Are you leading, or are you just trying to be liked?

In this episode of Leadership After 5, Kim gets direct about people pleasing in leadership and why it doesn't stop with new managers. At the executive level it gets quieter, more sophisticated, and more dangerous. Kim explores the fine line between good leadership and approval seeking, the parenting analogy that reframes it all, and why the leaders who are remembered aren't always the ones who were liked, but the ones who were trusted.

Transcript

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Welcome to Leadership After Five, where leadership gets real. I'm Kim. Someone once told me that if everybody on your team likes you, you're doing something wrong. And I remember thinking, that can't be right. I want to be liked. I want my team to enjoy working with me. I want to walk into a room and have people genuinely happy to see me. But the longer I've been in leadership, the more I understand what that person meant. Today I want to talk about people pleasing in leadership and why it's a common misstep and a dangerous one at that. It doesn't just show up in new managers, it shows up in the boardroom, at the executive table, in the rooms where the most consequential decisions get made. But let me be clear about something first. The desire to be liked is not weakness, it's human. And in leadership, there is a version of it that is completely appropriate. You want your team to trust you. You want them to feel safe, bringing problems to you. You want to create an environment where people feel seen and valued. That requires some level of warmth, some level of accessibility, some level of caring whether your people are okay. That's not people pleasing. That's good leadership. But there is a line. And when you cross it, you stop leading and start managing perception. Those are two very different things. I often compare leadership to parenting. If you're a parent, you know there comes a point where you cannot make your kid happy and do your job at the same time. You have to make decisions that protect them, challenge them, and sometimes disappoint them because you're thinking about the greater good of their well-being, not just the moment they're standing in. Well, leadership is the same. You are responsible for the greater good of the organization, not just the comfort of the people in the room with you right now. And just like parenting, there will be seasons where your people just don't like you. Call it the middle school years of leadership. You know, it happens. Especially when you're making hard calls, holding people accountable, or taking the team somewhere they're not sure they want to go. The question isn't whether they like you in that moment. The question is whether they trust where you're taking them. Now we see people pleasing most visibly in leaders who are new to the role. The ones who just move from peer to manager and don't want to lose the relationships they've built. That transition is hard and the temptation to over-accommodate is real. But it doesn't stop there because at the executive level, people pleasing, it gets more sophisticated. It gets quieter, and it gets more dangerous. At the executive level, it doesn't look like avoiding hard conversations with a direct report. It looks like softening a difficult truth for the CEO because you don't want to disrupt the relationship. It looks like performing alignment in the boardroom on a decision you fundamentally disagree with and never saying so out loud to the people who need to hear it. It looks like managing up so carefully that your actual perspective never makes it into the room. I've seen it up close. And the cost at that level isn't just personal, it's organizational. When the people at the top of the house are performing agreement instead of speaking truth to the entire organization, the organization ultimately pays for it. Decisions get made without the full picture. Problems that should have been named in the room get named in the hallway instead. And the culture that gets modeled from the top is one where silence is safer than honesty. Now I want to name both ends of this because neither one works. On one end, you have the people pleaser, you know, the leader who needs to be liked so badly that they can't make a hard call without softening it into meaninglessness. They avoid conflict. They give feedback that isn't actually feedback. They say yes when they mean no. And over time, their team stops bringing them real problems because they already know the answer is going to be whatever keeps the peace. On the other end, you have the bulldozer, let's call it that. The leader who decided they don't care if anyone likes them and they actually took it too far. They railroad, they dismiss, they leave wreckage at every intersection and call it decisiveness. Neither one of these leaders are effective long term. The bulldozer might move fast, but they can't sustain it. People stop following them. Talent walks, and eventually the very results they were driving toward fall apart because the people required to deliver them are gone. The people pleaser might have a happy room, but they can't move anything. Decision stall, accountability disappears, and the organization stops trusting them to do what needs to be done. The balance isn't somewhere in the middle. The balance is in the intent. So here's what I want you to hold on to. People will follow the leader that is going somewhere, not always the leader that they like. I learned about followership early in my career, not as a leader, but as an individual contributor. And what struck me was this you don't have to like everything about a leader to follow them. You don't have to love their communication style. You don't have to agree with every decision. You don't have to be best friends. What you need to believe is that they have the organization's best interests at heart, that they have a vision worth following, that when they make a hard call, it's coming from somewhere real, not from ego, not from fear, and not from a need to be liked. That kind of leader earns followership, not because everyone is happy, but because everyone knows where they're going and trusts the person taking them there. Now, this is not a pass for misbehavior, by the way. This is not permission to ignore organizational culture or bulldoze people in the name of vision. A leader who abuses their position, who creates a toxic environment, who operates outside of the values of the organization, that's a different conversation entirely. That's not leadership, that's an organizational crisis waiting to happen. I'm talking about the leader who is doing the right things, making the hard calls, holding the line, and occasionally making people uncomfortable in service of something bigger. That leader doesn't need everyone to like them. They need everyone to trust them. And at the executive level, that leader needs to be willing to say the hard thing in the room where it matters, not in the hallway afterward, not in the coaching session six months later, in the room where the decision is being made. That's leadership. So here's the question I want you to sit with after this episode. Are you leading or are you just trying to be liked? And if you're at the executive level, are you saying what needs to be said in the rooms that matter? Or are you managing the relationship so carefully that your real perspective never makes to the table? Because those two things can look the same from the outside for a while, but eventually the difference shows up in your decisions, in your conversations, and whether your team respects you or just tolerates you, and whether the organization is getting your best thinking or your most comfortable version of it. Check your intent. Are your decisions driven by what's right for the organization and the people in it? Or are they driven by what keeps the room comfortable? If it's the latter, then that's your signal. Not to stop caring about your people, but to start trusting that doing right by them sometimes means disappointing them. The leader your team needs is not always the leader they want in the moment. And knowing the difference and having courage to act on it is what separates the leaders who are remembered from the ones who are just liked. If this one hit close to home for you, I want to hear from you. Find me on LinkedIn or any one of my socials. Tell me what you're thinking. Tell me what landed for you. This is Leadership After Five, where leadership gets real. I'll see you in the next episode. Take care.