Grow Your Team with Challenge Questions Asked Well

I’m coaching a leader who is the resident expert in her field.  Like many leaders, she loves the industry and is a natural problem-solver. In fact, she is well-sought-out for her thinking and her expertise and is also a respected speaker.

She needs more time for strategic work, and she wants to delegate more to her team. Some of them are intimidated by her and they have a hard time stepping up. In Coaching, we talk about how she can grow her team members’ skills and teach them to trust their own thinking.

As always with coaching, we begin with self-awareness. We discuss her ways of listening. She typically listens for familiar signs that she can interpret for the speaker. She quickly sees patterns and assesses risks and possible outcomes. She points people in the right direction and tells them what to avoid. She has a brilliant, and busy, brain. She’s doing a lot of the thinking for others.

Listening differently is a skill to start with. More active listening means listening on two levels: the level of content (which she does so well) and the level of understanding. This is about understanding the speakers’ point of view. It means listening to what’s said and how it is said in equal measure. It requires suspending her executive brain and getting curious. Curious about the person’s way of thinking, feeling and behaving. Curious about what they are doing that supports their goals, and what they are doing that is getting in their way.

In this active listening mode, this leader is going to do something else that’s new.  She is now discerning when she wants to coach. She can do this anytime, by asking a “challenge question”.  The key is to ask it in a non-challenging way! These questions challenge the person to think and they help to reframe or widen their perspective. These are not the same as the challenges she has made in the past. Those questions were often delivered in frustration, challenging the “rightness or wrongness” of an action or decision. Or challenges the facts of the issue.

To grow her team members, my client begins to listen with curiousity. When a coaching moment arrives (a moment when they could grow or learn from their experience) she asks, gentle Challenge Questions:

  • What if there was another way?
  • What if you didn’t do that?
  • What if that wasn’t the whole truth?
  • What if you saw it differently?
  • Why would you want to do that?
  • Why is that so important?
  • Why is that the obvious choice?
  • What else is here?


Soon her team are gaining more than her technical knowledge, they are learning how to approach issues more broadly, and where to look for risks and opportunities. They are being coached by her.

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