Photo by Davide Baraldi.
Every headline for the last few weeks has been about either actual dictators or aspiring dictators or wannabe corporate dictators. You might get the impression that most leaders are nursing a bit of an evil streak. We understand that. We’re not here to stump for dictators.
The rise and noise of cartoonish, political strongmen has left many leaders worried that chest-thumping is a prerequisite for management. And that board work requires a sleeper build. Friends, we are here to tell you that nothing could be further from the truth. And we know because we ask this question of a lot of bosses:
Quick show of hands. How many of you would self-describe as being a people-pleaser?
In a room full of managers, what’s your guess? A few hesitant hands? Mostly from people who are either new-to-management or relatively early in their careers?
Guess again.
The best part isn’t the moment the first boss raises a reluctant hand. It’s the moment after that, when those leaders look around the (virtual or IRL) room and see that other hands have gone up, too. Not only are they not alone, but the majority of folks present have a hand in the air.
Now, maybe there’s some selection bias at play here. Perhaps leaders who voluntarily attend management training are the folks who didn’t say “Get out of my face” when the HR team told them training was coming up. Maybe. But we’ve done this with small orgs, big orgs, nice orgs, and prickly orgs. And the finding is pretty consistent.
You are not alone
Anticipate what your boss needs, what your peers need, and how everyone is feeling. Make their lives easier. Say yes. Some fights aren’t worth having. Don’t rock the boat. Most fights aren’t worth having. Get along with your colleagues. Say yes again. Totally understand where they’re coming from. No fight is worth having, really. Are you people-pleasing or just an affable, engaged member of the team? No wonder you got promoted.
In any management corps, you will find a good chunk of people-pleasers. And if you’re one of them, you have already figured out that people-pleasing is a superpower, but also has some limitations. It makes it hard to give feedback. In fact it makes it hard to do anything that you anticipate might cause hurt feelings. And while it got you promoted the first time, it often fails to get you subsequent promotions.
When we meet people-pleasers in our programs, they often ask if we can help them to be tougher, or stricter, or meaner. They read business books full of hard-chargers making tough, unpopular calls that are ultimately right for the business. They don’t want to make their teams cry, but they do sort of reluctantly feel like the lesson of a lot of leadership storytelling is to be more willing to hurt people.
It’s worth untangling a thing. Our people-pleasers are confusing “meaner” with “effective.” But…those aren’t correlates. If anything they’re inversely correlated. You can be an effective leader without screaming at your team. Promise. And you will be wholly ineffective if your team keeps hiding in the bathroom because you seem to be in one of your moods. Again.
The biggest issue for people-pleasing leaders isn’t that they need to be tougher. Or scream more. Or play a different boss on TV. It’s what they’re not doing. People-pleasers consistently fall down on one of the core responsibilities of management. And they do it in the name of harmony.
Not the feedback thing again
Everyone wants the answer to be better feedback. Our people-pleasers all know that they’re bad at it, and want to get better. And sure, that’s righteous. The feedback-is-hard struggle for a people-pleaser is real and, perhaps obviously, we’re so happy to help with it if that’s your particular struggle hut of the moment. But while feedback is the obvious place every people-pleaser struggles, it’s not the most consequential.
No, what we want to draw your attention to here, is decision-making. The way your people-pleasing factors in to those decisions, and is co-opted by those decisions. And we want to check in on how you feel about it.
Because, look. The thing most people-pleasers know but rarely say out loud is that people-pleasing is not about the other person, it’s about yourself. People-pleasing is a way to keep yourself safe. A way to camouflage, to avoid conflict or confrontation or rejection or failure. If you’re a people-pleaser you know that it’s not even a thing you think about, it’s a reflexive response. We heard someone, years ago, say “show me a people-pleaser and I’ll show you someone who was asked to carry adult things as a child.” And. Like. Damn?
But say what you will, those reflexes worked to get you here. You’re in the room where it happens now. Partly based on your straight up merit, no doubt, but also because a lot of more senior folks feel like you really get it, that you’re on-side, that you’re with them. Because you’re good at projecting those things. You have access, and standing, and trust.
Oh no.
See the thing with management that we come back to a lot is that it’s a completely different job. And one of the main ways it’s different is in the decisions you make. Individual contributors mostly make decisions about their work, but managers make decisions about people. Those management rooms, and zoom calls, and slack messages, and email threads are where decisions are made about who gets promoted and who gets a PIP. About doubling this team and laying off that one. About whether we fund parental leave, or cover same-sex partners with our health benefits, or have tampons in the bathrooms. About whether our AUP bans nazis.
Managers make those decisions. Debate those decisions. Argue about those decisions, sometimes threaten to quit over those decisions and sometimes actually quit. Those are rooms that have conflict and confrontation — sometimes as chest-thumping toxicity, but often as earnest disagreement about choices and direction. And now, you’re management.
Your camouflage let you dodge and avoid conflict as an individual. But as a part of the management team, your job is to surface risks, to push back on decisions that won’t work, to counter-propose, to represent the perspective of your team. When you people-please as a manager, your acquiescence is read as agreement. Your going-along-to-get-along is received as endorsement. If you didn’t agree, you should have said something.
We know. This sucks. You want harmony and chill vibes and to take care of your team, and instead you’re having your name attached to decisions you don’t agree with. And us telling you not to people-please feels a bit like telling you not to blink — it’s not that easy. It’s a reflex. Besides, it feels like the more senior people in that room still have all the power. That disagreement and pushing back and fighting will expose you, and cost you social capital, and feel super awkward, and might not get anywhere regardless.
And still, this is the job. Some fights are worth having. The more senior people in the room can’t make good decisions if they can’t see around corners. If they can’t spot and address risk. If they don’t get any pushback. Whatever the source of your dissent, papering over it doesn’t cause it to disappear, but it does sell out your team and maybe yourself. That doesn’t mean those senior leaders will listen to you. Or that speaking up will always be welcome or rewarded. But if we’re right, that many managers got there through people-pleasing, someone is going to have to raise that first reluctant hand.
— Melissa & Johnathan
