Is Challenge a Privilege or a Responsibility?

Nate Brown said in our Big Boss Biscuits conversation, “You have to earn the right to challenge.”

I understand the sentiment. In many workplaces, especially in the U.S., challenge is something you grow into. You build credibility, you learn the dynamics, and over time, you’re given a bit more space to question things.

But my perspective on that is… well, more German. I don’t think challenging should be treated as a reward you get only after you prove to be agreeable, trustworthy, or caring. It’s not something optional or something that can wait. The mere fact that someone speaks up and wants something to change should be testament enough that they care about the outcome.

I grew up in Germany, and culturally, challenge isn’t something you earn later. It’s something you’re expected to bring from the beginning of your education. Not in a confrontational way, but as a contribution. As part of how you participate responsibly in a system that relies on people thinking, not just agreeing, and especially not just following. Been there, done that, didn’t go too well, did it?

See, a mindset that challenges doesn’t come out of nowhere. It’s shaped by history, by a very real understanding of what can happen when authority goes unquestioned for too long. So over time, challenging ideas—especially those coming from leadership—became less about boldness and more about duty.

So challenge isn’t a personality trait. It’s a responsibility.

You don’t bring it once you feel safe enough. You bring it because the situation requires it.

And if you’ve ever watched a German political interview, you’ll see this in action. A journalist will stop a chancellor mid-answer and say, “That didn’t address the question,” and then ask it again—more directly. No drama. No outrage. Just… insistence. It’s understood that leadership includes being challenged clearly, sometimes uncomfortably, and often in public.

Now take that expectation and place it inside most organizations.

That’s where things get interesting.

Challenge vs. Alignment

Many organizations say they value challenge. But what they consistently reward is agreement—well-articulated, thoughtful, respectful agreement, but agreement nonetheless.

People notice that pattern quickly.

So they adapt. They wait. They choose their moments carefully. They ask themselves, “Is this really my place to say something yet?” By the time the answer becomes “yes,” the decision has already moved on.

In other words, people hesitate. They wait until they feel safe, senior, or certain enough. By then, the moment where challenge could have made a real difference has often passed.

You don’t get poor intentions in those environments. You get cautious ones. And cautious thinking rarely leads to great decisions.

Strong leadership, at least in my experience, isn’t about having the best answers in the room. It’s about creating a room where answers are tested before they become actions. It’s about making sure ideas are tested before they turn into decisions.

Steve Jobs was actually known for this—despite his reputation for being, let’s say, intense.

At Apple, ideas didn’t survive because they sounded good in a meeting. They survived because they could withstand pressure. Jobs would challenge assumptions, push teams to defend their thinking, and often ask the same question from five different angles until the idea either held up—or fell apart.

It wasn’t always comfortable. In fact, it was often the opposite.

The intent wasn’t to win the room. It was to make the product better.

Of course, that sounds great in theory. In practice, it’s more complicated. I learned that firsthand. In one of my previous roles, I joined a company as the leader of Client Experience. I was new, still building relationships, still understanding how things worked.

Early on, a sales executive proposed a new process to reduce churn. A reasonable goal. No one argues with wanting to keep customers.

But when I looked closer, the situation didn’t quite match the diagnosis. What I saw wasn’t primarily a churn issue. It looked more like an adoption gap. Clients completed onboarding, gained access, and then did not actively use the product. There was a drop-off between “ready” and “engaged.”

So instead of jumping into solution mode, I suggested we pause and get clearer on the problem: Map the client journey. Look at where onboarding might be falling short. Understand how Sales and Client Success were handing off clients. And importantly, look at the data behind the assumptions we were making. Or, as it turned out, the lack of data.

When I asked where certain numbers came from, there wasn’t a clear answer. We didn’t yet have dashboards, shared metrics, or a strong data foundation. The proposal was built more on intuition than evidence.

So I offered a different framing: what if we’re not solving churn, but conversion—from onboarding to active usage? And what if we measured that before redesigning a process?

Same intention. Better outcomes. Just a different starting point.

And still, it didn’t land well.

The sales executive felt undermined. From his perspective, I wasn’t strengthening, aka agreeing with the idea; I was questioning it in a way that felt personal.

From my perspective, I was trying to ensure we were solving the right problem before committing time and resources to the wrong one.

That gap is where most of the tension around challenge lives.

The Gap

This is where the distinction shows up: there’s a difference between challenging to improve and challenging to prove something.

One opens a conversation. The other closes it.

And here’s the uncomfortable part: even when your intent is to improve, it doesn’t automatically feel that way to the other person—especially when trust hasn’t been established yet.

Which is exactly why I don’t believe challenge should depend on trust.

At least not in the way we often think about it.

Yes, trust influences how things are said and how they’re heard. But it shouldn’t be the gatekeeper for whether challenge is allowed. Especially not in leadership. Because the more senior you are, the less direct connection you have to most people in your organization.

A CEO, for example, won’t have a personal rapport with the majority of their company. They won’t have built trust through frequent interaction. In many cases, they may never have spoken directly to the people closest to the actual problems.

And yet—those are exactly the people they need to hear from.

So if challenge is only welcomed from those you know and trust, you’ve unintentionally created a system where critical insights never reach you. Not because people don’t care. But because they’re paying attention to what feels safe.

Leadership at that level isn’t just about setting direction. It’s about creating access to truth, to perspectives, and ideas that don’t naturally rise through hierarchy or even domain expertise.

And those perspectives won’t always come neatly packaged. They won’t always come from familiar voices. Sometimes they’ll come from someone you’ve never met, phrased a bit too directly, raising something you hadn’t considered.

The question isn’t whether they earned the right to say it, it’s whether you’re willing to hear it.

The Right Behavior To Invite Challenge

When someone challenges you without a relationship in place, that’s not casual behavior. That’s a risk for them. And how you respond in that moment sets the tone far beyond that single interaction.

If the response is defensive or dismissive, people notice. Maybe quietly, but consistently. And over time, they adjust. They speak less. They filter more. Eventually, they stop raising things altogether.

If the response is open—even if it’s just a pause and a genuine “tell me more”—you create a different pattern. One where challenge isn’t reserved for the few who’ve earned it, but expected from anyone who sees something worth questioning.

That’s how you build organizations that actually think, problem-solve together, create stronger products, and achieve successful outcomes. It may not always be easy or comfortable, but it will make any organization stronger.

And sure, there’s responsibility on both sides. If you’re the one challenging, your intent matters—and so does your delivery. This isn’t about being blunt for the sake of it. It’s about contributing to a better outcome, not winning a moment.

But if you’re leading, the heavier responsibility sits with you — to make the challenge possible before it feels comfortable. Before trust is fully built. Before the message is perfectly delivered.

Because if no one is challenging you, it doesn’t mean everything is working. It usually means people have learned that it’s safer not to.

And that’s not alignment. That’s silent followership.