Uncertainty Wednesday: Leadership under Uncertainty

A startup founder I know likes to say that their leadership style is “frequently wrong, but never in doubt.” Often that expression is applied as a critique, such as in Cheryl Wheeler’s song Driving Home, but the founder meant it as a positive model along the lines of the idea that even a bad decision is better than no decision. Given the high degree of uncertainty inherent in startups, how to lead in its presence is one of the crucial founder/CEO challenges. So should a leader share their doubts about a course of action with the team?

That framing of the question has an implicit assumption: that the leader has doubts to begin with and hence needs to make a decisions whether to share those or not. To some this may seem like a preposterous question, after all, who doesn’t have doubts? Only an overly sure fool would seem not to. But the word doubt has a lot of connotations, including lack of confidence and even distrust. So what do we even mean by asking about doubt and sharing it?

To help narrow this down, I therefore want to use other words and distinguish between “second guessing” and “re-evaluating.” The former is questioning a decision without material new information. The latter is revisiting a decision after material new information has been obtained. It is second guessing which is destructive for morale, because it calls into question not just the decision but also undermines the legitimacy of the decision making process itself. A a leader you should keep any second guessing strictly to yourself.

Re-evaluating on the other hand is healthy but requires a good decision making process. In particular, there has to be a relatively clear way of assessing whether something is in fact material new information. There is a famous quote, often attributed to Keynes: when the facts change, I change my opinion – what do you do? If you have a good process for making decisions then it will be quite clear whether something is a material new fact and the team will be able to be quite dispassionate about re-evaluating the decision.

So as a good exercise, next time you feel doubt about a decision, ask yourself if you are second guessing or if you are re-evaluating. And if you find yourself second guessing a lot, then it likely says something about problems with the decision making process (and potentially about your own fears).