I’ve been managed in many jobs. I’ve got a pretty good idea I know what bad management looks like. But have those experiences prepared me to be a leader myself? I’m not so sure.
As a new leader, I’ve approached the role as something to be learned. Ari Weinzweig, co-founder of Zingerman’s, has written extensively on this learning process. In an essay on servant leadership, he urged new leaders to answer “a seemingly simple question, ‘What kind of leader do I want to be?’”
At first, I didn’t even know how to approach the question. What did an answer look like? What were my options? I didn’t want my thinking to be derivative of the management literature, so I avoided reading anything about it until I’d figured some things out on my own.
I spent months going through rounds of self-reflection, writing down my thoughts, and talking to others. I shared my thinking with people on my team and elsewhere, and I asked for feedback.
I don’t want to make it sound so straightforward and obvious. It wasn’t easy. I faced an enormous amount of self-doubt. The screaming skulls were always there in the back of my mind. But I sucked up my fear and pushed on, despite my anxiety about how others perceived me.
At this point, I’m ready to share where I’m at. I still don’t think I have all the answers, but I’m confident that I’m on the right path. What follows is an account of how I got here.
What the Hell Am I Even Doing?
In the spring of 2016, I became the head of the Data team at Kickstarter. Aside from a few roles managing student assistants at past library jobs, this was my first time in a leadership position.
I wish I could say I threw myself into the role with confidence and gusto, but the truth is I suffered from tremendous uncertainty. It felt like I was winging it day to day, with no solid foundation to fall back on, and I had far more questions than answers.
What did it mean to be a leader, both for my team and for the company? Where should I focus? How could I balance all the competing demands and make time for both short-term and long-term projects? What did I want to get out of this role, and what did I expect my impact to be? And, to be brutally honest, is this even something I wanted to do?
Thinking through all this led me to a central question about values: What were my leadership values, and how should I communicate those values and put them into practice?
Getting a Handle on It
I had the opportunity to participate in a series of coaching sessions during the summer of 2016. One of the goals I set for these sessions was to reflect on leadership. But it wasn’t enough just to think about it; I wanted to write about it and share my thinking with my team and with a broader audience.
I started off with some brainstorming, doing free writing to get my ideas on paper. When engaged in this kind of thinking, I work best with actual pencil and paper, away from a screen.
Scribbling in my notebook, I reflected on the differences and similarities between technical and people leadership. I thought about how I like to be managed, and I challenged myself to think about different ways other people might like to be managed.
I found myself gravitating toward a few key concepts: intellectual curiosity, love of learning, and a desire to have an impact. I explored these further in writing and in conversations with my coach and with folks inside and outside the company.
After a few months of reflecting, writing, and talking, I distilled my thinking down to several core ideas, and I drafted a document. I shared this with my team and a few others, got feedback, revised, rinsed, repeated.
As I thought about how to put these ideas into practice, I focused on an important question: How can I create a safe space for candid intellectual discussion? It’s one thing to say you value candor, but it’s another thing to foster a culture where candid speaking is the norm. This is something I’m currently focused on.
And so that leads us to the present day, and another important part of this process: sharing the document with the wider world.
Here it is:
My Leadership Values
What do I care about most?
Rigorous thinking. Candid speaking. In service to others.
My role as a leader is to foster these values on my team and put them into practice in my work for the company and the users it serves.
Rigorous thinking requires curiosity, skepticism, critical self-reflection, and continual learning.
Candid speaking requires humility, integrity, empathy, and the courage to speak honestly and plainly.
These values are in service to one another. Without rigorous thinking, candid speaking may be misdirected or biased. Without candid speaking, rigorous thinking may be ineffectual or uncaring.
These values are also in service to a larger cause: other people. Whether for the people on my team, in the larger organization, or the rest of the world, my ultimate goal is to put these values to work to make things better, for them. I measure my success by the success of others.
Fostering these values and putting them into practice requires constant diligence. They require careful listening, where I ask more questions than I answer. They require time and energy devoted to challenging my own assumptions. And they require direct, honest communication with the courage to challenge the assumptions of others.
As a leader, I am in service to my team, the company, and its community of users. My calling is to ensure that the work we do makes a difference in the world. My promise is to support that work through rigorous thinking and candid speaking, always mindful that these are in service to those around me and the world at large.
Where Do I Go From Here?
I expect this document to evolve over time, so I’ve also committed it to a Github repository. Because it’s under version control, it’ll be interesting to see what changes in this document and what remains constant.
I’m a private person, and so, honestly, it’s scary as hell to share something like this. But if I’ve learned anything about leadership over the past six months, it’s this:
- Self-reflection is essential. Take the time to reflect on what you’re doing, how you’re doing it, and how you could be doing it better. You can never stop learning, and you can never stop striving to improve.
- Document and communicate those thoughts. Write things down. Share them with others. Ask for feedback. Be brave because being a leader means being vulnerable.
Candid, thoughtful feedback is a central pillar of my leadership values. In the spirit of that, then, I ask all of you: What do you think?