Career Transitions

"PMF stands for people, mission and financials. And these are my three criteria... you should have a set of criteria that you are unapologetically rigorous around and you should learn how to evaluate companies against that set of criteria."

"My early career was pretty wild... it really comes down in a nutshell to this career concept of explore and exploit... You're either in a mode of explorer where you have a bunch of unknowns and you're testing to see whether or not you like it... Or you're exploiting, where you actually have found something that's really rich and really deep and then you're just trying to get more."

"It's really easy to be a victim of inertia. It's really easy for all of us to be the frog where there are little things that make us uncomfortable, and we sit with them... you really have to be aware of your surroundings. You have to be aware of which way is the direction of the temperature of the water trending."

"It was a difficult decision to walk away from my career at the peak of it, but I guess the takeaway, and then I'll stop for a bit, is it's important for people to understand that there are formative experiences in our lives which put us in positions to where we form adaptations in order to survive, just like my attachment to achievement and how my self-worth was entirely tied up in that."

"The transitions that I talk about are the big fundamental ones like the transition that I've been going through myself... me, for example, stepping away from my career, at the end of the day, I wasn't running from something, I was running back towards myself. That was an act of kindness towards myself."

"I realized that probably the most important thing is to just acknowledge that that is true for me. That I'm not going to be a person with a plan, and actually the thing that has consistently served me is to do the thing that feels right, go to the place that feels like home, work with the people who feel like my friends."

"I try to just put on the coat of the job. When I wake up in the morning, I'm like, what would it be like if I were doing this job? What would I think about on my commute? Who would I have lunch with? Do I like them? What problems am I going to solve today?"

"I convinced one of them to introduce me to everyone at the office. I'd made a trade, I said, I'll buy you a fancy coffee at Coupa Cafe in downtown Palo Alto, and in exchange just introduced me to everyone... And the only call I got back was from the Head of PR... 'But we need a temp to review our press releases, so if you want to come join a temp agency, we'll tell them to send you here.' And that's what I did."

"I think there's really two paths. I think one is more formal in nature. There are associate product manager programs out there and many scaled companies... I think another "more formal" way to get into PM is really by just directly applying to a junior PM role where there's no expectation of any sort of experience. I've usually seen this work best when you're already working somewhere in some product adjacency. Maybe you're in customer support, implementation, or maybe you're a sales engineer."

"I definitely think doing it within the same company is a lot easier than trying to switch companies and switch jobs at the same time because when you're within a company, you've already built credibility, hopefully."

"The framework is really that there's impact that you're really trying to drive and that is the thing that is the most important. And the impact is only achievable by looking at two sets of variables, a set of variables related to the environment, a set of variables related to your skills."

"I left Apple on a Friday and I started Pinterest on a Monday. I didn't give myself time to recalibrate to the Pinterest culture. I think at some level, a lot of the challenge is that Apple, and it's not just Apple, I think every major tech company, they have really powerful cultures. You get indoctrinated into all those standards and it's really deep."

"And you start to realize that all of these things where we think we have to pay more money, over 50% of the people who got new jobs didn't get more money. It's a lie. It's about progress. It's about what do they want to learn? What skills do they want to get?"

"The moment you stop making progress in your career is the moment you start looking for another job. And so over the last 15 years we've interviewed over a thousand people. I've coached almost a thousand people because I think there's a billion people a year who switched jobs and ultimately most of them end up with a job that's worse than the one they were at, but they don't know how to find it."

"I call it a jobcation, which is a job I can go do with one hand tie by hide my back so I can rest and recover to go do something else. It's about actually being able to go to the gym and work out and have some vacations. The moment you are comfortable doing nothing, you know who you are again, and you can actually figure this out."

"The thing that I think has been most powerful is, again, treating you like a product. How do we prototype different job positions for you? So how do we think of you? ... It's this notion of starting by doing what we call informational interviews to other jobs that are out there."

"Jump into new things, give it six months. If it's not the thing, no problem. You just built a ton of new skills that's going to come in handy, I promise you that. Keep going."

