This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes I’m often asked about by listeners. This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the traits and strategies required to approach these problems wisely. Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes I’m often asked about by listeners.
This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the traits and strategies required to approach these problems wisely.
Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
In today's episode, we discuss:
Timestamps
[00:00:00] Introduction and context on caller
[00:02:43] Caller’s question
[00:06:35] Nikhyl’s initial reaction
[00:09:11] Could she solve this problem if she wanted to?
[00:10:48] The relevance of patience/impatience
[00:12:40] The relationship between tenure and solving hard problems
[00:15:20] Earning trust as a leader
[00:16:30] Understanding the company’s expectations and timelines
[00:18:05] The advice discussed so far
[00:22:54] Why this matters for future opportunities at startups
[00:27:10] Advice for approaching this challenging leadership scenario
[00:31:08] Nikhyl's closing reflections
[00:33:45] Key links for this podcast
Where to find Nikhyl:
Where to find The Skip Podcast:
Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.
Nikhyl: Hi everyone, welcome to The Skip podcast, the podcast dedicated to helping you get ahead in your career.
I'm your host, Nikhyl Singhal. Today's episode is another live coaching episode. One of my listeners took me up on the offer to walk me through a challenge that she's having in working through a new executive role at a tech company.
And the question that she's mulling over is whether she made a mistake in actually joining the company because she's seeing a lot of red flags. Now conventional wisdom is you should trust your instincts. And if you start feeling like maybe you've made a mistake, it's probably not going to get better. But I don't actually trust conventional wisdom. Oftentimes, the hardest part of any job is in the first hundred days, and maybe even all the way to the first year.
And the important thing is to weigh, is the position that you have set up to fail, or is this just an opportunity for you to show some grit?
But if you think about your skip job, the next employer is going to want to see that you've solved some really messy challenging problems in your current role. And so if you presented with a position that is filled with a number of problems.
You have to weigh whether or not they can be solved over time, whether or not by having the right relationships, but certainly don't exist in the first 100 days, whether you can actually start nudging yourself towards a successful spot. And in fact, if you do solve those problems, there might be a very powerful story that you might be able to connect into a very career additive position.
When I spoke to this caller, she walked me through a very detailed background. Now, for the purposes of this episode, I'm going to summarize it. She started as an engineer, then moved to the States for business school, and then has really held over a dozen roles.
This is quite an experienced executive where she's had success in small companies. Mid sized and large companies, and she's been very proactive about her career, leaving when it didn't feel like there was much to be gained and actually has held over a dozen roles.
And so the lot of my advice is what makes sense for someone who does tend to have a number of different roles and is looking for the current job to be career additive.
So let's start our conversation with an edited version of her background and then some of the questions that she has.
Guest: Thank you for making the time. I definitely have been following your posts. I was definitely inspired to hear the very no bullshit, straightforward advice you shared.
So I think the question I sent you was hey, I'm not sure if my current company and this particular role is the right fit for me having been in here for 4 months and I was also talking [about like a CPO role at a series B startup and another director of product role at another series D or E, I can't even remember. And this to me was most exciting because it sounded like, hey, come in as a head of product. And then in 6 months, we'll set you up to be, the P&L lead. And it's a small contained business where it's at the series A to B stage that within a series E, and you get to run your own P&L, you need to you get to take this forward it's incubation business.
We wanna see 2-3x growth here on year. And you'll have a lot of autonomy on how you achieve that. Coming in, I think the two challenges I've found is one, the company that we acquired to first bootstrap this business, it was more of a acqui-hireand so they understand the domain very well, but they don't understand software development or SMBEs and not just like SMBEs when we say our average customer sizes, businesses with 10 employees, so like, really small, not even medium. And so there is an element of, okay, this is a interesting challenge where we now need to course correct and build a true MVP. But the part I'm struggling on is we have a bunch of folks that came to us with a acquisition and have golden handcuffs and so I'm stuck with a high will, low skill team.
And the second challenge is the hiring manager who brought me in left within 60 days. And so now I'm also like this independent island where I'm trying to build more relationships and credibility with the leadership side of the house and turns out
the person who hired me had burned their bridges and there was some animosity there, which I wasn't aware of till after her departure. And so now I'm trying to go talk to them and build that bridge of, hey, I'm not that person. Even from the four months I've been here, I can see your upsell business should not work in isolation.
