One of the hard realities of starting a business or coming into a new leadership position is that, unless you’ve done it many times before, you likely don’t know how to do your job well. This doesn’t mean you’re not talented; it’s just the nature of constantly confronting the edge of the unknown. One of the most important lessons I learned early in my startup career was that nobody else knows what the hell they’re doing, either (never mind their humblebrags on LinkedIn).
The most successful people are those who, faced with their own inadequacy, move forward anyway. They’re not blessed with special talents, they’re just people who keep going despite all the reasons not to. You grow into yourself as a leader when you learn to stop pretending to have all the answers and instead are willing to be yourself—warts and all—and step into the immense uncertainty of leadership. Scared, absolutely. But undeterred.
You grow into yourself as a leader when you learn to stop pretending to have all the answers and instead are willing to be yourself—warts and all—and step into the immense uncertainty of leadership.
In his book Crossing the Unknown Sea: Work as a Pilgrimage of Identity, David Whyte writes:
We have (a) strange idea in work… that we will engender love, loyalty, and admiration in others by exhibiting a great sense of power and competency. We are surprised to find that we garner fear and respect but forgo the other, more intimate magic. Real, undying loyalty in work can never be legislated or coerced; it is based on a courageous vulnerability that invites others by our example to a frontier conversation whose outcome is yet in doubt.
Whyte is not describing a leader who has all the answers, here. Rather, he observes that the most effective leaders lead not solely from a firm conviction in their beliefs, but from a deep and humble commitment to answering a worthy question.
Why We Need Vulnerable Leaders
If you’re up for a contemporary example of this type of leadership (if you’ll forgive the locker room setting; I do come from the world of competitive sports, after all), consider Al Pacino’s portrayal of football coach Tony D’Amato in Any Given Sunday.
Far from the rah-rah you’d expect given the setting, by the time Tony finally gains the support and loyalty of his team, after a ton of on- and off-field issues, he is all but a defeated man. It’s his leaning into that vulnerability—admitting to his personal shortcomings, the wrong choices he made and how he failed as a leader—that opens up the space between him and his team to create something new. It’s his owning his own vulnerability that gives his team space to embrace their own.
Tony never sugarcoats the challenge in front of them. He deals with reality as it is: raw, unforgiving, no chaser. This combination of personal vulnerability and the willingness to deal with the reality of a situation, however messy it is, bonds him to his team.
And despite his uncertainty, importantly, he moves forward. Knowing all the reasons not to. Knowing his own shortcomings, his own fears, knowing the long odds against them. Knowing all that, he marches forward anyway. And in doing so, he invites his team to do the same.
I work with leaders every single day, and the one thing they all have in common with Tony is that they all have problems. Big problems, little problems. Existential problems. Small problems that feel existential. Leadership, to a large extent, is simply a method to take on bigger and bigger challenges. Yet 80% of leaders don’t talk readily about their struggles with those they lead, according to a study of 21k employees published in The State of Leadership Development in 2020, and 21% actively hide their problems from their employees.
I get it. It’s scary to admit that you don’t have everything under control. People might leave, or worse, they might think badly of you. But as scary as it is, most leaders who bravely own their uncertainties and imperfections find the exact opposite: it makes them a more effective leader.
3 Reasons to Embrace Vulnerability as a Leader
1) You Invite your team to bring their whole selves to work.
As a leader, projecting the image that you’re “crushing it” sends the message that your team must do that, too, and since nobody actually crushes it all the time, what really happens is everyone just pretends they are. Many leaders ask for teams to dedicate themselves, but someone pretending to be something they’re not can’t truly dedicate themselves. To truly engage with the hearts of your team, you must give them the space to be themselves at work. You do this by being yourself.
By being honest about your failures, your imperfections and the things you don’t know, you give others permission to be their imperfect selves as well (they will be themselves one way or the other, your choice is only whether you’ll welcome them in all their glory, or whether by curating your image of success and certainty you’ll force them to wear a mask, too), and your commitment in the face of those imperfections and uncertainty invites your team to courageously make the same commitment in the face of their own fears.
2) You let your team make you smarter.
Nobody can see the entirety of the elephant. Leaders who communicate their opinions in the form of facts (a la “strong opinions loosely held” or similar) simply make it difficult for their team to help them see the bigger picture.
By taking pains to accurately represent your level of certainty in stating your opinion without selling it (an easy way to do this is to simply state your percentage of certainty. Think: “I’m 80% sure that we should go this way,” or “I’m 45% sure we should invest in this project”), and by publicly embracing the fact that you do not or cannot see the whole picture, you open the door for others to contribute to your understanding. And a more complete, nuanced understanding of the problem enables you and your team to make better decisions.
3) You get to be yourself. And that’s enough.
Finally, and in the end most importantly, by aligning your public persona with the real, fallible, vulnerable human underneath, you bring your thoughts, words, and actions into harmony, which no less than Gandhi has said is key to happiness (and I can attest).
Leading a team or a company is tremendously hard. Everybody struggles, despite what you see on LinkedIn. The best leaders in the world have bad days, weeks, and months. The best leaders in the world fail, sometimes. Everybody does. This journey that we’ve chosen can make you feel inferior, inadequate, like an imposter. It’s easy to internalize these feelings, and doing so can make the journey hellish.
David Whyte again:
We have an even stranger idea: that we will finally fall in love with ourselves only when we have become the totally efficient organized organism we have always wanted to be and left all of our bumbling ineptness behind. Yet in exactly the way we come to find love and intimacy with others through vulnerability, we come to those same qualities in ourselves through living out the awkwardness of not knowing, of not being in charge.
Compassion is key. Compassion for the inevitability that you will struggle, and you will fail, and that that’s normal and OK. It doesn’t make you a bad leader; it makes you human. Acknowledging that fact enables you to gracefully do what all great leaders do: Press forward.
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