Failure makes for great leaders, if it’s shared

My failures have been the gifts that keep on giving.

The time when my team almost mutinied. The time many of them did, leaving scathing reviews on Glassdoor. The time I went to jail. The time I got fired. This is not an exhaustive list. I’ve failed a lot.

Failures hurt like hell. But sharing those failures, moreso than sharing your press-releases, is the key to building great relationships. And building great relationships is the key to being a great leader.

Polished Competence

Most people communicate in the business context with an intention, unstated but permeating everything they say like bad incense. They say lots of words, but what they’re really hoping you hear and understand underneath all the words is that they’re competent. Independent of what they say, the way they say it is polished to shining, honed over many dozen or hundreds of conversations to produce that result.

You know it when you hear it. It’s the moment in the call when, after comparing your weather to theirs, one of you offers to give “a bit of background to help set the context for our call.” And then the next 3-15 minutes (depending on how dialed in they are) is that person rehashing a rehearsed presentation of themselves that they’ve (consciously or unconsciously) user tested and fine tuned to get you to think well of them. That’s polished competence.

This type of polished competence has a place. For my last business, I went so far as to prepare different versions of it depending on the situation:

  • 5 words: “ for high school sports”
  • A paragraph: VNN is the largest and fastest growing high school sports marketing platform in the country.  Already the Official web/mobile communication platform reaching over 15% of all US high schools (and 11million passionate fans) over 45 states, VNN is rapidly consolidating the $15bn high school sports market onto a single intelligent platform, enabling marketers to engage with nearly every aspect of local school sports on a national scale.
  • Personal: I’m the founder of VNN, the nation’s leading high school sports marketing company. In this role I raised $20m, built out a world class team of 100 professionals and scaled our company to nearly 20% of all US high schools. I also write about my experiences on, and lead meditation classes for founders and executives.
(My polished competence, best shown on stage)

Either way, the goal was to tell the other person about myself in the way I thought would best get them to like/admire/invest in/purchase from me. To present the parts of myself that would produce a result, and skip over the rest. That time I was uncertain about how to make payroll? That time I completely fucked up the investor presentation? That time I let a customer down? These are completely off limits in these conversations because they’re hairy, and scary.

They’re real.

I always thought nobody would buy from that guy. The guy who was uncertain and had the occasional pimple. People wanted the guy who had his shit together, who had all the credentials and who was polished and competent.


Maybe they did want that, to an extent. I was able to raise a ton of money and recruit some amazingly talented people to join me at VNN by being polished and put together. And I’m pretty sure they wouldn’t have joined me if all I had were failures, so being able to package myself well was useful, in the same way that a sharp jacket is useful if you’re hoping to meet someone at the bar (I’m married, I think people still do that?).

But on the other hand, crushing it all the time doesn’t make for deep relationships, just like if all you have is that jacket you won’t make it past the one night. The guy who always wins doesn’t connect with people emotionally, or develop the kind of deep friendship with his customers and partners that serves as the bedrock foundation when things get tough. Presenting the image of polished competence simply makes you look good. And in a race to look good, there’s always someone who looks better.

Authentic Connection

Everything will line up perfectly when knowing and living the truth becomes more important than looking good.

Alan Cohen

People want stuff that looks good, and that includes leaders. You need a jacket. But people only want that stuff as long as it keeps looking good, if there’s no substance underneath, so presenting myself as polished and competent was like hopping on a golden hamster wheel. People were attracted to me not because I was special or because I was me. People were attracted to me because I was running on gold.

It’s easy to get this confused, until you stop running or get off the wheel and see how many people stick around, and how many run to the next shiny object. We can call this the golden hamster-wheel experiment. It has a predictable outcome.

Connecting with people in the way that builds meaningful relationships, a requirement to lead people through the hard times, required a depth that my presented-self didn’t have. By definition, a presented-self is a polished surface, shone to brilliant with all the best stuff. The greatest hits album of one’s career. It’s impressive, but it’s got no substance. It’s not human. It’s shiny and attractive, but it has no staying power.

