If you knew you couldn’t fail, how would you lead? 

It’s the kind of question that unlocks something. 

It’s not just motivational fluff. It’s what coaching expert Nancy Kline calls an Incisive Question™—a question designed to remove limiting assumptions and free up clear, creative thinking. 

And it’s something you can use with your team.  

Especially when you’re juggling client demands and deadlines, and you don’t have time to take over every tricky task or presentation. 

Here’s how it works in practice. 

A familiar scenario 

Let’s say a team member comes to you in a panic. 

They’ve got a high-stakes presentation, and they’re convinced they’re going to mess it up.  

They want you to do it instead. 

Now, you could step in. Or reassure them. Tell them they’ve done this before, that they’ll be fine. But chances are, they’ll still freeze—or you’ll end up doing it anyway. 

That’s because fear doesn’t respond well to logic or instruction. But it does respond to the right kind of question. 

Swap the assumption 

What your team member is really saying is, “If I do this, I’ll fail.” 

That’s the assumption. 

Now, flip it and build a question around a more liberating belief. For example: 

“If you knew you couldn’t mess this up, how would you approach the presentation?” 

You’re not telling them what to do. You’re inviting them to think and you’re showing you believe in their ability to work it out. Which is exactly what they need in that moment. 

Use it on yourself too 

This approach works brilliantly as a self-coaching tool. The next time you’re stuck or spiralling, ask yourself: 

What assumption am I making that’s stopping me? 

What would be a more helpful, true assumption? 

What’s the question I need to ask? 

Here are some examples: 

• If you knew you were trusted, how would you proceed? 
• If you knew you were valued, what would you do next? 
• If you knew you were ready, how would you show up? 

Try it. And notice what shifts. 

The takeaway 

Coaching doesn’t have to be time-consuming or complicated. Sometimes it’s just asking one question that creates the space for someone to move forward. 

So next time a team member says, “I can’t”, try responding with: 

“If you knew you could, what would you do?” 

Till next time 

Jude