Jason Fried

March 29, 2023

The improv instinct

Last week I was talking with another business owner from a different industry. He was frustrated with an employee who kept asking him what to do if x, y, or z happens. This was a long-time employee who'd been in these situations before, not someone new who was learning the ropes.

With this particular employee, it's always the same set of questions no matter the situation. It could be a call with a client. If could be a meeting with another department. It could be a conversation with a vendor. What if they bring this up...? What if they bring that up...? What should I say if they say...? What about if they...? Essentially this employee wanted to be prepared for every contingency in a given situation. And they were great when everything went as anticipated.

Being prepared sounds like a good idea, and you could understand why they might ask these questions. Considering the edge cases ahead of time is certainly useful. You might read the above and say "Yeah, and? What's wrong with that?"

There are many ways to prepare for any eventuality, and one of them is to literally prepare for all possible outcomes. But another one, and I'd say the more valuable — and useful — one is to become comfortable with the unknown. To develop on instinct around dealing with the situation whatever comes up. To know, not just to say. More jazz, less rock. More improv, less script.

I'm not suggesting that someone who's specifically prepared for every situation won't perform well. They very well might be outstanding in their role. But you can't drop that person into any situation — you can only drop them into a certain situation.

I've found that those who develop a comfort with the unknown are the most delightful to work with. It's not that they know everything — they may know a lot less with someone who's studied every angle — but flexibility and independence is such a multiplier, that I'd take it any time over the alternative. The degrees of freedom you get with someone whose ability to work with "let's see what they say" vs. "what if they say?" are immeasurable.

To be clear, there's nothing wrong with asking questions about things that could happen. Preparation is essential regardless. And if you can know every move ahead of time, knowing every counter move might be the way to go. But in the murky realm of people and motivations and strategy and incentives, trying to map it all out will lead to you more blindspots, not less. And then when things go off the golden path, you're stuck needing directions with no one to ask.

At least that's how I see it.


About Jason Fried

Hey! I'm Jason, the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Subscribe below to follow my thinking on business, design, product development, and whatever else is on my mind. Thanks for visiting, thanks for reading.