Accelerating your Career Growth

🚀 ACCELERATE 2023: Virtual Summit for Product Leaders by Dragonboat
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Becky Flint: All right. It is my absolute pleasure to welcome Deb Liu into our session. Deb, with your experience in product management and business management and the growth in your career, we would love to hear you share with the audience. I know today we have covered a bunch of the business growth, the product growth and now it’s time to talk about our personal growth. So I would love to hear from you a couple of topics that most of our audience care a lot about. How do you grow from a product management role into a product executive role? And once you achieve a product executive role, how do you achieve and sustain success and how do you grow from there? And I’m going to turn off the screen share. I would love to just hear that from you.

Deborah Liu: Absolutely. Happy to talk more about that. It’s interesting, everyone starts out in product as an individual contributor. You have a product, you know exactly and you have complete control over your destiny, your product’s destiny. You run a cross-functional team and it’s incredible. And I remember those days I started out in product management at PayPal and it was exhilarating. And a couple years in, I was given the opportunity to manage and I managed a team of a couple people. And then very shortly thereafter my manager left and suddenly the VP asked me and tapped me to run the entire team. And I ran the team, the eBay product at PayPal, which was at the time the biggest business. And I was completely out of my depth. 

I think one of the things that I learned about going from an individual contributor to a manager and then a manager to a director and eventually to a more senior leader of a big product organization and then a kind of GM is that each single time you take that step the skills that you need are completely different. What makes you really, really good is an individual contributor PM will actually make you fail when you’re a product lead, and then when you’re a manager of a product team, and then when you’re a director where you’re managing through people, and then on when you actually move beyond just product and managing other functions. 

And so I’ll explain that a little bit, which is the skill that makes you an amazing product manager, especially as an individual contributor, no matter how big or small your product is, is you know everything going on. You have tapped everything, you understand end to end, you understand the history of the product, you know every quarter coming up and what you want to ship, what your strategy is and you have complete control. And once you start down the path of, say, product lead, suddenly you’re actually maybe not even managing, but leading a group of product managers to do something. And suddenly you have less control, but the control freak nature of every product manager is what actually will trip them up because suddenly you’re working through another person, but you have very little control over what they do. 

I remember when I first started to manage, I read the spec of my team for the first time. There was a new product manager. He was an APM, really amazing leader and has gone on to amazing things, but his first spec was objectively not good. And I didn’t know what to do because I thought, “How do I tell him?” And I could rewrite this for him, which would be very insulting. I could teach him, but it’s going to take a long time. And we were under the gun and I was really caught because I knew I could rewrite this in one evening, but it would actually not teach him the skills and I would not scale. And I remember actually going to my manager and saying, “Look, this is so frustrating.” I could do this faster and easier than him and it’s making me crazy. It’s going to take me a week or two to actually get this through to place. And he said, “Yes, but you’re never going to scale because now you’re leading through others.” 

And that’s where I think one of the things that we need to do as product managers as we transition to both of product lead or product manager of the product team, is that you suddenly have to go from doing yourself to leading through others. And that transition is very hard because we are control freaks. We are so good at knowing everything and you have to learn to let go. And so one of the things I tell people is the difference we always say, and there was a study actually, I wrote an article about this in my blog, which was we take our best salespeople and they actually make the worst sales managers because your best salespeople are good at one thing.

And then we think, “Wow, they’re going to be good at leading people,” which is a totally different set of skills. I absolutely believe the same thing about product management. 

And so you actually have to learn this as a completely new skill, just like when you first start a product, which is leading through others, managing, teaching others and actually learning to scale are so, so important. Learning to coach, learning to actually hope and want the best for someone else, but also knowing you do not have control. And that transition is the hardest and the first transition that I encourage everyone to really think about if you want to go into executive level. 

The next one is actually when you go from a manager to a manager of managers because even as a manager you can have the capacity to understand what eight people do, what they do on a daily basis. You’re very close to what they do. You can read their specs if you chose to do that and you can talk to their cross-functional teams, but imagine suddenly you’re managing managers who manage people. How do you actually lead through that process? 

