A version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.
Nobody wants to follow someone who made General in peacetime.
I’ve been thinking about that concept a lot lately (Ben Horowitz calls its Peace/War Time CEO). In 2017, after eight years of informally leading the tiny community journalism organization I cofounded, I named myself CEO. Up until that point, my cofounder Brian and I had survived together. We’d always find a way to last a bit longer, growing slowly and thoughtfully as we navigated treacherous waters.
That survival approach was rational for growing a local news company in the early 21st century, a time in which consumers maintain very high expectations for free and independent journalism but have not yet been fully trained to actually pay or otherwise support its work in a post-advertising world.
But in early 2018, as I was finally feeling the great responsibility of the CEO title, I took stock of where my company was.
Setting aside excuses of industry constraints, I am too competitive and ambitious and proud and passionate to be CEO of a company that just survives. A year ago I resolved to only spend my time being the CEO of a company that was thriving. I had work to do.
I spent most of 2018 throwing out the playbook of my nearly decade-old, 20-person local community journalism organization. I tested the fences on a half-dozen approaches. My fixation of a truly unique business model leveraging a local newsroom came into clearer focus: Technical.ly will compete in talent acquisition, Generocity.org in professional development and Philly Tech Week will continue on to being a more widely recognized innovation festival. I talked to every single teammate at least once, many of them several times, about updating their roles and focus and where I thought our organization had to go in order to thrive.
Remarkably most of the team was thrilled (if cautious at first) that I was growing into a more decisive, more strategic CEO. I replaced those few who couldn’t commit to this new phase with people who know exactly what they’ve signed up for. We set quarterly roadmaps and ambitious new goals. In the fall, I took over our sales team, guided by an experienced sales coach. For a few months there, I made my incredible team nervous. Still a few of them found quiet moments to say to me: I believe in you. They may never know how important that was. Today, we are in such a different place.
I led a year-long reorganization of a decade-old company, and last month effectively marked the immediate end of that transition.
On March 29, our team celebrated hitting the largest Q1 revenue goal we ever set, powered by our reorganization. (The photo above is my sales team and me stomping the Q1 goal number.) There was champagne and cheering and the secret antics that I love conjuring. We celebrated the impact we have, and the work we’re doing. We celebrated the final day for my 10-year business partner Brian (more on that another time), whom I enlisted to help make sure we got through this big transition, and the six-month mark of my Chief Product Officer Kristin, my newest, closest work confidante.
Here’s the more universal lesson: leaders are made by the lows, not the highs.
I was as scared as I have ever been professionally in the last 90 days. I put a considerable amount of weight on hitting that big revenue goal, after using the goodwill I had with my team to trust me as I reorganized our tiny company. And not, like,”haha im scared” scared but like “good lord what if everyone decides im a loser and leaves at one time and the world is exposed to my idiocy in such a way that i cant even get an internship” scared. (Yay entrepreneurship, right!?) I needed deliver to my savvy team a big piece of real evidence that the strain was worth it, that I knew what I was doing. A big revenue goal was just the thing to earn back any trust I spent during the reorg. If I didn’t, I’d certainly deserve scrutiny. So, uhm, yes, phew, I was pretty happy at the end of March!
I’ve written about fear before here, about how we don’t talk enough about it because we all experience it. In the most intimate conversations with my coworkers last year, I told them the truth: I trusted entirely my confidence in where I was taking us. The risk was whether I could get us there. I named that fear. I asked for help. We came together.
In the last year, particularly in the last six months, I had to have a lot of hard and serious and honest conversations. I had to lean heavily on a lot of strong relationships I built up in my organization to be patient and trust me. I had to articulate my vision slowly and persistently. I could not waver. I had to do everything in my power, with unyielding focus, to make sure we got to the goal as a team.
The last year our organization was at war, in transition, shifting approach with the limited financial security of a small bootstrapped independent media company. Now, we aren’t on the defensive anymore. Now we go forward, on to bigger goals and challenges. We won’t hit them all, but we’re as able today as ever. We’re back on the offensive, a remarkable feat, I’d argue.
I like to believe I’m now more worthy of being a General worth following than ever before. You’ve likely had moments like these too. We all do. That’s as worthy as any outcome.
