I've had this conversation a hundred times.
A manager comes to me frustrated. Someone on their team is disengaged, checked out, doing the minimum. The manager has tried everything... or thinks they have. "I understand what they're going through," they say. "I've been in their position. I know how it feels."
Do they?
We've all been taught the same framework for empathy: put yourself in someone else's shoes. Walk a mile in them. See the world from their perspective. It's one of those pieces of advice which sounds right the first time you hear it, and the hundredth time too.
The problem is, it doesn't work the way we think it does.
The Shoes Don't Fit
Think about it. Even if you once held the same job as your employee, you didn't hold it in their body, with their history, their family situation, their fears, their past experiences with bad bosses or broken systems. You wore the shoes. They wore different ones.
Brené Brown said it well in Atlas of the Heart: "Rather than walking in your shoes, I need to learn how to listen to the story you tell about what it's like in your shoes and believe you even when it doesn't match my experiences."
The last part is what most people skip: "believe you even when it doesn't match my experiences."
When someone describes their experience and it doesn't line up with what we've seen, the instinct is to edit their story. We hear them, filter it through our own experience, and end up listening to ourselves.
Not empathy. Projection with good intentions.
The Numbers Tell the Story
Research from Elevate Leadership found a striking gap: 92% of CEOs believe their organization is empathetic. Only 72% of employees agree.
Twenty points between what leaders think they're doing and what people experience.
The gap doesn't come from leaders being bad people. It comes from walking in the wrong shoes... their own.
And 58% of CEOs say they find it difficult to demonstrate empathy in practice. Not because they don't care. Because the "shoes" model gives them nothing to work with. You cannot replicate someone else's inner experience. You don't have access to it.
What Riding Shotgun Means
When you ride shotgun with someone, you're not driving. You're not navigating. You're in the car, in real time, as a witness to their journey. You see what they see. You feel the turns. You notice when they're driving tense or when they suddenly relax.
You're present. You're paying attention. And... you're in their car, not yours.
This is what genuine empathy looks like in practice. Not: "I know what this is like." But: "Tell me what this is like for you. I'm here. I'm listening. I won't rewrite your story with my experience."
It requires something most leaders find uncomfortable: park your own interpretation and sit in uncertainty.
The old-fashioned "shoes" approach is active. You're doing something... simulating, projecting, imagining. Riding shotgun is receptive. You're making space. You're waiting. You're witnessing.
What Changes When You Ride Shotgun
In practice, the difference shows up in small ways.
You stop finishing sentences. When you think you know someone's experience, you fill in gaps. When you're riding shotgun, you ask questions instead.
You stop comparing. Saying "I had the same problem once" sounds supportive. It isn't. It shifts the conversation to your experience. Riding shotgun means staying in theirs.
You stop solving prematurely. The urge to fix is strong in leadership. We're trained to diagnose and act. Sitting in someone's car means staying with discomfort long enough to understand the real problem... not the surface one.
You believe them. The hardest one. When someone tells you something disproportionate to the situation, riding shotgun means accepting their experience as real. You don't have to agree. You do have to believe they're feeling what they say they're feeling.
A Story I Think About a Lot
Early in my career, I managed an engineer I'll call Tom. Skilled, quiet, and increasingly withdrawn. He'd miss standup. Give one-word answers in 1:1s. Stop volunteering for anything.
I thought I understood why. Tom was underpaid relative to the market, and I'd been underpaid too at a similar stage. I knew how demoralizing it was... watching your rent go up while your salary stayed flat. It erodes motivation in a specific way.
So I went to bat for his salary. Got him a significant increase. Tom stayed withdrawn. I was puzzled.
I'd walked in his shoes and been completely wrong.
Months later, we had a real conversation... one where I stopped offering solutions and started asking questions. What I learned had nothing to do with money. Tom had requested a specific project assignment six months earlier. He'd been passed over without explanation. He'd taken it as a sign his technical judgment wasn't trusted by leadership.
The salary increase hadn't touched the actual wound. I'd been treating the wrong problem entirely.
I'd been so confident I knew the answer, I hadn't asked the question.
Two Types of Empathy
Most leadership writing collapses empathy into one thing. It isn't.
Cognitive empathy is understanding how someone thinks and feels. Emotional empathy is feeling what they feel. The "walk in their shoes" metaphor pushes toward emotional empathy... but it's a counterfeit version. You're not feeling what they feel. You're feeling what you'd feel in your version of their situation.
Riding shotgun is closer to cognitive empathy. You're not trying to become them. You're trying to understand them, on their terms, without taking over.
According to Chief Executive, 87% of CEOs believe financial performance ties directly to workplace empathy. Nearly nine out of ten top executives think empathy moves the bottom line... and yet the gap between how leaders show up and how employees experience it stays wide.
Cognitive empathy is learnable. Emotional empathy is partly neurological. Cognitive empathy is a skill: listening to someone's story without overwriting it with yours.
Three Questions for Riding Shotgun
If you want to practice, three questions will take you further than any empathy framework.
What does this feel like for you? Not "what happened"... what does it feel like. Emotions are data.
What would help most right now? Not what would help you in this situation. What would help them, right now. Listen carefully to the answer.
Have I got it right? After reflecting back what you've heard, check. The adjustment is where real understanding lives.
These aren't magic. They require you to slow down, stop solving, and trust understanding comes before fixing.
The Point
The "walk a mile in their shoes" metaphor isn't entirely wrong. It's easy to misuse. It gives permission to substitute your experience for someone else's without realizing you've done it.
Riding shotgun is harder. It asks you to give up the driver's seat. To be present without being in control. To listen without knowing where you're going.
People don't need you to have been where they are. They need you to be where they are, right now, with them.
Next time someone on your team seems unreachable, resist the urge to walk in their shoes. Ride shotgun instead.