Again, a whole new set of skills. And again, if you use the same techniques where you’re going directly to people, asking them questions, you actually are not necessarily going to get the answers because what you realize is that managers are very good at different things and they’re not uniform. And so leading through someone who has to lead through someone else is yet another skill you have to learn. And the other part I think that you forget is when you’re close to the metal, when you’re close to the product, you can have influence over design, you can have influence over research, over analytics. 

You talk to your engineers every day and as managers you get less. And then as a manager of managers, you get even less, but your influence is now across the organization. Who is your key team that you’re influencing? It’s no longer the IC who’s coding this. It’s really across the organization, getting things done, unblocking, working through others in a very, very different way. And again, this is a skill that we often lack when we get there. And so you have to learn that as yet another skill. This continues as product leaders go from director to maybe senior director or VP because suddenly there’s a lot of organizations where you might manage a TPM team, you might manage design, you might become a GM in manage engineering as well and suddenly your skillset has to change yet again.

I tell people the most successful people are the ones who have the biggest learning mindset. How do you take the skills that you learn that made you great at something, but then learn the next set of skills and the next set of skills and the next set of skills so that you can continue to grow?

Becky Flint: Wow, this is super helpful, especially rather learning my side. And then what get you here won’t get you successful in next row. It’s a super, super refreshing, especially around product managers. One of the key things we hear quite a bit from product leaders, product managers especially get to when they become senior managers, sometimes the directors, there seems to be an impossible gap for them to become a VP. What are some of the suggestions, advices for people get through the first level and then they really want to get to the VP, get to the executive level? What are the things they should do and think and improve, maybe shortcuts?

Deborah Liu: Yeah. What’s really funny is we in our schools teach all of our kids and we learned all the wrong way to be successful. And so I’ll give you an example. So my son just took the ACT. He’s applying to college and the ACT is objective, right? You study, you practice a lot and then you go take it and you get a score and it’s objective and then there’s a rating. You’re X percentile. Your GPA, it’s objective within your school. Somehow you get grades and there’s a GPA. And we teach that mastery is just being able to answer questions that are thrown at you. That is absolutely not what success looks like. And this is where I see a lot of people really get stuck in the workplace, which is they have 100% of the they check all the boxes for the hard skills.

I remember Schroepfer who was a CTO of Meta told me once, he’s like, “People don’t fail because of the hard skills because we hire for that. People fail because of the soft skills.” And that is absolutely true. It’s your ability to adapt. It’s the ability to live within the culture. It’s the ability to influence people. It’s the ability to really persuade and influence across an organization. That’s where the gap is between somebody with the hard skills. Yes, you’re objectively a great product leader. You have built these things, but have you built the relationship? Do you have the soft skills to influence? Are you able to get your ideas out there? Do people want to work with you? Those are all important things when people are thinking about the gap between somebody who is a mid-level executive and somebody to get to the top tiers. It’s your ability to actually be a whole person.

And so we teach the mastery. Check the box, get the ACT, SAT score. It’s objective, but it’s actually the soft skills that I see people struggle with the most and it was what I absolutely struggled with the most as well. 

Growing up in South Carolina, I grew up in a place where there was something like 16,000 Asian people in the entire state, registered three million people. And myself and Nikki Haley I guess are the two people you probably know, but I think one of the big challenges, though, was that I protected myself by never connecting with people. I said if people didn’t notice me, they might not comment. They might not make racial slurs to me all the time. And so I became smaller and I’m like, “I could just get really good at school, get good grades, get a scholarship to college and leave this place.” And I worked really hard at that. 

And then as you said earlier, that stopped working for me because people felt very distant from me. They felt very alienated from me and I didn’t realize that until my skip level manager said, “I’m going to get you a coach.” And he didn’t give me me a coach because I was high performing and I was amazing. He got me a coach because I had a really hard time connecting, working with people. And I had to deprogram myself, undo all of those things, which was I kept everyone at arm’s length, but I knew I was extremely competent. I was very objectively good at my job and terrible at the relationships, which actually made me bad at my job. And so part of the work of working with this coach was really unpacking that. Why was I not building connections? Why was I lacking those relationships? Why could I not influence?

