Real talk. Most leaders say that they want challenge. In truth, very few actually do.

So, starting with the basics, permission to challenge isn’t about a nod in the company values statement. It’s the day-to-day lived and observed experience of those who dared to challenge in days gone by.

They love the idea of healthy debate… usually right up until the moment someone actually challenges them. It’s often a different story at that point; suddenly, it’s “not the right time,” or “we’ll discuss that offline,” or the more subtle side eye, or no response at all.

Food for thought.

Nail the fundamentals

• Safety first – People won’t risk challenging if the perception is that the outcome could result in them being personally targeted, punished, sidelined, or outright excluded. So, respond with appreciation. That single interaction will be replayed in people’s heads when they’re deciding whether to speak up subsequently.
• Everyone is heard – If only certain people get airtime (often those who think similarly and concur with the boss), everyone else learns pretty quickly to keep quiet.
• Visible follow-through – If challenges go into a black hole, never to be mentioned again, the process becomes performative, and the message is clear: your input is purely ornamental. Not operational.

Create the environment

• Be wrong – Be open to being wrong. Invite disagreement… and mean it! If you can’t appropriately handle being challenged, you have no right to outwardly expect or demand that others challenge you.
• Create the space – Build opportunity to challenge into your meetings. Create the role of devil’s advocate. Ask: “What might I/we be missing?” and as a group, try and ‘break’ an idea or plan. And if you ask for a different perspective, stay silent for long enough to hear it.
• Shine the light – Celebrate the act of speaking up, even if the idea doesn’t stick. Focus the attention on the intent behind the action, not solely on the outcome. Use it as a teachable moment and coach for future opportunities.

What destroys it in seconds

• Retaliation – Whether direct or indirect, nothing kills challenge faster than watching a colleague pay the price for speaking truth to power.
• Performative invitations – Asking for input when the decision has already been made? Insert face palm emoji!
• Favouritism – If only certain people can get away with pushing back, whilst others are disregarded, it’s blatantly a two-tier system.

Here’s the bottom line: permission to challenge is a trust contract. It’s not about slogans.

So, think about meetings you’ve been in. What happens in the split second after someone says, “I disagree.”

If you meet that moment with defensiveness? Contract broken.

If you meet it with curiosity and respect? Contract reinforced.