Wil.README

Over the last few years years, I’ve found myself repeating roughly the same spiel every time I onboard a new direct report. When I ran across the concept of a Manager README a few years ago, it seemed like an obvious and good idea to spend some time writing it down.

Some Things About Me

  • I live in Chicago with my wife and son.
  • I was born and raised in Texas, and am a first generation American.
  • My father is a retired professor of Mechanical Engineering, which luckily gave me exposure to software engineering at a very young age.
  • I am a college drop-out. Some of my most formative startup years were when my close friends were getting their degrees.
  • I have two hobbies that balance each other out: fitness (tennis and olympic weightlifting) and learning about wine. I also occasionally play the piano.

My Role

Regardless of my current title, you can either think of me as a business-centric technology leader, or a technology-centric product leader. I am accountable for a lot of things, but ultimately I exist to serve you and enable our team to be successful. To keep us focused and happy, to remove obstacles, and to create a great working environment.

I believe that most people want to work on interesting problems alongside great people. They want to grow as individuals, make a big impact, and have fun doing it. I believe that leadership can come from anywhere in the organization, and it’s in everyone’s best interest to let them flourish.

Management

I am a firm believer in radical delegation. By deliberately handing full ownership of a task, project, or initiative, we empower leaders and teams with liberating levels of confidence, creative license, and the degrees of freedom to experiment with new approaches (many of which will fail, leading to important lessons learned). Some call this process “innovation.”

Of course, it’s important to pair ownership with clear expectations and full transparency. Visibility helps leaders stay informed, clear obstacles, and shield their teams from distractions. It also prevents surprises from occurring. Weekly updates are a simple yet effective mechanism to both reflect on the past week and to provide visibility into progress and roadblocks. Sharing them in writing eliminates the need for a status readout meeting.

I’m not afraid to get my hands dirty. I prefer not to, but if things aren’t working well, there’s a good chance I’ll get involved if a plan to fix isn’t underway.

I believe “doer leaders” are the most effective leaders: those who have demonstrated the ability to not only understand, but also do the work of their teams will have earned credibility with those they lead. It takes a lot of practice to keep ones skills current, but the result of this practice keeps leaders grounded and empathetic to the team’s day to day challenges.

“Disagree and Commit” is a concept I take to heart. While at times it can be difficult and uncomfortable to commit to an approach we disagree with, it’s important that teams stay aligned and row in the same direction. In any large enough group of people, it’s impossible to make everyone happy, and even consensus can be difficult to achieve. If I make the wrong decision, I will take accountability for it. Thankfully, most decisions in business tend to be easily reversible. In markets with high degree of change, there’s a lot of value in executing nimbly, and a lot of lost opportunity in moving slowly. Let’s bias towards action!

Hiring

My hiring philosophy is simple: I strive to surround myself with those who are better than me in what they specialize in. If we are the sum of our surroundings, then it’s important we surround ourselves with only those who make our team better. One of the best ways to make sure our approach is sound is to embrace diversity: diversity of background, race, gender, sexual orientation and viewpoint will help to make sure our ideas/plans are well-formed and credible.

I bias towards hiring doer leaders. In my experience, no company is too big to be lead by doer leaders. Many of the worlds largest technology companies have grown or maintained their success by hiring and promoting doer leaders.

Meetings

Over the course of my career, I have spent what feels like an eternity surviving through hours of poorly run meetings. Time is our most precious commodity, so we owe it to ourselves to spend it wisely.

I expect all meetings to have an agenda, objective, and if necessary, pre-read material. In meeting heavy cultures, this might seem like overkill. It’s not. Good preparation leads to better meetings, which leads to fewer meetings and more time for execution. When the agenda is over, the meeting is over. What happens after the meeting is even more important: clearly defined action items with assigned owners and committed deadlines, communicated to the right people, prevents the need to waste time revisit the same topic in the future.

I am skeptical of meeting with more than eight attendees. The larger the group, the less effective the communication, and the more distracted the attendees. A culture that requires large meetings regularly to drive execution suggests a deeper pathology: either strategic misalignment, too many competing priorities, ineffective communication, or a fundamental lack of trust and delegation.

Managers should take care not to interrupt the focus (“flow”) of those they oversee. Context switching is well understood to be disruptive to creative work (software development qualifies!), so let’s not sabotage ourselves by interrupting our teams frequently.

Writing

I am skeptical of PowerPoint as a communication medium for complex ideas. Bullet points are a low bandwidth form of communication. Without a written-out voiceover, PowerPoint presentations allows people to fill in the gaps with their own assumptions, and enables everyone to come away with their own interpretation. Long form writing is easy to share and collaborate in, easy to version control, easy to search, easy to catch up on while disconnected or mid-flight, is natively supported across many applications, and ultimately does a better job of ensuring all are on the same page.

Writing effectively is hard, but it’s one of the most useful communication skills to have, especially as the world begins to embrace widespread work from home practices. Being great at writing takes lots of practice, and I don’t claim to be even merely good at it. In fact, I’m told I can sometimes come across as harsh or angry when I believe I’m being emotionless and factual. I’m working on it.

Tools, Processes & Data

Most technology companies have dozens if not hundreds of tools and processes for their employees to work in. When designed in a silo, each of these tools or processes may make perfect sense, but when layered on top of each other, they can present a substantial burden on productivity, and prevent agile decision-making.

I believe that a good process is the most lightweight one that results in the desired outcome, and no more. Regularly reminding ourselves the difference between the work and the process that facilitates the work helps to reinforce where our focus should lay. “Meetings aren’t the work, and neither is JIRA” was a phrase frequently repeated when designing our implementation of agile nearly a decade ago.

Where we need them, our processes and tools should help us make better decisions based on the data, rather than relying on instinct. The absence of data in prioritization and decision-making usually leads to HiPPO, which can leave those closest to the work feeling unvalued. Starting with a common fact base will lead to better decisions.

Communication & Feedback

I am passionate about my work, and this frequently comes across in my communication. I believe that open, honest, informal, and caring communication (a la radical candor) can help us build trust and be on the same page. I believe that having the vulnerability and humility to look past organizational politics and share our failures openly – so that we can all learn from them – is a sign of maturity.

I try to give feedback early and often, as shortening the feedback cycle tends to lead to faster positive change. I will often ask “What can I do to support you?” and “What feedback do you have for me?”. I ask these questions earnestly. We’ll work the best when we have clear expectations of one another. Constructive criticism, if delivered well, should trigger introspection. I believe that “public praise / private criticism” is a good rule of thumb to follow when trying to change culture or behavior (with a few key exceptions, most notably strongly unacceptable behavior).

I believe context matters. Retrospectives and postmortems are important tools that help teams share a common fact base and learn from each other. Knowing the answer to “How did we get here?” is a prerequisite to not making those same mistakes again.

I place a high value on communicating accurately and choosing one’s words intentionally. This is an area of personal growth I am sensitive to.

Fin

This doc is very likely incomplete. I’ll probably update it from time to time. If you’ve made it this far, I’d appreciate your feedback. What resonates with you? Where do you disagree?