Item 13: Prefer Asking for Feedback vs. Asking for Advice
I've been in a lot of meetings where people ask "how would you like X" or "what could you do with Y?" or "what do you think is the most helpful way we could lay out this table?" If you're like me what you've noticed is that it takes people a while to answer that...it tends to look like a "tough" question to answer. If you read Item 1, you know that this is partly because people don't know what they want, and you're trying to help them figure it out. But helping them figure it out by asking them what they want, it turns out, isn't that helpful. Instead, try this:
Take a very solid, very concrete stance, and then ask them what they think. Instead of asking "what could you do with Y?", say, "What it seems like you want to do with Y is $thing. What do you think?". Instead of asking, "what do you think is the most helpful way we could lay out this table?", say: "we're going to organize this table by widget priority with all of the inactive widgets pre-filtered so you can easily triage which widgets need your attention. What do you think?". What I've found is that people will be much more likely to respond to that question with feedback that actually gives you a sense of what's important to them.
The science behind this is pure evolutionary biology. Brains are lazy; the harder they have to work, the sadder they are. When you ask someone an open-ended question, you're asking them to do a lot of work imagining the right way forward. When you tell them about the way the world is, you're asking them simply to react to that, which is much easier; a reaction is finite and discrete and closed; a world is open-ended.
Just remember: it's easier to edit than to write