If Everyone Likes You, You’re Failing

Why avoiding discomfort is costing you respect as a leader

For a long time, addressing poor performance, or any difficult conversation with team members, was my Achilles’ heel.

Any time someone on the team was underperforming, I’d feel uncomfortable before I even walked in the room. I knew what needed to be said, but once the conversation started, I’d lose my edge, second-guessing my wording, filling every pause with extra fluff, and dancing around the point instead of actually landing it. The more uncomfortable it felt, the more I tried to smooth it out.

At the time, it felt like I was handling it well, keeping things light, calm and positive. Team members would leave those conversations feeling upbeat and convinced there was little that needed to change, and that was the problem.

These days, I’m not like that all the time. My desire to avoid uncomfortable discussions or unnecessarily cushion them presents occasionally, but I catch it earlier and correct it faster. Like I always say, it’s progress over perfection.

Those leadership moments early in my career had little to do with the team members involved and everything to do with me. It was about me wanting to be seen as supportive, fair and easy to deal with. I didn’t want the conversation to feel heavy, so I shaped it to avoid the real issues and softened it with superfluous context, misplaced praise and random stammers. The succinct term is people-pleasing and I was a world class proponent of the people-pleasing sport.

There’s a version of leadership that rewards the behaviour I've described, at least in the short term. Its the version where you’re approachable, people enjoy working with you and every conversation feels smooth. In short, you're liked by all.

But leadership isn’t measured by how easy interactions feel in the moment and success doesn't come from pumping up your team when what they really need is a firm steer. True leadership is measured by what people are able to correct and achieve after a conversation and that’s where the difference between being liked and being respected becomes clear.

When you lean too far on being liked, you hesitate before speaking or soften feedback until it loses its usefulness. You may even delay or dodge decisions because you don’t want to disappoint people. None of it feels significant on its own, but it shapes how people experience your leadership. Standards start to feel flexible and your expectations become murky. Sure, you’re still liked, but you’re much harder to rely on

Respect isn’t built upon just being a likeable leader, it comes from clarity and consistency. People need to know where they stand with you and they need to understand what good looks like. When your people have this foundation, they trust that if something needs to be said, you won’t avoid or dilute it. That doesn’t mean every interaction feels easy, but it does mean your leadership feels more authentic and dependable.

What I’ve had to get better at is noticing the moment where the choice is evident and rarely is it obvious. The point of digression shows up as a slight hesitation before speaking, or the instinct to rephrase something that was already clear. It’s the pull to make things smoother when what’s actually needed is precision.

A few practical shifts have made a real difference for me, so allow me to share them with you.

First, say the thing you need to say in one clean sentence before you add anything else. To borrow liberally from Mark Twain, bite the head off the frog and get it done without hesitation or fluff, then only add more context if it genuinely helps. If you can’t state the core message simply, you’re more likely to dilute it.

Second, pay attention to what you’re adding just to make yourself more comfortable. Extra qualifiers, softening language, over-explaining, it all has a place, but a lot of it is just there to reduce your own discomfort in the moment.

Third, close the loop and don’t leave conversations open to interpretation. Make sure your team member is clear on what’s expected and what happens next. Clarity at the end of a conversation will build respect.

Finally, notice what you avoid, as counterintuitive as that may sound. The conversations you keep pushing out and the points you keep skirting around are usually where the gap between being liked and being respected is widest.

This isn’t about becoming blunt or ignoring how people feel, empathy should always play a role in how we communicate. Too many leaders mistake the need for directness and clarity for brashness. This is about saying what needs to be said without overcomplicating it, and holding the standard while still treating people with respect. Most people can handle directness far better than we think and what annoys them is a lack of clarity.

I still care about being someone people enjoy working with. That hasn’t changed and I suspect it never will. But these days I pay a lot more attention to what’s driving my choices in those tough moments. If I’m shaping a conversation to avoid discomfort, that’s usually a signal I’m straying and need to course correct.

As leaders, we can't be liked all the time, but we can be respected and that will carry us a lot further in the long run.