the incentive systems within the company.
I feel like if you don't know both the intrinsic and extrinsic motivators of the different functions, then you don't really know how they operate.
And so, you know, is this a boys club where it's like, whoever, you know, is in the boys club, you know, they make the decisions.
Is this a goal oriented, you know, money oriented culture?
Is this a data oriented culture, research oriented culture?
Like, you've got to figure out how are decisions currently being made if they're being made?
And what are the things that work or don't work?
And that tends to be a very critical point for you to then figure out what are decisions I need to make and how do I actually make them?
Now that we're kind of we've covered sort of a spectrum, I'm sure that there's so much more to learn.
And of course, I want folks to be able to know how to contact you.
But before we get into wrapping up, I would love to know a little bit about setting boundaries outside of your work hours.
We've talked about all of these things, these high pressure decisions.
There's a lot of pressure.
And even if you do have a fairly stable schedule, that's fairly predictable.
It can be very easy even for non -executives to let work responsibilities creep into our personal lives and make it difficult to draw boundaries.
What are some practical strategies that you've seen work well for leaders who want to maintain some boundaries while still being effective in their jobs?
I would say one of the positives about being an executive is that generally you're the one in control of your schedule.
Again, I say that with a big asterisk of like if you're in an industry where there's a lot of governance and legal and market changes, that's going to like emergencies that happen, disasters that might happen that might like change your schedule, that's a completely different ballgame.
In general, you're fairly in control of your time.
You can actually very much prioritize certain things that you want blocked off, right?
Like if you want to make sure that you're free from 6 to 7 p .m., generally speaking, if you're really strict about it, nobody's going to be like, no, I have to take your time from 6 to 7 p .m.
That said, it's usually we're our own worst enemy.
But we're like, well, maybe you start kind of slipping.
Maybe we just do this once.
OK, maybe we'll do another time.
It's a slippery slope, right?
You're like, OK, well, maybe I don't protect this time anymore and people can schedule.
That's the first thing I say is like if it is the thing that is important to you, it goes on your calendar and you and your admin protected at all costs.
Like this is not a thing that I'm going to do.
And then I do think having like different phones, like a work phone and a personal phone, a work schedule and a personal calendar is important.
That way you physically can like have separation, leave your work phone like somewhere else, like in a different room, right?
Like between six to seven.
So you're not getting pinged and distracted by whatever is happening.
So physically actually having different devices and different calendars will really help with that as well.
And then I think one of the last things is making it a norm within the company to respect people's calendars.
So you can help yourself, but you can also help others be able to set those boundaries.
And I feel like that's almost one of the most important things as a leader is like, if this is something you is valuable to you, then you want to make sure that it's also something valuable to the organization more broadly, not just out of self -interest, but out of like you believe this is a good way
to work, right? Like where you have that balance, where you have things that you do that is respected by the rest of the team, then you kind of going out and making it a part of your brand will both make it easier to do because others are doing it too.
And it makes you kind of stick to it because if your self -narrative is, I am the person who's advocating for protecting the time, it's a bigger dissonance if you don't protect your time.
And be like, wait, but I'm supposed to be the protector of calendars.
But if I don't protect it, that's a bigger dissonance.
I know make you think twice or maybe three times about like, oh, do I really want that when I tell my team and I tell everyone else?
No, like we need to respect the time blocks on other people's calendars.
Stand by that. I love how much we've covered today.
There's been so much practical advice.
I really appreciate your time here today, Yui.
Where can people learn more about you, your executive coaching, and connect with you online?
Yeah, so I'm on LinkedIn, backslash Yui Zhao.
I also run a newsletter called The Uncommon Executive on Substack.
And you can find that through Substack or through my coaching website, which is www .yuezhau .coach.
Or you can just Google my first name, last name, coach.
And hopefully I show up somewhere on the results.
You can find me that way.
Sounds great. Well, thank you so much.
We really appreciate your time today.
Thank you. Thanks for listening in.
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