The Leadership ReadMe: my favorite way to build understanding among coworkers
An instruction guide for how to work with your boss? Yes please. | Team Letter | February 9, 2026
Hello Alpaca and Happy Monday!
Happy Q1 Retreat Week! Happy NCE Week! WOW this is a big week!
I figured you might want some airplane reading/thinking topics today as we travel, so I wanted to introduce a concept that we’ll be talking about as part of retreat. Tomorrow, we’ll talk about how we’re going to grow as a company this year, and central to that conversation is leadership.
Leadership is a part of everything we do.
Our customers are all school and district leaders; our product is built around improving leadership and culture; and our team thrives when each of us acts as a leader of our work, our teams, and our goals.
One of my favorite leadership tools I’ve ever learned about is the Leader ReadMe. It’s a simple way to start speaking the same language with leaders in your company, understand the best way to communicate with your manager, and build expectations for your teams.
So what IS a Leader ReadMe? Well, thank you for asking.
First, a History Lesson.
A long long time ago when personal computers were rather new to most of us, many pieces of software were purchased in an actual store (yes and software came in an actual box) which you then installed on your computer. Once installed, you would very often find a simple text file in the software named “README.”
That file contained the operating instructions for the software. How to use it, which commands you’d need, the rules of play for a game. So whether it was business software like Microsoft Excel or a game (Oregon Trail? Anyone?), you’d have a simple way to know how to use the software as soon as you’d installed it.
I promise I’m going somewhere with this, and now you all know JUST how truly old I am.
Years ago, I learned about a leadership practice called the “Leader ReadMe.” The practice originated in the tech industry and was made particularly popular by the then leader of Netflix, back when Netflix still shipped DVDs to people in the actual mail. (Yes, I was around for that too).
Leader ReadMe: An operating guide for working together
The idea of a Leader ReadMe follows the same principle as a software “ReadMe” file, but for leaders and managers. Essentially, it’s a guide to how to work with a leader, setting up expectations and norms from the very beginning. A leader’s ReadMe can evolve and change, and can adapt to the company or team.
A ReadMe It isn’t a sales pitch or a resume but rather a simple set of things to know about working with someone as a leader. What they expects, what they care about, how they works, when they works, and how they help each team member be successful in their role.
At my former company, our Director of Engineering led off his very first day of work by sharing his Leader ReadMe — an operating guide to working for him — with every one of his direct reports. Right from the start, they knew how best to work with him. After reading his, I immediately wrote mine.
I found that the clarity of writing it was helpful for me as a leader, too — it helped me discover what I valued the most, and I found myself realizing “I don’t think I’ve ever said this to the members of my team.”
Every company and team is different, and my own leadership style has changed with time, so last week while I had the gift of a bit more time on my hands, I took a moment to write a new ReadMe. I now primarily lead other leaders, so mine is oriented in that way, but you can write a Leader ReadMe for any type of team.
You’ll find my Leader ReadMe here in a new space for them on Notion. (If you’re reading this and you aren’t on the Alpaca team, but you want to read my README, email me at karen at getalpaca.com and I’ll happily share it with you).
Why to write a Leader ReadMe
The simple answer is: clear is kind. To spend the time thinking about and writing about how you work, and sharing that with your coworkers is to give your coworkers a gift. It’s also a gift to you as the leader.
If you manage a team and they don’t know that you work best early in the morning or that you live and die by your google calendar, you risk misunderstandings, miscommunication, and a lack of alignment in expectations. But when everyone is on the same page (and it’s literally written down on the page), you can operate with the same understanding, even if you don’t work in exactly the same way.
We are all leaders here. Yes, you!
If you’re wondering how this applies to you if you don’t lead a team at Alpaca, worry not. You can also write a Leader ReadMe about the kind of manager or leader you WANT to become — it may help you identify the skill sets that you need to build or refine in order to earn a leadership role.
Also, don’t forget that there are more ways to be a leader than managing a team. If you lead a product, an office, a team, a key effort, or our culture, you’re a leader. So in a company of our size, we need everyone to be a leader, actually.
As part of our time together as a team this week, we’re going to talk about leadership and how we’ll grow as a team in 2026, and as part of that, we’ll help each person on the team develop the beginnings of your own “ReadMe.” Start thinking about what might go into yours, and do some exercises to help us each write our own this week.
Everyone buckle up — this is going to be a GREAT week together! See you in Nashville!
KB