"I think there's two really good places to be. I think one is carrying a lot of water in areas that the company's not paying attention to but you are important... The second-best place to be, or maybe equally, is on the most important thing."

"Don't stop being a hands-on technical until you feel like it's in your bones... I do think it's probably somewhere in the 10-year range of really having spent a lot of your time over those years writing code and really understanding how to be a technical expert."

"The fact that you really don't own your time as a manager. Your team and your management and the company owns your time... individual contributors often think that if they become a manager, they will still have some of the freedom that they have as a senior individual contributor."

"I'm seeing more PMs, like I said, go into the space. So, it's no longer being seen so much as a threat. It's being seen as this partner... if you love creating that healthy team environment and one where there's cross-functional collaboration and it fuels you to empower the team more, it's a wonderful fit for you."

"I strongly advocate for product ops leaders to have done that role, to have actually had hands-on product experience building and understanding customer problems and feeling that pain, because you very quickly realize where to place your efforts."

"What I love to see is not so much what roles you've had... Give me, in a paragraph, a thorny problem you faced. What was the problem, and what skills you used to actually accomplish it, and what was the result of that?"

"When you're interviewing, you're also interviewing them. When you're interviewing, it's not about you having to prove yourself. It's also for them to actually prove themselves as a company."

"the founder was just like, 'I've read that the cure to all our problems is going to be hiring product manager,' and you heard that and you googled, what is product management, and then you asked them, 'Can I do that?'"

"choosing where you want to break in is almost as important as choosing that you want to break in the first place. Thinking about who you're going to be reporting to, thinking about what's the track record of success for people at that company, breaking into product management, trying to think five years in advance and work backwards"

"PM is such a generalist role, it's okay to go a little left and a little right to go up. I took this marketing growth role... It wasn't only for product, it was for marketing. And I had to learn marketing... but it was a foundation on which I could build a broader leadership career."

"I chose to come to Stanford because... I was okay to take a risk of restarting my tenure clock. Becoming the first female director of SAIL, I was actually relatively speaking a very young faculty at that time, and I wanted to do that because I care about that community. I didn't spend too much time thinking about all the failure cases."

"I always balance learning and impact, which was you can have the most impact, the job you know the best, but then you stop learning. And if you're learning all the time, you're not necessarily having impact. So how do you keep going back and forth and back and forth so that you're not going straight up a lot or you're actually laddering back and forth into different things where you're having an amazing time where you know everything and then you're the newbie again and learning new things."

"The people who were most successful were the ones who actually through adversity, learned to turn stumbling blocks into stepping stones. They were the ones who got hard feedback and then came back stronger because now they learned what to do differently."

"Pull your superpowers out of your stories from your past and your present, and then eventually figure out how to apply them and transpose them to your future. But if you look at your peak experiences from life, from work, but especially from life... when you can look at these three stories as moments in time and you can lay them on top of one another, what you see at key moments is your superpowers popping through."

"It's a quite substantial part of product owners who eventually become very successful by the way. So it's like a positive self-select, so it means that someone already succeeded in another role. So it's a guaranteed culture match, it's a guaranteed domain knowledge, and then they simply grow. Usually it could be operations managers or engineers."

"I have been surrounded by amazing people in all these roles and I have a feeling that I learned a lot by osmosis and observation and then have been able to leverage that to be stronger in the roles I was sitting in."

"Full-time jobs are not the best way to monetize the skill that you have... My goal professional is actually to have options so I can choose what I want to do... Career optionality, being the ultimate north star for anybody in their professional journey."

"Build that growth advising muscle by staying on your day job. Don't quit your day job, and moonlighting and practice selling, closing, working, retaining, and that's where if you're successful there, you can be successful on your own."

"pivot is defined as a change in strategy without a change in vision. So we have this idea that the founder has the vision, then they try to figure out how to make the vision happen and they find a different way, but the vision stays constant."

"We are seeing a larger percentage of our executive network... working on things like newsletters, podcasts... full-time advisors, fractional heads of growth, fractional heads of product one day a week... they love it because of the flexibility that it creates for them. They love it because of the high upside and non-linearity of possibility."