We should be a plug into the platform, not a separate standalone app. But that's where I'm wondering, A, what is this doing for my career and beginning to question like is track to leadership, the right choice, even.
And what does that set me up for? Does that really set me up to be— oh, sorry. Actually, I didn't even tell you why I thought it was a good idea. I think the reason I thought it was a good idea was because ultimately I do see myself taking on a role as a CPO at a series B or C, where like you're at the stage, you've managed to prove product market fit, but then you don't know how to keep it trading in order to scale.
Or you may have found yours because you found a sweet spot in one segment or one market. But then now it's more about sequencing, strategizing and continuing to grow at a sustained pace. And I think that's the kind of area where you get to be equal amounts of strategic and equal amounts of scrappy, and I think I enjoy that and you get to set your own best practices, you get to build a team and set the culture.
And so that's where it also felt like a good opportunity to take this role, because I felt like there was a VP level person who would help mentor me, help me step into that role. And I would get to emulate and learn by seeing none of those things seem to be in place now.
Nikhyl: I think that the thing that you noted to me, if I'm playing it back is I joined a company, the company set up was for me to sort of establish as a product leader.
This new business started with an acquisition and it was to take that core nucleus, build it out. And if things go well, my role as the product leader could move to more of a general manager. And that is the sort of success. And that's what drove me to take the role. And I'm seeing challenges. I'm seeing challenges where some of my air cover is gone.
I'm seeing challenges that the acquisition is maybe not suited for the business that we need, and that this requires a pretty fundamental rebuild. And so what I would say to you is that, you know, and you're asking this question of, is this even worth it?
My, my take is that, well, I think that this is a hard challenge, and it possibly impossible.
It's, it's conceivably that this setup is not possible for a new person to come in and establish a fairly substantive pivot given some of the constraints you've mentioned. But I would say that, you know, one of the things that we want to do in career is to do hard things. And to build harder things to the point that people look at that and say, boy, these are the types of challenges that are pretty common across industry today.
You know, if you look at all of the companies that are out there, whether they're late or early, they all have very unusually hands on hard problems and you happen to have one in front of you. So the calculation of is it worth it for me to stay is predicated, in my opinion, on could you succeed? And if the first question is this is foundationally impossible to succeed, I don't think I am set up to succeed.
I don't think I have the endorsement. I don't think I have the right, you know, expectations and I don't have enough time. Then I think it's a fairly easy decision to like, why would you work on something that's not possible as a leader? But if you're like, hey, I could actually succeed if I grind it out.
I have a point of view on the sequence of things that have to happen. I can kind of lay out the one pager of what changes need to be put in. But I just feel like if I succeed, this may not be worth it in exchange for what I've been interested in career wise. That's a totally different question. And we can comment on that second question in a moment, but maybe I'll start with the first question is, could you succeed if you wanted to?
Guest: I think in the current setup, that is very tricky. I think, If I was fully empowered to make the decisions that require to create the right theme, then yes, I can see us succeeding on a two to three year time horizon. But the fact that I've inherited these folks that have these golden handcuffs on and the whole subculture within these ten to twelve folks permeates through all the subsequent hires they've made over the last two years.
And while some of that I can undo, I can't let go of that basic nucleus. Without accruing a lot of bad will, ill will.
Nikhyl: And what's been the response when you presented this to leadership? This concern.
Guest: It depends on the leader I talk to more newer leaders that have come to my current company um, they are super supportive. I think the people who have been there and were part of the acquisition, the reaction can be a bit like, are you sure you're not being too aggressive?
Like maybe, you know, we can, phase this out. Maybe there are other ways to deal with this, which is what gives me pause where I'm like, we can do that. It depends on how quickly you want to get to success.
Nikhyl: Are they willing to be patient?
Guest: I think maybe that's something that I should clarify. I know that they are definitely willing to be patient for, like, the next, um, 2 years. I don't know how much longer after that.
