From Pleasing to Challenging: The Leadership Shift That Drives Real Growth

Not long ago, I had a conversation with a manager in the tech industry. Let’s call him Adrian. He led a high-performing engineering team, the kind of group where expertise ran deep, but so did the resistance to change.

Adrian shared his frustration over a coffee break. “I don’t get it,” he admitted, his voice laced with weariness.

“I do everything I can to keep the team happy. I approve their ideas, stay out of their way, and avoid any feedback that might come across as harsh. But it feels like we’re stuck. The team isn’t hitting the goals we need.”

He paused, searching for the right words. “I feel like I’m on their side, but it’s like they’re not on mine.”

Adrian’s words hit on a common struggle: the tension between being a leader and being liked.

Why Pleasing Doesn't Work

Many managers see themselves as advocates for their team, and there’s truth in that. A good leader does support their people. But when the desire to be liked takes priority, it comes at a cost.

When we need approval, we avoid tough conversations. We hesitate to address underperformance or push people beyond their comfort zones. It feels easier to keep the peace, but in doing so, we inadvertently lower the bar.

The truth is, you can’t lead people when you need people to like you. Leadership requires the courage to challenge—not because you want to criticize, but because you believe in their potential.

The Courage to Challenge

As Adrian and I talked, I asked him, “Think about your own career. When did you grow the most? Was it during the easy times, or was it when someone challenged you to do better?”

He thought for a moment, then nodded. “It was when someone called me out. Not in a harsh way, but in a way that made me realize I could do more.”

That’s the essence of this shift.

Challenging others isn’t about being critical or overly demanding. It’s about showing your team that you believe they can achieve more—and helping them get there.

How to Shift From Pleasing to Challenging

Making this shift starts with understanding that growth doesn’t happen in comfort. Here’s how you can move toward challenging your team effectively:

1. Start With Trust

No one responds well to challenges from someone they don’t trust. Building trust means showing consistent support, communicating openly, and genuinely caring about your team’s success. When trust is in place, challenges feel like an investment, not an attack.

2. Challenge the Behavior, Not the Person

When addressing issues, focus on actions, not identities. For example, instead of saying, “You’re not a team player,” try, “I noticed you didn’t involve others in this project. How can we approach it differently next time?”

3. Be Clear and Actionable

Vague feedback doesn’t help anyone. If you’re challenging someone, make sure they understand exactly what needs to change and why. Then, provide steps or resources to support them in making the shift.

4. Balance Challenge With Support

Challenging your team doesn’t mean abandoning them. Offer guidance, resources, and encouragement as they stretch themselves. It’s this balance that keeps morale high while driving growth.

5. Celebrate Progress

When your team rises to the challenge, acknowledge it. Growth is a journey, and celebrating small wins reinforces the value of stepping out of their comfort zone.

The Payoff

Adrian decided to have an open and honest conversation with his team. He shared the gap between their current performance and the potential he saw in them. He didn’t frame it as criticism but as an opportunity to aim higher together.

The initial response was quiet—uncomfortable, even. But then one of his senior engineers spoke up: “I’ve been feeling the same way. Let’s go for it.”

That conversation marked a turning point. The team didn’t just meet their goals—they surpassed them. And it wasn’t because Adrian pushed harder. It was because he challenged them in a way that made them feel seen and capable.

The Shift That Matters

The shift from pleasing to challenging isn’t just about achieving better results. It’s about creating a culture where growth is the standard, not the exception.

So here’s my challenge for you: Take a hard look at your leadership style.

Are you holding back tough conversations because you fear conflict?

Are you prioritizing being liked over being effective?

Leadership isn’t about being the most agreeable person in the room. It’s about being the one who believes in others enough to push them out of their comfort zone.

And that’s where the magic happens.

Are you ready to step up and challenge—not just your team, but yourself?

Drop me a message and let’s start today.

Kindly,

Florin