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Crafting a more beautiful question
Inspired by Warren Berger's book: A More Beautiful Question
Every few years, a technology inflection (like GenAI) sweeps everyone off their feet. We’re reminded that all the exciting technical skills in our toolkit today may be banal tomorrow. Every impending automation leads to a flurry of articles by the Harvard Business Review warning of job losses and reinforcing the importance of “soft skills”. These soft skills can never be automated, and therefore are more important than ever. While I’ve never liked with this “soft skills will save you” take (IMO, technical skills will never not be important), I do value the importance of them.
There are the usual suspects of soft skills: communication, executive presence, empathy, teamwork, etc, etc., but one that I think I’ve come to appreciate more than ever before is the ability to ask really good questions.
It’s a skill prioritized by journalists, sales teams, founders, and user researchers, but seemingly under-prioritized by the average knowledge worker. If you don’t (yet) appreciate the power of good questions, go learn from the master: Ezra Klein.
As I work on this skill, I’ve come across three questions that I’ve found to be especially impactful:
What haven’t I ask you about that I should have?
Ending a user interview with this question has led to some fascinating responses. After 25 minutes of pointed questions in a user interview, this “catch-all” question opens up the conversation and gives the interviewee the chance to express what is really top of mind for them. You’ll almost always learn something interesting.
What are you feeling?
You may have heard this one before. The question of “How are you?” has become so common and expected that our partner in conversation will almost always unconsciously respond with a lie: “Good”. A small change in wording from “How” to “What” prevents the interviewee from giving a canned response. The question is unique, and therefore their answer will be as well.
Using the inverse. What does your team do really well? What does you team do poorly?
Anchoring is powerful. If you ask someone what their team does very well, they’ll be quick to give you a detailed response with pride. If you then follow that question with the inverse, they will feel the need to provide an response that is equal and opposite in nature. They’ll really dig to figure out what their team does poorly.
What are your favorite
Raman at Rhetoric