Stop being so nice all the time

The price we pay as leaders for optimizing for “being nice” – and how to avoid being too nice without being a jerk.

👋 Howdy!  Claire here, CEO of Canopy.  Fun news:  Our Canopy newsletter now has a home here on Substack 🎉 Feel free to whitelist “canopynewsletter@substack.com” to make sure you receive these newsletters in your inbox going forward.  Read on below for our newsletter…

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You don’t have to be so nice all the time.

It’s one of the most unobvious truths of leadership:

When you over-optimize for being nice, you prevent yourself from being an effective leader. 

Now I’m not advocating to be crude or disrespectful. Few things are as harmful.

Rather, I’m calling for us as leaders to resist the rampant desire for our team to be liked all the time. To release the expectation that every single interaction with our team should “feel good.”

After all: Feeling good as a leader doesn’t equate to be being most helpful to our team.

I was most recently reminded of this the other week in an interaction I had with a team member. 

It’s been an intense season of progress and change at Canopy these past few months – and I wanted my team member to feel confident and supported.

So when she presented her work to me, I showered her with positives: 

“This looks great. I love what you did here.” 

Being so affirmative felt good to me. And I hoped it felt good to her.

I did notice a few errors, but told myself in the moment:

“It doesn’t feel right to rock the boat. Those small mistakes don’t matter right now…”

A few weeks later, there were more errors in the work she had put together – the exact errors I’d justified to myself “weren’t worth bringing up right now.” Those mistakes had then gone out to the client.

I shook my head… at myself. I’d let my team member down.

I’d fallen into the trap of wanting to be nice. I’d wanted her to feel good.

But most of all, if I was being honest with myself, I wanted myself to feel good. 

Optimizing for being nice as a leader becomes a selfish act. 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 your identity perceived as positive by them.

When you care about “being nice,” you’re essentially saying, “The needs of my team don’t matter as much as their perception of me as an individual.”

This is the reality I found myself in the other week as a leader: My preoccupation with being nice had distorted my helpfulness. My withholding of feedback didn’t help my team member, or the client.

Now, I had to go back and explain how I should’ve said something earlier. My team member would understand – but undoubtably, at minimum, be a little perturbed on why I didn’t mention it sooner. 

The price of being nice had hurt her, hurt the team, and the client.

Sound familiar? 

To get a sense of if you are over-optimizing for being nice, ask yourself these four questions:

(1) What happens when someone messes up?

When someone makes a mistake, do other team members avoid telling you directly? Now I’m not suggesting you encourage “tattle-telling” but the opposite is detrimental to a team. An unwillingness to acknowledge each others’ mistakes contributes to over-optimizing for “nice.”

(2) How long does it take to let someone go?

How much time passes between the moment you’ve decided a current team member is not the right fit for the team, and the moment you tell them? If it’s longer than a week and you find yourself stalling, you’re guilty of over-optimizing for being nice.

(3) Do people bring up failure?

When is the last time someone (other than you) brought up that a project that fell short, or quality of work was not up to par? If your team members focus only on what’s going well and are reluctant to be critical, you could be inadvertently encouraging folks to be too nice.

(4)  Do people disagree with you in public?

When you ask for people’s opinion on an important issue, do you get passive head-nodding? Or even complete radio silence? If so, people may not feel comfortable voicing their disagreement, and you may have enabled both yourself and your team to be too nice.

Nice can be toxic because it’s hard to see.

Hiten Shah, co-founder and CEO at Nira, underlined this truth to me, in a podcast interview we did a handful of years ago. 

He warned “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team” when you focus on being nice all the time.

We don’t want to see the nefarious second-order effects of being too nice — let alone do the hard work to have hard, honest conversations. It’s much easier to see the beautiful field of pleasant coworker smiles, the flowers of kudos and petals of positive recognition, and pretend that being nice doesn’t have consequences.

We only want to see what we want to see. That’s toxic.

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. 

The seminal read and one of my favorite books, Crucial Conversations, extolls how being nice and being honest are not mutually exclusive. You can be both.

The best leaders embrace this duality.

Let’s stop being so focused on being only nice all the time.

Let us see this reality clearly, together.

-Claire