Leaders, stop being so nice all the time.

“Being nice” can be a crutch to avoid hard choices and uncomfortable conversations. Don’t fall into this trap.

Leaders, stop being so nice all the time.

I don’t mean to sound like an asshole. But when it comes to leadership, it’s true: Prioritizing “being nice” keeps us from being good leaders.

Now I’m not advocating for us to be mean. Disrespectful or dismissive leaders help no one. Rather, I’m calling for us as leaders to loosen our grip on “being nice.” To stop wanting our team to like us all the time. To let go of the expectation that every single interaction with our team should feel good.

Truth is, our team isn’t going to like us all the time. Our team isn’t going to feel good all the time. And trying to be nice to everyone all the time isn’t going to change that. Nor is it actually helpful for your team.

When we’re preoccupied with seeming popular instead of fair, when we optimize for pleasant conversations instead of honest ones — we hurt our teams.

I was reminded of this most recently while I was reading The Watercooler, our online community with almost 1,000 leaders. One manager revealed he was facing this exact dilemma. He was seen as “The Nice Guy” in his company, always complementary, never critical. As a result, he was struggling how to start giving his team difficult feedback — and his team was floundering.

He’s not the only one.

Have you ever found yourself in one of these situations?

  • You avoided giving tough feedback to a coworker… and now the person has made even bigger mistakes than you previously imagined.
  • You didn’t tell someone that you disagreed with them… and now you have to figure out how to course-correct without blindsiding the person.
  • You postponed firing someone… and now have to do damage control for the low morale they infused throughout the team.
  • You said something was “great!” even though it actually wasn’t… and now you have to fix the level of quality for what was produced.

Many of us focus on “being nice” as a leader more than we should. And we pay a price for it.

Hiten Shah, founder of Kissmetrics and Crazy Egg, emphasized this point to me, in a recent interview. He warned that when you’re concerned with being nice all the time, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.”

Prioritizing “nice” as a leader is an easy trap to fall into. Being nice fits into our desire for belonging and companionship as humans. We’re social creatures. We want to be liked. Inherently, there is nothing wrong with that.

But “being nice” becomes problematic when it becomes your rudder as a leader. It leads you astray. You lose sight of your purpose as a leader: To help your team accomplish a specific mission. Your barometer for success as a leader morphs from “Are we accomplishing our mission?” into “What does the team thinks of me?

Over time, “being nice” becomes your crutch. It’s a convenient rationalization to avoid hard decisions, uncomfortable conversations, and controversial actions. It’s easier to “be nice” than it is to have tell someone to their face that they’re rubbing a client or colleague the wrong way.

Ultimately, being nice as a leader is selfish. It doesn’t serve the team. It serves your ego. The team is looking to you to help them achieve a goal. And instead, you’re looking to have your decisions, actions, and yourself perceived as positive by them.

A leader is the only person’s whose sole job is help a team achieve the outcome they want to achieve. When you care about “being nice,” you’re essentially saying, “The needs of my team as a whole don’t matter as much as their perception of me as an individual.”

Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.

Or even better, we can seek to be nice and honest, nice and rigorous, nice and consistent. One of my favorite books, Crucial Conversations, discusses how being nice and being honest are not mutually exclusive. You can be both. The best leaders embrace this duality.

Let’s just stop being so damn focused on being only nice.

P.S.: If you enjoyed this piece, please feel free to share + give it 👏 so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)


Leaders, stop being so nice all the time. was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

Teaching iteration

I’ve written about the class I’d like to teach, but what I’ve been thinking about lately is the class I’d like to attend. Not necessarily now, but when I was growing up. In the 6th grade, let’s say.

I don’t know why people ask me this, but I’m often polled for my opinion on the American education system. What’s my take? What would I do to fix it?

I don’t know, really. “It” covers too much ground to be addressed accurately. Education is delivered at every scale, from an individual reading a book, to a 1:1 tutor, to a small home/classroom setting, to a larger university auditorium-sized class, to online classes that can be theoretically taken by the entire planet at once. From one to 7 billion.

You can’t fix anything that’s so big and so varied. You can, however, fix small parts of things. And hopefully, as the small, fixed parts add up, you have a chance at chipping away at a big problem.

So here’s my one small idea: I’d begin to teach iteration. Iteration as a subject, equivalient to math, science, history, language, art, music, etc. How do you make something better over time? How do you return to something that you’ve done and see it with fresh eyes? How do you apply new perspective to an old problem? Where do you find that new perspective? What trails do you follow and which do you ignore? How do you smash the familiar and reassemble something new from the same pieces?

Once you’re done with school, and cast out into the world, your job is likely to involve iteration. No matter what you’re doing, you’re probably going to have to do something over. And often times again and again. You rarely simply deliver something and move on. You’re asked to refactor, to build on it, to “make it better”.

Making anything better is iteration. When you put something out there, it’ll often land right back in your lap. Sometimes that feedback boomerangs back directly, other times you have to infer the problems by disciphering other people’s behavior when they interact with the thing you gave them. This customer struggled with this, this manufacturing tolerance didn’t line up with that, this printing process looked better on the screen than it did on paper. Or after a certain amount of time passes while working on something, you reflect on what you’ve done and don’t like the reflection.

Either way, someone’s probably going to ask you to take the state of your art, and make it the state of the art.

Now that you’ve got it back, what do you do with it? This is something you have to learn how to deal with. But in school — save for writing a few drafts before handing in the final version — you don’t get to iterate much. You move on from assignment to assignment, rarely getting a chance to revisit your work earlier in the semester. I think that’s a missed opportunity.

So, perhaps for a final assignment (no matter the subject), students should be able to choose something they did earlier in the year and get a chance to improve on it. Make version 2. I think working on four things, and getting a chance to redo one of them would be more valuable than working on five separate things. It would be a better education.

Or another take would be a single assignment for the entire semester. Every two weeks you hand in a new version of it. In time you may slam into diminishing returns, but that’s all part of it too. That would be a better education.

Or maybe you work on something and hand it in. Then the teacher shuffles the deck, so to speak, and hands you back someone else’s assignment. Now you have two weeks to improve on that. And that cycle — improving on someone else’s work — continues for the whole semester. That would closely mirror what work on the outside is really like. That would be a better education.

I don’t know, something like that.

So there, I guess that’s my initial idea to improve the educational system. Teach problem solving through iteration. Bounce things back to people for a second or third try. And then a fourth and a fifth. And so on. Require them to bring new perspectives. Demonstrate how time, space, and chance are on your side — they give you the opportunity to wander around with an idea and take it in new directions. Iteration is evolution. Hopefully what’s next is better than what came before it.


Teaching iteration was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.