"I told myself, if four years later Uber exits and I make a bunch of money, I owe it to myself to take a risk, because then I'll have four years of savings in my bank... I decided to leave Uber. And we'll talk about it a little later in the podcast, but I didn't plan like this, but I started writing a newsletter."

"In your career, it's just a lot like building a product. You have theories and hypotheses, you find ways to experiment with them, and then you were successful or you failed."

"I think great careers are built by knowing a lot of people doing great work so they know and want you on their teams, and just waiting for serendipity and then seizing it and jumping."

"I would much rather be the number two or number three person... in the leader in a space, than the top person. Say Google versus Yahoo. I saw even if you're the VP of product at Yahoo or the head of product at Yahoo versus a ICPM at Google, you probably want to be the ICPM at Google."

"People who are joining the workforce new should generally join mid-stage companies because mid-stage companies you get some mentorship and it's not just basically whatever needs to be done and ultimately you don't build any deep skills. So mid-stage company I would define as something that is a multi hundred person company, but not maybe a thousand person company."

"Imagine that you're walking home from work and you see this bright, shiny object. You walk over and you realize it's a magic lamp. And you rub the lamp and this genie comes out and the genie says, 'Hey, I haven't been in this bottle for 10,000 years yet, so I'm not fully formed. So I can't give you three wishes. But what I can do is I can give you one wish. And the wish I can give you is whatever you throw yourself into with your whole life and your career, it's going to turn out great.'"

"The biggest question I think with respect to your career is, within reason, what would you do if you knew you wouldn't fail?"

"You basically come up with nine lives. So you say your first life, life one is the life you have now... The first rule is all the lives have to start from today... And the second rule is you have to be excited about all these lives."

"I'd really start zoning in on roles where you might see if you don't have the functional experience, the industry experience. I think that would go a long way as how to help you differentiate from yes, what's probably more candidates, or more applications going into each role."

"Being a manager is not as much fun as being an IC. It's a lonely job. When your team goes out for drinks, they treat you differently when you're the manager than when you're one of the other ICs. It's more painful and less fun."

"I think understanding that there's different ways to grow your impact and grow your career, other than getting promoted to people management... you can make a lot of money without getting that promotion title. If you're working at a small company, if you're working with other companies that isn't the highest paying company, you'll make a lot more money by switching companies than you will by getting promoted at your current company."

"One mistake I see people make early in their career is they are trying to overdo it... A lot of times you've been assigned a problem where a huge creative solution is a bad idea. If you're in one of the situations, just do the simple thing, get it done really well. And that'll earn you the trust to be able to take on bigger things in the future."

"Being a PM actually provides you with a lot of the skills and background to be a founder, to be a CEO. It gives you a lot of chance to work with a lot of the different teams and see a lot of the underpinnings of how business works."

"The framework I like is ladder versus map, and I think that you can be either person that any point in your life... Ladder is about moving up. It's more influence, more power, a higher title, things like this, whereas map is I just want to go wherever's interesting... I'm okay with discomfort because it's interesting."

"making that initial transition is really hard. What I've seen is the path that we just talked about, join a startup and then from there go into different companies. And then the other path that is typical is being at a company and then switching product management, especially if you develop domain expertise and there's a need for a PM."

"I do have an unusual background, but it doesn't surprise me that people who are interested in product are also interested in investing and vice versa. For me, I've always had three interests broadly and that's an interest in business, an interest in technology and an interest in markets. And I get to express those interests both in investing and in product, but just with different weights."

"When I first came to Anthropic and I was like, "Oh my God, I really love front-end engineering." And then the reason why I switched to research is because I realized, "Oh my God, Claude is getting better at front-end. Claude is getting better at coding. I think Claude can develop new apps.""

"I think it's so easy for a young person to go into their career and everyone is telling them... 'You need to get that manager title.'... I think sometimes people opt into this without knowing what they're actually signing up for. What are the trade-offs? And is that really what you want to do?"

