The Wrong People Have Imposter Syndrome

One of the most distressing things that happens to me at work is seeing someone who is clearly capable and competent and able to do a task doubt themselves. And it’s not because “I need the work to get done” or any of the typical “business needs to operate” bs. I don’t REALLY care about that stuff (I care, but it’s a byproduct of leading the right way, not the product itself).

But what I care about is people purposefully limiting themselves because they know too much.

We’ve institutionalized rewarding overconfidence and bluster, and punished thoughtful reflection and acknowledgment of uncertainty. As a result, we enable the wrong people to rise through the ranks and gain more power and control and the right people are stuck in a continual state of questioning themselves into paralysis, not knowing how to get ahead.

And so, I want to talk about Imposter Syndrome.

But, the more I thought about it, the more I realized that you can’t talk about Imposter Syndrome without talking about the other side of that coin — the Dunning-Kruger effect.

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In both of these cases, the problem is that we can’t accurately see or assess our own abilities. And while it would make a lot of sense for us to continually feel like as we learn more we’re more confident, it’s actually the opposite. (I’m literally feeling it right now, because I’m sitting here going, is this a thing everyone knows? Am I just preaching to the choir? Is this even a thing anyone will care about? Let alone care about enough for TWO posts on this topic that I have planned for this week? Whatever push through the discomfort Scott)

Essentially, the point of the Dunning-Kruger effect is that people with low capability in a specific area overstate their ability in that area.

Some great examples are all the dudes out there that think they can hit a Serena Williams serve. Or beat a gorilla in a fight. You’re just too ignorant to realize how insane your comment is, but you’re also ignorant enough to say it with confidence!

But that posited that there’s a counter argument that people who are eminnetly capable also know all the things that they DON’T know and over compensate by caveating and seeming like they lack in confidence when really what’s happening is that they are knowledgable enough to know that there are pitfalls and issues that they can’t anticipate or account for and rightfully call it out! As a former boss told me, if any of us could predict the future we’d be rich from all our gambling winnings and not here at work.

The problem is, these are both the internal reactions, and not accounting for the external perceptions. People judge themselves by their intentions, inner monologues, and judgments, whereas people judge others by their visible outputs whether that’s the way they’re standing, the tenor of their voice, or the confidence that they’re presenting.

But that external output isn’t representative of anything other than their persona! It’s all an act.

None of this is new. And I also want to acknowledge that originally “imposter syndrome” was almost exclusively used to discuss women, and that it was just a sexist way of saying “women are more thoughtful and less willing to pretend to know things that they know nothing about”. It’s honestly shocking as a person who likes to think of himself as neither sexist nor racist, that our institutions are still both sexist and racist and make it harder for people to get ahead. Which is a different discussion, though it’s related!

Because the feedback loop at work has always been about the boys club. The guys that go out to the bar after work, or stay late jamming on code while sipping on whiskey and smoking cigars, or go take 2 martini lunches. “It’s all about connections, and making sure people know your name!” we’re told.

And that was the best way to get ahead. I know that I personally benefited from bosses just knowing who I was because I was loud and forceful in meetings. I like to think that I was forceful in a knowledgeable and thoughtful way, but I wouldn’t blame anyone who saw it and thought “that guy is probably full of shit”. Hell, I bet in the moment I FELT like I was full of shit. I’ve pinged people on the side during calls HUNDREDS of times to ask “did I sound like I knew what I was talking about just then, or sound like I was full of shit?”

But basing our work life around “knowing people” and “people seeing you a lot” is a terrible way of judging who is competent or capable! And you’ve all experienced some variety of it, whether it’s the one guy who always has to question the strategy in every meeting, or the one who says they think we’re all overthinking things and it’s much easier, or the one who says we’re all dumb and it’s much harder than we think! They’re always the loud people that we remember, regardless of whether they’re RIGHT.

What we often miss as a result is the quiet person reflecting in the corner who then asks a thoughtful question via email or chat later that shows true understanding.

And our promotion cycles and processes reinforce that. It’s a zero sum game, where we have a certain number of available promotions and a certain number of available dollars, and inevitably pure skill and ability aren’t the only factors. Do I know that person? Do I think they’re more likely to feel valued by a larger amount? Or are they more motivated by the title? Or by the kind of work they do? Or, or, or, or…

And then we get to the person who never talks during meetings, but has a velocity of 1.5 times the person we were just spending all the time thinking about. But they’re quiet so they get the median raise. They get put on the next cycle for promotions. They get ignored.

