As leaders, we often dream of the high points—recognition, growth, vision-setting, and impact. But then there’s the other side: the tough conversations, the team reshuffles, the calls that keep you up at night. As Brene Brown says, “We can do hard things.” And yet… doing them with grace, empathy, and strength? That’s the real art.
I get this question from clients all the time:
“How can I be the bad guy and still do good things?”
Whether it’s laying someone off, shifting team roles, or delivering tough feedback—there is a way to do it that’s good for the person (and you!), good for the team, and good for the culture. But you have to be willing to get uncomfortable.
Let’s be honest: most people don’t want to be “the bad guy.” So they try to be liked. They tiptoe around hard truths. They avoid conflict, hoping things will fix themselves. Spoiler: they don’t.
This kind of clarity vacuum is how you end up with a snake-pit culture—where people talk behind each others’ backs, trust breaks down, and resentment simmers under fake smiles. And it almost always starts at the top.
Why Avoiding the “Bad Guy” Role Hurts More Than It Helps
If you’re a chronic people-pleaser, here’s your growth edge: get to know the “bad person” you’re scared of becoming. Not to become them—but to move past them.
It’s like going to a dietitian and being told to avoid chocolate. Suddenly, all you want is chocolate. When we avoid discomfort, it grows louder. But when we face it, we gain power.
Many of us are driven by old fears: “I don’t want to be like that boss who was a bully.” Or, “I hated being treated like that, so I’ll never do it to someone else.” Noble intent. But if you avoid hard truths in the name of kindness, it’s not actually kind—it’s avoidance dressed in empathy’s clothing.
On the flip side, some leaders lean into being the tough guy. They wear it like a badge. I once sat in a job interview where the first question was: “How many people have you fired?” The expectation was clear: toughness = effectiveness. But this mentality can breed cold, disconnected teams. When being “the heavy” becomes a point of pride, you miss the human opportunity in the moment.
The Truth: Good Leaders Do Hard Things—Kindly
If someone’s role no longer fits their strengths, or they’re underperforming, the kindest thing you can do is help them move on. That doesn’t mean being mean. It means being real—with compassion.
You can tell someone, “Hey, this role isn’t playing to your strengths—but I see so much value in what you bring. Here’s what I’ve noticed you’re great at…” That one moment can shape how they see themselves for years to come. It can be the difference between someone walking away feeling ashamed… or walking away with their head held high. You give dignity—even in the hard moments.
And guess what? The rest of the team is watching. They learn what leadership looks like. They learn that performance matters and that people matter. It’s not about a show of strength. It’s about being an authentic, empathic leader.
The Real Opportunity
Every tough leadership moment is a breakthrough in disguise—a chance to build trust, set the tone for your culture, boost someone’s confidence (even as they walk out the door), and model what it looks like to lead with both courage and kindness.
Yes, it’s hard. Yes, it can hurt. But that emotional sensitivity you feel? Use it. That’s not weakness—that’s your superpower. It lets you connect, uplift, and lead with integrity. I look forward to hearing your experience of uncomfortable moments like this.
Best,
David Lesser