by: Sim Sitkin

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Many leaders believe they understand the people they work with. But the real question is not whether leaders think they understand—it’s whether the people around them feel understood.

That distinction matters because understanding is one of the least discussed parts of leadership, yet one of the most important.

Without understanding, even leaders with good intentions can make poor decisions. They may assign work badly. They may overlook strengths. They may misread motivation. They may miss what kind of support, feedback, or development would actually help.

Understanding shapes all of that.

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Understanding Is Often the Missing Piece

When people talk about leadership relationships, they often focus on concern and fairness.

Those matter a great deal. But understanding is often the missing piece.

If you do not really understand someone, then even if you care about them, you may still make choices that do not serve them well. You may think you are helping when you are actually misreading what they need, what they value, or what they are capable of.

That is why understanding is so important to trust.

If you do not understand me, how can I trust you to evaluate me fairly, assign me wisely, or help me develop?

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Surface Knowledge Is Not Real Understanding

Real understanding goes beyond knowing someone’s title, responsibilities, or resume.

It includes knowing their strengths and weaknesses, their experience, their priorities, their values, and what parts of the work energize or frustrate them.

  • Do you know what they already know how to do?
  • Do you know where they are still developing?
  • Do you know what they care about?
  • Do you know what they are motivated by?
  • Do you know what parts of the work they find meaningful and what parts they find draining?

That is the kind of understanding we need if we want to lead people well.

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Misunderstanding Leads to Poor Decisions

When we do not understand people, we make poor leadership choices without realizing it.

We may overexplain things to someone who is already highly capable. We may assign someone work that does not fit their strengths. We may fail to notice a development need or fail to recognize a particular talent that is being underused.

Or we may misunderstand someone’s priorities and assume that what motivates one person will motivate another.

That is where trust starts to erode.

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People Need to Know They Are Understood

It is not enough for a leader to believe they understand someone. The other person has to feel understood.

Without that feeling, people often protect themselves. They hide weaknesses, disguise preferences, or pretend to be more comfortable or confident than they really are.

But when people genuinely feel understood, they can be more honest. They can say things like:

  • “You know, and I know, that I’m not strong in this area yet.”
  • “This is the part of the work where I add the most value.”
  • “I’d like help developing here.”

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Respect Matters Most When Imperfections Are Visible

Understanding, by itself, is not enough. It has to be joined with respect.

If you only respect me when you see the polished version of me, that is not real respect. Real respect means you know my weaknesses and still value me as a person. You know the disagreements and still treat me with dignity. You know where I differ from you and still respect me.

That matters because otherwise people feel they must hide the parts of themselves that are imperfect or different. And when people feel they have to hide, trust goes down.

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Differences Do Not Have to Undermine Respect

Leaders and team members do not have to agree about everything in order to work together well. They may have different priorities, different styles, or different beliefs about how things should be done.

That does not have to erode trust. In fact, when people know they are understood and respected, they are often much more able to put those differences on the table and work through them openly. They can disagree honestly without feeling dismissed.

That is one reason understanding is so powerful. It makes direct, realistic communication much more possible.

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The Bottom Line

Leadership relationships become stronger when people feel truly understood.

That means understood in a practical sense: their strengths, weaknesses, values, priorities, and perspectives are known. And it means understood in a relational sense: they know that understanding is joined with respect.

Understanding is not a soft extra. 

It shapes how leaders assign work, evaluate performance, support development, and navigate differences. When people know they are understood and respected, they are far more likely to communicate openly and work through challenges constructively.