Nikhyl: Yeah and maybe this is a core conversation based on the background is from what little I know and what you shared with me, there's there's a degree of impatience that has governed your career. And it has worked in your favor and perhaps it has worked against you. And I would say that that is career limiting as you become later in career, because more and more people are like, look, I want to build something that's hard and complicated and growth is not available. And so you run the risk of growth being a great tailwind to your career, you combine growth and impatience and what ends up happening is you keep it, you keep having more at bats. You keep having more opportunities and growth was lifting everything with 0 percent interest. And so you could go from one good setting to another setting and maybe it works out.
But if it doesn't, you can quickly move on because you're impatient and that has worked in your favor in the next 10 years. It could be a dramatic headwind against your success. And so one of the things and one of the reasons I asked this question is in some ways, you're trying to get some justification.
Like, look, I found that this setup is pretty far from what I had hoped my impatience is like, well, isn't there a better job for me? I haven't invested that much here. Why not pull the ripcord and that might be the right thing, but if you read between the lines and if they're like, look, you are coming in.
You have a pretty good sense of what's not working. You You have a point of view of what might be the next sort of set of steps. And they they may say, look, we're not going to make a 180 degree change based on decisions we've made. Frankly, you haven't even been there for 180 days, but why don't we start heading in the direction you're suggesting, but do it at a little slower pace, you might come back and say, I'm not patient enough to go through that process, but that is not on the company failing you.
That is not on you not being a general manager. That that is you having to take the time to prove out your idea, build some confidence. They need to make sure that they can trust you and you might fundamentally think this is not a company I don't want want to invest in and that was just a bad career decision.
But I'm cautioning you that you don't want to keep, you know, avoiding tough, challenging, tenure based problems simply because the market allows you to get new jobs, because at some point people are going to be, why would I invest in her as the lead? Because as soon as the company hits its first jitters, she's going to move on and And I need someone who can be a leader when things are not good, not when things are good. And and perhaps that's an unfair comment, but I just think that that that can be a narrative for folks that move quickly.
Guest: The tenure based piece really resonates me with me. I do think when I look back at my career, like the places I can speak to with confidence, both in terms of having grown in and have had the ability to show measurable impact are places where I stuck around for more than 3 years and so. And like, I didn't come into my current company with the idea that I was going to think about an exit this quickly. Right? Like, I definitely came into it, with like, I'm in for at least the next 4 years and possibly the next 7 to 8 years. I'm just at a stage of life where, like, I don't want to just keep jumping around. And, and yeah, I guess I need to think a bit more on that point about impatience, like, because I think what I'm hearing is, hey, making tenure based career choices is not just about spending time in the role and being able to point to impact every 6 months, it's really about solving the harder problems that might take a year or 2 years, 3 years to solve because shifting orgs and culture is not a 6 month, put it on your PSC task.
Nikhyl: I mean, I couldn't have said it better myself. I think maybe another way to look at it is let's start the conversation with I've joined this company and my expectation is to be a leader at this company. I need to be here for three to five years. That three to five year period is when a leader can make it's, you know, his or her greater impact.
Now, in your example, what I would say is maybe the the role that you start when you join the company is not the same role as when you have the greatest impact. And so the way I look at these longer tenure leadership positions in established companies, and certainly your current company is a very established one. I would say that, you know, you need to first build confidence in yourself and your translation of your skills to the company culture, and and they need to build confidence in you that you are a leader. They're not going to do that based on a resume or an interview. Or in three months, that's perhaps possible in an IC role or in a more junior role, but not obviously in leadership.
And as you pointed out, you've had more of your impact when you've had longer tenures, which is not surprising. So think about it as okay, I'm going to join this company for five years. The first job I'm taking is the starter role. That job will take me a couple years for me to essentially have trust and confidence bi-directionally Now what will happen is the company will pull me forward into a better, more impactful role. And that's where I have maybe my greatest tenure, impact, joy, and that's where I've really found my fit. So this entire conversation is like, could you have impact in this first two years? And as you point out, what you're describing is incredibly difficult for anyone. We just bought a company. We need to establish a new business line. We're asking people that are new that have never worked at this company to be the drivers of that. And by the way, the customer needs to change from what the acquirer or you know what the acquisition team is used to seeing.
