We’ve all been there—the magnetic pull of wanting to be liked, to keep things smooth and agreeable. It feels good, doesn’t it? And as a leader, connecting with your team, showing empathy, and building trust are critical. But here’s the truth: if you’re leading solely to keep everyone happy, you’re playing small. Leadership requires you to know when people-pleasing works—and when it holds your team back from real progress.
A wise saying reminds us, “You can either experience the pain of discipline or the pain of regret. The choice is yours.” As a leader, this choice plays out daily. Picking the right pain means asking yourself: is this discomfort helping me and the team grow? If not, maybe it’s time to lean into discipline over approval.
When People-Pleasing Becomes a Superpower
Being a people-pleaser gets a bad rap, but it’s not all negative. A leader who listens, empathizes, and shows up for their team builds a foundation of trust. Trust is your secret weapon—it keeps your team open to feedback, willing to accept challenges, and invested in your vision. It’s what lets you connect on a personal level, so when you make tough calls, they know it’s for the team’s good.
But here’s the catch: discipline is also part of leadership. At times, leading effectively requires you to step out of the people-pleasing zone and embrace tough calls. Knowing when to transition from empathy to discipline is key.
Avoiding the Trap of Ruinous Empathy
Empathy is valuable, but too much can slip into a pitfall known as “ruinous empathy.” This happens when you’re so focused on keeping everyone happy that you avoid hard conversations and accountability. Leaders who shield their teams from tough feedback or allow subpar work to go unaddressed aren’t doing them any favors. Real kindness means holding people to standards that push them to grow—even if it stings in the short term.
When we avoid conflict or let underperformance slide, we compromise the team’s potential. True leadership means setting expectations and sometimes making uncomfortable decisions for the good of everyone involved.
Finding Balance: Discipline and Empathy Working Together
Effective leaders can toggle between empathy and discipline based on what’s needed. This doesn’t mean you disregard people’s feelings or trample over their needs. Instead, you balance your compassion with a disciplined focus that drives results.
Use People-Pleasing Wisely
Building trust and gaining buy-in from your team are powerful tools. People-pleasing has its place when it serves a greater purpose, not just a desire to be liked. So, go ahead—show empathy, but don’t let it derail the big picture.
Embrace Discipline When It’s Necessary
Recognize when staying “nice” might be harming the team’s success. Making the tough calls can be intimidating, but it’s often what the business needs to grow. The discomfort of discipline is easier to handle than the regret of missed goals.
Communicate With Clarity and Compassion
Discipline doesn’t have to be cold. Share the “why” behind decisions, set clear expectations, and communicate thoughtfully. Your team may not always agree, but they will respect a leader who’s transparent and accountable. And remember—bad news is better shared openly than left to rumor and assumption.
Leading With Both Heart and Resolve
Leadership isn’t about a fixed formula. It’s a blend of empathy and strategic action, and knowing when to lean on each. Yes, being liked feels wonderful, but respect—and the results born from discipline—always last longer. When you lead with this balance, you empower your team to achieve more, trust deeper, and move forward together.
Ready to lead with clarity and purpose? At StringCan, we help business leaders sharpen their marketing strategies to inspire and drive growth. Let’s chat so you can grow your business!