The Leaflet #137: greatest hits & new quotations

managing those with more technical skill; i do - you do - we do at work; essence and maintenance

Welcome! We've added a lot of new readers in the past few days, so in this week’s issue we're running back three of our most-read pieces from the archive to give a flavor of The Leaflet at its best. Compelling Quotations down below, as always, are new :)

You’ll see on the homepage that we now have a lineup of our most popular recent stuff and links at the top for collections on frequent topics: feedback, hiring, AI/Claude, mvps, etc. We’re tagging and organizing the 136 other issues in our full archive in Kermit-at-the-keyboard fashion; for now those links will give you a first sampling.

As always, we love hearing what you find useful and what challenges you want help with. If you have a moment, reply here and let us know or forward this one on to a colleague who could make good use of it.

Enjoy!

ben & eric

1. Managing people who have more technical skill than you do (from Leaflet #116)

Critiquing people who far exceed your technical skill set in the thing you’re critiquing is a very common part of management. It may become even more a part of your management work the higher you go in the org chart. A CEO usually has emerged from a specialty, like operations or sales or product, rather than having been a generalist who has done all of those. Despite how common this responsibility is, people are often terrible at it for the reasons we’d guess.

I was very lucky that I had a management mentor early on in my life, when I was a 28-year-old principal managing teachers who had double the experience I had. I was very nervous about that all the time. And that mentor just gave me this phrase: your job is not to be better than them, it is to make them better. I held that in my head and repeated it, over and over.

If you share that story with those you manage, they will likely agree with you and they’ll be glad they agreed. It can help to do this explicitly: our story, by the way, is not that I’m better at this than you, and that’s why I get to tell you what you need to do to improve. The story we share is that I am the person we have both agreed can make you better at this. And that is what allows me to push you the way I’m about to.

The next step can be talking with them about the ways in which they can envision that happening. You can identify some things where I don’t need to be inside the technical skill set to tell you whether it’s improving or not. I don’t even need to know what hacks, tips, and procedures make somebody better at that thing. We can brainstorm those things together. It’s my job to make sure we have the brainstorm. It’s my job to hold you accountable to what we produce in that brainstorm. Who else is going to do it if not me?

What I’m sketching here is manager as coach. I’m holding us both accountable to you identifying, with me sort of stamping and agreeing and perhaps even critiquing and vetoing occasionally, the next level you want to get to. I can hold that. If you say, “Today I would correctly assess myself as a six,” I can say to you, “Okay, by next quarter you should be an eight.” You might know way more about what that six-to-eight leap is going to require than I do, so I’m going to ask you to identify what those things are. Whether it’s additional guides who aren’t me, or resources I can give you, or focus and accountability I can give you, or the opportunity to thought-partner — I’m going to provide every single one of those things.

That is my role as manager: to marshal the resources and the clarity to make you better.

-ben

2. I do - you do - we do for the workplace (from Leaflet #115)

There’s a common approach in K-12 teaching called “I do, we do, you do.” You can imagine how this approach works just from reading the handle. The part that can easily get lost when you apply this in the workplace is that all three steps require full attention from both parties. Too often, a leader delegating something skips straight to “you do” and only looks at the output of the delegate’s work.

When handing off a skill and practicing it, the “I do” part doesn’t mean the teacher is just doing it in a vacuum. “I do” means the teacher is doing it and the student is paying attention to how they do it. It’s still a two-way street. “We do” can take a few different forms: we’re either sharing the task by taking different parts of it or we’re literally holding hands on the same pencil and doing it together in lockstep. Obviously, this step requires full participation of teacher and student. In the “you do” phase, the student does it and the teacher is paying careful attention, giving feedback.

When you’re transitioning a skill set or a set of structures, you’re roughly using that framework. It’s worth noting that all three steps of this can be done in a pretty short amount of time, depending on what the skill or task is that you’re delegating. You may not need a detailed work plan or calendar gymnastics to get it done. Watch me open this meeting, then we’ll open the next one together, then the one after that, you open on your own (with me observing).

-ben

3. essence and maintenance (from January 23, 2025)

In one bewildering season of my time as CEO, Ben made a typically perfect book recommendation. He suggested I skim The Four Disciplines of Execution. I did and then carried chunks of it to my team and said - we are doing this. Let’s try it.

I liked the realism of the recommendations in the book. Specifically, the authors recognize that there is inevitably a “whirlwind” of responsibilities blowing around and through any brilliant central stratagem you and your team have come up with. Total, exclusive focus on the most important thing isn’t really possible or advisable. Someone has to file all the state taxes, answer customer calls, make sure that the right number of rooms are booked for the conference (anyone who works in operations knows this list could stretch to another 50-100 items before you have to think hard).

For his part, Greg McKeown recommends making a daily list of essential items and maintenance items: 2 essential and 3 maintenance. Richard Rumelt’s writing about the cost of having a strategy at all presumes that you’ve got beaucoup maintenance on your hands and may have to tradeoff on some of that maintenance to execute your strategy (so think twice, dear reader, before you commit to having a strategy at all).

The through line here is essence and maintenance. Classifying the two in your own work, giving them both their due. Especially in fast-paced early days, where you’re scrambling for survival or, happily, scrambling to keep up with rampant demand, you can lose sight of one of these two halves.

Often, essence feels sexy and maintenance feels safe. Different people on the team will be drawn to one of the two, so much so that they’ll see it as the sole guarantor of success. A challenging truth is pretty much every day of an organization’s life (and of your own) requires attention on both.

-eric

COMPELLING QUOTATIONS

Buddhist scholar Geshe Shawopa with an admonition:

Do not rule over imaginary kingdoms of endlessly proliferating possibilities.

Austrian poet Elfriede Jelinek flipping the script:

They remain at the edges of things, not because they’re afraid of the light but because the light, understandably, is afraid of them.

Poet Rosanna Warren on source and destination:

The stars are a wheel of fire
broken off from earth fire, surrounded by air.
We came from the unlimited, to it we return. So taught

Anaximander of Miletus, who thought we would be destroyed.