And if they're asking you to do that, if their expectation is we expect to see progress relatively quickly, well, then you're set up to fail and you should move to another role within the company. But if instead they're like, yeah, we think it'll take a while. And, obviously the leader that came in is no longer here, but you, you know, have the best position.
Now, if they don't trust you, then you're sort of set up incorrectly, but if they're like, we we want to hear from you, we want to give you time, we believe that you might be the right person to drive kind of the right direction. And frankly, we need someone, but you need to basically work through it in your mind.
You're like, career wise, if I can have effectiveness in 2 years. Then I can really get the plum role to really drive my main impact. And so this is a two year starter position, you know, and that, that to me is a much better framing. And then you can decide, do I opt in for an additional two years or not?
If this wasn't meant to be, but I think that mentality will be much better to govern your tenure than whether or not this was met your expectations in joining.
Guest: Just to play that back. I think what I'm hearing is you went in thinking you were going to inherit a problem, you were going to invest 4 years, turn it around, learn things, et cetera, et cetera, and come out and be ready for, like, the next big jump in your career for having done this. What you're finding is that part is very unclear and even the nature of the problem you thought you were inheriting is quite different.
And so there might be an opportunity to learn and grow and have an impact, so A don't be hasty in assessing what can be achieved or not achieved. And instead, like, align on what the time horizon in leadership's mind is so that everyone is on the same page about, hey, is this impact going to be achieved in the next year or 2? What's your expectation? Will this area get defunded if we don't get to a certain scale in 2 years? And if the answer is, nope, you have time, you have 3 to 4 years. Then go and do what it takes and reassess personally where you stand after 2 years.
Nikhyl: It is, I think I have slightly different, um, words to get to the same sentiment. What I would say to you is, you had an expectation that in the next few years, you can show impact and it can be very additive from a leadership point of view and career point of view. And what I'm suggesting is that absolutely still exists, perhaps even more so.
But I think when you look under the covers, What it takes to be a leader was much harder than you realized, and I'm suggesting to you as this is the job and this is the best thing for your career, is to prove you can succeed in a hard job so that the next job, by the way, these series B CPO roles ain't so easy.
They're not, hey, I join and things just go up into the right. They are very similar to the problem that you just described. So what I'm saying is you have an opportunity with some level of grace for you to show that leadership. I don't think that the company needs to commit to you that we will write a blank check for four years.
I think that's very unlikely and that's crazy. I mean, you wouldn't want to work on a project for three and a half years and then find out it doesn't work. I think you need to do is you need to say, hey, I think this is a tricky problem, but I'm going to come up with a two year plan to optimize and I'm going to believe in that plan.
And then I want to get told that I can't get to that plan. Now, if your plan is so aggressive, we're going to change the team, we're going to change expectations, we need three years before we show any kind of impact. That's not a reasonable plan. It has to have some degree of risk. But at the same time, you, you are not going to be able to wave a magic wand and turn it around.
And one of the trigger words I heard is that, hey, if I was the GM or if I was in charge, I'd be able to do things. But, that's not really reasonable. You all of us live in some degree of constraints and you're new, but you could come up with a very viable two year plan and that two year plan you can believe in.
And if you get through that plan, get the team to a better place, get the business off the ground, perhaps see a promotion along the way, you'll have a ton to show and add to your career. You'll be able to say, look, I ground it out as a leader of a new business. And it's a, it would be an absolute diamond in your career.
If you were then say, give me the CPO of a series B where I'm doing something quite similar constraints, but I'm figuring out a way to take this business forward and I'm inheriting something, I'm not starting it from scratch, but it's certainly, a bunch of strategy, a bunch of complexity and upward communication and downward communication, and it has a ton of accountability challenges.
So it's very, very viable as a setup for your next role. It just requires a degree of grind, which is going to take a while. And that's what I'm asking you to be patient around.
Guest: I'm sorry. Yeah, I think I'm letting that sink in, but, um, framed that way. That makes a ton of sense. It's good to hear someone reflect back to me that, yes, there is opportunity here. This is a viable role and as additive would be, you're being impatient, slow down and it'll be okay. I think maybe I just needed to hear that from an external voice.
