If Everybody Keeps Misunderstanding You, Check Your Communication

I watched a video of a business owner complaining about having to explain the same things to his workers over and over again. According to him, he shows them what to do, tells them what to do, explains it repeatedly, and somehow they still ask questions or do it incorrectly. My first thought was pretty simple: if everybody who works for you keeps having the same issue, I think it might be time to investigate the common denominator. You.

Aside from the fact that owning a business that requires hiring, managing, and training people is not for everyone, leadership requires more than knowing how to perform a job yourself. Knowing something and knowing how to teach it are two completely different skills. You can be brilliant at what you do and still have no idea how to explain it in a way another person can use.

When I went to college to pursue my PhD in Industrial and Organizational Psychology, I learned something that I personally believe should be taught everywhere, including workplaces, schools, marriages, friendships, and families. The way we communicate should change depending on who is receiving the message. That does not mean changing what we mean. It means recognizing that the same delivery will not reach every person the same way.

Years ago, I managed a call center for a large transportation company in Orlando. I noticed that workers on the floor were frequently confused after receiving instructions, changes, or suggestions from management. It happened often enough that I became curious about what was actually going on, so I started paying attention to the pattern instead of assuming the workers simply were not getting it.

I quickly realized we did not have one problem. We had several different issues producing similar results. One group misunderstood what had been said. Another group was not fully listening. Yet another group heard the details but could not connect them to what they were expected to do. From the outside, all three could easily be labeled as, “The worker doesn’t get it,” when that explanation completely ignores how the message was delivered.

A company has different levels of responsibility, knowledge, experience, and access. The CEO speaks to board members differently than a floor manager speaks to call agents because those people are operating from completely different positions inside the same organization. That does not make one group smarter than another. It means their jobs require different context.

Imagine a CEO discussing quarterly projections, operational efficiency, market positioning, and long-term strategy with the board. Everyone in that room already has a certain amount of background knowledge. They know what happened last quarter, which decisions are being considered, why those decisions are on the table, and how everything connects to the larger operation. There is an entire layer of shared context sitting underneath that conversation.

Now take pieces of that discussion downstairs and deliver them to a call agent without translating any of that context. What the hell are they supposed to do with it? The worker does not necessarily lack intelligence or comprehension. They may simply lack the background necessary to understand what those words have to do with the job sitting in front of them.

Relevance changes as a message travels through the structure of a company. The higher someone moves within an organization, the more likely their conversations are to involve strategy, projections, policies, systems, and decisions affecting the entire operation. Someone working directly with customers needs to know how those decisions translate into what they are expected to do. Those are two different conversations about the exact same company.

That experience taught me to pay attention to the person standing on the other side of my words. Some people need the entire picture before individual instructions make sense. Another person wants the directions first and the explanation afterward. Some need to see the task performed. Others understand immediately but prefer having it written down so they can reference it later. A new hire may require background that a ten-year veteran automatically fills in without even realizing it.

Personality enters the equation too. One worker may comfortably interrupt a manager and say, “I have absolutely no idea what you mean.” Another may nod, walk away, and spend the next twenty minutes trying to figure it out because admitting confusion feels uncomfortable. Ironically, management may assume the quiet one understood everything simply because they did not ask a question.

This is where repeating yourself can become ridiculous. Saying the exact same thing louder, slower, or with increasing irritation does not magically turn it into a clearer explanation. Sometimes you are simply delivering the same ineffective message six different times and becoming annoyed that attempt number six produced the same result as attempt number one. At some point, change the delivery.

We need to normalize learning who we are dealing with. How does this person process what they hear? How familiar are they with the subject? How much background do they already have? Would an example help? Would written directions work better? Are your expectations actually clear, or are they only clear to you because you already know what you mean? That last one will get us every damn time.

We speak from inside our own heads while forgetting that nobody else lives there. We know what we intended, the tone we meant, the backstory, what happened yesterday, what we expect tomorrow, and where the conversation is supposed to end. Then we hand another person the middle of that mental conversation and become confused when they do not arrive at the conclusion we already reached.

And this definitely does not end when we clock out of work. The same thing happens in friendships, families, marriages, dating, parenting, and damn near every other relationship involving another human being. Think about how many arguments eventually arrive at some version of, “That’s not what I meant.” Well, what did you mean, and did you express it in a way the other person could reasonably interpret?

Relationships become especially complicated because people bring their histories into every conversation. One person prefers direct language while another softens everything. Someone needs time to process before responding, while their partner wants to resolve the issue immediately. One person uses silence to mean, “Give me a minute,” while the other interprets that same silence as, “I don’t care.” Nobody has to speak another language for two people to completely miss each other.

Fear complicates it even further. People avoid saying what they actually think because they fear rejection, confrontation, embarrassment, judgment, or hurting somebody’s feelings. Instead, they hint, soften, dance around the point, and expect the other person to read between lines that were never clearly written in the first place. Then both people walk away carrying completely different versions of the same conversation.

This is one reason I am so convinced that honesty without judgment needs to become normal. We need environments where people can say, “I don’t understand,” “I disagree,” “That approach doesn’t work for me,” “Can you explain that differently?” or “What you said is not what I heard,” without the conversation immediately becoming a battle. Honesty does not always tickle our ears, nor is it supposed to. Sometimes clarity is uncomfortable, but at least everybody knows what the hell was actually said.

The person speaking has a responsibility to express themselves clearly, while the person listening has a responsibility to pay attention, ask questions when clarification is needed, and be truthful about what they heard. Both people have to participate. Otherwise, we spend more time defending what we meant than making sure the meaning actually arrived.

This becomes especially important for leaders. If one worker repeatedly misunderstands instructions, evaluate what is happening with that individual. If an entire department repeatedly misunderstands instructions, evaluate the system being used to deliver them. If nearly everybody you manage seems confused by what you say, eventually you have to consider the possibility that you are extremely consistent at explaining yourself unclearly.

Repeating yourself is not automatic evidence that you explained something effectively the first time. Sometimes the answer is not another explanation using the same words. It is a different explanation designed for the person who actually has to receive it.

Learn how you express yourself and pay attention to how the people around you process what they hear. Ask questions instead of assuming comprehension. State expectations instead of expecting people to magically know them. Give context when context is necessary, be direct when directness is required, and allow people to tell you they misunderstood without making them regret admitting it.

Communication without the proper ingredients is a word salad expecting to be understood, correctly translated, and somehow turned into the exact result sitting inside your head. That is a hell of an expectation to place on another human being. If we want clearer results, perhaps the first question should not always be, “Why the hell don’t they understand me?” Sometimes we need to ask ourselves, “How am I explaining this?”

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