Great Leaders Ask Great Questions

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I am mildly obsessed with studying great interviewers given their skill at asking incredible questions. My five favorite interviewers are:

1. Barbara Walters

2. Patrick O'Shaughnessy

3. Oprah Winfrey

4. James Lipton

5. Kai Ryssdal

This obsession stems from the fact that asking great questions is a superpower, particularly for leaders. Over time I’ve come to see that, like anything, asking great questions is a skill which can be learned. While I’ve hardly mastered it yet, here are four tips which will help you ask better questions.

Listen

The old Kindergarten teacher standby of having, “2 ears and 1 mouth for a reason” holds true here. You’ll never be a good questioner if you think you already know the answer to the question you’re asking. Put differently, kill your ego.

A useful way to check yourself here is to think about your talk time. As a general rule I like to shoot for a 3 to 1 ratio. The person you’re speaking with / asking questions to should be speaking 3 times as much as you are.

Ask questions because you are genuinely interested to learn, not to show how smart you are.

Common questions, uncommonly asked

In sales (my chosen profession / obsession) this technique is often referred to as a “pattern interrupt” which can be particularly useful when trying to ask good questions. A pattern interrupt is a question which breaks an individual’s natural pathway for automatic responses. If the person you’re speaking to needs to pause to think, you’ve executed a pattern interrupt correctly.

It’s worth noting there’s an important difference between an effective pattern interrupt and a confusing question. The goal is not to “stump” the person you’re speaking to by confusing them, rather your aim is to ask an uncommon question which genuinely makes them think.

Oprah is one of my favorite people to study for learning to pattern interrupt successfully. See the following example of a great question, rephrased, which Oprah uses to break through the “surface”:

What common questions can you ask in uncommon ways in order to garner a deeper response?

Ask questions like a fan

One of my favorite pieces of advice with respect to asking great questions is to do so as a fan, not a journalist.

This tip comes from the aforementioned James Lipton and his famous piles of blue notecards used during his interviews on Inside the Actor's Studio. Lipton once famously quipped to a reporter from the New York Times that his show was, “not journalism.”

Lipton saw himself as a peer and a fan of those he was interviewing which led to an intimacy in his interviews which is worth studying by any would be question master.

On the surface asking questions like a fan rather than a journalist seems counterintuitive. Journalists, after all, are in the business of asking questions. While this is true, I’ve come to find that journalists value a level of detached skepticism with their subjects that, while I’m sure is useful for their profession, deters two individuals from connecting with each other ultimately preventing an honest discourse.

In asking great questions there is no substitute for genuine curiosity. There is no better source of genuine curiosity than someone who is a fan of another person. Cultivate this sense of fandom or admiration as a questioner and you will always have a more interesting conversation.

Simple words, used directly

Our final questioning tactic harkens back to the fact that to ask great questions you need to be a great listener. It’s worth repeating, the goal of asking questions is not to confuse your subject nor show how smart you are, it is to genuinely learn something new about the world.

This balance between not confusing your subject while still making them pause to think (see Oprah’s example from above) is an important one. When asking questions you are in pursuit of a genuine conversation punctuated by thoughtful dialogue. There’s a difference here between thoughtful dialogue and trying to, “stump” your subject. Your aim should be the former.

To that end, questions should be asked directly using simple words. Now is not the time to show off your command of the English language or provide ten different qualifiers for why you’re asking your question.

Formulate your question simply, ask it directly, and then listen.

Conclusion

Asking good questions is a leadership superpower and the ultimate life hack for curious people. In your own journey to ask better questions:

• Be a great listener

• Ask common questions in uncommon ways

• Ask questions like a fan not a journalist

• Use simple words, and ask your questions directly

See y’all next week.