Most leaders say they want people who challenge them. Then someone does, and we find out whether they meant it.

In sales, that gap gets expensive. Reps want the deal to close. Managers want to hit the number. The VP has a forecast to defend. The CEO wants predictability. Nobody has to be lying for everyone to start believing the better version of the story.

That's why someone needs to be able to say, "I don't think this deal is real."

Nobody announces that disagreement isn't welcome. Leaders teach it in smaller ways. A manager questions the forecast and spends ten minutes proving they aren't being negative. A rep flags a product gap and gets told to stop making excuses. Someone pushes back on the CEO's favorite idea, and everyone watches what happens next.

People learn quickly. They notice which questions get considered and which ones irritate the boss. They notice whether bad news gets examined or pinned on the person who brought it forward. Eventually, they adjust. They keep talking, but they stop saying anything risky.

And that's where leaders can get fooled.

A quiet room can look like an aligned team. A clean forecast can look like confidence. But if the first time leadership learns the truth is when the quarter closes, you don't just have a forecasting problem. You have a candor problem.

The higher you go, the easier this becomes to miss. A rep may tell another rep exactly why the new process isn't working. By the time that information reaches senior leadership, the sharp edges have been softened. People aren't necessarily being dishonest. They're thinking about how the news will land with someone who has influence over their career.

That's also why "My door is always open" doesn't mean much by itself. Your reaction matters more. If someone challenges your thinking, do you get curious or start defending yourself? When bad news arrives, do you examine it or immediately ask who screwed up?

And when someone changes your mind, do you admit it?

You hired smart people because they know things you don't. If they never change your mind, you're paying for an audience.

None of this means every decision becomes a debate. Someone still has to make the call, and sometimes that person is you.

The goal isn't unanimous agreement. It's making sure the uncomfortable facts and strongest arguments are heard before the decision gets made. A good team can disagree about what should happen and still move forward once the decision is made.

People don't need to win every argument to keep speaking up. They need to know that telling you what they actually think won't cost them standing with you.

That's a much healthier standard than agreement.

The responsibility isn't only on the person in charge. If you're a rep, manager, or future leader, learning how to challenge someone well is part of learning how to lead.

Don't just object. Bring information.

The most valuable disagreement often comes when everyone else has already accepted the premise. Maybe leadership believes the answer to a missed quarter is more pipeline, but you're seeing plenty of pipeline and a much bigger problem with conversion. “I don't think we have a pipeline problem. I think we have a conversion problem, and adding more opportunities to the top won't fix what's happening further down.”

The same principle works beyond sales. Bring the facts, explain your reasoning, and be willing to challenge the diagnosis, not just the decision. Then be willing to change your own mind if someone else has better information.

On your next forecast call or team meeting, try changing the order of the conversation. Ask what other people see before you tell them what you think. Once the boss gives an opinion, it gets much harder to know whether the agreement that follows is real.

Then ask one question:

And listen.

Pay attention to who challenges you. The person who pushes back most often may be giving you information everyone else has learned to hold back. The person who never disagrees may genuinely agree with you, but don't assume it.

If every meeting ends with everyone agreeing, get curious about why.

We return to this idea often on On the Shoulders of Giants because some of the most valuable information you'll receive as a leader will contradict what you already believe. If you want better decisions, you need people around you who are willing to tell you what they actually see.

Whether you prefer to watch or listen, we'd love to have you join the conversation.

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Built. Not Born. is for people who want to lead better, whether you're running an organization, managing your first team, or learning how to lead from where you are today. If someone came to mind while reading this, send it to them. And if someone forwarded this issue to you, subscribe and join us each week.

It’s easy to say you want people who challenge you. The real test comes when someone questions an idea you believe in, a decision you’ve already made, or an assumption you’re convinced is right. How you respond in that moment matters because people are paying attention. They’re deciding whether disagreement leads to a better conversation or simply makes their job harder.

Poor leaders hurt people. Great leaders change lives.

Until next week, keep building.

- Jeff Wells