The best answer requires some aggravation

by havoc

Once you think you have a good answer to an important problem, it’s time to drive everyone crazy looking for an even better answer.

Here’s a scenario I’ve been through more times than I can count:

  • I thought I had a pretty good approach, or didn’t think anything better was possible, and wasn’t looking to spend more time on the problem.
  • Someone had the passion to keep pushing, and we either stayed in the room or kept the email thread going beyond a “reasonable” amount of effort.
  • We came up with a much better approach, often reframing the problem to eliminate the tradeoff we were arguing about at first.

Steve Jobs was legendarily cruel about pushing for more. But in my experience good results come from more mundane aggravation; there’s no need to make people cry, but there probably is a need to make them annoyed. Annoyed about spending three extra hours in the meeting room, annoyed about the length of the email thread, annoyed about compromising their artistic vision… if the human mind thinks it already has an answer, it will fight hard not to look for a new answer.

That might be the key: people have to be in so much pain from the long meeting or thread or harsh debate or Jobsian tongue-lashing that they’re willing to explore new ideas and even commit to one.

It shows just how much we hate to change our mind. I often need to be well past dinnertime or half a novel into an email thread before my brain gives up: “I’ll set aside my answer and look for a new one, because that’s the fastest way out of here.”

The feeling that you know the answer already is a misleading feeling, not a fact.

Some people use brainstorming rules, like the improv-inspired “yes, and…” rule, trying to separate generative thinking from critical thinking. First find and explore lots of alternatives, then separately critique them and select one. Avoid sticking on an answer prematurely (before there’s been enough effort generating options). Taking someone else’s idea and saying “I like this part, what about this twist…” can be great mental exercise.

To know you’ve truly found the best decision possible, your team might need to get fed up twice:

  • Brainstorm: stay in the room finding more ideas, long after everyone thinks they’re tapped out.
  • Decide: stay in the room debating, refining, and arguing until everyone thinks a decision should have been made hours ago.

A feeling of harmony or efficiency probably means you’re making a boring, routine decision. Which is fine, for routine stuff. But if you have an important decision to make, work on it until the whole team wants to kill each other. Grinding out a great decision will feel emotional, difficult, and time-consuming.