November 29, 2022

The Power of an Honest Question

In a hilarious courtroom scene in My Cousin Vinny, a spiteful district attorney in an Alabama murder case tries to discredit the glamourous, if unorthodox, automotive expert witness, Mona Lisa Vito. His attempt backfires when his smug attempt at a “gotcha” question reveals her encyclopedic knowledge of cars, gleaned from growing up in her father’s Brooklyn auto repair shop. He underestimates her, at his own expense.

Seasoned trial lawyers abide by an age-old rule: “never ask a question if you don’t already know the answer.” In a context where questions are part of a choreographed dance to make or defend a point, surprising answers are never a good result.

While this technique may prevail in court, it falls far short in all other workplaces. Yet leaders use it all the time. They ask questions designed to verify what they already know or believe, rather than learn something new. If you use questions just to gather data to prove your point, you leave far too much on the table.

Good questions are power tools for collaboration and innovation. But only when they are grounded in honest curiosity and a genuine desire to hear the answer - even if it’s not what you expect. Asking good questions unleashes new ideas by surfacing the hidden insights of others. And it signals your respect for colleagues and the value of their contributions.

Teams that understand and use the power of honest questions are more collaborative, innovative and inclusive. Here’s how to do that:

  1. Change it up.  Many leaders have predictable patterns of behavior, especially in meetings. Your colleagues will prepare to answer the questions they know you will ask. If you stick to your usual script, the answers you get will never stray from the familiar. Think about why you ask a particular question and frame it differently. Instead of narrow questions about facts or deliverables (what is, what are), ask broad, open-ended questions that make people pause and reflect (what if, what could be). These open questions are designed to invite broader thinking and surface innovative responses: “If we could remove all constraints, what might be possible?” Probing questions deepen exploration. There is no better question to refine someone's thinking and expand a conversation than a simple “please say more?”
  2. Slow down. Asking better questions requires you to change how you ask: being ready to challenge your own belief systems, to acknowledge that you don't already have the answers. Being willing to ask a question whose answer will cause you to pause helps you think about a problem or a situation from another’s perspective, and models genuine collaboration. It's the subtle shift from a fixed to a growth mindset, where the ask itself signals your willingness to learn something new. Resisting the push to get quickly to an answer allows you and your team to be curious, to explore diverse possibilities and embrace out-of-the-box ideas without fear: “What could we try that might not work?” In a time-starved culture, this is hard. But good ideas - especially novel ones - take time to build and freedom to mature.
  3. Don’t be afraid to ask hard questions. Author Peter Block defines three attributes for a good question: it must be personal, ambiguous and evoke anxiety. Anxiety, in this case, is not about intimidation, it's about importance: the things that make us anxious are the things that matter. A personal question engages the heart as well as the head, encouraging the listener to bring more of themself to the challenge. And an ambiguous one requires you to rely on the listener to provide the meaning. This framework invites you to rethink what you ask your colleagues. Hard questions introduce vulnerability and produce deeper, often unexpected answers. These questions jostle the status quo, encouraging you and your colleagues to push beyond your comfort zones: “What are we doing today that no longer serves us?” These are fundamental or existential questions that encourage your team to dig deep and put the inquiry before personal interest. How do you know that you’ve asked this kind of question? When you have no idea how to answer it yourself.

It’s easy to fall into a transactional trap: using questions to gather the data you need to confirm a decision or point of view. Too many leaders assume – like that Alabama district attorney – that they already know what others have (or don’t have) to offer. They underestimate their teams, at their own expense.

The world is just too complex for anyone to have all the answers. Build a culture of genuine curiosity that embraces this. It sounds extreme, but try asking questions like you know nothing and it will not only change the conversation – it will change your team, your productivity, and boost your innovation for the better.

Image Credit:
Saul Steinberg, Untitled (Question Marks), 1961 via
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