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I get asked all the time about the differences between operating roles in startups. On the surface, operators share a common mandate: get things done. But how we do it, and who we do it for, varies. In this week's essay, I explore the four roles in the "operator spectrum" - biz ops, chief of staff, exec ops, and COO - in 5 visuals. This one is for you Nicole Titus, Abdul Bombata, Ciarra Balsomo Maria Lynch, Megan Carlson, Farah Cohen, Jamie Savage and Allison Donn. Let me know what you think. ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #35.

When it comes to retaining information, is it easier for you to remember what you read or what you heard? I'm a visual learner. Which is exactly why the rise of AI-generated documents at work has wrecked my comprehension lately. Ironically, this is the exact problem most writing cultures try to address. In this week's essay, I lay out our collective responsibilities as both writers and readers, and why outsourcing writing to AI risks the very things writing and reading are supposed to give us. This week's post is inspired by Clay's AI Writing Policy, written by Sophie Alpert, and by others leading the charge on our responsibilities as writers now that AI can do it for us, including: Jessica Z. at Leapsome Kathryn (KG) Treser at LinkedIn, and Mishti Sharma at Clay + S/o to Mike Maseda for introducing me to the concept of "meat proxy" ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #34.

I used to compare Chiefs of Staff to air traffic controllers... wide visibility, lots of coordination, and timing. But then I started working closely with product people, and my analogy evolved. Now I believe Chiefs of Staff are more like product managers. In this week's essay, I explain how I got here and why I believe the organization is the product. ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #32.

Why are execution and follow-through not improving alongside our rate of AI adoption? Well, that's because we assume we can automate the work that accountability and execution require. We can't, and shouldn't. In this week's essay, I argue that accountability requires friction, and that the annoying task of creating clarity is the first step to actually getting the work done. And that's way to valuable to be outsourced. ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #31.

Today is my birthday 🥳 And to celebrate, I'm walking Manhattan tip to tip with some of my favorite people. This year, in addition to blisters, I'm giving myself the gift of reflection. In this week's essay, I share 36 lessons I would give to my 26-year-old self. Consider this my version of a Sahil Bloom post :) ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #30.

I learned how to listen from a band. Unintentionally at first, but upon reflection, intentionally. Which makes me stop to wonder: how have others developed soft skills like listening? Has it been intentional? In this week's essay, and in honor of seeing my favorite band tonight at Madison Square Garden, I reflect on how Phish taught me how to be a better listener, and what I took from them into my work. Knicks in 4, Phish in 5! ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #29.

Congrats on the huge milestone Clara Ma Ask a Chief of Staff! Thanks for all that you do to empower, develop and support this role 🙏

There's a lot to not like about early stage startups: they can be chaotic, under-resourced, and constantly changing. But over 9 years and 6 different founders, I've figured out what keeps me coming back: the energy early stage founders bring. This week's essay goes out to them: the dreamers, believers and preachers. ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #28.

A core responsibility for any leader is to ensure alignment, and one of the best ways to do that is to foster a curious environment...one where asking questions is assumed, not requested. Which means there's a big difference between: "What questions do you have?" and "Do you have any questions?" In this week's essay, I reflect on a lasting lesson I learned in an improv class about the power of assuming questions. ---- In 2026, I'm publishing one essay each week about work, personal growth, and the relationship between the two. Here's essay #27.