Live from Lenny's Summit | Career advice highlights

JZ: Now, the next speaker is someone who gave me career advice during one of the most tumultuous times in my own career. As WeWork was imploding, um, as I was drawing up layoff lists, and I was actually pregnant with my first child.

I met Nikhil, and to this day, I still remember the conversation that we had, and he's taken what he's done for me, and he's done it for so many other product leaders. He's mentored them, coached them, created a community, the Skip community, around supporting product leaders. And for that, I'm incredibly grateful.

He just has the most insightful, real talk takes on career. And so I'm incredibly excited to bring the Bill Campbell of coaching product leaders to the stage.

Nikhil Singhal.

Nikhyl: JZ. That's like the first time Bill, Bill's kind of a mentor of mine. And it's so, um, humbling to be compared to him.

I'm here to talk about your career. I think your career is the most important product that any of you work on.

but if you're like the hundreds of executives and leaders that I've spent time with over the past ten years, uh, you probably feel pretty alone in trying to build your career.

And in some ways, that was the inspiration for this channel. For me, putting together the skip earlier this year, I left meta after a 25 year operating career with this expectation that we shouldn't be alone when it comes to building careers. We should look at collective wisdom and in some ways today's presentation is kind of the greatest hits of four or five things that I've learned over the last six months in particular in coaching and building communities for leaders.

before we get started, I have to say that, you know, I spent a lot of time at home and maybe you do as well, but because I don't have the same pay schedules I did before my, my two wonderful dogs sit next to me. And when they saw that I was putting together this presentation, they really wanted to use their gen AI skills.

So Saffron and Mipha are two dogs really helped me put together today's presentation and you, you know, if you like it, you can kind of credit them. I'm going to start with a really simple question. I want all of you to think about the question of how many jobs you're going to have. You know, if you're like most people I've talked to, they haven't given it a lot of thought, but they kind of think it's going to be like a half dozen or so.

if you think about it, you're actually going to live a lot longer than perhaps you may realize. You know, I've always said that with the expectations around life expectancy doubling every century. And going up, I always thought that someone of my age would live to a hundred, perhaps the next generation would live to 130.

The anthropic CEO published a statement that he thinks the number is 150. That's a long time. Then if you think about retirement, retirement is actually a bit of a antiquated concept. The idea that at 65 that we will stop working, you know, what are you going to do with all those extra years? So. And if you think about retirement, it was based on the idea that we physically labored, but all of you basically sit all day.

You know, you don't really need the actual physical respite. And so what you will find is actually you'll want to retire differently, perhaps pursue different hobbies or interests or even careers. And most tech jobs, And I suspect that if you ask your neighbor, most tech jobs actually last fewer number of years than you may think.

Two to three versus five to ten. So if you put the math together, we're looking at easily dozens of jobs. And when I say jobs, I'm not necessarily saying employers. Many of you transition from position to position within the same company. But when you think about. Dozens of jobs, perhaps multiple careers.

We need a bit of a framework to think about these positions. And so I thought about this framework kind of like a building. You know, I think that there's this foundation phase that I think is at the beginning. Then there's these power years that you end up having where you have the greatest impact. And then in the penthouse is kind of that second career.

Right. And if you think about the investments you make in the foundation years, it's to find a superpower. It's to diversify your strengths and experiences. But in the power years, you're actually leveraging that superpower. You're not broadening as much as leveraging that. You care about the largest, most impactful role you can get.

And if you think about compensation as a leader, for a moment think about the fact that this year you'll probably make the equivalent of two or three years early in your career. So compensation is a hell of a lot more important in these years But then when you get to the penthouse, you might pursue joy.

You might pursue a problem that you want to work on for a decade. You might want a different style of pace. And so this formation is critical for you to think about how you achieve which job. And then just as important, you have to make sure that each job sets up the next one. And that's actually why I call the property the skip.

So I want to talk about two specific points on the foundation itself. Second big topic was a mistake that I think many of you are making today is you're not thinking through the story that you're going to tell about the role you hold right now. Okay. When I think about a story, I'll be specific. It's what product are you building?

