Welcome, entrepreneurs. This week is part-2 of a two part examination of leadership. Last week we debunked the fallacy of the successful and certain leader. Leaders who are always “crushing it” (there are many and I was one for years) look like they’re running a company that is headed up and to the right, but in reality they make worse decisions, make it harder for their team to innovate, and saddle themselves with a crippling case of Imposter Syndrome.
If you’re in leadership and find yourself in pitch-mode all the time, consider that doing so may cause more problems than it’s worth.
To continue the conversation, since Unsuccessful and Uncertain leadership is not the answer, what is? This week we dive into the unique recipe of vulnerability and commitment that makes for an extraordinary leader.
VULNERABLE AND COMMITTED LEADERSHIP
One of the hard realities of starting a business 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 entrepreneurship that you’re 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 successful ones are those who, faced with their own inadequacy, move forward anyway. That’s all successful entrepreneurs are. They’re not blessed with special talents, they’re just people who kept going despite all the reasons not to.
You grow into yourself as a leader when you learn to embody this fact. To stop pretending to have all the answers, or to be constantly successful, and instead to be willing to be yourself — warts and all — and step into the immense uncertainty of running a company, undeterred.
From David Whyte:
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.
My favorite example of this type of leadership (if you’ll forgive the dude-bro setting; I do come from the world of competitive sports, after all) is Al Pacino’s football coach from Any Given Sunday, Tony Damato. Here’s what I’m talking about:
This is not a person who you’d look at and say “man, he’s crushing it.” The opposite is true, in fact. By the time he finally gains the support and loyalty of his team, after a ton of on- and off-field issues, he is a broken 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.
This works because deep down everyone in that locker room is broken. We all are. Every person has their demons, their dark places that they don’t talk about, and when a leader steps up and cops to his, people listen.
Nor does Damato sugarcoat the challenge in front of them. He says they’re in literal hell. 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. They are all broken, in a shitty, scary situation, together.
And yet, 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.
Dramatic, sure. But this speech is also quite instructive.
So why does Vulnerable & Committed work?
YOU INVITE YOUR TEAM TO TRULY DEDICATE THEIR WHOLE SELVES
As a leader, “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 fully themselves at work. You do this by being fully 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.
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 (see this excellent article for an easy way to do this), and by publicly embracing the fact that you do not — 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 company to make better decisions.
YOU GET TO BE YOURSELF, AND THAT BECOMES ENOUGH
Finally, and in the end most importantly, by finally aligning your public persona with the real, fallible, vulnerable human underneath, you bring your thoughts/words/actions into harmony, which no less than Ghandi has said is the key to happiness (and I can attest).
Building a company is tremendously hard. Everybody struggles, despite what you see on TechCrunch. The best entrepreneurs in the world have bad days, weeks, and months. The best entrepreneurs in the world fail sometimes. Everybody does. This journey that we’ve chosen can eat you alive. It can make you feel inferior, inadequate, like an imposter. It’s easy to internalize these feelings, and doing so can make the journey hellish.
Compassion is the cure. 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 CEO; it makes you human. Acknowledging that fact enables you to gracefully do what all great leaders do. Press forward.
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.
IT TAKES COURAGE
As we saw with the rat experiment last week, your brain is wired to avoid this type of vulnerability. Many of us are culturally conditioned to avoid it as well. There’s a reason the veneer of success and certainty is so prevalent in business.
It takes tremendous courage to push through all that and lead our company as the uncertain, vulnerable, committed beings we are. Without presentation and without hedging.
But while certainty isn’t a requirement for success, bravery is.
The compounding impact of doing little things fast
No less than Paul Graham said if it’s him reading the signs he thinks Stripe will become the new Google (perhaps the only Google by that time), and as a former tech executive I can say that when building a product that requires payment processing, it’s all but a foregone conclusion that you’ll use Stripe.
Things are going well for the payment processing company not because they are particularly unique, but because they are out-executing everybody in a crowded space. As such, there are many things entrepreneurs can learn from them.
That in mind, I really enjoyed this account, written by a serial-entrepreneur-turned-Stripe-employee, of what life is like at Stripe. The whole article is worth the read, but from my perspective one factor of the Stripe culture stands out as particularly relevant and worth emulating: the compounding impact of doing little things fast.
From the article:
The returns to pushing your cadence to faster are everywhere and they compound continuously, for years. Don’t send the email tomorrow. Don’t default to scheduling the meeting for next week. Don’t delay a worthy sprint until after the next quarterly planning exercise. Design control and decisionmaking structures to bias heavily in favor of preserving operating cadence.
I don’t think Stripe is uniformly fast. I think teams at Stripe are just faster than most companies, blocked a bit less by peer teams, constrained a tiny bit less by internal tools, etc etc.
A stupendous portion of that advantage is just consistently choosing to get more done. That sounds vacuous but hasn’t been in my experience. I have seen truly silly improvements occasioned by someone just consistently asking in meetings “Could we do that faster? What is the minimum increment required to ship? Could that be done faster?” It’s the Charge More of management strategy; the upside is so dramatic, the cost so low, and the hit rate so high that you should just invoke it ritualistically.
There are layers and layers of depth to implementing this, but it’s also the type of thing you could start right now.
What to keep in mind when giving feedback to a young entrepreneur
I first raised outside capital at age 25, with no prior business experience, my primary asset being an apparently compelling blend of ignorance and hubris. But someone first invested in me at 22 when, while working as an online truck salesperson and trying to get a sports blog off the ground, my boss (the GM at the dealership) told me that he thought I could really make a run of it in high school sports. In that moment what had been mostly a frustrating dream became real. Someone “successful” believed in me, and that was what I needed to invest in myself.
In building entrepreneurial communities we talk about the three types of capital:
All these types of capital are critical. But my experience is there’s also a fourth kind of capital that can be especially important at the early stages:
As important as it is, the beauty of Belief Capital as opposed to the others is that we’re all, every last one of us, a potential investor.
A powerful question if you’re wrestling with a tough situation
What would a wise investor want out of their CEO in this situation?
This perspective has a tendency to clarify things.
An easy, free way to begin investing time into your growth as a leader through meditation
I’m on record saying that meditation is more valuable than business school for leaders. It’s the most direct path I’ve found to concentration, equanimity, and insight, which are among the most important qualities in a leader.
But how to get started?
If you’re looking for a way to try meditation out, or to expand your practice, I really can’t recommend the Waking Up app, by Sam Harris, enough. Many meditation practices seem esoteric to those of us in the West, and Harris does a great job of making meditation accessible and straightforward, without sacrificing depth as many other approaches do. It’s easy for beginners to get started, and I still use the app regularly after more than 1,500 hours of meditation across many practices.
Whether you’re a regular meditator or just curious, I encourage you to give Waking Up a shot. They’re offering a free month of the app here. (No, I don’t get paid for this, I’m just a fan).
Like this article? Check out this list of my top posts, read and shared by thousands of entrepreneurs.
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.
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 — laser focused on results, without the fluff.
If you’re interested in developing yourself and your business beyond what is currently possible, I’d like to talk to you.
To find out more, click here or simply reply to this email.
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