Looking Back on Year One as a Team Lead

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It’s been a little over a year since I took on a team lead role at Automattic. The past year has been both fun and challenging. I’m fortunate to work in a culture where mistakes are viewed as opportunities and learning can happen rapidly. Last week, I was thinking back to everything I’ve learned over the past year, and I thought it might be helpful to share some of those ideas here.

One caveat I’ll mention before we take off: I share these ideas not because I’ve mastered the concept of leadership (or the concepts mentioned here to be clear). Read this not as “Jeremey shares the key secrets of leadership.” I’m still figuring it out, but I like to do so in public so everyone can level up together if they so choose. Another benefit: I can revisit this post in six months as a reminder to myself.

I subjectively chose five things below to focus on. Realistically, I probably made 1,000 mistakes that aren’t coming to mind right now. These are just the big ones that came to mind as I reflected on the past year.

1. Reinforce the “vision” a lot.

I’m reading Leading Change By John Kotter, and I was reminded of this in his eight failures of transforming organizations. He spells it out as “undercommunicating the vision by a factor of 10 (or 100 or even 1,000). Teammates need to understand what the future will look like and how to get there. More importantly, that future has to be reiterated over and over again through both words and actions (the latter being most important). Follow this rule of thumb from Kotter:

Whenever you cannot describe the vision driving a change initiative in five minutes or less and get a reaction that signifies both understanding and interest, you are in for trouble.

Create a survey (informally, we refer to these as leadback surveys at Automattic). Ask your team to explain the “vision” in their own words. Compare across team members. If everyone isn’t on the same page, had back to the drawing board. Rinse. Repeat.

2. Act as a funnel.

One role of a leader is to narrow the field of vision for their teammates. Meaning, of all the information coming at a teammate on a daily basis, how do you assign urgency and decide what’s important? What are we focused on? What matters?Realistically, this list has to be short.

This concept was further reinforced in the book Extreme Ownership:

Leaders must be careful to prioritize the information to be presented in as simple, clear, and concise a format as possible so that participants do not experience information overload.

Your job as a leader is to narrow that priority list so that the team can make decisions as a cohesive unit.

3. Be overly explicit in communication.

The “Say vs. Hear” paradox. Leaders assume that what they say and what teammates hear are on in the same. That assumption can prove false for a number of reasons.

The only way to solve this issue is to overcommunicate especially around the “why.” Whenever there is an information imbalance (that is, you have access to more background information than someone else), solve that first. Explicitly tie the action items back into the future vision. Recap in text.

4. Help teammates align projects with strengths.

Success and fufillment intersect when teammates are working on projects that align well with their talents. Cal Newport highlighted this in So Good They Can’t Ignore You when discussing three basic needs to feel intrinsically motived:

  • Autonomy: “The feeling that you have control over your day, and that your actions are important”
  • Competence: “The feeling that you’re good at what you do”
  • Relatedness: “The feeling of connection to other people”

If you’re doing #1, #2, and #3 well, the autonomy portion is mostly addressed. There are many ways to help teammates feel competent. One way is to understand everyone on your team, what makes them tick, what gets them excited. Then, find work that capitalizes on their strengths. This is only part of the puzzle (there’s also challenging them to work on their weaknesses), but it’s an important piece.

How do you find out what teammates are great at or what gets them excited? Observe what they’re working on day-to-day when they have free time. Or, better yet, just ask them. These questions from Lara Hogan are a good starting point for your first 1-1. Give this spinoff a try that I adapted from the altMBA application:

Tell me about a situation or project where you went above and beyond, a time where you felt really in love with your work.

5. Build a team, not a collection of individuals.

A few months back, I read this awesome quote about “superstar teams” in Charles Duhigg’s Smarter Faster Better:

There’s a myth we all carry inside our head…we think we need superstars. But that’s not what our research found. You can take a team of average performers, and if you teach them to interact the right way, they’ll do things no superstar could ever accomplish.

I’m not implying that our team is full of average performers just that with the right recipe the sum is indeed greater than the parts. This vision is either weakened or reinforced during every piece of communication including when you’re setting goals and giving praise.

Using pronouns like “we” versus “I” or “you” go along way. Reiterate that the team is going to succeed or fail together; no one singular person is at fault.

Find times to get to know one another on a personal basis. We started with an adaptation of Friday Fikas from Help Scout (kudos Dean for the implementation).

The benefits to this kind of approach go beyond fulfilling the relatedness component Newport mentions above. When done right, this team atmosphere goes along way in addressing accountability. Teammates are accountable to the larger team, not to their “boss.” Teams can celebrate wins together and capitalize on everyones’ various strengths.


It would be remiss of me not to give a thank you out to Sparta, the awesome team I’m fortunate to lead at Automattic. Thank you all for pushing me to grow and learn over the past year. I’m lucky to work with such smart and talented individuals. Here’s a premature “thank you” for all the lessons I will undoubtedly learn the hard way in upcoming years!

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