How to Lead People You Don’t Understand (Yet)

The room was warm. Not just the thermostat-warm of a mid-morning meeting, but the kind of Midwest thick, sticky, muggy, uncomfortable warmth that hinted at a growing, quiet tension. Dana sat at the head of the table, her notepad untouched, her smile fragile. Across from her, Jamie leaned back, arms crossed, offering nothing but silence in response to her fourth attempt at connection. She took a sip of tepid coffee, willing it to soothe the silence. It didn’t.

If you’ve ever led a team, you know this moment. You’re in charge of someone you just can’t read. Their motivations, their reactions, even their silence feels like a puzzle with pieces missing. And you’re left holding the bag, wondering if the picture on the outside even matches what’s inside.

So, what do you do when you’re tasked with leading someone you don’t understand? Someone whose worldview, background, communication style, or even work habits are so different from yours that you feel like you're speaking two different languages.

Let me walk you through it—not from a pedestal of perfection, but from the well-worn path of experience, missteps, learning, and coaching hundreds of leaders through this exact scenario.

Step One: Drop the Assumption That You Should Already Understand Them

Here’s the truth: leadership is not about mind-reading.

Too often, we enter new leadership dynamics with a silent expectation that we should just "get" people. That good leaders are natural people readers. That connection should be instant, intuitive, even easy.

It’s not.

Understanding people—really understanding them—takes time. It requires curiosity, humility, and above all, intentional effort. So, before you launch into trying to "fix" the lack of connection, check in with yourself: are you judging the distance, or are you exploring it?

That mindset shift alone can change everything.

Step Two: Get Curious Before You Get Critical

Imagine you’re watching a movie, but you started halfway in. Characters are acting in ways that make no sense, and you're trying to guess motivations without the context. That's what it's like to lead someone without understanding their backstory.

Your job? Rewind the tape.

Start with questions, not conclusions. Questions like:

• What do they care about?

• How do they define success?

• What drains them?

• What lights them up?

One executive I coached—let's call him Maurice—was frustrated with a new team member who always challenged his ideas in meetings. At first, Maurice saw her as combative, even disrespectful. But when he finally asked what was driving her, she said, "I thought I was doing what you wanted—you said you wanted critical thinking and honest feedback."

That one insight turned their relationship around. She wasn't challenging him; she was trying to support his vision. But he couldn't see that until he got curious.

Step Three: Observe, Don’t Just Listen

People speak in more than words.

Pay attention to body language, pacing, energy shifts, vocal tone. Does your team member lean forward when discussing certain projects? Do they go quiet when the topic turns to recognition or competition?

Understanding often lives in the subtext. The way someone enters a room. The cadence of their speech. The notes they take. The moments they flinch.

I once worked with a manager, Alisha, who felt her direct report was disengaged. But when I observed their interactions, I noticed the employee always perked up during brainstorming sessions but faded during one-on-ones. We shifted their check-ins to be more collaborative, using whiteboards and visual thinking tools. The result? A dramatic shift in engagement—and not because the employee changed, but because the approach did.

Step Four: Learn Their Language

No, not just English. Their motivational language.

Some people thrive on recognition. Others on autonomy. Some want to be in the spotlight; others want to quietly master a skill. As a leader, your ability to adapt to these preferences can make or break a working relationship.

There are tools that can help—Color Code, DISC, StrengthsFinder, even informal values exercises. But the best tool? Observation + conversation.

Try asking: "What’s one thing that makes you feel really seen at work?" or "Can you tell me about a time you felt most successful in your last job?"

These aren’t trick questions. They’re doorways.

Step Five: Build Psychological Safety One Brick at a Time

People don’t open up when they don’t feel safe.

If someone doesn’t feel seen, heard, or respected, they’re unlikely to show you their full self. So your job as a leader is to build a foundation of trust—slowly, intentionally, and consistently.

This looks like:

• Keeping your word, even on small things.

• Owning your mistakes.

• Inviting feedback about your leadership.

• Protecting your team’s dignity, especially when things go sideways.

I coached a Director of Food & Beverage who didn’t understand why her staff was guarded around her. She had inherited the team from a leader who led through fear. Once she realized that, she made a point to over-communicate safety: celebrating small wins, making space for vulnerability, and showing up consistently.

Trust didn’t appear overnight. But it did appear.

Step Six: Share First

If you want someone to be open with you, go first.

Modeling vulnerability is one of the most underused leadership tools out there. When you share a challenge, a mistake, or even a moment of doubt, you create space for others to do the same.

This doesn’t mean oversharing or turning every meeting into a therapy session. It means being human.

• "I remember when I started in this role, I didn’t feel confident either."

  
  

• "This project feels a little ambiguous, and I’m still figuring out the best way to approach it."

These moments invite connection. They send the message: you don’t have to be perfect to be valued.

Step Seven: Commit to the Long Game

Understanding isn’t an event. It’s a practice.

Leading someone you don’t understand yet means embracing the journey of discovery.

It means showing up with curiosity today, tomorrow, and the day after that.

It means asking again. Listening deeper. Changing your approach when it doesn’t land. Owning the missteps and trying again.

The best leaders I know didn’t become masters of empathy by accident. They worked at it. They got it wrong. They stayed in the discomfort of "I don’t know yet" long enough to actually learn.

Final Thoughts: The Power of "Yet"

There’s a small word that makes all the difference here: yet.

"I don’t understand them." vs. "I don’t understand them yet."

One is a wall. The other is a door.

Every time you choose yet, you leave space for growth. You make room for possibility. You lead not just from authority, but from humanity.

So, when you find yourself across the table from someone whose behavior feels foreign, whose silence feels loaded, whose energy feels disconnected—don’t pull away.

Lean in.

Ask a better question. Offer a piece of your story. Stay in the room.

Because the leaders who connect most deeply—who build the most powerful, high-performing teams—aren’t the ones who understand everyone instantly.

They’re the ones who choose to understand.

And they start by saying:

"I don’t get it…yet. But I’m here. And I’m not going anywhere."