Nikhyl: I think it's, it's more than it'll be okay.
Maybe the question, let's assume that I'm a CEO of a series B company. Let's assume that I'm interviewing you to be head of product. The question I would want to ask you is, give me an example of a series of hardships that you've dealt with in the professional setting and how you overcame them.
Now, I'm not suggesting, given your very broad career, that there's plenty of hardships that you've faced and that you've overcome. I'm looking for the level of complexity, because the role that I have for you is going to be faced with all kinds of hardships, and it's going to test you. And I want you to overcome.
And when I hear your background, one of the things I hear is hardship came and I made a move. And we call that impatience. But I actually think that actually that could also mean that you are perhaps challenged with grit.
And the Series B role that you desire is a role filled with grit. Why I'm suggesting leaning into the current role is to show a degree of grit that you've not shown to date, and that is a career unlock, because if you can transcend that, if you can say the chips were down, and I was able to get something that no one believed that required me to build on lots of levels, influence, product strategy, taking some, you know, circuitous path to success.
People are like, that's exactly the person I need in my company, because those are all the skills I'm going to need knowing very little about your background, perhaps you have many of those examples as well, you know, and certainly going from where you started early in your career and going through all that reeducation and rethinking requires a ton of courage.
So I'm not pushing back on that. I'm just saying grit is the important feature in the roles that you desire next. That requires perseverance. And that requires hardship and it requires you to overcome and frankly require some degree of tenure. And so that's why I'm pushing you in the direction I'm suggesting.
Guest: Got it. No, and can that resonate, and I think, I mean, while I'm also taking away that I need to work on how I narrate my story, I don't think, I don't think of a jump ship when the going got tough. But to your point about what if, what if I was sitting in an interview for the role I desire, and I think the examples I would be leaning back into were all in larger, more structured setups. Whatever I achieved in the last 5 years was at post IPO companies and that would not resonate with, um, um, the IPO founder. I mean, I wouldn't want to hire me.
Nikhyl: Yeah, I think that combination of that insight, plus the fact that growth, because it existed for so long, people are very skeptical of anyone's background, not just your own, that they always look, well, maybe they were just present while, you know, they had a boat on the tide and the tide rose and that was the success.
So you're combating two of these memes. Hey, I had a structured, you know, success and then is it possible that growth really was the factor to some of your success. So now you sit in a role there. You don't have the growth piece inherently
and you know, ultimately you are not in a super structured environment. You need to be the leader of that structure. That's why I like the role.
Guest: Yeah, I think framed that way I can, I guess, and I know this is like getting to the next part, maybe, but I'm also then wondering, like, when you say, two year plan together and think about, like, what might be that structure, what's a good way to approach, a challenge like this, where you like, you know, you have this entire set of individuals who pretty much know are the evangelist of this business, but over the last 2 years have pretty much become redundant and are potentially almost a liability and don't want to demotivate the rest of the org, nor do you want to make too many aggressive sweeping moves because I don't think that's the right way to set up a org this size for success. What's a good way to thread the needle between upskilling versus cleaning shop?
Nikhyl: I would probably say is the product strategy that needs to exist in the next two years needs to first ignore them, which I worry is blinding you to your ability to look at all the other parts of the problem. Like if the problem was as simple as everyone's on board with the strategy, but we just have the wrong group of folks, and I just need to work through that. That's pretty far along everyone in leadership is aligned on here's our 2 year plan. Here's what we can achieve. Here's what's meaningful going to matter. But I have a problem with my P&L paying for X and not Y that's pretty far. My hunch is that you're not quite there.
My hunch is that's one of many, many, many problems. And so my counsel is for you to say, well, let's put that aside for a second. Let's figure out what this business needs. Let's align that with leadership. Let's find a champion for you of someone who's in the old guard. Who's actually has good trust with all the leaders, but is actually also someone who's willing to adopt you and work with you.
Or maybe that's someone in the new guard who has that translation then put that as one of your challenges on your plan. Maybe the one that you have least control over to your point but I think if the rest is actually then this is my counsel is if the rest is actually pretty well established, then I think that you can bring the leaders together to solve that problem.
