Want to Really Help Others at Work? Talk About Your Failures

By being real with someone, it’s possible to create space for a different type of connection. Ryan Vaughn offers insight on why it’s important to foster authentic relationships in the workplace.

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Most people communicate in a 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 is that they’re competent. Independent of what they say, the way they say it is polished to shining, honed over dozens of conversations to produce a certain result.

You know it when you hear it. It’s the moment in a 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) fine-tuned to make an impression on you. For my last business, I went so far as to prepare different versions of my pitch depending on the situation: five words about the company for a first introduction, a paragraph touching on the market, unfair advantage and traction for investors, and a personal description of my greatest accomplishments for volunteer work.

The goal was to tell the other person about myself in the way I thought would get them to like me, admire me, invest in my company, or 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 botched the investor presentation? That time I let a customer down? These were completely off limits in these conversations because they’re hairy, and scary. They’re real.

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.

I always thought nobody would buy from that guy. The guy who was uncertain and had the occasional blemish. People wanted the guy who had it all together, who had all the credentials, and who was polished and competent. Right?

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. And I’m pretty sure they wouldn’t have joined me if all I had were failures. But sharing failures, more so than sharing press releases, was what enabled me to build my best relationships. And building great relationships is the key to being a great leader.

The person who always wins doesn’t connect with people emotionally, or develop the kind of deep friendship with 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.

Why Career Success Depends on Fostering Authentic Connections

Connecting with people in the way that builds meaningful relationships, a necessity 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, the greatest hits album of one’s career. It’s impressive, but it’s got no substance. 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. The time my team almost mutinied. The time many of them did, leaving scathing reviews on Glassdoor. The time I got fired. The time I went to jail.  When I talk about those things, the person I’m talking to really listens. Maybe for the first time.

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

By being real with someone, it’s possible to create a space for a different type of connection. We can finally stop presenting at one another and actually connect in a way that both of us might remember the next day. 

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, 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 create bonds between people, well beyond the surface of their manicured competence. And they don’t usually show up in a professional context. Not in my experience.

Being Vulnerable Makes You a Better Leader

The thing is, we need to hear these stories more often. Strong bonds enable you to lead people through hard times. So great leaders can’t save their vulnerability for close friends and bonfires. We need to bring it to the office.  

Strong relationships are built on real, honest, authentic, and vulnerable communication. 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 that we can really connect with another person. And it’s that level of bonfire-type connection that builds great leaders and great companies.

If we as leaders don’t emulate this at the top, we shouldn’t be surprised to find transactional, brittle relationships all the way down. In vulnerability as in everything else, leaders go first.

Mindful Leadership Starts with People 

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, or customers. The key to your success, the force multiplier present in everything you do, 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 title. Like it or not, you are a leader. So it’s worthwhile becoming a good one.

From the outside, it looks as though doing well means 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 but feel no reason to stick around when 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 the slightest pressure. And if you’re up to something meaningful in the world, you’d better be prepared for more than just a slight pressure.

To lead a team through the tough spots, the spots in which even you don’t know what to do, you need authentic relationships. To build those, 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. 

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


Keep On Moving 

We don’t have to like everything life throws our way. If we can learn to truly accept—not ignore or resist—the hard stuff, it won’t feel as hard. Read More 

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