And it took me years, but I was able to unpack all of those things. And one, for example, I’ll give one salient example was that for women to be leaders they have to be competent and warm and men only have to be competent. And I just wasn’t warm. And when you say warmth, I mean connection, opening up to people, being vulnerable. I was terrible at that objectively. I fought for everything I wanted for my team. I was a fighter and Cheryl Sandberg called me aside and said, “You can stop fighting now if you want.” Because I was combative. I had a chip on my shoulder. And so, yes, objectively was I doing the job? Did I build amazing products? Absolutely. And was I limited in my success in my career because of the behaviors that I had? Absolutely.

Becky Flint: Wow. I can’t actually really relay quite a bit of the things, Deb, you’re saying. And this is very refreshing. Like you said, when people are starting out, they do have to prove their hard skills. They have to really do a great job. And that really helped. And then later on you mentioned about have you built relationships versus have you built product? This is so refreshing. So now as we go through the first journey and from product managers to directors and maybe get to the product executives being VPs and chief product officers, we also know that role is challenging, right? It’s alone in some ways at the top. Especially you look at a stats actually stat shows that product leaders has a lifespan in a company, somewhere around 18 months or so. So how do you go through the transition thinking you’re on both sides of the table, right? So you’ve been as a product executive role and now you’re CEO. What’s your advice and how do you evaluate product leaders, product executives? How can they be more successful?

Deborah Liu: Well, as you rise in your work, your first team was very clear. It was the engineering manager or the engineers you worked with. It was your data scientist, it was your designers, your researcher. It was the group of people who you built stuff with. And yes, you had a product team, but you worked parallel to each other. You might even have had a product meeting maybe once or twice a week with the rest of your team. But you spent day-to-day 80% of your time with a very clear team. And then you became a manager and then a director and your team was now your direct, but also your peers. And suddenly your first team is no longer just the people you work with day to day. It’s like another team. And this gets harder and harder as you go up because to be a successful executive in the C-suite, so a CPO, your role is to lead a company while leading a team.

And you could be so good at leading the team but really bad at leading a company or vice versa. And you’ve seen people thrive in one and struggle in the other. And it’s because when you lead the company you are both an executive company, you are reporting to the board, you might be involved in a lot of strategic decisions, but you’re also asked what should our return to work policy be? Something that you never spent any time thinking about before you reach the top of the company. And I think that’s part of the challenge, is that you don’t make the mindsets shift from VP of product or director of product to chief product officer, person who is deciding how do we think about compensation. If we have to layoffs, what are the choices we have to make? What’s our location strategy? You’re actually asked to weigh in on things that as any other employee at the company you would probably have never been asked.

And even when I became CEO of this company, there were a lot of questions I never really considered. They had asked me before I joined, what should our return to work policy be? And I just was never involved in HR issues outside of recruiting and so I didn’t have any answers. And I think that’s true of a lot of people who rise through organizations, is that the altitude now which you’re expected to function and the team at which you’re expected to persuade is no longer the people you worked with day-to-day. You’re paralleling with all these other folks, but suddenly how do you actually talk to the general counsel about a tough issue that you’re facing? We have to put this in this privacy issue has to come in or is it going to push out a roadmap or not?

And suddenly those choices aren’t made from the top. You are making this choices every day. And I think it’s that transition that fits that ability to function within that team, where it’s both an opportunity but it’s also a pitfall. And I think if you’re too focused on your own team, you’re too focused on just the product or just the strategy, that’s an important part of the job, but that’s only half the job. The other half of the job is leading the company through difficult circumstances, through growth, through growing pains, all of those things. Influencing the board, influencing external parties, partnerships, and suddenly you’re playing this on hard mode and everything is just that much more complex.

Becky Flint: So I think, Deb, this is super, super helpful. In your career, you’ve gone through product and went to business and now you’ve been on the board of Intuit for a while and being the CEO. So as the product leader navigate through their career path, we can see clearly it’s not a linear straight line. So what are some of your thoughts around how product leaders should think about do I say in product, do I go to business? What kind of path opportunity presented potentially in front of product leaders like you and how do you evaluate and decide which direction you want to go and how do you pick up some of the skills you mentioned in different roles?