"I was fired from Slack three different times... I spent that year being fully out of integrity with myself. Never saying what I really wanted, how I really felt because it didn't feel safe. I was too scared. I kept it all inside. And it took me six months or a year even after that to really feel safe and okay again."

"I discourage people from going straight into product management. If they want to become product managers, you encourage them to start somewhere else first. Why is that? ... The people that should be doing that are the people who are building it. That's an engineer, that's a designer, that's a sales person or a support person."

"I land my first official, by title, PM job at a startup. I made it. I've arrived... the company is really struggling and so we go through a series of rolling layoffs and I'm round 4 something... my identity that has been completely crushed... I thought I was a product manager. This is evidence I am not."

"Moments that stretch you or moments that you feel uncomfortable in or you find yourself saying, "Oh shit. I shouldn't be here," or, "I'm under qualified to be here," those are the moments you should be seeking out. Those are the moments that stretch you and give you a new foundation. So oftentimes you'll hear a career question like, "Hey, do you feel like you're growing in your role?" And that's a very ambiguous, in my opinion, way to ask this question. A much sharper way is like, "Hey, how many, oh shit moments have you had in the last six months, year, two years, and what are they?""

"I think breadth is incredibly important. It's so critical, especially if someone has an end goal of wanting to step into a product leadership role to have been able to have touched lots of different components, as opposed to specializing in one specific thing."

"Logo collecting is never something that you want to be known for... but there's also something to be said about staying somewhere too long though. And I will say that. I think sometimes you find people that are almost loyal to a fault... I think sometimes in your career you do have to be a little bit more selfish and think about what's going to be best for you in the long haul."

"Work backwards from a goal for sure, but don't allow titles or valuation bubbles or other things to derail something that feels good. If you're in a role and you feel like you're making an impact and you're learning and you're growing and are excited about the work you're doing, do not allow a title of some other company to make you feel like what you're doing isn't worthwhile."

"One inflection point that I've seen is, when you go from being a manager, a first line manager, to becoming a manager of managers, and if you're able to navigate that with very strong effectiveness, then you know... Because managing ICs is so different from managing managers, because then you now need to create a structure. You need to be able to determine how much you delegate. How do you coach? How do coach your managers to do the right thing?"

"If you can get someone to stamp you with the product manager role, take it. Because... it's what we screen on... once you get that first job, it all gets easier."

"You can raise your game so that you actually can contribute at this level. That's what you should do for your own career, but by the way, and not accidentally, that's what your company needs you to do... At a minimum, your company will appreciate it and probably promote you because you will be one of the few that actually understands these things."

"It's why as an early career product manager, or it's why frankly at any stage of your career when you want to learn, you should join a winning team... I want to hear what they learned from being part of a winning team. And that's sort of one of my go to heuristics when I'm looking at candidate profiles."

"I think that people who get acquired, especially founders, actually go through a relatively deep depression and existential crisis after getting acquired... you're like, wait, what is my job now?"

"The best thing you can do is find companies that are growing fast because it compounds your learning at a much faster interval."

"Do not optimize for compensation, especially early in your career. If you're truly on a track to become an executive someday... you will make 90% of your compensation in the last five years of your career."

"Early career you want to be in intensely talents dense areas... For general tech, there's no better place than West coast of the US."

"The way a lot of people do careers is a set of stairs. Just walk up the stairs and you'll get promoted every two years. But that is boring. The much more fun careers are like jumping off cliffs and you do fall, but then you climb out way beyond where the stairs could ever get you."

"They were extremely careful about only making people PMs who had first proven themselves out as forward deployed engineers. You basically could not become a PM any other way... the reason for that's pretty simple, it's going to be someone who understand how customers work and has that customer empathy."

"It's your job when you're in the interview process to figure out what that burning problem is. So, put on your discovery hat and go figure out what is the actual job to be done of the hiring manager when they're bringing on a new PM onto their team? And if you can do that and then make a good case that you are the person to solve that problem, then hiring you becomes a binary choice."

