Three questions to ask (or not ask) your team

English is a funny language. You look up words in a dictionary, you get things that are presented as synonyms—but which, in practice are anything but. How you ask something is as important as what you ask.

Here’s a pattern you might notice in your own teams. Three questions, very close in the asking, but quite far apart in the effect they have.

It’s rare, luckily, for question-answerers to go flying off the sides of rickety bridges.

1. “What could we do here?”

This one’s for when you want your team to think about possibilities. It’s part of the kickoff for a brainstorm: it widens the scope of possibilities.

A former coworker of mine was fond of saying, “It’s software—we can make it do anything we want.” Which isn’t strictly true, but it’s close enough in many cases. There are a lot of coulds, limited largely by time.

2. “What should we do here?”

This one’s when you want them to think about constraints: ethical constraints, legal constraints, or the capabilities and preferences of your customers.

Should is funny word, and most of us realize that it means different things to different people. Expect to have a follow-up question about what you mean by ‘should’, and be prepared to answer.

3. “What can we do here?”

This one’s for when you want your team to think about implementation: what can we, with the tools and knowledge we have, actually get done?

The question usually has an unspoken second half, something like “…in the time allotted.” Again, be prepared to help define the scope for the team, or you’ll get a lot of useless flailing.

What question is right for your team? What do you want to achieve? Are you looking to widen the scope or narrow it? Think about constraints, possibilities, implementation, or ethics?

Obligate infovore. Antiviral blogger. All posts made with 100% recycled electrons, sustainably crafted by artisanal artisans. He/him/his.

Obligate infovore. Antiviral blogger. All posts made with 100% recycled electrons, sustainably crafted by artisanal artisans. He/him/his.