Communicating Ambiguity

It feels like it should go without saying that startups always entail a healthy dose of uncertainty. It should come with the territory, right? However, for a few years as the tech industry skyrocketed, startups became ‘too’ secure. As it was so easy to raise money, it was rare to see startups closing. That resulted in plenty of people joining startups who didn’t consider the ambiguity a startup entails. As this is no longer the case, many leaders find it difficult to balance the daily uncertainty in the startup environment with providing their employees with safety and confidence. What is a leader to do?

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Fake It Till You Break It

Let’s start with what seems to be the most common behavior: executives decide to ‘fake it till you make it’ and pretend they actually know what they’re doing and have all the answers. This is chosen because they fear making people worry or scared. Unfortunately, this rarely holds for long and creates a whole set of different issues.

The self-imposed need to seem as if you know what you’re doing will prevent you from declaring things are experiments, and thus require different execution levels. Not being able to openly prioritize learning means you’ll be harming your efforts to cover those knowledge gaps. If you force yourself to come up with roadmaps that radiate more confidence, you lower the odds of people in the team participating in ideation and maximizing their potential (after all, how can you let them in on a discussion where you talk about things actually being guesses). And, of course, eventually, your guessing will turn out to be wrong some of the time. If you tried to pretend you were confident of the path forward, you’re only going to get your people even more worried.

Embracing Reality

Instead, I claim that the only sustainable solution is to be candid. Don’t run around flailing your hands in the air yelling, “We have no idea what we’re doing!!” I doubt that’s going to get you many points in the leadership department. However, you also shouldn’t feel compelled to always have the right answer. There’s a huge difference between not knowing something and pretending that you do, and proactively handling not knowing something by taking steps to iterate and gain insights. The latter shows your team that you are addressing your “known unknowns” and working systematically to improve the situation.

That’s why I really love it when leaders fully embrace this and talk to their teams about work as experiments, learning iterations, etc. Whatever you want to call it, by naming it and framing it correctly, you’re setting the entire stage differently and in a healthier manner. Especially for startups that are pre-PMF, learning ought to be your objective. Optimizations, scaling, and other issues should be reserved for once we’re certain of our path forward.

The advantages of openly discussing ambiguity are multifold. First, you’re making it much easier for people to question decisions and thinking. If you don’t know, then poking holes in your current guess is a lot easier, as opposed to telling an “expert” that they might be wrong. You’ll also get more ideas from your motivated engineers, who will realize what is the real problem that needs to be solved, and their minds will automatically start thinking about it.

Another advantage of open experimentation is it makes it ok to change your mind. Instead of people feeling like you’re capricious and change your mind every week based on nothing, when you’re experimenting it is entirely acceptable to gain an insight and change course given it. It also makes iterations much faster because we’re all aligned on the needed quality and robustness levels. There’s a difference between a feature we’re sure will be needed and be used by everyone and a little proof-of-concept that will be used by the sales and marketing teams to gauge interest before doubling down on it. Experimentation makes descoping easy—leverage that!

Don’t Stifle Motivation

I’ve written at length about how the best engineering teams in the world usually have a terrific connection with the business. Engineers who come up with great ideas and drive dramatic impact do so because they can see the results of their efforts and gain motivation from them. That’s why it’s incredibly important to connect engineers with feedback from users and show them the impact of work delivered over time.

That’s of course, much harder to do in pre-PMF and while experimenting. In those cases, being open about the uncertainty can help you gain similar motivation even before your experiments are successful. To do so, have retrospectives dedicated to discussing what the company has learned from an iteration, the current hypotheses, possible directions, etc.

I’d go as far as saying that you can fully embrace it and have KPIs, OKRs, and goals dedicated to learning at these stages or when you’re working with an experimental team. Perhaps this quarter, the team’s measurement of success would be learning which marketing tool seems more effective, or even as simple as executing ten experiments. I’m not sure what yours should be, but that’s fine.