And the further up you go in organizations the more rampant it is, because now not only are you expected to execute your goals as a leader, but you’re EXPECTED to be a good hang. You’re expected to be at all the team building events. You’re expected to make work your life if you want to get ahead. And the people who are the least qualified often are the most ready to jump at the opportunity for face time, because even if they’re not incredibly skilled in their field, 1) they don’t know they’re not skilled and so think they deserve the raise or promotion more than the person who knows a ton but doesn’t want to advertise themselves and 2) they know how the game is played!

There’s an immediate connection to the empathy tax.

People paying more of the empathy tax end up being the same people that are more introspective, careful, thoughtful, and not prone to bluster. And those who are exacting the tax tend to be those who are more willing to take risks assuming things will turn out ok and talk a big game without needing to back it up with anything because someone is going to come in after and ensure things are working correctly.

And I think it comes across as sounding like there are people being malicious and people being kind, and I don’t think that’s exactly right, even though for SURE it’s how I read my own thoughts on paper lol.

But it’s not people that are being good or bad - let’s be real we’re all good sometimes and bad sometimes and if you judged me by my worst moments you’d think I was the devil and if you judged me by my best moments you’d think I was a saint. The reality is somewhere in the middle, as it is with most people.

The problem isn’t the people, it’s the institutionalization of rewarding Dunning-Kruger’s and penalizing impostor syndromes.

So how do we fix it? How do we change the way our institutions and institutions work in order to make it so that we’re valuing the right things in the right contexts?

I think there’s a few things that could help:

More leadership training, especially on items like unconscious bias I know this is going to sound insane, but I went from being an individual contributor to running a team of 250+ people, managing a $15 million/year budget, and a $150+ million/year revenue product and never received any leadership or financial management training on the job
My training was all on the side, and that’s not reasonable if we’re entrusting our employees and our companies with people who don’t have the background to do their jobs

Clearer expectations from leaders

If you manage 5 people, how much of your time should be dedicated to managing them vs other responsibilities?
How do we run feedback sessions?
How do we ensure we’re getting detail that expands beyond one on one conversations?

More time and space for learning about our employees and what they’re capable of

More opportunities for individual contributors so that the only path to more money and more recognition isn’t managing people

The problem is, that these are less about specific “here’s the thing you do to change” and more in the realm of “we need to create more space for people to be people”. And a part of that requires slowing down. Because it’s impossible to go at a breakneck speed and always need to produce and consume more and have the bandwidth to really understand someone beyond the facade you see in meetings or in chats.

And this is very anecdotal, but I’d say every manager that I’ve talked to and worked with doesn’t have any of the tools or time to do what’s needed to make a shift. Which means that as leaders, we need to not only enable our employees, but enable OURSELVES to find space to have the important conversations that go beyond the facade and figure out how to help people to grow in their careers.

My example that I always draw on, is that I had an Android developer who was great, and did amazing work, but his vision of himself was as an individual contributor. I kept pulling him up and asking to make architectural decisions, and he kept trying to tell me that he didn’t have the experience to do what I was asking for. And he was right! But it also DIDN’T MATTER. Because I spent time working with him, and saw his ability through his work and his way of thinking, and knew he would be great.

And even afterward he would tell me that I saw things in him that he never saw, and that’s really what SHOULD drive someone wanting to be a leader or a manager. Finding opportunities where people didn’t see them! Giving people opportunities they never considered for themselves but would be great at! Doing cool and fun shit with cool and fun people! (I crossed that out after writing it, because it’s actually the OPPOSITE of my intent — you should want to do cool and fun things, and you should see your co-workers as cool and fun people, but I don’t want to give the impression that they need to be outwardly fun and cool with YOU to be cool and fun. But you should be able to see it in them as a leader!)

This isn’t a prescription for how to fix the fact that too many Dunning-Kruger’s are in leadership positions and too few Imposter Syndrome folks are not. Nor is it even saying FIXING that is the key thing to deal with, but rather that our lack of intentionality leads to results that we don’t want.

The competence gap that I’ve been discussing is not about individual psychology - it’s that it’s been systematized! We need to stop equating confidence with competence. We need to be more intentional about getting more voices into the mix and not only getting those voices in through meetings where it’s intimidating to stand up and talk. We need to create psychological safety so our teams reach out in the ways that make THEM feel comfortable rather than the ways that make leaders feel comfortable.

By creating that psychological safety and creating a culture that is more focused on learning about people than making assumptions about people we can create a more equitable and in the end enjoyable workplace! And guess what… that’s how business thrives. It’s not just screwing people over to get every penny we can; it’s about creating sustainable and maintainable businesses that make money while caring about the people helping to make that money.