Rule of thumb: Learning about a customer and their problems works better as a quick and casual chat than a long, formal meeting.

“So here’s that top-secret project I quit my job for... what do you think?”

you need to be the one in control. You set the agenda, you keep it on topic, and you propose next steps. Don’t be a jerk about it, but do have a plan for the meeting and be assertive about keeping it on track.

Rule of thumb: You always need a list of your 3 big questions.

The measure of usefulness of an early customer conversation is whether it gives us concrete facts about our customers’ lives and world views.

You can't outsource or hire someone to do customer learning.

Rule of thumb: Some problems don’t actually matter.

I’m not going to try to set up a meeting. Instead, I’m just going to immediately transition into my most important question: “Hey, I’m curious—how did you end up getting this gig?”

What does it mean if you reach out to 100 people and 98 of them hang up on you? Well, nothing, except that people don’t like getting cold calls. No surprise there. More importantly, it means you’ve now got 2 conversations in play.