My Journey Towards Authentic Leadership

I’ve been reading and listening to Jerry Colonna for five years now. I was fascinated by the first post he ever wrote, disappearing into the fire. It captivated me. Like many bloggers, Jerry was able to talk with authenticity about the experience of entrepreneurship. But unlike anyone else I’ve read to date, his perspective somehow managed to combine eastern philosophy with the harsh realities of capitalism in a way that spoke to me. There are others. Brad Feld thinks this way, although he hasn’t made it his life’s work to teach others going through this journey. Parker Palmer thinks this way, although he doesn’t live in the entrepreneurial world to the same extent. Jerry is, in my experience, unique.

While I was fascinated by the concept of “authentic leadership”, I didn’t really know what to do with that thought process. In the ensuing years, I’ve been on a continual journey to re-shape my ego and shift the way that I build relationships. I think I will be involved in that process forever, because I know just how far I still have to go, and yet I have begun to see the fruits of my labor. I’m fascinated, and humbled, as I start to see this happen.

I’m writing this because I want to share what I’ve learned so far from my attempts at practicing authentic leadership. My hope is that these practices will become more widespread.

Admitting that you are human — limited, fallible, imperfect — is a superpower.

It absolutely changes the way you relate to everyone you work with. The people that work with you are empowered, because they’re not counting on you for answers all the time. They’re also able to admit their own failures and imperfections and have honest conversations about them, because you have created a safe space to do so. These egoless conversations give everyone the opportunity to get better, and improvement becomes a collaborative process where both sides bring something to the table.

Human fallibility is an absolute, incontrovertible fact. You are not perfect. If you truly embrace that, openly and publicly, it is amazing how dramatically it will change both individual relationships and the dynamics of an entire team. My team today is the most honest, non-defensive, straightforward, hardworking group of people I have ever had the pleasure to be a part of. We’ve found that the people who join this team and get exposed to this culture blossom in really dramatic ways. Comparing this to teams that I have led in the past prior to my exposure to Jerry is like night and day.

The practice of mindfulness is an absolute requirement of a leader.

I’ve heard Jerry describe mindfulness as the practice of creating a space between a stimulus and a response that you can use to make a decision. I thought that was absolutely brilliant, although if you’re not familiar with mindfulness it might not sound like much. Here’s what this means. Going through your day as a leader, you’re bombarded with stimuli: people asking for things, data on performance, to-do lists, disagreement/conflict… As this is happening, you’re often in a flow state, just handling one thing after another after another. You’re very much relying on system 1 to do a lot of this processing, and as such most of what you’re doing feels very instinctual.

Mindfulness is the ability to recognize, in the moment, when a situation requires you to pause, come out of that flow state, and process it with system 2. Stop, pause, destress, think, pause, pause. Then react. Say something or do something, but only after that period of mindfulness. This can still happen all in the space of a few seconds, but it requires extreme mental effort, because you’re exerting a very high degree of self-control in pulling yourself out of flow and exercising a much more effortful mode of thought. But it’s the difference between acting annoyed and acting calm, between shooting from the hip in an important decision and stopping to gather more data. It’s the process that allows you to question a long-held belief.

Stop, pause, destress, think. I’ve specifically trained myself to recognize certain situations that require mindfulness. When I feel combative, or particularly stressed, or annoyed. When someone feels particularly strongly about a viewpoint that runs contrary to something I believe. I’m not perfect by any means, but I’ve made massive strides using this tool over the past year.

You only have one self, and you have to share it all.

To truly be authentic, you can’t just share your “work self” with your team, you have to share your whole self. People trust, and identify with, people. Your authenticity will resonate with them, but it requires you to share your entire self, not just some edited version of yourself that you’ve decided is safe-for-work. Eventually, most people will get comfortable sharing their complete selves in return when they realize that it is safe for them to do so.

Once you have developed two-way true-self relationships, communication, productivity, and happiness begin to climb for everyone on the team.

—

That’s all for now. Authentic leadership is absolutely the most important and impactful competency I’ve developed over the past six years working in startups, and I have a lot more to learn.

Thanks Jerry.