How to Be a Strong Leader Without Becoming a Jerk

When you’re a natural people pleaser, stepping into leadership can be challenging. Here’s how to build on your strengths, not deny them.

My client wanted to be a great boss. He just didn’t want to be a jerk.

Evan could be described as a classic people person—his co-workers say he’s empathetic, an active listener, and genuinely invested in helping others. A high performer, Evan quickly built a reputation as someone in his company with strong leadership potential.

When Evan did get that promotion, though, he was surprised by the feedback from his team: He micromanaged, was unclear in his communication, and was often irritated when people didn’t act on his vague, confusing directions. Evan was troubled. Why was this happening?

The People-Pleaser’s Leadership Trap

The answer lay in what happened in those most challenging leadership moments when Evan would have to make tough decisions or deliver critical feedback. Evan held back because he felt doing these things went against his core identity as a good person—he didn’t want to be the bad guy.

This meant Evan’s team was often left in the dark, wondering what he really wanted from them. He’d dance around difficult topics or deliver sugar-coated, vague feedback. When his team couldn’t read between the lines to decipher what he really wanted, Evan would become irritated and snap into micromanager mode. His team didn’t have a consistent, supportive leader, but someone who’d swing like a pendulum.

Why Assertiveness Is the Missing Ingredient

Evan realized that in his efforts to not be a jerk, he’d become another kind of bad guy entirely. Instead of the pendulum swing, he needed to embrace a middle ground: assertiveness.

Here are the four actions Evan took that helped him go from people pleaser to assertive leader:

1. He stopped sugarcoating. Like many people pleasers, Evan didn’t want to cause any hurt feelings by delivering difficult feedback. Instead, he’d dance around or sugarcoat his feedback, leaving his team confused and frustrated. Assertiveness, meanwhile, calls for delivering all feedback with clarity and directly, not by burying it in a mountain of qualifiers. Evan realized he could still be true to himself and be direct—he could deliver critical feedback with respect, authenticity, and empathy. That way, his team would know exactly what they needed to work on. As author Brené Brown writes, “Clear is kind. Unclear is unkind.”

2. He held people accountable. For many people pleasers, the idea of holding people accountable can bring about panic, as they would rather avoid conflict. Accountability, though, means setting clear expectations and having the confidence to enforce them. Evan had to learn that holding people accountable isn’t about being the bad guy, it’s about developing a team that functions well.

3. He got comfortable with conflict. Assertive leaders know that conflict is part of the job, and they don’t shy away from it. Evan realized he had to learn to face conflicts head-on instead of ducking for cover. In conflict, being assertive means standing up for his ideas and rights without belittling or overpowering others.

4. He kept his eye on the big picture. In his shift from people pleaser to assertive leader, Evan redefined what success looked like in his role. Instead of thinking, How can I make everyone happy? he started asking, How can I lead my team to do great work, even when it’s uncomfortable? Once he saw that leadership was about moving the team forward, not avoiding tough conversations, he stopped seeing assertiveness as a threat to his identity and embraced it as a new strength.

Evan learned that assertiveness is exactly what he needed to be the supportive, empathetic boss he aspired to be. By communicating directly and clearly, holding his team accountable, becoming comfortable with criticism himself, and keeping his eye on the big picture of his team’s success, he not only avoided becoming a jerk, he became the leader his team was inspired to follow.