This Week #14: Transitioning from startup founder to product manager

Hello and welcome to another edition of my weekly newsletter 👋

Each week, I’ll tackle reader questions (keeping your name and company anonymous) about building product, driving growth, and anything else that’s stressing you out at the office. Send me your questions (just reply to this email or DM me) and in return I’ll give you free actionable real-talk advice  🤜🤛

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Q: I just sold my company to another startup and now I'm transitioning from startup founder to product manager at this new company. I’ve never had "proper" training as a PM, so I'm a little worried about the integration with the new team. Do you have any tips?

This EXACTLY the situation I found myself in when I entered Airbnb. I was the CEO of a little startup called Localmind which we ended up selling to Airbnb in 2012. Up until that point I’d been a software engineer my entire professional life, so I had no real idea of what product management was. And looking back, I was really bad at it. I knew very little about managing up, keeping scope in check, leading teams within a larger org, and basically everything else a PM should know. Also, having just run my own company for 1.5 years, it took me waaaaaay to long to remember that you had to actually listen to your boss when they said no. 🥴

If I could go back in time and give myself some advice, here are the top five things I’d tell myself:

  1. Being a PM is very different from being a founder — Although being a PM is actually much closer to being the CEO of the product than people acknowledge, there are enormous differences between these two roles. One of the most interesting is that as a founder your job is essentially to win at all costs. You are rewarded if your company succeeds — everything else gets swept under the rug. Even if you create constant chaos, repeatedly change course, and piss people off. As a PM, your job is to avoid chaos, to avoid changing course, and particularly at a large company to avoid pissing people off. The team looks to their PM to keep things running smoothly, productively, and happily. Thus, as you transition into this new role, focus on these softer skills — teamwork, collaboration, execution, buy-in, and communication. Don’t expect that hitting your goals will be the only thing that matters to your career as a PM, particularly as an IC.

  2. Don’t lose your entrepreneurial spirit — Companies generally acquire other companies because they want to move faster on a given opportunity. Thus, they want (and need) you to help them move faster. It may seem at times like the larger company is almost designed to move slowly. Don’t let that discourage you. As a balance to the first point, be the change you want to see in the world. Take risks. Move fast. Push folks to think differently. Don’t be afraid to share your thoughts on what the company should change in order to move faster and work better. This is why they brought you in.

  3. Find a PM buddy (or two) — Build a strong relationship with a successful PM at the company. Ask them to give you the inside scoop on how things get done, who you should get to know, and what it takes to be successful. If you’re the first PM in the org, then find a peer in a different function.

  4. Be humble, ask questions — Startup founders often enter a company with a huge ego and an assumption that they know a lot more than everyone else. I suggest doing the opposite. Assume everyone else is smarter than you. Spend most of your time asking questions, hearing people out, and studying the business. Then, once you have a clear picture of what’s going on, share your (informed) pespective.

  5. Listen to your boss – You are no longer in charge of your destiny. Your boss’s opinion actually matters for your career at this new company. In exchange for this loss of control, you get a steady salary, benefits, and not having to worry about every possible thing that can go wrong. It’s not a bad deal.

Finally, check out this guide I wrote for new PMs, and this book many people recommend to help you during your first few months.

Good luck!

Inspirations for the week ahead 🧠

  1. WatchA twitter thread collection of the best stand-up comedy bits of all time by Erik Torenberg — There goes your afternoon 🤷‍♂️

  2. ReadTech in 2020: Standing on the shoulders of giants by Benedict Evans — Now that tech has connected most of the world, what comes next? 🧐

  3. ListenMarc McCabe: A Deep Dive Into Startup Fundraising — The most in-depth dive into the startup fundraising process I’ve come across, courtesy of my former Airbnb colleague Marc 💰

That’s it for this week!

(Photo source)

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Lenny 👋