Building Trust with a Founder

First of all, make sure that you understand the founder's context, the things the founder cares about and worries about, and the overall vision.

One of the most important things is to get to the bottom of what the business goals are. In a startup, you'll typically have a short runway and run out of cash. Understanding that runway is super important because it defines how much time you've got, creates a constraint, and limits some options because of that constraint.

Understand what success looks like for the founder. At what point of the startup or what success metrics should be in place for them to get another round of investment or whatever that is.

Once you get this, it needs to be written down somewhere, so when you catch up with the founder, you have documentation to capture these goals and make sure they are visible. You have to prioritise what is important. If they are not, the founder will call it out and say, "This is not what we're trying to do. We're trying to do X." That's what you want. Understand the true goal so you can then adjust the product or your approach and strategy to achieve these goals.

Make sure there is a regular check-in with the founder. Ideally, it's once a week for half an hour to an hour, but it needs to be regular. During these check-ins, build a relationship with the founder. Especially in the beginning, you need to be aligned. The founder will have many priorities and ideas, and the art of product management is to say no, or not yet, to most of them and only focus on what is really important.

You need to be a sounding board for the founder. The founder might not see results as fast as they want and may say, "Let's stop this and do something else." As a product person, manage that and ensure the founder fully understands the impact of the switch, the impact on the team, and the consequences of starting too many things without finishing them.

Provide weekly snapshots of the week, typically at the end of Friday, and share them with the team. It's a quick snapshot of what happened in the week, so the founder can quickly scan what's happening. If there are any questions or follow-up, they can call or email you.

Regular catch-ups where the founder picks one topic you need their input on are also beneficial. It's a good opportunity for you to learn.

Certain decisions fall under product management per se. The founder might have an opinion and can override it. But decisions like hiring a new team member need to be discussed with the founder, who needs to decide. As a product person, you'll provide the rationale for why the person needs to be hired and what happens if you don't.

Some decisions could be quite subjective. Even if there is enough data, organisations are typically data-informed rather than data-driven. Communicate problems and solutions clearly using frameworks like SCQA. Convey the problem and solution on one page, and provide evidence and considerations in an appendix. The appendix might be multiple pages, but if you give this one page to anyone, they should be able to quickly understand the context, problem, and solution.

It might be frustrating, but from a professional perspective, outline your recommendation and why you think this way. Ask the founder why they made this decision and why they're overriding it.

It could be an emotional decision by the founder due to stress about funding. Having empathy for the founder makes sense. Keep the log, provide your recommendation, and don't be attached to it.

You can disagree and commit, and that's fine. It took me some time to get to the point where I'm not attached to my recommendations. I've learned to let it go if it is overridden by the founder or boss.

If you find yourself constantly disagreeing with the founder, it could indicate a mismatch in product or culture. It might be a good time to find a new job if you can't resolve this for months.