Team Players Are Not People Pleasers

Tell me if this scenario sounds familiar: You're designing a feature. You've carefully explored various directions, talked to customers, and analyzed competitors. In sum, you've put in a lot hard work to create a well supported and well reasoned solution.

But suddenly... A wild executive appears.

You're trying to be a team player. You want to make people feel heard and build relationships, right?

So you create a half-baked and unholy simulacrum of Acme Co's horrifying designs. What you've created is Frankenstein's monster. It haunts your nightmares.

And when your little friend comes to life and goes on a murderous rampage, guess who will be blamed? Not the executive.

Team players are incredibly valuable, people pleasers are incredibly dangerous.

Team players vs people pleasers

Team players and people pleasers look very similar on the surface. Both go out of their way to support other people's ideas, seek buy in, are generally well liked, and focus relentlessly on building relationships.

But there's a crucial difference.

A team player is willing to incur personal, reputational damage for the benefit of the team. They'll push back when they think it counts, in a respectful way, in order to secure a better outcome for everyone even if it hurts them in the short term. Their ultimate goal is to make the team successful.

A people pleaser will avoid pushing back at all costs and hoard relationship capital in order to avoid discomfort. They won't push back, even when they think the outcome will be disastrous in the end, because they don't want to be the bad guy. Their ultimate goal is to be liked.

Subtlety

One of the qualities of a great designer is subtlety: The ability to orchestrate and delicately balance a host of precise decisions to produce a beautiful, coherent experience.

That same quality applies here. It takes subtlety to say 'yes' to other people's ideas 80% of the time without becoming a 'yes man'. It takes subtlety to realize now is the time to push back and go against your instinct to be liked.

As you get better at this, it'll become automatic. But what does it take to reach automaticity?

Timing

You don't need to push back in the moment, especially in a group setting. In fact, you often shouldn't since it can present a status threat to the person you're disagreeing with.

You can simply say 'I appreciate your feedback. I'm going to think through it and see how we might incorporate it.'

Then... think through it! Write down what you agree with, what you disagree with, and why. Spell out the possible impact. And make sure you really steel man their idea.

Talk through your analysis with a colleague to gut check it. After that, talk to the decision maker one on one.

Start by asking questions. Try to see if their idea can be salvaged. If they are still completely blind to the burning issues despite your gentle questioning, escalate in directness gradually. Your prior analysis will inform how much you need to push back.

Keep escalating until the cost makes further escalation untenable. If this is a decision that could destroy the company, it's reasonable to keep escalating until you get fired.

If this is a decision that is largely reversible, you're not certain your way is better, and uncertainty can be massively mitigated by quickly testing their idea, then stick with asking questions and see if you can knock out a design quickly to validate your stakeholder's idea.

If you're someone who is generally averse to conflict, taking time and convincing yourself that an issue is worth pushing back on is especially important. It's much easier to push back (successfully) when you've done your homework and don't blow up in the moment.

Silence and violence

In the quasi-scientific ramblings of the cult classic book "Crucial Conversations" the authors introduce this notion of silence and violence:We often don't speak our minds and let concerns fester until we're unable to contain ourselves. At that point, we lose all tact and blow up at people, heavily undermining our credibility.

Perhaps you are better adjusted than me. In fact, I know for a fact many of you are. But maybe some of you have experienced this phenomenon. Pushing back when you believe it'll the benefit of the team is a release valve. It'll stop you from building up and venting resentment in an unconvincing and inopportune manner.

Touchy Feely

There's a legendary Stanford business school course called Interpersonal Dynamics (also known as touchy feely). The course is always booked out and students often report that it's one of the most transformative experiences of their professional lives.

There are several concepts taught in the course that apply here.

Stay on your side of the net. You don't know what the other person is thinking or feeling. All you know is how you feel and the impact their actions have had on you or on the team. You may not even know the latter with certainty. By focusing on what you know to be true and not speculating about the other person's motives, you disarm them and are able to make progress. That's part of why I put such a heavy emphasis on questions: They're disarming. They help you get into a collaborative and truth seeking mode.

Focus on the person, not the issue. Ignoring an issue might help you avoid discomfort in the short term, but can stall out your relationship in the long term. Especially if it's an issue you can't ultimately ignore. Obviously bringing up every single thing that bothers you makes you an impossibly sensitive person. So you'll need to draw the line somewhere. As we discussed previously, you can figure out where to draw the line by taking a step back, writing out the implications of the issue at hand, and discussing it with a reliable third party. Skillfully bringing up issues that truly matter one on one will enhance your relationships rather than damage them, more often than not.

Credibility

But how do you build enough credibility to push back meaningfully? This is something I've gotten much better at over the years. I've gone from doing it terribly to doing it mostly well. And let me tell you, doing it badly is not fun. Losing credibility leads to being sidelined and creating work you're ultimately not proud of. Building credibility lets you do meaningful, creatively fulfilling work. In two weeks, we'll talk about a consistent, simple way to build massive amounts of credibility with your team.

I'm going to be in Iceland. So hopefully this excessively long article will you hold you until I'm back.