How To Ask Tough Questions In Conference Calls


What’s the best way to ask the tough questions – especially in online meetings, conference calls etc?

Tough Questions: Like Juggling?Asking difficult questions can be a real challenge even in face-to-face meetings – and it often feels like the problems are multiplied when you’re meeting online.

But effective communication is essential for collaborative problem solving. And so, while it might seem scary to ask those tough questions, doing it well is a useful skill to master.

I’ve taught questioning skills online to hundreds of coaches and facilitators over the years. Here are my top tips.

Tip 1: Practice With Easier Questions First

People learn to juggle by throwing one ball, then two, then three: starting off with seven tends not to work well. Asking “How was your weekend?” is the equivalent of throwing one ball from hand to hand. The trick is to step it up to questions which are slightly harder for you to ask, and for people to answer: questions which force them to think.

For example, you might ask, “What were our top three successes this week?” or, “What’s an idea you’ve had about this that you’ve never mentioned before?”

Context is important, but it’s usually the case that “appreciative” questions, looking at the positive, require a bit more thought to answer than questions that address what’s gone wrong.

Gradually build your question-asking muscles until you feel almost – but not quite! – ready to ask the “meaning of life” questions. Then ask them anyway.

Tip 2: Notice The Feedback You Get

With juggling, feedback is difficult to miss: the ball drops to the floor. With questions, you need a bit more attention. And you can never ask the same question, of the same person, twice!

So, make sure you keep track of what happens.


  • What kinds of responses do you get? Words, or silence? Smiles, or funny looks?
  • What kinds of answers do you get? What you expected, or something else?
  • If you’re asking a group, who responds, and who doesn’t?
  • What are your feelings about asking the question? before you ask, as you ask, and afterwards?

Tip 3: Challenge Yourself To Sit With Silence

Here’s where it can get really tricky, particularly in conference calls.

What do you do when you ask a question and it’s greeted with silence?

Sitting with silence can be a real challenge, even for experienced facilitators in face-to-face meetings. But those experienced facilitators teach themselves to do it, because they know that silence is often where the big creative breakthroughs are born.

Silence allows many people to think, to make connections, and to come up with new ideas, in a way they can’t do when listening to others talking.

I recommend that you take the juggling approach once again. If you ask a question and nobody replies instantly, how long can you sit with the silence before asking another question, or requesting an answer from a named person, or giving your own opinion?

Five seconds? Ten? Twenty?

At what point do you start to worry that the line’s gone dead?

Could you invite the group to take an entire minute to reflect in silence before sharing their ideas?

Share Your Tips For Tough Questions

What have I missed? Please share your ideas for asking tough questions in the comments area below.

1 thought on “How To Ask Tough Questions In Conference Calls”

  1. Getting comfortable with silence and uncertainty takes time and does increase your confidence to speak and ask effective questions

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