My condolences, you are now running a multi-billion dollar company

Halfway through a relaxing winter break with my family, I opened Slack for a quick dopamine hit. The message I saw waiting from Matt, the CEO of Automattic, was quite a surprise:

“Would you be interested in running WordPress.com while I’m on sabbatical?”

To be honest, my first reaction was, “No, not really.” It seemed like a lot of work, stressful, etc. But I didn’t name my last team YOLO for nothing: the answer is always ‘Yes’, because you only live once.

Many teams at Automattic use the “red/yellow/green check-inas a means of communication. Now that I’m almost a month into running WordPress.com, I can safely say that I’ve experienced the entire program rainbow of emotional states. Today I want to share some of my lessons with you in the hope that they will help you in your leadership journey.

Another pro tip: don’t open Slack on vacation.

Problem #1: I’m receiving 50x more pings

My former team is mostly based in Europe, so their day started much earlier than mine. When I logged in for the morning, I usually had a few things to respond to before getting to work.

Nowadays I drink from the fire hose. I wake up to dozens of P2 mentions, Slack DMs, and other communication threads. I clean them up and then they pile up again.

Solution: Delegate, delegate, delegate

Ideally, I would like to run the business while skiing on fresh powder snow. To do this, I need a great team that I can rely on to get the job done.

For our recent efforts, the WordPress.com leadership team traveled a total of 160 hours to meet in New York. While we were there, we focused on identifying goals that answered the question, “If we did this in the next 90 days, would it be transformative for the company?” Everyone went home with a specific set of goals that he or she had. Knowing what we are trying to do and who is responsible for what are two important elements of delegation.

In addition, I encourage the team every day to:

• Actively collaborate before they come to me. On a football field, the team wouldn’t get anywhere if they had to ask the coach before every pass.
• Come to me with “I plan,” not “What should I do?” Actively acting on your own and reporting progress represents the highest level of initiative.

Ultimately, I should be the critical point of failure in very few things. If something comes up, there must be a clear 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 is always something broken. Whether it’s bugs in our code, overloaded customer support, or a botched marketing email, entropy is a very real thing in a company of this size.

Even more amazing is the game of “whac-a-mole”: when you make a small change in X, it can be difficult to detect a change in Y or turn off Y altogether. There’s always something!

Solution: Focus on the next most important thing

In dealing with the constant fires and constant fire hoses, I have found great comfort in asking myself, “What is the most important thing I need to work on right now?”

Leadership is about results, not about the hours you put in. Typically, achieving these results comes from finding leverage points that deliver outsized returns.

Ultimately, the best I can do is give it my best shot.

Problem: We move too slowly

By default, nothing ever gets done in a large organization. There are always reasons why something shouldn’t be done, additional feedback that needs to be gathered, or uncertainties that someone may not be comfortable with.

If you’ve reached the point where you’re a large organization, congratulations! You must have done something good along the way. But remember: standing still equals death. Going too slow can be even riskier than making the wrong decision.

Solution #3: “70% confidence”

I think “70% confidence” has been hanging around for a while, but Jeff Bezos put it well in his Letter to shareholders from 2016 (emphasis mine):

Most decisions should probably be made based on about 70% of the information you want to have. If you wait 90% you are probably slow in most cases. Moreover, you have to be good at quickly recognizing and correcting bad decisions. If you’re good at course-correcting, being wrong can be less expensive than you think, while being slow will certainly be expensive.

In the field of leadership, I find ‘70% trust’ a particularly effective communication tool. It explicitly invokes risk appetite, encourages a level of uncertainty, and identifies a sweet spot between inadequate planning and analysis paralysis. Progress only happens when there is some degree of risk.

I’m happy to share what we’ve been working on. Stay up to date with new developer tools, powerful updates to WordPress.com, and tips for making the perfect pizza dough. If you would like some additional reading material, Here is a list of my favorite leadership books.

Original illustrations from David Neal.