Lessons from Big Company -> Startup Product Management (Part 2)

I am running a virtual workshop in August 2023 for product folks considering the transition from big companies into startups. It’s the stuff in this article, combined with a community of supportive peers, concrete tips for navigating the transition, and a personalized action plan for helping you thrive in your new role. There’s limited spots, so sign up for yours here.

This is part one of a two part series focused on my learnings going from a big company to startup product management. For part part of the article, click here.

Hello! Welcome back to the second part of my article focused on learnings from big co -> startup product management. In this part, I focus more on team and self management… which was definitely the largest part of my learning experience!

People Management

Trying to do IC work + management long-term is not sustainable: it doesn’t matter how good you are at product. At some point, you will drop the ball somewhere. The key to this stage (which every growing PM reaches in their career at some point) is being explicit about how long you have to balance the two, and transition to one permanently. This is not a steady state, but a moment of disequilibrium.

• I thought for the longest time at Propel that doing both well was the key to a successful PM. The more I reflected on this, the more I realized that this expectation is not sustainable long-term. IC work looks fundamentally different from management, and excelling at either requires a completely different set of skills (and often opposing instincts). It’s important to be clear to yourself on which one you want to focus on longer-term, and how far away that “long term” path looks like.

Support has no singular definition: Julie Zhuo said in her book that what support means to you might mean something different to whoever you’re managing. I found this to be extremely true when I started managing. I was so surprised how often just saying something like “That sounds like an interesting idea, you should post in X channel” or “Wow, that sounds like a tough situation” was helpful to my report. In my head, I would often beat myself up after those interactions, thinking that I hadn’t done enough to help this person because I didn’t have the exact answer to their problem. Sometimes, people just need acknowledgement or a gentle nudge to take the next step.

• I found this difficult because the way I often provide support is by putting myself in someone else’s shoes and thinking of what I might need in their position. I’ve realized now that the two are not mutually exclusive approaches, but rather need to be combined. As a manager, you have to use the combination of understanding who the person is and what kind of support they need in addition to understanding the particular task/challenge t and the roadblocks they’re facing to best support the person. This is why management is such a complex beast!

Have a pulse on the watercooler convo: People are always talking about leadership (good and bad), even if it’s a small company. The key isn’t to stifle that conversation (because you can’t) but to try your best to keep a pulse on the conversation. The higher your title, the tougher it can be to cultivate those relationships. There’s a TON of value in investing in what people at all levels and functions of the company are thinking.

• In my experience, the best way to do this is to build a relationship of trust through vulnerability (i.e. sharing what you really think and/or struggles that you’re having) to create a safe space for people to share. Then, treat their feedback with respect and try to act on it. That will speak for itself, and further reinforce trust with folks.

Self Management

Burnout is easiest to treat when caught early: startups often feel like a never ending sea of things to do, and therefore can make certain perfectionists (like me) more susceptible to burnout. I only took burnout super seriously when it started impacting my productivity. However, I’ve learned that burnout is like cancer: early detection is key. Even if it’s minor, it’s important to flag to your manager and team, take action against it, and track progress ASAP. Otherwise, it’s going to fester and get worse.

• When it’s caught and treated too late, it can be more difficult to get back on track, and often requires more extreme interventions (like taking 6 weeks off).
• On a side note- if you’re facing burnout, I recommend not just telling your manager, but also your team. They can help you in ways that might be tougher for your manager, since your manager is usually less involved in your day to day. Further, the shared vulnerability is a great way to build a deeper relationship with your team. For example, during the worst phases of my burnout, one of the senior engineers on my team would Slack me at 6 PM everyday to make sure I had logged off and took time for myself. This shared accountability really helped me get better at respecting my own boundaries!

Boundary breaking needs clarity: my biggest problem with boundary setting was that I let my to do list dictate whether I respected my boundaries, rather than my energy levels. There were some times when this was necessary (like when something would break and all hands are on deck) and other times when it was completely unnecessary, and created more long term harm than good.

• I am now setting clear expectations with myself and my team on when I’m willing to break my boundaries. For me, this means that I work a consistent set of hours, and only work nights and weekends if there’s a big launch or fire. Your definition can be whatever you want it to be, as long as it helps you manage your energy!

Don’t forget your life outside of work when optimizing your schedule: I’ve realized that I need a lot of things to replenish my energy levels and feel like a whole person (and not a working automaton). Specifically, I need time for writing, mini side projects (like this article), workouts (yoga/tennis/strength), reflection, meditation, and salsa dancing.

• Therefore, I’m now changing my schedule to wake up at 5 AM (!!!!) because that’s when I’m most productive (by evening I’m a puddle of sadness). In the morning, I’m planning to spend 3–4 hours working out, journaling, writing, and meditating before starting my work day. I’m also planning to block time in the afternoon to take a breathing room and meditate at work instead of letting the stress pile up for the evening.
• I tried doing this in my last job and felt so guilty- shouldn’t everything about being productive the whole time? I’m working on reframing this narrative in my mind because I know if I don’t do this, I’m headed for another burnout, which is not what I want for myself (nor my team).

Startups are a tough beast, both on the body and mind. But they’re also incredibly exhilarating. I hope that some of these experiences will help you in your startup journey, especially if you’re pivoting into the space from a bigger company. I’d love to hear if you have any thoughts on the above. Reach out to me here to share your thoughts!