Stop Trying to Please Everyone — This Is Real Leadership The real leadership challenge isn't charisma or consensus, but emotional clarity under pressure.

By Sam Rockwell Edited by Micah Zimmerman

Key Takeaways

  • Real leadership is staying grounded, not absorbed by team anxiety.
  • Self-differentiation means setting boundaries without breaking the connection.
  • Don’t fix everything — lead with calm, clear emotional presence instead.

Opinions expressed by Entrepreneur contributors are their own.

Every few years, a new leadership style captures the collective imagination — often because it flatters our kids. Right now, it's "Conscious Unbossing," Gen Z's polite refusal to manage anyone because, bless them, they're too emotionally self-aware to boss and too exhausted to be bossed. A decade ago, it was "servant leadership," before that "transformational," before that something military-sounding.

These style debates aren't wrong; they're just surface-level. Most leadership breakdowns aren't about choosing the wrong approach. They're about emotional fusion — when leaders lose track of where they end and their teams begin.

The real challenge? Not charisma or consensus. It's self-differentiation.

Related: This is the Kind of Leadership That Will Transform Your Team

What family systems teach us about leading at work

Edwin Friedman, rabbi and leadership contrarian, once said that leadership isn't about style — it's about managing emotional fields. Not in the "group hug" sense, but in the "this place is dripping with anxiety and I just absorbed it through my pores" sense.

He built on Murray Bowen's family systems theory, which starts with this uncomfortable truth: Organizations don't just feel like families — they function like them. We over-function, under-function and triangle into drama that isn't ours, and call it "teamwork."

The real leadership work is what Friedman called self-differentiation — the ability to stay connected to others without getting absorbed by their emotions. It's staying calm when your team is spiraling, setting boundaries without cutting people off, and declining that passive-aggressive meeting invite with a clear conscience. Let's explore these concepts using a real-life example from my coaching practice.

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Rachel's dilemma — Leading from the middle

Rachel had just been promoted — her first big leadership role. She'd built her career by being the go-to person: collaborative, competent, never the center of attention but always essential behind the scenes. Now, suddenly, she was in front of the room, expected to set the direction. And she was stuck.

When her team hesitated, she carried the load herself (classic over-functioning). When conflict flared, she tiptoed around it, hoping it would resolve itself (under-functioning). And when two peers butted heads, she jumped in to smooth it over, only to get blamed from both sides (triangulation).

Rachel wasn't lacking skills. She was saturated in her system's anxiety, trying to prove she belonged by pleasing everyone.

The problem wasn't her competence. It was her blurred emotional boundaries. She'd fused with the team she was meant to lead. She needed something more potent than assertiveness training. She needed self-differentiation — the capacity to stay grounded, clear and connected without being emotionally hijacked by the room — even when it means disappointing people.

The charisma–consensus trap

I illustrate this dynamic using a leadership spectrum. On one end of the spectrum is the charismatic leader: a disembodied head rolling down the road, bold and certain, hollering "Follow me!" as the body (their team) flails behind. On the other end is the consensus leader: Humpty Dumpty, fully fused with the group, rolling slowly because everyone's feelings have to come along too.

Most of us default to one end or the other when anxiety rises. Charisma says, "I'll go, even if you don't." Consensus says, "I won't go unless we all do." Both are forms of emotional reactivity—one over-separates, the other over-fuses.

But real leadership lives in the messy, unglamorous middle. The goal isn't to lead like a messiah or a middle manager—it's to become a self-differentiated presence. A good head, on solid shoulders. Connected, but distinct. Clear, but not combative.

Image Credit: Sam Rockwell

Because when the system gets anxious (and it will), what it needs isn't another brilliant idea or a soothing voice. It needs someone who can hold their shape. Who can say: "This is where I am. I hope you'll come with me. But I'm going either way."

Related: The 3-Step Framework for Leaders to Lead with Confidence

Three practices to lead with differentiation

Self-differentiation isn't something you achieve and then laminate for your desk. It's practiced, in real time, under pressure. Here are three places to start:

  1. Track Where You're Over-Functioning. Over-functioning is leadership's sneakiest self-sabotage. Ask yourself: Whose work am I doing for them? If you're writing the deck, solving their problem, feeling their feelings (Ding! Ding!), you're fused. Let go of other people's responsibilities so they can step into them. That's not abandonment, that's respect.
  2. Notice the Triangle. Triangulation is what happens when two people are in conflict and, rather than face it directly, they pull in a third to manage the tension: You. If you're suddenly the middle of someone else's drama, press pause. Try this phrase: "Sounds like something you two can work through." Stay kind, stay connected, but don't get recruited.
  3. Practice Non-Anxious Presence. This one is the secret sauce. Don't react. Breathe. Reflect. Let your nervous system model the calm you wish to see in your meetings. People don't follow logic under stress: They follow signals. If you bring presence without panic, others often rise to meet you. The key is: Self-differentiation isn't detachment. It's staying fully present in a hot system without letting it boil you alive. And in a world that rewards urgency, your calm might just be the most disruptive leadership move you can make.

The system shifts when you do

Organizations don't transform when policies change. They transform when people do—when someone, somewhere, stops playing the anxious game. That someone could be you.

You don't need a new leadership formula. You need a steadier footing in the middle of the swirl. More charisma won't carry you. More consensus won't protect you. Leadership with staying power doesn't wait for the system to settle down. It stays in the room and keeps its shape.

Let your presence be the calm center that doesn't demand agreement but invites coherence. You don't have to fix everything. You just have to lead like a person who knows where they end and others begin. And sometimes, that's enough to change the system. Or at least hold it together long enough for change to become possible.

Sam Rockwell

Entrepreneur Leadership Network® Contributor

CEO at Rockwell&Co

Sam Rockwell is a consultant, coach, and author specializing in helping medium to large businesses across sectors, industries, and the globe dramatically scale their results and profits by using the lens of identity to optimize their strategies, leadership development, and team performance.

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