Managing Your Career and Beyond: a Conversation with Shreyas Doshi

How to think about your career differently in 2023

A couple of weeks ago, I sat down with Shreyas Doshi, who recently taught a cohort on how to Manage Your PM Career in 2023 and Beyond for Maven. Our goal was to chat about some of the most common challenges Product Managers face in their careers, both early on and as they advance. During our conversation, we discussed topics like building a learning mindset, managing upward, going from a PM to a CEO, and more. 

We wanted to make this information available to everyone who didn't take the class. I’m sharing it with you here now so you can benefit from our conversation as well. Without further ado, here are the highlights. I hope they are a useful resource to you—in 2023 and beyond!

SHREYAS: Let’s start by talking about the importance of communication in your career. You mentioned that presentations make up five percent of your job, but fifty percent of how you're judged. What advice do you have for those of us who are very talented, thoughtful PMs and leaders, but who have challenges with communication? 

There’s this misconception that we should just focus, put our heads down, and focus on the work, but there’s a huge bias in the workplace that favors those who communicate well. This is particularly prevalent for Product Managers, who are judged on every piece of communication, whether spoken or written. Managing upward is also an important part of the job, and this, too, requires significant communication skills. 

I would encourage you, if you're uncomfortable with speaking up and presenting, to learn by doing. Practice, practice, practice. Try joining Toastmasters, or getting into a coaching circle. Strive to make yourself comfortable speaking on a variety of topics and answering questions around your product. This is important, because every time you speak, you are representing your team and your product. Often, your presentations are what decide how resources are allocated. 

You mentioned coaching circles. What are those? How do I join one? 

There are a number of different organizations that you can join where you can get access to coaching circles: groups where people who have similar goals and interests gather and have conversations. I think they’re really powerful because it allows you to connect with potential mentors, hone your speaking skills, and make new connections. 

Some companies provide these for new hires. We had them at Meta, where we would put new PMs into coaching circles. That said, if your company doesn’t have a formal program, there are also organizations like Women In Product that help people connect to host informal mentoring circles. 

Are coaching circles usually my peers, or people who are maybe ahead of me career-wise? 

It tends to be peer coaching. I once hosted Speaker Idol with Ha Nguyen and Dan Olsen. It was a three-session class where we taught PMs and Engineers to give talks so they could become speakers at events and conferences. Each class formed its own cohort, and I heard they still keep in touch with each other. You can find these kinds of mentoring coaching circles in a lot of different places, some of them specifically for women, like LeanIn circles. Others are within your organization. You could even form your own!

A big theme in your philosophy is the importance of learning. I think you have an entire chapter in your book dedicated to learning. For us busy senior PM and PM leaders, who have a thousand things to do and not enough time to do them, how do you suggest we use this philosophy? 

There's something called temptation bundling, where you add something fun to something that feels like a chore. This encourages you to make the thing a habit and stop putting it off. 

I find this works great with learning. For example, if you feel like you don’t have time to listen to a great audiobook on its own, do it while you're working out. That way you're learning and doing something good for your body at the same time. It also forces you to take a thing you want to do (listening to the audiobook) and tie it to something you may dread (working out). Most importantly, it allows you to get two things done in the same chunk of time, which is huge for people who don’t have much free time. 

I like to listen to podcasts about politics or economics while walking my dog or cooking dinner for the week. Doing one active activity and one passive one works well, since you’re making maximum use of your time. 

Speaking of not having enough time, one of the things I encourage everyone to do is to study your time use for a week. From the moment you wake up to the moment you fall asleep, track how you are spending your time. You will find that there's actually a lot of open space, perhaps when you’re mindlessly watching TV or scrolling through the news. Then you can decide whether to time-box those things so you learn new things during those open periods. 

Do you have a certain structure or an approach to learning, whether it's through audiobooks or other media? Do you pick an area that you want to focus on and consume content related to that area? Or are you consuming multiple things at a time? 

I have a stack of books that I'm constantly trying to get through. I'm currently reading the book You Don't Have to Carry It All by Paula Faris, which comes out next year. I also just started Killing Comparison by Nona Jones. Both are by friends of mine, and it’s wonderful to see their words and stories on the page.

