A client and I were talking recently about productive challenge. Her organization is doing the Dare to Lead work, and they’re making a real investment in creating a culture where people are willing to challenge one another.
By productive challenge, I mean the willingness to question a decision, name a concern, or offer a different point of view while there is still time for it to make the work better. It is disagreement in service of the mission, and it depends on people believing they can tell the truth without paying for it later.
We can announce that we want productive challenge. We can teach the language and build it into meetings. But people decide whether we really mean it in much smaller moments.
I learned this a few weeks into command in Iraq.
My organization was responsible for morale, welfare, and recreation for roughly 25,000 people, along with housing, feeding, fitness, laundry, and a list of other things I was still learning. That included the swimming pool.
I had closed the pool during my first week in command, which made me wildly unpopular. The hate mail was immediate and thorough.
Honestly, I understood it. People were deployed far from home, in a place where we were still losing people regularly. Even inside the wire, fear was part of the environment. An hour at the pool offered a little bit of normalcy in a place where very little felt normal.
When we reopened it, women were required to wear one-piece swimsuits. At one of my first commander’s calls, I stood in front of the organization and said no question was off the table.
A young airman stood up and asked why bikinis had been banned at the pool.
My immediate thought was, Seriously? This is where we’re going?
I was responsible for taking care of 25,000 people in a war zone, and he wanted to talk about bikinis. Everything in me wanted to tell him we had serious things to discuss and ask him to give me a real question.
But I had just said no question was off the table, and everyone in that room was now watching to see whether I meant it only for questions I considered worthy.
So I asked him, “What about it bothers you?”
I want to be honest about this. I wasn’t being especially wise or generous. I was curious, and I didn’t have a good answer. I was brand new. The Army had asked us to change the policy, and I didn’t fully understand why.
As we kept talking, the answer began to change. This wasn’t really about bikinis. Things kept changing, and no one told them why. They felt like they were navigating in the dark. Decisions were happening around them, and they didn’t feel trusted enough to understand them. In an environment already filled with uncertainty and fear, the pool policy had become the place where all of that frustration landed.
I couldn’t reverse the policy. The bikinis did not make a triumphant return. But I could stay with the question long enough to understand what was underneath it.
By the end of the conversation, I don’t think anyone remembered that we had started with a swimming pool.
Where a Speak-Up Culture Gets Built
That is where productive challenge is built. Formal programs give people language and practice. Leaders make that language credible in the everyday moments when someone raises a concern awkwardly, emotionally, or through a question that seems far too small for the moment.
People don’t always begin with the most important truth. Sometimes they begin with the truth that feels safest to test. A policy. A scheduling change. A complaint that sounds petty. They’re watching what happens next.
A culture of productive challenge allows people to question a decision without first finding the perfect words. It allows a leader to remain curious without surrendering authority. You can keep the decision and still honor the question.
One Thing to Try This Week
This week, when someone asks something that feels beneath the moment, notice how quickly you want to sort it into “worth my time” or “not worth my time.” Ask, “What about this bothers you?” Then stay long enough for the second answer.
The decision may stay exactly where it is. Trust can still grow because the question was taken seriously.
Your people learn whether challenge is truly welcome from what you do with the questions you think are a waste of time.
P.S. This is the work I do in keynotes and leadership sessions.