Deborah Liu: Yeah, I’ve been wanting to write this. I actually created a paths for product leaders, which is where could your career go? Because I think we were just like, “Okay, does everyone just end up as a CPO or VP of product someday? Is that the terminal path?” But actually, you have so many other roles and opportunities, but you have to make the choices around that. I’ll give you some examples. For example, maybe you want to be a founder. Are you crafting your career, as you’ve done, to become a founder? Do you have the opportunities on your resume where people see you in executive leadership roles? Do you have the background to build the team that you want to pull? Are you able to raise money? Those are skills that you can learn and check those boxes along the way so that you’re not doing this kind of on the fly at the time.

Other people are like, “Hey, look, I just want to go to high flying startups. I want to do amazing things, but I don’t want to start something on my own. I kind of want to see some traction.” I’ve had product leaders come to me and said, “Look, I want to join a company with 100 and get it to 10,000.” I’m like, “Great.” Then you know what you’re going after. So I think sometimes we think the path is just our current job, just higher up, but actually thinking about how you want to mold what your future is. Other folks are like, “Hey, I want to do nonprofit.” Some people become product evangelists and creating organizations. Others want to invest in other people’s products. They want to be longtime investors, create a seed fund and still always want to take the nonprofit route. They want to lead an organization, but maybe not in corporate side.

They care about, say, climate change or something else. And so I think oftentimes we can only see what our manager does and say, “Okay, what’s the next step,” but what if your next step is completely different? And so one of the things I’ve done is the other option is maybe become a CEO of someone else’s company. I’ve had several product leaders I know who are fractional product leaders and do fractional work and then invest on the side. I know others who basically now just sit on boards and have incredible careers sitting on boards, advising some of the best companies in the world. And so really thinking through those paths and then saying, “Here’s what my career could look like. How do I fill the bingo card to get there?” What are the key steps to get there and work your way backwards where you are today?

But I always tell people if you don’t know where you’re going, that’s where you’re going to end up. And so if you have an inkling, I was talking to a former CEO and he was deciding what he wanted to invest and he just said, “Here are three things I could do. I went and talk to a bunch of people and try to figure it out.” And then he ended up in the place that was perfect for him. Because he had talked, he’s like, “This is not for me. This one might be an opportunity. This one is probably further out. And so I think you having a sense of who you are and where you want to go will give you a better chance of deciding what are the steps you need to take.

Becky Flint: This is super helpful, Deb, especially if you don’t know where you want to go to evaluate options. It’s definitely going to be very difficult. Just take what’s coming at you, so that type of planning and the self-discovery is super, super helpful. I know we covered quite a few topics today. Obviously learning is ongoing process, but before I move on to talk about additional resources that we could have learn from you, Deb, I would’ve like to if you were to say, “Hey,” take a step back where you are today, super, super accomplished and successful. I’m sure there’s a lot of great things in front of you as well. If you go to look back to say, “Hey, a couple of things that I could have done to let’s say my director level self or people at a slightly different stage,” director level and executive product level and then maybe getting to business level executive. What are some key takeaways? A couple of them maybe that people can put it on their desk and look at it in a morning, something like that.

Deborah Liu: Yeah, it’s interesting. Some of the best product leaders are also the ones who really understand the dynamics of their product. Not just from the customer perspective or from a product perspective, but from a business perspective. Because look, ultimately, no matter how awesome your product is, it has to pay for itself or the company will not continue to grow. So I’ll give you an example. Facebook Marketplace, which I built when I was at Facebook, has a billion people using it, but they don’t do it for free. We built an ads team within it so that we could start monetizing it from the start and we could figure out the business model so that when the time came people weren’t asking, “Well, what’s the value of this?” And so really having a full understanding of the business that you’re in and what you’re trying to accomplish is really important.