"Just act like you already worked there. What would you do? ... During the interview loop... you can ask, 'Hey, can you put me in touch with an engineering manager who's working on the same problem?' And if no one else is asking, again, you're going to have an extra piece of feedback."

"I think getting into startups as a product manager is a pretty awesome way to get into product because it's just a lot of problem-solving. The problem with that is you don't have anyone to teach you the right way, but the product will teach you the right and wrong way if you're with a team that is moving quickly."

"I tend to help and coach hundreds of folks through transitions. So if they're in a moment where they're trying to decide between another job, if they're trying to decide to leave, if they're having sort of an alert at work, I call them 911 calls. I take a few 911 calls every week and from a relatively large group of people. So I find those are the most substantive times to help people, is when they're in moments of dilemma or forks in the road"

"I always try to prioritize putting myself in positions that are going to cause a lot of growth and learning. And growth and learning can be very painful. ... I can find situations that are going to stretch me, that are going to force me to do things that I haven't done where I'm going to grow and learn significantly."

"A three month sabbatical is much more attainable than people think. Companies are desperate to keep people and are much more open to things like this these days. And the way I frame it is if you're assuming you're going to work continuously in adulthood, that's about 500 months. Try to find three months of that where you can create space and reconnect with yourself, explore things, just see what emerges, see how you feel."

"I've found it takes six to eight weeks just to unwind."

"I always tell people you need a boomer compatible story for what you're up to, as just give them something. Just say, 'I'm an entrepreneur,' or, 'I'm a business owner.'"

"I call it ship, quit, and learn, which is what is the quickest way I can ship something designed to quit, but as soon as I ship it, I learn about what to do next?"

"I talk about this in the book. Sometimes you need a two-step strategy. Let's say you want to be a VP of product at a top streaming company or whatever it is, but you not a fit for that today. So the question is how do you step there?"

"I had a ton to learn about marketing, with what I knew really well... I spent my life in engineering, and in any product, it's not the go to market side, even. I was never part of the go to market, or I have never heard of a lead in my life. I did not know the word "pipeline.""

"I do feel like an imposter, and I know there's always those statistics about many people feeling that way. So I think, maybe just, "Let's embrace it. I feel like an imposter, you feel like an imposter, everybody feels like an imposter," It's kind of, maybe embrace it, but don't let that stop you from making a decision."

"When people are in their gifts and their strengths firmly, most of the time, they have more energy... I try to help my leaders see that they can design their lives so they're spending 80% of their time in their gifts."

"The advantage a smaller company has really is in latency. You can have an idea one day, you can test it the next day, and as a result you can have this really short cycle time between an assumption or a hypothesis and being able to validate that hypothesis. That's just not true at larger companies where there's a lot more momentum."

"I think it's important to plug into an early stage network as soon as possible... the people sort of really build their lifestyles and their careers around a particular stage. And there are some people that like to move between stages, but the majority of people don't."

"There's many different ways to invest. There's, you know, angel investing is one... there's scouting... there's SPVs... raising a fund... one thing you can also do is just like pretend angel invest... write memos, or you can like almost create a fantasy portfolio... she was doing the job before getting the job, and anyone can do that today."

"The decision to move as well, I think, was really focused not just on what GitHub was and maybe is at the time, but what GitHub also can be. ... to get to an opportunity to work on so many V1 products, like that is creation itself, to be able to build an entirely new product, get it out to market, test it, iterate on it, and really feed on the energy that's coming back from the community."

"For about a year, I was doing the product job without having the title and I was also the engineer. So I was in this great state where I'd figure out what needed to be built and I would just build it myself. So, that's how I started. And at some point during that one year, I realized that while I was a good engineer, I was perhaps a top 20% engineer. I realized that I would never be a great engineer, that I would never be a top 10% engineer because I saw those engineers, the fortune of working with them, and I just could tell that I couldn't be that."

"I have to abandon the traditional path, that like, 'Oh, after this level, I'm supposed to do this, and then I'm supposed to do this, and then this is what society expects... Identify your superpowers, because if you identify your superpowers and work in accordance with them, you will do the best work of your life.'"

