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Apr 30, 2021 · 3 min read

I'm collecting great questions: questions that elevate discussions and our thinking and are different from the questions that we are used to hearing and asking ourselves. This is a list of the questions I have found so far. Enjoy.

Questions are in alphabetical order and I'll keep updating them every now and then.

How could we do this?

Ask, "How could we do this?"—not, "Can we do this?" or "Is this possible?"

"How could we do this?" urges people to get creative with possible solutions. "Can we do this?" asks if something is realistic or not and can result in a knee jerk "no" if a problem seems unsolvable on the surface.

How is your week going so far?

The single best question you can ask strangers at networking events. It's an invitation for others to tell you what's on their mind at the moment.

What caused the problem?

Ask, "What caused the problem?"—not, "Who caused the problem?"

Mistakes are inevitable. But you can avoid turning blunders into blame games by focusing on the what—not the who.

What do I want?

Ask, "What do I want?"—not, "What don't I want?"

This question is from David Emerald's The Power of TED and according to Emerald, it's maybe the most powerful question you can ask yourself.

"What don't I want?" is the question that's usually easier for us to answer. The problem with it is that it puts the focus on the problem and not on outcomes.

"I find that I know all too well what I don't want in my life. I'm not sure how to get clear about what I do want"

—David Emerald, Power of TED

What do I hope to learn?

Whenever you're entering into a discussion or debate about a topic that's important to you, it's easy to get fixated on your own talking points instead of focusing on listening and learning about your counterpart's point of view.

Ask yourself, "What do I hope to learn?" and write down the answer in bullet points on an index card. This primes you to listen—not just talk—when you get the chance to meet your counterpart.

I read about this exercise in Nilofer Merchant's article about listening.

What do you think I should change?

"What do you think I should change? What do you think should be left alone? What do you fear I wouldn't understand?" are the three questions Nokia's former CEO Stephen Elop asked in a mass email sent to all employees on his first day at Nokia.

What does a good day look like?

I find that it's easier to be content with life when you have figured out the things that put you in a good mood on a daily basis.

What questions do you have for me?

Finish your presentations with "What questions do you have for me?" to get more questions from your audience.

What three things are working for you right now?

If a colleague approaches you for advice, Marcus Buckingham and Ashley Goodall—authors of Nine Lies About Work—suggest you to avoid jumping immediately into problem solving mode and follow these steps instead:

  1. Start with the positive: "What three things are working for you right now?"
  2. Go to the past: "When you had a problem like this in the past, what did you do that worked?"
  3. Turn to the future: "What do you already know you need to do? What do you already know works in this situation? What do you actually want to happen? What are a couple of actions you could take right now?"

What's next for my field?

Tim Brown (former CEO of IDEO) keeps asking himself, "What's next for design?"

Where do you disagree/get confused/drop off?

Use these questions to discover weak points in your writing or presentations when looking for feedback:

  • When you ask someone where they disagree, you'll learn about the objections that you may need to address in order to make your arguments more convincing.
  • When you ask where they get confused, you'll learn which parts need more clarity and explanation.
  • When you ask where they drop off, you'll learn which parts to cut, condense, or make more fun.

Where's the fire?

I got this one from an interview with coach Christopher Sommer and use it to guide my own fitness goals.

There's no point in thinking about all the exercises you skipped in the past and trying to overcompensate by taking on way too ambitious goals for your future self. Where's the fire? Where's the rush?

Who am I becoming?

We are much more like vectors with direction and magnitude than fixed points in space. Don't get too fixated on who you are now.

Why? What if?

Author Nic Stone says that an important source of inspiration for her is her tendency to ask, "why?" followed by, "what if?"

Why do you think this is a good strategy?

In strategy work, when a team presents its strategy, the typical questions are "what" questions: "What are your primary objectives? What is your action plan?" But the question that really forces people to think is, "Why do you think this is a good strategy?" —Risto Siilasmaa, Transforming Nokia

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