Chief of Staff Network

Most of what makes this community useful never shows up in a headline. It's the person who answers a question in the group at 11pm because they just dealt with the exact same thing. It's someone sharing the exact template they used to build a stakeholder map, not a watered-down version of it. It's the honesty about what didn't work, which is rarer and more valuable than any story about what did. If you're a Chief of Staff or an operator who's tired of doing this job in isolation, this is what COSN is for. Join COSN → https://lnkd.in/eBXdUzFz

Alex Craig’s blog post about building an AI Chief of Staff was written by the AI Chief of Staff. That’s not a gimmick. Peter, the system Alex built to run his Command Centre, drafted the post. Alex read it, gave feedback, decided what shipped. The byline is Alex’s. The labor wasn’t. Which makes the central admission more interesting: “This system has made my job harder, not easier.” Strip out the calendar reconstruction, the 1:1 prep, the ticket that appeared before Alex even remembered the commitment, and what’s left? Back-to-back decisions. No recharging work, no context-switching that actually gives you a break. Just the hard calls, one after another. The other thing worth noting: Alex ended the post with “You can’t have mine.” Not because he’s protective of it. Because it only works as a system built around his specific friction points, incrementally. A copy of Peter wouldn’t be Peter. That’s the real lesson Chiefs of Staff should take from this one. The tool is the process of building it. Full write-up linked in the first comment.

AI adoption is solved. The harder problem just started. Most organizations spent the last two years getting people to use AI. PortSwigger did it fast and across every function, including kitchen and front-of-house staff, not just engineers. But Alex C., their Chief of Staff, points to a more uncomfortable question now sitting on every leadership team's desk: when output volume explodes and accountability doesn't move, what does that mean? Alex frames it with a test worth stealing. If your manager could open a fresh browser window, no context about you, and produce the same output in five minutes, what exactly did you contribute? That's not a question about effort. It's a question about judgment. AI has compressed the distance from zero to a first draft. It hasn't compressed the distance from a first draft to a real recommendation. That gap is where Chiefs of Staff earn their seat. Structuring output. Pressure-testing analysis. Making sure what reaches a Principal is decision-ready, not just polished. Phase two of AI is harder than phase one. Full episode in the first comment.

If you're a Chief of Staff in Berlin (or anywhere in Europe), I've got two dates for you this summer ☀️ Our last event in May was a Show & Tell (pic below): a few CoS walked through real systems and processes they've built. No polished decks, just what's actually working behind the curtain. And couple of things stuck with me: Everyone in that room had built something worth "stealing". Which reminded me that growing into this job is a lot faster when you're not doing it alone. That's the thing about being a Chief of Staff: there's rarely someone in your own building doing quite the same job. These rooms fix that. So I'm really happy to keep hosting them, and to keep growing into this role alongside people who actually get it. If you'd like to be in these rooms too, I've got two chances for you: ☀️ Berlin Chief of Staff Summer Happy Hour — July 16th, 6 PM No agenda, no slides. Just drinks, good conversations, new connections, and the chance to exchange ideas with fellow operators in a welcoming environment. RSVP: https://lnkd.in/dpiKS-G7 📅 Chief of Staff Connect Berlin — September 14th The first CoS conference in continental Europe! A full day built for operators: - 50–75 Chiefs of Staff, not 200+. Curated room, you'll actually meet everyone. - Sessions tailored to the European operator landscape. - Annual Chief of Staff Network PRO+ membership included: be part of a 900+ global community. RSVP: https://lnkd.in/dpwYript Info: https://lnkd.in/dMH9UcaM There will be more interesting formats are coming after these, so stay posted. 👀

The Chief of Staff Network’s next Australian event is a networking event in Sydney on the 9th of July.🇦🇺 Our last event in Sydney was a success - a room full of Chiefs of Staff and company leaders engaged in conversation about the current landscape, business challenges and changes, and the role we play in all of it. If you’ve been looking for community, here’s where you’ll find it.🤝🏼 Register at the link below. Our last event filled up quickly, but there are still some spots left for this one. Grab them quickly!😊 https://luma.com/jrs37g7f

Most companies aren't failing at AI because they picked the wrong software. They're failing because they don't actually understand how their own company works. Kanika Choudhary put it simply on this week's episode of The Chief of Staff Podcast: "You cannot automate what you can't see." Chiefs of Staff are increasingly handed AI transformation by default. Not because someone designed it that way, but because the role sits at the intersection of everything. That's an opportunity. But only if you start in the right place: - Describe your actual processes - Find where time and money leak - Then look at tools The episode is called "Map Before You Buy" for a reason. Full episode linked in the comments. #ChiefOfStaff #AITransformation #OperationalExcellence #Leadership #FutureOfWork

We’re building the COSC NY stage and we’re looking for Chiefs of Staff with a story worth telling. COSC NY is the year’s biggest gathering for the Chief of Staff community. The best sessions don’t come from job titles, they come from people who’ve done something specific and hard. We want to hear from you if you’ve: → Deployed AI across the office of the CEO → Built something real — a product, a revenue line, a new market → Used the CoS role to accelerate your career in an unexpected direction → Got a sharp POV on what the role should be in 2026 Nominate yourself or tag someone who belongs on this stage. Link in comments. 👇

Eric Nehrlich never interviewed for the Chief of Staff role that defined his career. A VP he had worked with for three years just turned to him one day and said, come help me run my business. No job posting. No six-round process. An easy yes, because the trust was already there. Here is how that trust got built. Eric sat on Google's revenue forecasting team, which meant he was the person everyone went to about the numbers. When the Great Recession hit in 2009, he was the one standing in front of Larry, Sergey, and the entire leadership team every month, explaining what was happening to revenue when nobody actually knew. Stressful, exhausting, and the single best thing that could have happened to his career. You earn a lot of trust when you are the one staring at the hard problem nobody else wants to own. He was not the only one. Roughly five people from that same team went on to become Chiefs of Staff, because each had become indispensable to a leader on something that mattered. The role is rarely won in a hiring process. It gets earned, usually before the title exists, by becoming the trusted person on the thing a leader cannot afford to get wrong. Full episode linked in the first comment. #ChiefOfStaff #Leadership #Career #Operations

Attention Chicago-area Chiefs of Staff, Founders' Associates, and operators: mark your calendars for June 25 for our upcoming Chief of Staff Network meetup. This time, we are introducing a practical "show & tell" format. Attendees will have the opportunity to share real examples of how they are tackling challenges, building systems, and supporting their leadership teams. We look forward to seeing you there! Details and registration: https://luma.com/b5qz8v53 #ChiefOfStaff #Operations #Leadership #BizOps #Strategy #Chicago