Working with founders
Joining an early-stage startup can be an exciting opportunity to be part of something new and innovative. However, depending on your role and how early you join, there's a strong chance you'll be reporting to or working incredibly closely with the CEO or founder. This relationship can be challenging because it's not a conventional manager-team member relationship. At this stage of the company, you're expected to be pretty self-sufficient and independent. Any coaching you get will be few and far between because this person's time is spread across the entire business and working with external folks like investors and early customers.
So what's the best way to build a strong relationship with your founder, and navigate this unique working dynamic effectively?
Your support network
Start by establishing a network of folks to support you in this journey. Joining the founding team can often feel isolating because you're often the only person in your function so it's important that you have people outside the organization who can help. This can come in many forms, with the most common being mentorship from former managers or more experienced folks within your network. I've found this to be most helpful when you have mentors who have built a strong expertise in a particular area. For example, there's a senior executive I've worked with closely in the past who built strong teams and has an incredible history of hiring high potential individuals. Throughout your career, identify who these people in your network may be so you have someone to reach out to when you encounter those specific hurdles.
Another great source of support is community. This is generally made up of peers who are going through a similar journey as you but in a different organization. You can start by joining existing communities or you can establish your own over time through networking. I've heard of friends who have a text group that they use as a safe space to bounce ideas of one another. I'm personally part of several Slack communities. If you're a founding product manager, feel free to shoot me a message here or on LinkedIn to join our monthly virtual discussions!
Finally, there's coaching. This is likely the most expensive option (but something worth negotiating into a contract) but I've personally found this to be immensely helpful. A great coach isn't there to give you answers but is able to help you reframe your thinking or approach by asking questions that guide you along that process. You can check out a great list curated by
here! As you work with founders and go through your journey at a startup, there are so many instances where this relationship helps you be much more effective as a leader.Communication is key
Working with a founder is like managing up on steroids because you have to be extra diligent about providing the right level of visibility without impeding on the founder's time — you accomplish this with strong communication and alignment. This isn't just about what you say, it's about how you say it, when you say it and sometimes...if you say it at all.
The response to each of these can be determined by having a deep understanding of how your founder likes to work and communicate. Folks I've spoken to often make the mistake of figuring this out through trial and error while working together. The easiest way to understand this is by having an explicit conversation upfront and I've found user guides to be a handy tool that makes this step as straightforward and transparent as possible.
While each founder is unique, there are still aspects of communication which are universally appreciated for someone who is time poor but still needs to have a good understanding of what's happening across the business. Here's a few things that I've seen work really well:
Push vs pull communication: The rule of thumb here is for the founder to feel like they have a pulse on the most critical and strategic initiatives that you're responsible for without a need to ask. It's a fine balance to strike but when done well, it means they won't be pinging you constantly for updates and insights because you've preempted what they want to know. Make sure you're aligning with the founder on exactly what matters to them most at the beginning of each cycle or quarter. There will always be things that catch on fire or items that just pop-up, but the majority should be proactively shared.
Set expectations and be specific: This ranges from simple things like always including an agenda and ideally a pre-read ahead of a meeting, to more nuanced behaviors like being explicit about what is needed (eg. I'd like your approval here vs this is an FYI) and by when (eg. By the end of this week vs by the end of the quarter) in your messages or requests to the founder. This allows your founder to prioritize your ask, come prepared and also respond accordingly and in a timely fashion.
Make it digestible: Always optimize for what's easiest for your founder. Generally this means async updates over long meetings that give them a sense of what's happening. Reserve meeting and face time to dive into deeper topics or open items. Use bullet points to summarize the key takeaways from any long form docs or blocks of text.
Be adaptable
Now forget everything I just said about communication 😅 Startups are in a state of flux, and priorities can change quickly. This applies to how great founders operate too. They're moving fast and constantly challenging themselves to re-think their approach. This means that you need to be prepared to shift gears just as quickly — no matter how much alignment you've done and how transparent your communication is, last minute changes will happen.
There are two things that I've found make this reality easier to stomach. The most important is to acknowledge that this is inevitable and set that expectation for yourself and the teams that you work with. Understand that the shift likely has no reflection on how you've performed thus far and was always outside your control. That said, it doesn't mean you shouldn't just accept everything that gets thrown your way. It's equally important to ask questions and challenge the shift — understanding the 'why' behind a sudden change will help you and the team get behind it far better, even if you don't necessarily agree with the ask or decision.
Working directly with founders is not for everyone, just as working at an early stage startup isn't for everyone. For a lot of folks, it might feel like you're getting the short end of the stick because you're dealing with founders who are under significant stress or uncertainty. You'll need to approach your work with empathy and compassion and try to be a positive force in the founder's life. If you're able to operate under these conditions, the experience is incredibly rewarding because not only are you getting front row seats to the building of a startup, you're also being exposed to a mindset and experience that will make you an incredibly scrappy and effective founder of your own company or an invaluable employee at your next gig.
So…would you work directly with founders?