Overcoming uncertainty through conviction and decisive leadership
It’s been a few months since I last posted - I’ve spent the last 4 months focusing on a few in-depth consulting engagements, and now that those have wrapped up, I’m able to come up for air and get back to writing.
I have some availability the next few months for product coaching and consulting. My focus is on founders, product leaders, and experienced PMs who are stretching into new roles and scope, re-evaluating product strategy or product-market fit, or building/scaling their product team for the first time. If you’re interested in chatting, I’d love to connect - feel free to reply to this or go ahead and book some time with me.
Uncertainty, conviction, and decisiveness
Today I want to dive into the inescapable uncertainty that founders and product leaders face, especially in early and growth-stage startups. This has been a major theme in my work and recent conversations with founders and product leaders, and one specific challenge has stood out to me: the question of how to be decisive and provide clarity to your team when you’re not sure of things yourself.
If you’re feeling stuck in the uncertainty you’re facing, I’d love to help. Drop me a message or schedule a free consultation and let’s dig into it together.
You can’t get around uncertainty, but you’re not alone.
Building something new always involves a high degree of optionality and unknowns. Which customers should we focus on? Which solutions should we prioritize? Which metrics will be most useful? How fast should we hire, and in which parts of the company? Every founder faces these questions, and has to come up with answers quickly despite not having the insights they need to know which answer is right. If there’s a way around this, I haven’t seen it (if you have, let me know!).
You and your team need clarity, which comes from decisive leadership.
In the face of this, founders have to find a way to create clarity for themselves and their teams on what is most important to focus on. Lack of focus will kill your chances of success. This is especially true as your team gets larger, but it also applies when it’s just you in your proverbial garage.
This kind of clarity does not and can not emerge in a bottoms up manner. Founders can’t delegate it, and can’t expect their team to come up with it on their own. The team should absolutely contribute insights and ideas, but ultimately the founders need to be the ones to determine strategic priorities and focus areas, because that unlocks alignment and empowerment for the rest of the team.
Conviction enables decisiveness in the face of uncertainty.
If you set strategy on a quarterly basis, another way to think about it is that you’re betting the equivalent of 3 months of burn on that strategy. This is far from trivial, but unless you’re running out of money, it’s not an existential bet. (If you’re running out of money, that’s a different matter altogether.) Let’s say you have 2 years of runway - that’s 8 quarters, so you have 8 strategic bets to make.
You can’t possibly know everything you need to know to be certain of the outcome of those bets. So how do you decide? Rather than looking for certainty, look for conviction.
Conviction can come from a variety of sources, including hard quantitative evidence, past experience, intuition, bottoms-up insights from your team, conversations with customers, etc.
What’s important here is not that you have bulletproof evidence behind the decisions you make - that’s impossible. The aim is for you, as the founder or product leader for your company, to feel strongly enough about the direction you’ll take that you’re willing to bet 3 months of burn on it, and to be confident that even if you get it “wrong,” you can learn enough along the way to meaningfully increase your odds of success on the next bet.
Once you feel enough conviction to set the direction, your next task is to communicate it clearly to your team and get them aligned with it. This is critical, because if they don’t understand your thinking, and if everyone isn’t properly aligned, then it’s too easy for an otherwise solid strategy to fail.
When you lack conviction, step back and reassess what you know, what you believe, and what you’re unsure of.
There will be times when you need to question your core assumptions/hypotheses for your product, especially, but not exclusively, in the early days. Maybe you’ve been pushing in one direction for a while, and you’re worried that you’re trying to climb an impossible hill. Or maybe external factors have changed in a way that requires you to reorient your strategy. Whatever the context, it’s essential for you to get to a high enough degree of conviction that you’re comfortable making the next strategic bet.
Here’s a few tips on how to do that:
Try to narrow down the uncertainties. Make three columns on a whiteboard for what you know, what you have conviction on, and where you’re uncertain. Chances are, the first two columns won’t be empty - that’s where your strength lies.
Focusing on the third column, think through how the items in the first two columns interact with your areas of uncertainty. Do they eliminate certain paths you could take? Are there hints on a direction that might be viable given what you know and where you have conviction?
If there are still major areas of uncertainty, stack rank them from most to least important to the success of your company. Throw out everything but the top 3 items. Come up with a handful of ideas for how you can get some new insights for each item in the next week, and then go do those things. With those new insights, take a fresh look at things and evaluate your new level of conviction.
Trust your intuition and your ability to learn. They will lead you to the right path eventually, even though you’ll get some things wrong along the way.
Remember that you’re making a non-trivial bet, so take this seriously. Don’t settle for indecision here, because it will only increase your odds of failure. Make the important calls, and make sure you can communicate your decisions clearly to your team so they can focus on executing well.
Remember that you’re only betting 3 months or less, so don’t let decision paralysis set in. You can change course next quarter, or even sooner if it becomes clear that things aren’t working. Creating clarity and focus is way more important than getting everything right.
I would love to hear how others have navigated this in their work - feel free to comment or reply and let me know what you’ve learned. My previous articles on Hypothesis-driven leadership (here and here) dig into this even more, and if you’d like to go deeper in a 1:1 context, you can schedule some time for us to chat.