"How to Get Your Team to Challenge You (Without Forcing It)"

As leaders, we often say things like “Please push back on my ideas” or “I want to be challenged.”

But in practice, challenge rarely comes, because permission isn’t enough.
Power dynamics override good intentions.
People still wonder:

Do you really mean it? Will it cost me something if I do?

If you want challenge, you have to be intentional about for it.

Here’s how:

1. Expect challenge—don’t just allow it

“If no one disagrees with me, I assume we’re going to miss something.”
“Pressure-test this, I expect you to find the cracks.”

Make it part of the job, not a favour.

2. Handle pushback well, in the moment

“That’s a great catch, let’s dig into that.”
“Good challenge. Keep going.”

Everyone’s watching how you react. Stay curious, not defensive.

3. Add structure to make it easier

  • Run pre-mortems: “What could go wrong if we go with this?”
  • Assign a rotating “challenger” role in key meetings

Make disagreement part of the process, not a personal risk.

4. Invite critique of your thinking, not your authority

“Where’s my logic weakest?”
“What am I underestimating?”
“What would you do differently if this were your call?”

Lower your guard first to make it safe for others to follow.

5. Reward it when it happens

  • Celebrate when someone improves your thinking
  • Point out when challenge led to a better outcome
  • Show people that dissent is useful, not disloyal

It turns out you don’t get challenge when it’s allowed.​
​You get it when it’s safe, expected, and rewarded.

Be intentional about it. Model it. Thank people for it.
That’s how challenge becomes a team habit, not a leadership wish.

Until next time,
Dermot
​The Messy Middle

​

✉️ Enjoying The Messy Middle?​
If this sparked something useful, consider forwarding it to a colleague or friend, it might help them too.

If someone sent this email your way and you’d like to get it direct, you can sign up here.