And what it will probably look like is reducing the team to a smaller group, probably not retraining and probably looking to use that P&L in some thoughtful way or expanding the P&L in an attempt to just sort of manage this constraint. But I wouldn't put all your energy there without all the clarity on what's after that, right?
Because that's that can become a quite a distraction.
Guest: Yeah, no, I think I, I am at a place where I've pulled a strategy together and set the new metrics. I'm now in the process of shopping that around, which is where some of these gaps were I'm like, hey, if you're going to optimize our ops heavy workflows and build in, AI chat assistant or do all these things.
Where is the ML skill? Where is the AI skill set? Like, you know, and so that's what brought to surface some of these conversations. And I sort of then realized there are, almost two guards, I like the way you put it, like the old guard and the new guard and that's where I was like, holy shit. This is not as simple as we need a strategy.
Nikhyl: Well I think that if everyone agrees to the strategy. The tactics is what you need help with.
And so what you want to do is get everyone aligned that this is the correct product, the right strategy and the right business. then you want to essentially say in the light of us agreeing to that, here are my tactical concerns, help me through this here, the constraints I have, how many of these constraints exist?
Do you see the gap? I think that if you go too fast through the strategy and too quickly to the problem, you'll end up people feeling like, hey, I made that call and now you're asking me to change my mind. If, on the other hand, you go slow through the alignment of the strategy and get everyone excited. Then they all stay on your side of the table when you effectively work through the constraints and you can kind of openly talk about, well, I mean, if these constraints exist, this is what we get. You just need to bring people to solve this with you as opposed to trying to make that the centerpiece of the conversation.
Guest: That's good advice. I think I need to be and it keeps bringing me back to your point about patience. I think I need to be patient just because I've created the strategy and three leaders have blessed it doesn't mean everyone understands. And I think the part what resonates is get everyone excited about it.
Nikhyl: Correct, and that creates influence and that influence as well carry you through that 2, 3, 4, 5 years and the level of impact that you look for.
Okay, so as we wrap up, I think we all can agree that grit is a really critical factor to career progression. If you have a really hard problem in the office, And you're able to show success in solving those problems and your next employer will match that to the problems they may face.
And if they turn out to be similar or perhaps even easier than the problem that you faced in your current job, it's a huge factor to being successful in that role, obviously getting that job and so on. So the trick that we want to balance is ensuring that the problem that's in front of you is actually solvable and solvable over some reasonable period of time.
Now, if it requires you to compromise your values or stay for years or essentially play politics in a way that makes you uncomfortable. That's not maybe a job for you. Or if you're just set up to fail without any possibility of success. Well, those are roles that you want to move quickly past, but really hard problems do require effective relationships, trust, context that everyone has that shared, and all of that points to gritting it out for some reasonable period of time. Maybe that's two or three quarters. Maybe that's a year. But if you feel like you've been given a really hard challenge and it's going to take quite some time to solve, that may be okay.
Because the payoff is the role you get next is going to be filled with even more challenging problems, but will be a lot larger with a lot more responsibility.
Finally, I'll end by noting that this patience that we're talking about is something that wasn't as necessary in the past as companies were growing so fast that the problems tended to get more complicated, but also responsibility tended to grow organically for anyone that was trusted or anyone that was really present in the building because growth was coming for free.
Now you really have to grit it out and show this progress and this patience in a way that wasn't needed before. So if you're struggling to work through some really gnarly challenges, but the challenges do seem like challenges that other companies have, it might be exactly what you need to actually stay gritted out and overcome.
I'm Nikhyl Singhal. This is The Skip Podcast. Thanks for listening in.
If today's episode resonated with you, please consider leaving a review or sharing it with the people, you know, who want more out of their career. To get the latest content from The Skip, you can subscribe to the podcast on Apple, Spotify, YouTube, wherever you currently listen. You can also follow my newsletter on Substack.
And if you have questions or feedback, particularly related to this new format, I'd love to have you drop me a line on Twitter or LinkedIn and perhaps you can be one of the next guests on The Skip podcast. As always I'm Nikhyl Singhal and this has been The Skip.