Understanding: Two Ways Leaders Can Connect Better with Their Teams
I broke ChatGPT the other day.
Well—I didn’t actually break it, but I might have given it PTSD. I gave it a prompt it simply could not answer.
Usually, whenever I prompt it, I get an answer almost immediately. It’s astonishing how quickly it can access information, process it, and produce high-quality output. It has become an outstanding tool in my daily work.
But this time was different.
I wrote the prompt in plain English—as I always do since I don’t speak “coding”—and asked my usual follow-up: Do you have any questions? Do you need anything else from me before getting started? It asked a few clarifying questions. Nothing unusual. Then it asked if I was ready for it to proceed. I said yes.
And then… nothing.
For hours.
After a while, I followed up. It reassured me it was still working and would reply in its next message.
More hours passed. Still nothing.
My request wasn’t complicated. I simply wanted it to ingest some text and extract the top insights. I’ve done that hundreds of times with zero delay. Why was it choking now?
So I tried an experiment: I opened a new chat window and made the exact same request.
The response came instantly.
The Problem
ChatGPT knows a lot about me at this point—what M2 is, what projects I’m juggling, how I write, how I speak, what I like, what I don't, and what I want from it. That’s by design. I’ve taught it all those things because I want it to act like a thinking partner, not a digital vending machine.
But that personalization comes with a cost.
When I asked the original chat why it struggled, here’s part of what it told me (paraphrased):
This conversation has accumulated a massive amount of Model Set Context.
The model must cross-check every new answer against months of history.
Even simple tasks become heavy when the model tries to honor all of that context at once.
Long threads with multiple simultaneous projects can cause overthinking, hesitation, or paralysis.
A new chat has none of that baggage, so it answers quickly.
In other words, my prompt didn’t break it.
My history with it did.
I accidentally asked it to emulate my thinking with too much precision. And the more it tried to “be me,” the more overwhelmed it became.
Why tell you all this?
Because as powerful as AI is, as helpful and advanced as it has become, it is still just a tool. It tries to comprehend my requests. It attempts to replicate my preferences. But when it comes to truly understanding me—that’s where it failed.
And that’s what brings us to leadership.
Two Essential Aspects of Understanding
To truly connect with people, leaders must practice two different—but complementary—forms of understanding: empathy and perspective-taking.
1. Empathy
I’m writing this in early December 2025. As best I can tell from quick research (and a lot of hands-on experience), AI can imitate empathy, but it cannot actually experience it.
Empathy requires two things:
Understanding another person
Sharing their feelings
AI can mimic the first to some degree. But it cannot do the second. Machines do not feel. They can predict emotional patterns, but they can’t experience emotion the way humans do.
Leaders, on the other hand, must feel.
John Maxwell puts it beautifully: “People don’t care how much you know until they know how much you care.”
Competence matters. But trust grows when people sense you understand how they feel—and that you care enough to respond with compassion.
Empathy is one of the most powerful trust-building tools a leader has.
2. Perspective-Taking
Perspective-taking is different from empathy.
If empathy is emotional, perspective-taking is cognitive.
It’s the ability to step outside your own experience and mentally view a situation from someone else’s point of view—how they might be interpreting it, what pressures they might be facing, how their background shapes their thinking.
Perspective-taking doesn’t require emotional labor.
It’s not “feeling with” someone; it’s “thinking with” them.
Because of that, leaders often find it easier to sustain. It helps them avoid over-empathizing or slipping into “fixing mode.” And interestingly, AI is fairly good at perspective-taking—it can consider different viewpoints, identify possible interpretations, and help leaders better understand how others might be seeing an issue.
Empathy makes leaders relatable.
Perspective-taking makes them wise.
Together, they make leaders effective.
Practical Application for Leaders
Understanding your people isn’t a soft skill—it’s a strategic advantage. Empathy and perspective-taking aren’t abstract concepts; they’re daily practices that help leaders build trust, reduce conflict, and create environments where people do their best work. Here are three practical ways to put them into action:
1. Ask One More Question
Most leaders stop after the first answer, which is usually the safest and least revealing.
Try this instead:
“Tell me more.”
“What am I still missing?”
That extra question signals genuine interest—and often uncovers the real issue.
2. Schedule One Meeting per Month Focused Only on Understanding
Not performance.
Not metrics.
Not updates.
Just understanding.
A simple prompt:
“What’s something I should know right now that would help me lead you better?”
You might be surprised by what surfaces when you carve out protected space for honest dialogue.
3. Use AI as a Perspective-Enhancer, Not a Relationship Substitute
AI can help leaders imagine how different groups might interpret a decision or message.
Try asking your AI tool:
“How might frontline employees react to this announcement?”
“What concerns might high performers have about this policy change?”
This improves communication and reduces blind spots—but still requires you to show up as a human.
Final Thoughts
AI is no longer “the future.” It’s here. And yes, it will reshape the workforce—especially roles built on routine or predictable tasks.
But no matter how advanced technology becomes, people still need people to lead them.
Connection is human.
Understanding is human.
Trust is human.
And those are the things leadership is built on.
If you want to become a more effective—and more HUMAN—leader, practice the twin skills of empathy and perspective-taking. They will help you connect more deeply, lead more confidently, and build teams that know they matter.