That’s where failing, and talking about my failures, has been eye opening.

A funny thing happens when I tell someone something revealing about myself. Something human, vulnerable and real like “I built a culture that almost caused our company to implode,” or “I went to jail for a DUI.”

The person I’m talking to really listens. Maybe for the first time.

By being real with someone, particularly in the business context wherein real communication is exceedingly rare, it’s possible to create a space in which a different type of connection can happen. A new kind of conversation, in which we can finally stop presenting at one another and actually connect in a way that one or both of us might remember the next day. A new kind of relationship, not between talking heads repping agendas, but between people.

And more often than not, the person hearing my vulnerability responds in kind. They tell me about the death in their family that they’re still processing, or the struggles they’re having with their boss or friend. Or they may even tell me something they never tell anyone, like maybe even that time they went to jail.

These are the types of things that people only tell their friends, and usually only their close friends around a bonfire, after they’ve passed numerous tests of acceptance and empathy. These are the stories that truly bond people together, well beyond the surface of their heavily manicured competence. And they certainly don’t show up in a professional context. Not in my experience.

The thing is, they need to. It takes strong bonds to lead people through the hard times and WFIO moments. So great leaders can’t save their human vulnerability for close friends and campfires. We need to bring it to the office.

Strong relationships are built on real, honest, authentic and vulnerable communication. Mostly we keep this type of communication heavily guarded, lest we be hurt by someone truly knowing us and, heaven forbid, judging us. But it’s only when we let our guard down and take the risk of sharing something that makes us look imperfect, something about which we don’t know how the other person will react, that we can really connect with another person. And it’s that level of connection, bonfire connections, that build great leaders and great companies.

(besides, business is a blast when you’re working amongst bonfire people, and it is a sparkly version of solitary confinement when all you’re doing is running around trying to look competent)

So What

If you’re up to something meaningful in the world, you can’t do it alone. You’ll need people. Whether that’s employees, partners, investors, customers, whatever. The key to your success is in enrolling other people into what you’re doing, and into you yourself. Even if you don’t think of yourself as a leader, or nobody has appointed you with a Manager/Director/Executive/etc title, the key to your success is being able to lead others in the direction you want your life to go.

Like it or not, you are a leader. So it’s worthwhile becoming a good one.

From the outside, it looks as though doing that well means putting on a suit, or a pair of fuck-you flip flops, having all the answers and an air of been-there-done-that confidence. I fell for that line for a number of years early in my career, and while it does get you in the papers what it also gets you is a team of employees who work hard for their own sake but will leave as soon as a better opportunity comes along. What it also gets you are partners who will look for opportunities to cut corners and pinch percentage points. What it gets you are transactional relationships, which will fold under a modicum of pressure.

And if you’re up to something meaningful in the world, you’d better be prepared for more than just a modicum of pressure.

To get through the tough spots, you need to build authentic and deep, bonfire level relationships. And to do that, you have to be willing to be vulnerable, to share the things about yourself that make you uncomfortable, thereby opening up the space for other people to do the same.

And you have to do this first, because the other thing about leaders is that leaders go first.

So I’ve been to jail. And I got fired. And I am an alcoholic. And I’m a founder and CEO. And I raised $20m. And I led a team of 100 people, built an industry leader and did all the rest. The competence is way more comfortable to talk about, but it’s the failures that have been the genesis of my best relationships.

Leaders go first. And that goes for being vulnerable, too. Leaders set the paradigm for what it’s ok to share in an organization. Who it’s ok to be.

Want to know what work would look like if done around the metaphorical bonfire? What your team and your company would be capable of if everyone stopped trying to look good and instead brought their whole souls to the work?

Getting there takes giving up your competence and telling your story. The real one.

Leaders go first.

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