Stop asking boring questions

Two Dummies
3 min readMay 25, 2022
Photo by Jonathan Brown on Unsplash

I joined a new team recently and have been having a lot of one-on-one introductory conversations. Introductions are a funny thing. Usually when you join a call and know that you’ll have to introduce yourself, you have a canned response ready to go.

In professional services the intro is usually something like “Hi, my name is [insert name], I’m a [insert title], and I’ve been with [insert company] for [insert length of service at company].

I find these types of introductions to be blasé and shallow. They illuminate very little about a person.

I like to start these conversations a little differently. I ask people to begin their introductions with this question: How would you describe yourself in three words.

The reaction to this question has largely been the same — a pause.

Pauses, whether verbal or non-verbal, signal that a question is both thought-provoking and unexpected. Pauses indicate that you’ve asked a question that someone hasn’t answered before (or at least recently) and doesn’t have a prefab response.

So strive to ask questions that make people pause and think. Do the following:

  1. Create scarcity to force brevity
  2. Be unexpected

Create scarcity to force brevity

Response brevity is best captured in this often used quote by Mark Twain, “I didn’t have time to write you a short letter, so I wrote you a long one.” It’s easy to be verbose, to talk aimlessly and endlessly, and to carry on without knowing the destination.

That’s why you need to force brevity.

Scarcity helps you do that.

For gathering more information, open-ended questions are typically the way to go. But well-crafted close-ended questions can be just as impactful.

If I simply ask you to describe yourself, you can choose anything as a jumping off point and ramble on because there’s no constraint on how you describe yourself or the order of your descriptors. If you forget something in the beginning, you can always include it throughout.

If I ask you to describe yourself in three words, you don’t have the luxury of starting anywhere and adding things as they come to you. Because you are constrained, you have to be judicious, intentional, and purposeful with the words you choose.

Be unexpected

You can be unexpected by being fresh.

“Tell me about yourself…” and “Introduce yourself…” elicit staid and stale answers. We usually know when they are coming and because we’ve answered them before, we can comfortably answer them again without expending too much brain power.

You need a fresh question to get a fresh answer.

“How would you describe yourself in 3 words” has worked well for me and “What’s the story of your name?” has worked well for Garett only because they’re not already frequently asked in the environments in which we’re asking them. If everyone in the world read this article and started asking, “How would you describe yourself in 3 words”, then answers will become tired and dull.

There are no silver bullet questions — you have to keep iterating, innovating, and inventing to engage your audience and get thoughtful answers.

Most conversation is improv. But, the more you find yourself saying the same script, the less dynamic — and interesting — a conversation becomes.

You’ll have to spend some time thinking and building a repertoire of questions but it will be worth it. It will make your conversations — and your introductions — more lively, fun, and illuminating. You’ll start to see a newer, richer side of people.

Curiously Yours — Seb

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Two Dummies

I’m Garett. I’m Seb. We help courageously curious organizations identify and realize bold ambitions through co-creative experiences.