And that business mindedness, I went to Stanford for business school and then I joined Tech, and so it’s a little bit different, but if you haven’t, I actually encourage you to take a few. Read The Portable MBA or take a couple of business classes at Coursera or any of these other services. I think it’s just important to understand how do you fit into the larger ecosystem? Because one of the things that a lot of product leaders are so great as they build a beautiful product, but you see this in a lot of startups, but their monetization model is broken. There isn’t a path to profitability and suddenly they’re constrained. They can’t acquire customers, they don’t have dollars, they can’t raise money. And so I think learning that upfront and really building the business mindset towards your product will ensure that you have the longevity you need to actually scale.

Becky Flint: This is super, super cool. Now, I also know, Deb, that you have invested a ton in coaching the future leaders. You’re the founders of Women in Product, one of the co-founders. And it’s also one of our partners is super grateful for having that community about Women in Product. I am also a subscriber of your subsec and your book. Would you like to share a little bit about these two resources with our audience can find from them and what your recommendation for them to get started in some of the topics?

Deborah Liu: Yeah, so one of the things I did was I have a new year’s resolution every year. And by the way, I encourage you to do this. I have a new year’s resolution every year and one of the things I said was I was going to write a book and I was going to write a newsletter. And I thought, “That’s crazy. I’ll do it for a year. We’ll figure it out.” So the book took four years, but it’s out. It’s take Back Your Power: 10 New Rules for Women at Work. And it’s really about all the lessons I wish I had starting out in my career, which was all the mistakes I made, all of the experiences and then the stories of a couple dozen women who I’ve learned from and just have incredible stories that I think you should read about.

Nothing in there is so revolutionary, you haven’t heard it before, but it is an important reminder that every single day we could have more influence if we just showed up. And a lot of the book is really about intentionality and making really conscious choices, something that’s really hard when you’re just kind of on the treadmill. And I joke that my perspective newsletter is kind of like a career coach in a box. Again, nothing I say is revolutionary, but I’ve been coached by the same coach for I think 12 years now and I have learned so much from her. And not everyone has the luxury of having a career coach for a dozen years, but each day I’m like, “I wish I could just grab someone by the shoulder and just tell them this.” And that’s what I write about. It’s like I write about the things that I wish I did more of.

Last week I wrote about pruning, for example, because one of the things is trees are healthy if you prune back and you actually make space for something different. And so one of the things I’ve been actively doing is pruning more in my life. We’re actually moving shortly, maybe someday. And pruning is really taking we have too much stuff in our house and I just need to clear it out and to make space for more. And so one of the things that I’ve been really … What are those conscious things that I wish I did more of? And how do I coach myself and others to do the same thing? And so this week it’s really about patience and planting the seeds of something really special and it references Crazy Rich Asians, a movie I love, and something about my father and something that he invested in. And so one of the things that I hope for each person is if you could just have a career coach whispering in your ear, what is that person saying to you?

That’s what I write perspectives for, which is just a reminder. And I get really great guest writers, too, about their career journeys, some of the things they learned. One of my very popular posts was recently about creating your own first fractional practice, which Hadnaman worked with us at eBay. She was on the eBay side and I was on the PayPal side. She wrote about how she just started a fractional practice and how she hustled and got tons of clients and how you can do the same thing. And so there’s so much that I wish I could share. And it’s funny because I’m three years in almost and I thought I don’t think I have more than 50 articles in me. I think I’ve written 200, so it’s been pretty incredible.

Becky Flint: Yeah, I definitely found quite a few of them are very, very helpful and I really enjoyed the latest one you mentioned about trimming, making space. And thank you so much, Deb. I know you’re super busy and thank you for joining our summit. It’s called Accelerate, so accelerate product, accelerate business and accelerate our personal growth. And actually, they’re all connected, so thank you so much, Deb, for joining us.

Deborah Liu: And thank you for the invitation. It’s great to see you, Becky.

Becky Flint: Thank you.

Power your team with Dragonboat

“You’ve built products, but have you built relationships?”

Deborah Liu, CEO of Ancestry joined us at ACCELERATE 2023 for a session on accelerating your career growth. Hear Deborah’s advice on growing from a product management role into a product executive role, and how to achieve and sustain success along the way. She also shares the skillsets, mindset shifts, and transitions necessary for both professional and personal growth.

Watch Deborah’s session on-demand now to hear firsthand advice and candid tips to grow in your product management career.

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