"My career has been a little bit like a bingo card. I've always been looking to fill in boxes I didn't have filled because I felt like that would make me a better professional. It's like if I didn't know anything about that specific type of sales model or that type of marketing or that type of product management... well, if I learn about that thing, I will become more versatile."

"It's to constantly be choosing things that are either outside that, not totally outside the lines. Don't jump out of a plane if you've never parachuted before. Obviously you want them to be in some way and adjacency, that you want them to have something in common with what you know, but you want them to stretch you and change you."

"We had somebody in our user research team. We had an opening for a PM on the growth team... She used all those tools, and she's now a growth PM on the team. And really, you can start thinking about her more as a full stack builder ultimately."

"When I look back on my career and think about the things that I've done, my professional satisfaction is not well correlated with those external metrics and very, very coordinated with do I love the thing we were building and do I love the people I was working with?"

"My advice is if you're coming from design and research background, then you pick data or tech. If you're coming from a data or tech background, then you pick design and research, and that gives you the maximum leverage because that's a skill that you will necessarily not have developed over the years."

"It also makes a big difference if you are transitioning when you are slightly younger in your career. If you are already senior in a function and then you are transitioning, sometimes it can take a lot of time in transitioning and picking up those skills."

"I think that it's, first of all, a really great empathy building exercise of understanding that point of view, and also pushing yourself to push on the product from a different angle. Because I think as a PM, you're in the center facilitating all these different trade offs, and when you go into design, you have to ignore some of those other aspects to really be insistent on pushing on the best experience possible."

"I genuinely think that some of the best product managers come from something else because you have empathy for being on the other side... already start product management, doing product management before you're a product manager. Open up your favorite apps. What are the top 10 problems you see?"

"If you don't have a written down framework of the things you actually care about, it's very hard not to be distracted. ... I actually sent my framework to a recruiter one time and I said, 'Hey, this thing,' because they kept going back and forth to me and I go, 'Hey, this doesn't align with my framework.'"

"I sort of took the same approach showing up at the office asking if there were any roles... I had been doing the job voluntarily, almost informally for a few months. And I remember this because I had a seat on the third floor. I picked up all the stuff on my desk, put it in a box, walked down to the second floor once I got the job to become a PM."

"I actually went through my calendar and I changed the colors of all of the meetings on my calendar to red, yellow, and green after I had the meeting. And I looked. And basically if it was yellow, I was like, okay. It was a fine meeting. My energy was baseline. If it was red, I was either bored or I was stressed, or I was not having a good time. And if it was green, it gave me energy and I felt excited and I wanted to keep working on that."

"I evaluate whether I'm in a healthy role and in a good setup by asking myself about my learning curve... thinking about whether the environment is positively impacting your ability to grow your career... and the third piece is really around just the problem, the problem your product is solving."

"My advice to people is go get a job which will make you the fastest learner in the field of product management. That is what will help you a lot. No course, no degree, none of those things will help. The most important thing will be how quickly can you jump in, learn the auto product management."

"You got to figure out what are you optimizing for, what goes well with you. I've seen many successful leaders who will get choked up in a big company environment, and I've seen many big company successful executives who want to choke up in a very startup environment."

"If I knew then what I know now, I would not have done this... Then, quit. Your life is short. You have a great team. Pivot. Do something completely different. If you've lost conviction, you should not be doing what you're doing in the world of entrepreneurship."

"I never had a five-year plan... follow people. You learn the most from people. I don't look for domains... you follow people who are the best at what they do. So it's not good enough to follow somebody who you like. You want to follow somebody who's either the best product thinker or the best engineer or the best salesperson."

"Take a job where if you hire people, it's going to make their careers... you want to make sure that it's going to be a good place for them and that they're going to learn and they're going to grow. And so you want to do right by them. And you really earnestly want to say you can make your career by coming here."

"I think the executive track isn't for everyone..."

"If you're a product owner... try to take some ownership over strategic work."

"You should go do the thing that you feel guilty to get paid for."