Build a Challenge Culture: The Secret to High-Trust, High-Performance Teams
Why the best leaders don’t just hire well or set goals—they design environments where challenge is expected, feedback flows, and the best ideas win.
One of the most under-appreciated leadership responsibilities is designing the right culture for your team. Most leaders focus on hiring the right people and setting the right goals. Both are critical, but incomplete. The missing piece is how you shape team culture where those people and goals collide.
A high-performing team is not just a collection of talented individuals. It’s a complete system of the right people in the right roles using the right systems making the right decisions and executing the right way.
One of the best ways to create a high performing team is creating a Challenge Culture.
What is a Challenge Culture?
A team environment where:
Expectations of each other are clear and high. The bar is set at excellent.
Feedback is direct, respectful, and continuous. Teams know where they stand and what to improve.
Debate is encouraged, not feared. Healthy conflict is centered around ideas and are never personalized.
Results are measured in real time. There’s a scoreboard, and everyone can see it.
Leaders coach. Coaching is about growth and improving and pushing to make it to the next level.
My Personal Leadership Rule
For years, I’ve told the teams I’ve led as well as the clients I am now coaching 1:1 to specifically challenge me. It’s ok to challenge me and it’s expected. I go further and say “If you aren’t challenging me and you aren’t challenging each other (respectfully), then we aren’t operating at our best.” Moreover, just because I’m your leader or coach doesn’t mean I’m always right. In fact, I can guarantee you that I’m wrong many times.
I remind everyone that one of our core team principles is: “Best ideas win.” But if no one is speaking up, then by definition, the best ideas aren’t surfacing. If people aren’t challenging what they believe to be incorrect, or wrong, or what could be improved, then we aren’t getting to our “Best”.
I remind my teams of a simple truth: none of us are ever 100% right. At best, we’re 80% right. Which means we are up to 20% wrong in our point of view or our decision-making. That 20% is where blind spots live. It’s where each of our personal biases live. I make it very clear that it’s every team member’s responsibility to respectfully challenge not only me but each other so our collective “20%” doesn’t drift into bad decisions or poor outcomes.
When this principle is lived every day, decision quality skyrockets. More importantly, respect is earned and team trust is created through transparency of being willing to challenge each other without fears of rocking the boat.
Why Challenge Matters
Without challenge, organizations drift into comfort and mediocrity. People mistake the leaders at the top or the loudest or most passionate person in the room as being “right” nearly all the time because of their title, their years of experience, or simply because they have a clear point of view.
The goal is not to create stress by challenging but rather to stress test the assumptions. Think of it like elite sports: the best teams practice harder than the game. The challenge in practice makes performance under pressure feel natural.
The CFO/COO Role: Architect of Challenge
For CFOs and COOs, your job isn’t just to “run the numbers” or “manage operations.” You are the Chief Architect of Team Culture. You ultimately decide:
What is measured (scoreboards).
How feedback is structured (reviews, 1:1s, pre and post mortems).
Where healthy conflict happens (leadership meetings, strategy debates).
When accountability is enforced (missed targets, underperformance).
Stress testing assumptions and course-correcting them.
When you are doing this right, your team stretches beyond their current perceived capabilities. You are now multiplying team potential.
How to Build a Challenge Culture:
Here’s a starter playbook: Yes, challenge even this playbook. It’s likely only 80% right for your team or your company culture. But it’s a start:
Set Standards of Excellence: Define excellence. Define winning (and losing). Define good behaviors vs bad behaviors.
Design the Scoreboard: If it’s important, measure it. If it’s measured, share it.
Coach Relentlessly: Recognize both progress as well as failed efforts where something was learned to make the next effort or attempt more successful.
Normalize Debate: Model respectful disagreement. Kill “silent consent.”
Close the Loop: Tie every plan, activity, and goal to the winning definition.
Final Thought
If you want to grow leaders, not just employees, build a challenge environment.
If you want to scale to the next level of great, build a challenge environment.
If you want to create consistently excellent team performance, build a challenge environment.
