Becoming a Wholehearted Leader

I recently picked up In Other Words, the latest publication by Jhumpa Lahiri. She has always been one of my favorite authors, but I have gained an even greater appreciation for her after the first ten pages of this book. She begins by explaining why she chose to write an entire book in Italian, a language that she is just in the beginning stages of learning. She explains how she wanted to immerse herself even if her ability to write in Italian did not even come remotely close to her Pulitzer level writing in English. She writes,

You can’t float without the possibility of drowning, of sinking. To know a new language, to immerse yourself, you have to leave the shore. Without a life vest. Without depending on solid ground.

To sound cliché, she jumped in with both feet, publishing something that may seem sophomoric to a native Italian writer, but to her, is a major accomplishment. It is actions like those that are wholehearted, vulnerable, and powerful.

I have been working in technology for more than a decade now. I’ve led teams, mentored product leads, architected systems, recruited top talent, and helped build products used by millions. Despite all of those successes, I have played it safe for most of my career, and only recently decided to leave the mothership to start my own company.

The sheer action of that, I now view to be wholehearted, vulnerable, and powerful. Besides building a product that I hope will have an impact on many, I get to shape a culture that has an affect on a few — my team.

It took me a several years into my career before I realized that I am my best as a leader when I lead with love rather than fear. In a recent episode of the Longform Podcast, David Remnick, the editor of The New Yorker, shares a similar sentiment when he talks about moments when he has led with fear rather than love. He says that leading with fear can work, but blows up soon. He continues by saying,

You’re learning all the time if you haven’t gotten so arrogant and self enclosed that you think you’ve mastered everything.

In a nutshell, that sums up what I had learned roughly three years into my career. To that point, I had been leading teams with strict deadlines, harsh criticism, and the false belief that I knew more than they did. I was the master and they were just the puppets. I had been conditioned to lead by arrogance. I thought it was effective, and selfishly, thought it would help me climb the ranks.

After just a few years of leading that way, I began to get increasingly more uncomfortable and unhappy. I was exhausted from going into work every day with an adversarial attitude. I was not inspiring my team. I was not accomplishing anything more quickly or of higher quality. I was sacrificing my own inner morals and values for some grandiose future of success that would be impossible to attain with my approach. And so, roughly seven years ago, I started to embrace the idea of wholehearted leadership.

Prominent social worker, Brené Brown, defines the concept of wholehearted living by writing,

Wholehearted living is about engaging in our lives from a place of worthiness. It means cultivating the courage, compassion, and connection to wake up in the morning and think, No matter what gets done done and how much is left undone, I am enough. It’s going to bed thinking, Yes, I am imperfect and vulnerable and sometimes, afraid, but that doesn’t change the truth that I am also brave and worthy of love and belonging.

Leading a life that way, let alone, leading others, is not easy, but the rewards are incredible. To get there, I had to get to know myself, know my team, and learn to be vulnerable.

Get to know yourself

I realized that in order to lead wholeheartedly, I had to get to know myself really, really well. I had spent practically all of my life dreading that. I didn’t want to feel my feelings or feel vulnerable. I never wanted to feel scared or uncomfortable. Whether it was an after work drink, hours at the gym, binge watching TV, playing my guitar, or turning to one of my other hobbies, I was always trying to escape my feelings, and thus missing out on getting to know myself. What I failed to realize was that feelings are an incredible source of information, and that experiencing them is actually a gift.

I made learning about myself the number one priority in my life. I learned to sit with my feelings, name them, understand them, talk about them, and foster a deep connection with myself. Over the years, I have realized that that simple action has had the single greatest positive impact on my career. I had learned to know and love myself, and therefore was able to lead teams from a place of love rather than fear. I began leading with emotional stability rather than anxiety.

Get to know every single member of your team

Through the course of learning about myself, I was able to develop deeper sense of empathy for others. I became aware of what team members were feeling, what they were going through, and was able to create a safe environment for them. I was able to be supportive, encouraging, and a strong mentor. I was able to give my teams autonomy while holding them accountable.

Getting to know each person really well allowed me to truly offer them individual support. My weekly 1:1s became far more than superficial checkins. I was invested in their growth, both personally and professionally.

Learn to be vulnerable

For my whole life, until that point, I viewed vulnerability as a weakness. Now I think it is one of the strongest characteristics of a leader. The ability to be vulnerable is both brave and powerful. It shows a great deal of confidence and knowledge of oneself. The more I was able to say I don’t know, can I help you, and I’ll give it a try, the more I was able to grow and foster a deep connection with my team. It broke down the divide between manager and team, and created a great level of trust between us all.

Once again Brené Brown nails this when she writes,

Now as adults we realize that to live with courage, purpose, and connection — to be the person whom we long to be — we must again be vulnerable. We must take off the armor, put down the weapons, show up, and let ourselves be seen.

Leading teams with courage, purpose, and connection creates an environment of immense trust, and that trust is crucial for teams to build great products.

I won’t sugar coat it by saying that any of that is easy, but it is rewarding. It builds confidence, trust, safety, stability, and ultimately forms the basis to build strong products, communities, and companies.


***Update: Recently, I was part of a panel discussion at Startup Island focused on this type of leadership. It made me even more certain that not only can this style of leadership work, but can really be the basis of empowering and positive work places.
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