Why it's so hard to hire people better than you

The unconscious bias driving loads of subpar senior hires

Welcome Entrepreneurs. I’m so glad you’re here.

In my experience, the patterns that show up in our lives and our companies are very rarely coincidences. We might once hire an older man who talks down to people by accident, who in hindsight reminds us of our dad. Sure. But when that same relationship shows up more than once (and usually if it’s a pattern, it runs deep), it’s a good guess that we’re doing something to perpetuate that dynamic. Even if we don’t know what. Even if it seems we can’t possibly be.

Unearthing the ways that we unconsciously create the very dynamics we say we don’t want is one of the most fascinating parts of coaching (and one of the most high leverage learnings for a CEO).

Today, I want to dive into one of those common dynamics.

Why it’s so hard to hire people better than you

Ask ten CEOs whether they hire people smarter than they are. I’ll bet that all ten say yes. 

They all probably believe it, too, never mind the way some folks might look at them if they said no. That very specific mixture of surprise and pity, the sheer impact of which teaches any CEO to say yes to questions like that without consideration, if only because it’s the right response to maintain a sense of competence as a leader. 

But in my experience, many high achievers don’t hire people smarter than them. Not because they’re asleep at the wheel. Because the downslope from the CEO of a hyper growth startup to a kid who wasn’t enough to make their parents happy is just too slippery.

The Drama of the Gifted Child

I read a book a while ago that made me cry. 

It’s called The Drama of the Gifted Child by Alice Miller. It walks through one of the most common personality patterns of high achieving adults. In its pages, I saw what had happened to me — the ins and outs of how I’d become so successful but also so existentially unhappy — and I cried because it was sad, but also because it was a huge release. 

It goes like this:

Kid is born, and kid is smart. She’s so smart that she intuitively picks up on the fact that one or both of her parents are not okay. It could be that they’re emotionally unstable, or they’re distant and unhappy, working all the time. Just exactly how the parents are not ok is not important. The important thing is that the kid sees this, as an infant or toddler, and knows that making her parents ok is a matter of life and death. The thing is, the only version of her parents that she sees are the versions in which they’re interacting with her directly, so in her existential quest to interpret exactly why her parents are not ok, she doesn’t know to consider work, or friends, or money or any of those things. The only thing she can conclude is that they are unhappy with her. She is not what they wanted, and she must be different.

So she experiments. She tries to be this way. Or that way. She tries on being different ways, different people, and gauges the reaction from her parents. As she gets bigger, she finds that if she can just do the right thing, whatever that is, her parents seem ok. If she learns how to ride her bike, if she rides it faster than the other kids, she sees her parents’ faces light up with pride, and for a moment they seem ok. Happy, maybe. They tell company how advanced she is. That feels good. It quiets the voice that’s been telling her she’s not enough her whole life, and that’s important. 

So finally, she learns who she needs to be. She needs to be better.

As she grows up, she sees (or rather the adult part of her sees), that her parents are unhappy not because of her, but because of the myriad other reasons people are unhappy. But she also knows that when she wins, whether it be a spelling bee or a wrestling match, they look at her with admiration. Everyone does. And she doesn’t know why, but that look is the thing that makes her feel ok about herself. It fuels her. So she pushes herself to achieve, to be better, in everything she does. 

What starts out as winning a bike race around the block evolves into winning the class spelling bee evolves into winning a state championship in high school evolves into a high-paying career and an impressive spouse and even, for many, starting a company. Feeding on the looks of admiration she gets along the way. 

In this way, Alice Miller described my childhood in her book, a story that resonates with those of so many high performing people.

You might think this is sad. A kid that, deep down, feels so inadequate or powerless that they organize their entire lives to have the world tell them the opposite. And you’d be right.

But it’s also very productive. There’s nothing quite like an existential feeling of not-enoughness to motivate a person to work that extra hour. To sacrifice luxuries like sleep or friends for just a little more effort. For one more deal, one more raise, one more gold star. 

And for those high performers who work alone, the story might end there. But for leaders—for people who lead other people to accomplish big, daring, audacious things—this pattern of achieving has a catch. 

