For most of my adult life, I have experienced leadership from the person-in-charge seat. More than 20 years as a CEO, along with years as a head basketball coach, meant I was usually the one setting the vision, building the game plan and deciding how we were going to get there.
Recently, that changed when I became an assistant coach, and I didn’t expect the experience to teach me this much about being a CEO. As a head coach, you have information other people don’t have. The reasons behind how practice is structured and what the game plan is supposed to accomplish are clear because you helped create them. You have also been part of conversations and spent time thinking through decisions that the rest of the staff never experienced.
Being an assistant has allowed me to experience leadership from a different seat. I am learning how much I value clear communication, intentionality and the opportunity to debrief. Understanding what we are doing matters to me, but I also want to understand why we are doing it. Afterward, I want the opportunity to talk about what worked, what didn’t and what we need to adjust.
Something else has surprised me. When communication isn’t clear or consistent, I can feel myself starting to disconnect. It isn’t because I don’t care. In some ways, it is because I care so much and want to contribute. But when you aren’t sure where you fit, what the plan is or whether your perspective is wanted, something starts to change. You ask fewer questions. Maybe you offer fewer ideas. Eventually, you can find yourself waiting to be told what to do.
That has made me reconsider some of the people I have led over the years. What looked like disengagement from my chair might have felt completely different from theirs. Maybe someone wasn’t clear about what I wanted, or I expected ownership without giving them enough information or authority to really own anything. Sitting in this chair has made me wonder how often I interpreted the behavior without understanding what was underneath it.
The more I work with leaders and executive teams, while also experiencing leadership from this different seat, the more I realize how many leadership problems are really communication problems. Most leaders know how to talk, but that isn’t the same thing as knowing how to communicate.
Good communication requires listening, explaining and asking questions. Sometimes you have to say something more than once. What matters isn’t only what you thought you said, but what the other person actually heard. There are moments when leadership requires telling people something they don’t want to hear and others when we need to be willing to hear something we don’t want to hear.
All of that shapes culture, including the things we don’t say. Leave a decision unexplained and people will create their own explanation. Unclear expectations force employees to guess, while bad news that isn’t communicated usually finds its way through the organization anyway. Avoiding a difficult conversation doesn’t make the frustration disappear either. It usually moves somewhere else.
Eventually, the real conversation starts happening after the meeting instead of during it. Leaders tend to judge communication by what we said, while employees experience communication by what they understood.
There is research behind this too. Gallup’s 2026 workplace research asked workers what would help them have greater clarity about what was expected of them. Thirty-five percent said better communication, by far the most common answer. The next highest response, more direction from leadership, was only seven percent.
That makes sense to me because I have seen what happens when people don’t have clarity. We can assume they aren’t bought in or aren’t executing when the real problem is that they don’t completely understand what we want them to execute. Before deciding someone doesn’t understand the strategy, I need to ask myself a question first: Did I communicate it well enough?
Communication can’t only be about whether people understand us. What people are willing to tell us matters just as much, and I think that gets harder the higher you rise.
People don’t always talk to the CEO the same way they talk to their coworkers. When somebody has influence over your salary, promotion or future in the organization, you choose your words a little more carefully. Criticism can get softened and bad news cleaned up before it reaches you. It doesn’t take long for people to figure out which subjects make the boss defensive and which things are probably better left unsaid.
A leader can eventually believe everything is going well simply because people have stopped telling them what isn’t. That is one reason I pay attention to the conversation after the meeting. Everybody agreeing with you in the room and disagreeing afterward is telling you something. So is a workplace where employees regularly learn important news through gossip. If people are willing to bring their problems to everybody except you, that is probably worth paying attention to as well.
It is easy to get frustrated when we believe people are talking behind our backs, and sometimes that frustration is fair. People have a responsibility to address problems directly. Leaders also have a responsibility to ask a harder question: Why couldn’t the real conversation happen in the room?
A healthy culture has to make room for people to tell the truth. That doesn’t mean everybody gets to say whatever they want however they want. Respect still matters, and leaders will make decisions people don’t like. Listening isn’t the same as agreeing with every criticism or turning every decision into a vote.
Disagreement isn’t automatically disrespect, though, and questions aren’t necessarily disloyalty. The person willing to tell me something I don’t want to hear may be helping me more than the person who agrees with everything I say.
Listening might actually be the part of communication leaders struggle with the most. In some meetings, the best thing we can do is stop explaining ourselves and ask another question. Maybe the quiet person needs room to talk, or perhaps the same concern has come from enough different people that we should pay attention. We don’t have to agree with everything we hear, but people should know they can tell us the truth without paying for it later.
None of that excuses poor performance, and communication is not solely the leader’s responsibility. People have a responsibility to ask questions, seek clarity and address problems directly too. But leadership requires enough curiosity to find out what is really happening before deciding we already know.
I used to think about communication mostly as a leadership skill. I am starting to see it as something bigger. Over time, the way we communicate becomes part of the culture we create because people are learning whether honesty is welcomed, disagreement is safe and difficult things can actually be said out loud.
The goal isn’t to stop people from having conversations when we aren’t around because they’re going to have them. What matters is whether the culture we’ve built allows the important conversations to happen when we are.
If the real conversation always starts after we leave the room, eventually we have to ask whether the problem is the people talking or the culture we’ve helped create.
