Tammy Lenski

How to ask questions like a pro

How to ask questions like a pro

Watch a good mediator at work and you’ll likely notice that good questions are her stock-in-trade. Watch a masterful negotiator and you’ll see the same. If you want better conflict resolution results, learn how to ask questions that shift thinking and prompt fresh ideas.

What people think of as the moment of discovery is really discovery of the question. - Jonas Salk


Marty Cooper, a young engineer at Motorola, had a new assignment: Lead the team that would build the next generation of car radiotelephones. It was the early 1970s and car telephones looked like they could become the next big advancement in telephone technology.

But Cooper didn’t just roll up his sleeves and get to work on the assignment given him.

Instead, he stepped back and asked a question: Why is it that when I want to call a person, I have to call a place?

That question changed not just telephony, but the world. After a century of telephones attached to wires, the two finally became untethered. On April 3, 1973, Cooper stood on Sixth Avenue in New York City and placed the first cell phone call in history. (Source)

The power of good questions for conflict resolution

When faced with a problem, it’s tempting to tell people what to do. It feels efficient and makes us feel important and useful. In emergencies, this is not necessarily a bad approach.

But if the goal is understanding and discovering not-yet-visible solutions and opportunities, telling will not help you reach it. If the goal is real buy-in and commitment to a solution, telling doesn’t work very well. With goals like these, you can lead the discovery of better solutions and influence lasting outcomes by learning to ask good questions in the right way and at the right time.

During conflict, good questions have great power:

  • They help you get information you’re missing — information that can lead to solutions you could not have imagined.
  • They invite deeper reflection about vexing problems — reflections that push you past pet solutions and obvious ideas that won’t do much for vexing problems.
  • They spark insight and creative thinking — the kinds of insights that enable new solutions and that make invisible options visible.
  • They break you out of old molds — the kinds of molds that aren’t doing the job and leave you in that hopeless place mediators label “impasse.”
  • They enable curiosity to replace certainty — an essential shift for the kind of problem-solving necessary when the usual solutions just aren’t working.

Learning how to ask questions fruitfully

Learning to ask questions that are useful at the right time is very learnable, though it takes practice. Here are some guidelines I’ve found useful in teaching mediators to ask better questions:

Ask one question at a time. This seems obvious, but watch television news interviews and you will see how frequently it isn’t done. Don’t fill the space, don’t blather on, don’t ask three questions when one good one will do.

Listen to the answer! It is important not to listen with your answer running; you don’t want to miss the answer because you’re inside your head. If you asked a question because you believe it has merit, then don’t waste it by missing the reply.

Don’t fill the silence. When you’ve asked a very good question, the other person may well need time to process it and consider their reply. This is a good thing! Good questions deserve good answers, so stay out of their way and let them think.

Ask the thing you really want to know. When I am teaching new and even experienced mediators to ask elegant questions, I will often hear a question that seems to beat around the bush. I’ll ask the mediator, What is it that you really want to know? and they’ll tell me very clearly. It is often not the question they asked and equally often, it is the question they really should have asked. It is possible to be kind and direct and clear all at the same time.

Try not to rely on a question queue. When you’re learning to ask good questions, it is tempting to jot down a series of things you want to ask and then work through those questions. This is a mistake. First, your conversation will start to sound more like an interrogation than an exploration, and this may put people off. More importantly, what you do or say next is born from their reply to your good question. You cannot know what your next question or response should be until you listen fully to what they’ve said. If you are curious enough, you will not be at a loss for good questions. If you fear you will not know the next right thing to say if you don’t have questions queued up, practice at home at the dinner table or at work at the lunch table. When you relax into it, it isn’t difficult.

Be transparent. Don’t try to hide the intention behind your question, though do try to have intent that isn’t manipulative. If you are wondering something inside your head, consider asking it. I find myself wondering… is language I find very honest and useful in moments like this.

Avoid multiple choice and run-on questions. They confuse and convolute. I’ve noticed that run-on questions tend to surface when the asker is nervous, so practice asking a simple, clear question and then stopping yourself. Multiple choice questions assume you know all the options — and you probably don’t. Don’t limit the response possibilities.

Avoid leading questions. Leading questions aren’t good questions; they’re statements or your solution masquerading as questions. They’re not artful and they come off as manipulative, degrading the discussion.

Remember that close-ended questions have use sometimes. We tend to value open-ended questions (questions that have multiple possible answers) over close-ended questions (questions that usually have one possible answer). That’s not a bad rule of thumb, but sometimes close-ended questions fill in a much-needed tidbit.

Timing is important. A wonderful question asked at the wrong time may yield little. They may not be ready to answer it, they may not trust you yet with the answer, they may not know the answer yet. I’ve found that the best way to develop good timing for good questions is to practice and be patient — your ability will improve with experience. And even then, you will not always get the timing right. People are complex.

See if you can figure out the missing question you haven’t thought to ask. You don’t have to be omnipotent. Sometimes they have the better question or the missing one and that is a very good thing. What question haven’t I asked can be very useful.

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