What challenges are you facing? What opinions do you have to overcome those challenges? And then, are those opinions actually landing? Are they succeeding? And if they're failing, what are you learning about them? So this idea of product, challenge, opinion, outcome, is your job story. Now, what I find is each story that you collect is like a tool that we add to our tool chest.

And now down the road, someone will ask you, I have a problem. I'm looking to hire someone. I need someone who can solve, said problem. The most infa impressive thing you can do is say, well, I have a story to tell you. I have the ability to tell you that I have seen said problem. I've held this opinion, I had this constraint, and it really worked out.

And I think that the more stories you can collect. The more jobs you can open up in your power years. Now this same tool is very powerful for career management in other ways. So, several of you in this audience right now are probably thinking, now that we're in the afternoon session, you're probably thinking, boy, I'm not sure I should stay at my current gig.

There's all this great stuff happening out in the industry. Maybe I should take off. I get these calls probably once a week if someone's like, I'm stuck in my career, I'm thinking about leaving, but I'm trying to decide, should I stay or should I go? Many of you have asked that question yourself. The technique I use is, ask yourself what story you will tell in 12 months.

In 12 months, tell me if that story is different than today's story. And shockingly, a large number of people will say, actually, I think the story is going to be roughly the same. I've been in the role for a while. We have a bunch of constraints. Some VP is going to make a decision on what to fund. I'm not sure I'll have a much better story.

Well, that's what we call career stagnation. You should probably transition. But some people will say, actually, I don't know how good the company is going to do, but we're going to ship 11 products. And during that time, I'm going to learn a hell of a lot. I'm like, well, you're definitely not stagnating. I'm When your story improves, you're helping advance your career.

Similarly, when people come to me and say, I have this IC role at this hot company and I have this management role, it may be something that's not so hot. Which do I take? I always counsel them, think about the story you'll tell in 18 months after you take the role. Now, the second thing I thought about is as I've talked to most of the executives and even the folks that are on stage today.

Almost all of them will cite, there is one bend the curve role I took. There is a peak role that happened to me that sort of changed the trajectory of my career. For me, it was I had founded, uh, three times, and when Google bought my last startup, I joined the Google Plus team and I was associated with Hangouts and I was associated with Photos.

And the way I thought about my career up until that point and afterwards was vastly different. It was clearly the unlock for my career. So now the question is, for each of you, you need to find one of these peak roles. And so when you ask folks, well, how did you find it? The dissatisfying answer that most people will say is they'll say, you know, it's kind of mostly luck.

And I'm like, well, how helpful is that? And then they'll say, well, actually, when I looked into the data, almost all of it, luck is sort of always predicated on your professional brand. You know, this professional brand is something that almost all of you know about, but you all really struggle to invest in it.

Some of it's like hard to invest in. And some of it's just like, I don't even see my kids. I'm so busy with my one on ones or not making my workouts. You want me to start a podcast? Who has time to go to a conference? Actually, don't worry about that last one. But the point is that brand is what gets you luck.

But brand is this long term amorphous thing that's hard to control. So instead, I ask you to think about the reputation you're building today. Because the reputation you're building today is the brand you'll have tomorrow. So what that means is figure out what values you want to demonstrate. I suggest that in the day's market, being hands on, being gritty, being opinionated, but loosely held, being a team player, not in it for yourself.

These are all very clear values. Now the question is, do the best people that you work with around yourself know that about you? Do you have a relationship with them? Can you find one 30 minute meeting once a week to go and connect with those people? Make sure they know what you do. Make sure you know what you stand for.

Make sure they know your story because they're going to have dozens of jobs. They're going to go places. They will take your reputation with you. That is how all of us delivered and built our personal brand. Okay, two big topics on leadership pitfalls that I want to hit on. Okay, so this is one of those personal stories.

You know, I think almost everyone at some point during the year uses the word burnout and product management in their own mind. You know, for me, I have a superpower, which was I could bring a lot of force to work. I was highly opinionated and I was willing to prioritize work above everything else in my life.

I think a lot of people that are here probably feel that way too. And what would happen to me is after about two or three years, I would get to a point where I'm like, I don't know if the company sees me for who I really am. I'm doing great. They say I'm doing well, but I'm not getting everything I want.