They say one of the most important things a leader can do is to hire people smarter than themselves. For some leaders this is a benign platitude. Wise advice so obvious as to be nearly meaningless. 

But for leaders like our valiant heroine, who have built their lives on their own achievement and power and competence in all situations, hiring someone better than they are is a direct threat to their value as a human being. 

“Until you make the unconscious conscious, it will direct your life and you will call it fate.” — Carl Jung

I work with incredibly successful CEOs every day. Everyone wants to, and tries to, surround themselves with the best talent. At least consciously. 

But people also want things unconsciously. Love, safety, approval. Respect. Admiration. And it’s in the service of these unconscious desires that leaders hire people they think are the best they can find, but who ultimately aren’t so good that they might challenge the leader. Rinse and repeat, over and over again.

Though they say they are disappointed, and in many cases they might even feel disappointed, deep down these founders are getting exactly what they want: by hiring people who look fantastic, they get to feel competent at the hiring process, but when the new hire eventually underperforms, they can continue to feel like the most competent, accomplished person in the office. People look at them as though they’ve just won the bike race around the block all over again, and even 20, 30 40 years later, that look makes something inside feel ok. They are intentionally (albeit unconsciously) creating the precise circumstances they say they don’t want.

If this story resonates with you, like reading “The Drama of the Gifted Child” did with me, it’s worth asking whether or not the team you’ve built is the best team possible. And if not, as easy as it is to blame an anemic talent pool or balance sheet, it might also be worth looking in the mirror. 

The patterns that show up in our lives are very rarely coincidences.

(HT: Julie Mosow, Zac Thomas, Daniel Sisson & Foster for editing!)

Liked this article? I’d be honored if you’d share with others who might find it valuable. 


Who is Ryan Vaughn? 

I am an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO and a decade of meditation & mindfulness training, I have helped leaders from companies across the world, funded by some of the world’s top venture funds, to design a more conscious life and make key changes to improve their performance and satisfaction. More detailed bio, here.


One: IRAs and Wealth Creation

I was as grossed out as the next person to see Peter Thiel using a Roth IRA to amass billions of dollars tax free, so I’m glad that the US govt is thinking about how to limit that kind of behavior (really, really seems like the proverbial finger-in-a-dike, but you gotta start somewhere). That said, tax policy, if nothing else, requires nuance, and I know a lot of people using IRAs for retirement savings. I’m not an expert here, but I liked Fred Wilson’s perspective on a more targeted approach. 


Two: What We Think We Know About Metabolism May Be Wrong

Just when I thought I knew some stuff, according to a "groundbreaking, foundational" new paper, metabolism doesn't actually slow down after college. It declines from birth to age 20, then stays steady from 20-60 years old. 


Three: $1k grants to high schoolers / college students / dropouts for ideas

Attention all early early stage founders: reminder that there are at least a handful of orgs like the one linked below that will give you a no-strings-attached grant of $1-5k for you to work on your idea. StartGarden.com local to Grand Rapids, 1517fund.com/take-action, and another one that's still in stealth which I'll share in a later issue. The most important thing is to start.


Four: You Have to Make Adjustments

I'm less of a Ryan Holiday fan than I think most would expect (gotta think about why… I think it's because he translates ancient wisdom, and I prefer it untranslated). That said, his "Daily Dad" newsletter has become the one email I read every day. If you're a father, I highly recommend subscribing for a daily dose of what's really important.


Five: How the Pandemic Changed Me as a Parent

Well, maybe I was too harsh. Maybe my ego (as a writer on similar topics, and, if we're being honest, a fellow translator) blinded me to a kindred spirit. I read this article immediately after the Daily Dad, and I saw a kindred spirit, learning the transformative lesson of COVID in parallel. I see you, Ryan. Maybe I'll go read your book now.



Top Posts

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites: 

Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

At Inside Out Leadership, I’m privileged to work with amazing humans every day to help them grow into extraordinary leaders, and support them in building the company of their dreams. As a 3x founder and CEO for 15 years myself, I coach entrepreneurs how I want to be coached:

  • Focused on the person, not the role.

  • Focused on results, without the fluff.

To find out more, click here or simply reply to this email.