A couple months ago, I finished The Conversation by Dr. Robert Livingston, which discusses how we can talk about race. After that, I read Quiet by Susan Cain. 

When it comes to the media, I feel like I’m always behind. I find travel very useful for that reason. I often find myself sitting in a lot of airports with long waiting times for flights, or sitting on a flight with terrible wifi (which seems like every flight). Those are great times to read and consume audiobooks without interruption. 

Are there other ways to learn that you’ve found effective for yourself or people you've managed, mentored, or coached? It sounds like the way you like to learn is podcasts, books, audiobooks. If I learn by doing and I learn best on the job, how should I go about getting access to learning opportunities?

Try testing and using products you know. Do product takedowns of both your product and competitors’ products. Force yourself to be active in your company’s “user feedback” channels, and share your perspective on other product lines. Read the feedback in those groups to understand the frustration areas and user experience gaps. This will teach you to develop user empathy through doing. 

I make a point to write down feedback and send notes to people I know who work on the products I use (usually other companies). For example, I recently sent a note to a founder who's a friend of mine. I said, “Here's the feedback I have about your product. I hope you don't mind.” It was really interesting to go back and forth on why I experienced what I experienced. We started a conversation around some of the things that were working and some of the things that weren't. 

Actually using products helps you get better at your job, because you are more aware of the experiences your users are having. It hones your product sense and your ability to understand the user experience, and it allows you to learn in a hands-on way. 

Many ambitious PMs want to devote all their time to projects at work. They feel compelled to do that, instead of making room for learning. If I am doing that, how would you coach me to make some room for learning?

You learn so much by comparing what you are doing to what other people are doing. There’s a tendency among PMs to want to do everything themselves, but by learning from five other companies, you can compare and contrast what works and what doesn’t. This gives you a bigger picture to look at. You also learn what gaps you have and how your product decisions affect the experience. 

When I first got to Ancestry, I tested the onboarding flows of multiple subscription companies—both inside and outside our space. This helped me understand some of our challenges and opportunities. Our onboarding has evolved a lot since, thanks to our team who does this work. 

The best PMs aren't the ones who are always looking inward. They look outward. They're the ones who are seeking opportunities outside their own product to get better at what they do. 

The same is true of people. I've encouraged my team to choose five people they should learn from. For example, my team wanted to learn more about debit payments, so I put them in touch with the former COO of Affirm, Huey Lin. She and I worked at PayPal 20 years ago. I had her meet my team, and afterward, they said, “She's still incredible. She had so much insight into areas that are challenging for us.” 

There are so many people to learn from, and I feel like if you take those 15 minutes to look at a different product, look at how someone else solves the problem, or talk to someone new, you can actually expand your horizons. This is what makes a strong PM.  

You talked about managing upward earlier. What are some effective ways to do that? What are some effective ways to make your manager feel more responsible for your career growth?

Let’s say you ask your manager point-blank, “When are you going to promote me?” What does this do to the dynamic? Suddenly, your manager is on their back foot. They can only say yes or no. You are putting them in an adversarial position.  

But what if you made them your ally instead? What if you framed the ask as, “I'd like to get to the next level. What is the gap between there and where I am now? How can we partner to get me there?” It may seem like a small adjustment, but this makes a huge difference. Now you're on the same side as your manager, and you’re working towards something together. You’ve enlisted them as your partner in achieving your goal. 

There are three ways people approach getting promoted:

1. Hoping their manager recognizes their brilliance and suddenly promotes them, like a surprise coronation. A lot of people live with that strategic ambiguity because they are afraid to hear an answer they don’t want. 

2. Putting their manager on the spot. “When are you gonna promote me?” Now the burden is on their manager to do a thing for them, turning them into adversaries. 

3. Making their manager their ally. This is the strategy you want to take. It means getting them on your side, looking to the future together, and asking, “How can we partner?” Whether it takes six months or a year, your manager is focused more on the plan than they would be if the answer was a simple yes or no.

As an employee, your career growth is on you, not your manager. You have to own it. The question then becomes, how do you enlist your manager to help you get there? 

As people you know get more and more senior in their PM careers, one of the things that becomes important is the relationship with the skip-level manager. What about promotion committees?