I'm not sure I'm getting the promotion that I deserve, the compensation I need, the scope that I desire. I'm going to transition out, you know, next company comes along. And the same thing happens. I push really, really hard. Three years go by sort of have it a break, three, four, five companies went by. So I finally sat down with my therapist and I said, listen, I have this pattern where I give so much to work and I never feel that I get enough back.

And her question was, whose fault is that? It's kind of a tough one. I was like, I'm paying you and now you're making me feel bad. And I realized that I'm over investing in a relationship and all of us know when we over invest in a relationship and we will never get the return we need. And so the question is, are you over investing in your work today?

Now what's interesting is when we hear all the rhetoric around avoiding burnout What we know is that we need to create boundaries. The challenge is, none of us do it. And the reason why none of us do it is we don't understand why it's important. But what you realize is that if you overinvest, you are going to create resentment.

You start to enforce those boundaries. You hold back those 10 15%. Because you know that they'll never be able to return the kids practice that you missed that workout that you couldn't get to, perhaps that company that you could advise to branch out. So I've always suggested that you should take pressure off of your employer by enforcing boundaries, despite what they ask.

Because if you succeed, they will give you more stuff. And then when you get that more stuff done, your reward will be more stuff. It keeps happening until you find the ability to put those boundaries and recognize that it will only create resentment when you leave if you don't do it today. This is an example of one of the talks that I've given around shadows and superpowers.

The superpower here is your ability to create great force. The shadow is the resentment that that creates. Okay. There are lots of examples of this where when you become senior, what you realize as a leader is you stop getting feedback. Nobody wants to give feedback to you because you're a leader at that point.

Yet what gets you to leadership isn't what takes you forward through leadership. And so when you get no feedback but you need to change your strengths ever so slightly in order to succeed, you're in quite the pickle. Now what I've asked these folks to do is I've asked them to look deeply at their strength areas and seek the shadows.

You know, you might be a great storyteller, but you might struggle to get in the detail, the detail. You know, you're straight shooter. You know, I got to where I am because I'm very opinion in. I'm very direct. I'm like, great, now you run a 400 person organization, not everyone is at your level. 300 of those 400 people have never really met you.

You're a straight shooter, they call you an asshole. That is a shadow of your strength. You need to recognize that what gets you here isn't what takes you there. You know, the idea of a process person not being opinionated and creative, this process of seeking these. shadows under your superpowers is highly effective because what you realize is that since you're never going to get feedback, you need a place to seek feedback around.

So, go out, think about your superpowers, think about the opposite, go ask people, Hey, because I'm a graded process, do you know where I stand? The answer is probably no, and then you think through, wow, I know I need to create a little bounce. that adjustment expands your leader. Okay, so as we wrap up, I want everyone to recognize that this career that you have, though it very lonely and it gets more lonely as you become a leader, will not always be this way.

You are not alone. With folks like Lenny, with folks like Shreyas, folks like the properties of the skip, we're all trying to find ways to connect all of you together. Find ways not only to help each other. But also make sure that you're connecting with as many other product leaders as you can. Because we're the only ones, in my opinion, that can help change our industry and catapult our careers forward.

Now, to wrap up, I want you to divide those dozens of jobs and recognize that you'll probably be in your hundreds when you're still working. I don't know if that's actually true, but I'd wish and hope it will. Um, into these foundational roles, these high impact roles, and these roles that have this joyful giving associated with it.

Make sure that you're thinking about the stories you're acquiring today. Make sure they're career additive. Make sure they're filled with great opinion and grit. That the reputation that you're making today is your brand tomorrow. Make sure you tell people about what you stand for, and make sure they carry that signal going forward.

That boundaries will only get enforced when you realize that your employer is incapable of returning essentially unconditional effort. And so that's what creates the mentality to hold back, and it gives you longer tenures. Find your superpower. It's essential to have those high impact years, but beware of the shadows that sit underneath it.

And most importantly, continue to invest in each other, We're all in this together and we're going to have a great product career going forward. Thank you very much. It's been a pleasure.