My Condolences You Re Now Running A Billion Dollar Business

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Halfway through a relaxing winter break with my family, I opened Slack for a quick dopamine hit. The message I saw waiting from Matt, Automattic’s CEO, was quite the surprise:
“Would you be interested in running WordPress.com while I’m on sabbatical?”
In honesty, my initial reaction was “No, not really.” It seemed like a lot of work, stressful, etc. But, I named my last team YOLO for a reason: the answer is always “Yes,” because you only live once.
Many teams at Automattic use the “red / yellow / green check-in” as a communication tool. At nearly the one-month mark of running WordPress.com, I can safely say I’ve experienced the entire rainbow of emotional states. Today, I’d like to share a few of my learnings with the hope that they help you during your leadership journey.
Also, one pro tip: don’t open Slack on vacation.
Problem #1: I’m receiving 50x more pings My former team is largely based in Europe, so their day started much earlier than mine. When I signed on for the morning, I’d usually have a few things to respond to before I dived into work.
These days, I drink from the firehose. I wake up to dozens of P2 mentions, Slack DMs, and other communication threads. I clear them out, and then they just pile up again.
Solution: Delegate, delegate, delegate Ideally, I’d like to run the business while skiing fresh powder. In order to do so, I need a great team whom I can trust to get the job done.
For our recent efforts, the WordPress.com leadership team traveled a collective 160 hours to meet in NYC. While there, we focused on identifying goals that answered the question: “If we did this in the next 90 days, would it be transformative to the business?” Everyone went home with a specific set of goals they own. Knowing what we’re trying to do and who is responsible for what are two key elements of delegation.
Additionally, I also encourage the team on a daily basis to:
Actively work together before they come to me. On a soccer field, the team would get nowhere if they had to ask the coach before every pass. Come to me with “I intend to,” not “What should I do?” Actively acting on their own and reporting progress represents the highest level of initiative. Ultimately, I should be the critical point of failure on very few things. When something comes up, there should be an obvious place for it within the organization.
Problem: Something is always on fire I am a very “Inbox Zero” type of person. Running WordPress.com breaks my brain in some ways because there’s always something broken. Whether it’s bugs in our code, overloaded customer support, or a marketing email misfire, entropy is a very real thing in a business this large.
Even more astounding is the game of “whac-a-mole”: when making a tiny change to X, it can be difficult to detect a change in Y or take Y down entirely. There’s always something!
Solution: Focus on the next most important thing When dealing with the constant fires and the constant firehose, I’ve found a great deal of comfort in asking myself: “What’s the most important thing for me to work on next?”
Leadership is about results, not the hours you put in. More often than not, achieving these results comes from finding points of leverage that create outsized returns.
At the end of the day, the most I can do is put my best effort forth.
Problem: We’re moving too slowly By default, nothing will ever get done in a large organization. There are always reasons something shouldn’t be done, additional feedback that needs to be gathered, or uncertainties someone doesn’t feel comfortable with.
If you’ve gotten to the point where you’re a large organization—congratulations! You must’ve done something well along the way. But, remember: stasis equals death. Going too slowly can be even more risky than making the wrong decision.
Solution #3: “70% confident” I think “70% confident” has been kicking around for a while, but Jeff Bezos articulated it well in his 2016 letter to shareholders (emphasis mine):
Most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow. Plus, either way, you need to be good at quickly recognizing and correcting bad decisions. If you’re good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure.
In leadership, I find “70% confident” to be a particularly effective communication tool. It explicitly calls out risk appetite, encourages a level of uncertainty, and identifies a sweet spot between not enough planning and analysis paralysis. Progress only happens with a certain degree of risk.
I’m excited to start sharing what we’ve been working on. Stay tuned for new developer tools, powerful updates to WordPress.com, and tips for making the perfect pizza dough. If you’d like some additional reading material, here is a list of my favorite leadership books.
Original illustrations by David Neal.

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