I have been on these kinds of promotion committees. A random Director from another team will say, “We don’t want to promote so-and-so because of that terrible presentation she did. Promote this person instead.” But does that person really know what her work is like? Is that one bad presentation representative of her impact? What ends up happening is you have the same bias I talked about earlier, which favors people who can speak articulately to large groups. But this works against those who speak English as a second language, those who are not great at presenting, or those who are introverted or quiet. The work and impact are what matters, but most people would be surprised at how much emphasis is placed on other things. 

If you want to get promoted, make it easy for your manager and your skip-level manager to get everyone on board. When I wanted to promote someone, sometimes I would have to go smoothly the way with half a dozen or more people. Your relationships and partnerships across the company matter when it comes to getting their support.

Let’s talk about the topic of giving credit. How can senior product folks follow this advice of giving credit to other team members while still advocating for themselves and their contributions? 

I think credit is infinitely divisible, and the atomic unit of success is a team, not an individual. You succeed or fail as a team. As a PM, your job is to ensure that recognition goes to the people working alongside you. In many companies, there's a bias favoring the PMs, because they're often the people who put together the presentations and post the status updates. They get way more credit for successes than those who work more behind the scenes. 

As a PM, you need to ask yourself, “Am I giving others opportunities to shine? Am I helping my team level up? Are I building potential energy?” The ones who up-level the teams around them don’t burn those relationships; they build them. Over long periods of time, people follow those PMs from product to product. They build amazing teams that have impact over time. 

You are now CEO of Ancestry. What parts of the PM role helped you transition to the CEO role? 

Have you heard the saying, “The product manager is the CEO of the product”? I'm sure all PMs have heard that, and I would say it's true to some extent. It’s somewhat true, in that you carry the ultimate responsibility for the success or failure of your product. A CEO, regardless of what happens, answers for everything that goes wrong and right within their company. And so part of that echoes the sense of accountability you carry as a PM. That taught me so much, as a product manager and eventually as a GM. I would say that being a PM was amazing training to become a CEO in a lot of ways because I knew what accountability meant. 

That said, I also knew that success or failure was really not controlled by one person. You are the conductor of the orchestra. You’re guiding the people who are playing the instruments. You don't have to be able to play every instrument well, but you need to make sure everyone is on the same beat. That's the role of the PM. You don't have to play the violin better than all the violinists. You don't have to code better than your engineers. You don't have to design better than the designers. But you have to make sure everybody is working in tandem. What’s important, both in the CEO role and in every product role, is your coordination and your orchestration. That’s what is reflected in the final product. 

Your career is very inspiring. You’ve gone from a PM to an executive and now a CEO. Should people be, you know, planning ahead to be CEO say, five to ten years from now? 

I'll share a story that I shared on my blog, which happened five or six years ago. I went into Fidji Simo's conference room, upset about something that had happened at work. She looked at me and said, “Deb, you and I will be CEOs one day.” It was so salient and obvious to her, and it was so not obvious to me, and yet we ended up in the same place, right? She's now the CEO of Instacart. I reminded her of that story when she took the role, just as she reminded me of it when I took my role. 

My biggest advice would be to actually ask yourself what you aspire to. What does success look like for you? I always tell people, “Don't look at where you are today.” Instead, you should be asking yourself, “What do I want the future to look like in five years?” Five years from now, maybe you want to be a VP or director, but it's not just about the next promotion that’s six months away. It’s about the arc of time. “Where do I want to go? What can I do today to get me closer to that?”

The trick is asking yourself these questions every single day. There are days when it feels kind of like a rat race, like, “My product hasn't shipped yet. We're behind. We're trying to get it out by the holidays.” You need to put yourself in a different mindset, which is, “Five years from now, what will I wish I had done today?” When you focus on getting yourself a little closer every single day, suddenly five years will have passed, and you’ll be surprised by how much progress you’ve made.

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As Product Managers, our career arcs are dynamic and full of opportunities to learn and grow. I hope that this conversation provides you with some useful insight into how to find and leverage those opportunities, in your current role and beyond. 

Thanks so much to Shreyas for hosting this chat! If you’re interested in learning more, check out his next class here.