Show them your Pokémon Cards: Seeking Relevance as a Young Leader

I learned an invaluable and deceptively simple lesson when I asked John Ciancutti for advice about growing our team at Philanthropy University. What’s his secret to organization-building? What’s his trick for consistently building high-performing teams across companies like Netflix, Facebook, Coursera, and his most recent startup, 60-db? I was struck by the simplicity of his response:

“I never stop hiring people better than me,” he said.

I’ve regularly invoked this wisdom as our nonprofit educational initiative, Philanthropy University, continues to scale, and so far, it’s served us remarkably well. Never before have I worked with such an intelligent, keenly mission-driven, and relentlessly dogged team (they’re also hilarious, but that’s icing on the cake). Never before have I learned so much, so quickly.

But I’ll confess that continually hiring people who push, question, and challenge me isn’t always easy. Putting John’s advice into practice means striving to make myself the dumbest person in the room, a difficult prospect for a young leader, especially when some may be predisposed to judge me for having fewer years on the field.

It’s no wonder, then, that I often observe other young leaders posturing and compensating for their youth with overt displays of dominance or arrogance. After all, when surrounded by scores of savants and seniors, who wants recognition for being a mystical millennial, for growing up watching Power Rangers and collecting Pokémon cards? Who wants to be infantilized in the midst of such humbling talent and unrelenting pressure to perform and lead? What often results in these moments is a pretend leader: a child in a parent’s baggy suit playing CEO in a school play.

The psychologist Alfred Adler stressed that a most fundamental human desire is that for group belonging, and nowhere is this need more acute than at the helm, where the pressures to lead and embody your group’s ideals are most strongly felt. For young leaders, the fear of rejection, of having your youthful incompetence or unpreparedness revealed to your tribe, is a terrifying prospect, and can hinder a sense belonging with employees across the age spectrum.

But being a young leader doesn’t have to be lonely and terrifying*. What’s required is a willingness to truthfully, humbly identify and embrace where you’re most relevant.

There are two steps to this process. The first is being unapologetic about your strengths and unique value. Unless you’re an heir (or Donald Trump), your leadership position likely wasn’t a fluke. Even though crippling moments of imposter syndrome might tempt you to believe otherwise, you probably have real skills and insights to contribute, regardless of your age. Take the time to properly identify these strengths by continuously seeking feedback from peers and mentors. Regularly engage in written self-reflection (e.g. “Here are the things I did this week that were successful; these are the skills that I think underpinned this success”). Once you identify the skills and characteristics that make you relevant, own and hone them. These will serve you far better than trying to remediate your weaknesses.

The second step is knowing when to get out of the way, which begins with recognizing and embracing your limitations. In these situations, your value-add is less your ideas, and more your ability to catalyze and develop the ideas of your team. Ask probing questions, encourage equal participation across teammates, and foster a safe environment in which vulnerability flourishes.

Most important, reject all internal or external pressures to feign expertise. Remember that if you’re following John’s sage advice, you should never be the most intelligent person in the room, and that your team already knows your age and time spent in the work force (likely through a combination of social media stalking and noticing you still can’t grow a beard). Relatedly, remember that most high-performing employees, especially those older and wiser, are usually quite good at identifying when people don’t know what they’re talking about. With this in mind, pretending to be an expert is often the easiest way to compromise your perceived legitimacy and trustworthiness. (Read: you’re not fooling anyone.).

After accepting these truths, you’ll realize the only path forward is paved with painful candor and vulnerability. You’ll also realize that walking this path is anything but intuitive, and that combating your very reasonable instincts to hide and reframe your greatest shortcomings (and to use your positional authority to push your relevance where it isn’t needed or appropriate) will be an ongoing struggle.

So what does this look like in practice? Regularly say “I don’t know” or “I don’t understand” and other elusive phrases that often escape the insecure leader’s lexicon. Call out teammates who do the same. Openly recognize when you’ve learned something from a teammate; if you’re honest with yourself, this will happen daily. Stay quiet when you have more to learn than contribute. Relentlessly ask for and act upon feedback from your direct reports. Admit when you make mistakes (again, should happen daily!). Support your leaders to own and drive decisions and processes. Continually hunt for opportunities to get out of the way. Channel Dweck’s Growth Mindset, and share reflections about being a young leader and your exciting opportunities for learning and growth (perhaps even in a blog post**). Proudly share your Pokémon cards.

Ultimately, the error many young leaders make is in equating their own lack of experience with a lack of competence, which can interact in uncomfortable ways with a deep-seated desire for belonging in the very group they’re expected to lead. The solution? Embrace that you are (in real, tangible ways) relevant and insufficient, a fact that no amount of years, experience, or Pokémon cards will change.

*At least not all the time.

**Meta.

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