The first conference that changed the game for me was the inaugural ShopTalk in 2016 hosted in Las Vegas. ShopTalk managed to balance relevantprogramming with a selective, intimate audience of senior e-commerce leaders. The space was designed for connection (roaming coffee cart, lounge seating clusters, rapid-fire introductions where organizers connected you with relevant peers). People arrived eager to meet, share their challenges during interactive workshops, and help each other. It was one of those rare events where everyone there felt relevant, and the connections I made remain part of my career even today.
I think about that experience often when designing Chief of Staff Connect.
Conferences can be hit or miss. Panels that sound promising can end up being lightweight. Big crowds can make it hard to meet the people you actually want to learn from. It’s easy to walk away feeling like you spent a lot of money and time for a few slides you could have seen online.
But when done right, nothing beats being in the room. In-person events still hold unmatched potential for learning, building relationships, and accelerating your professional development. For Chiefs of Staff, who often operate alone in their organizations, these gatherings can be especially powerful.
With two COSC events under our belt, we’ve learned a lot about creating great experiences for our attendees. Here’s how we’re designing COSC NY and COSC EU to be that kind of conference and the real outcomes participants have seen from past COSC events.
Everyone in the Room is a Leader
Most Chiefs of Staff could be on stage themselves. We know that, and we design for it. You won’t find endless panels with limited Q&A here. We build sessions and workshops where your insights matter. You’ll share your perspective and learn from the person sitting next to you.
In this year’s "Conflict as a Growth Engine" workshop, we won't just talk about managing strategic disagreement—we role-play actual moments of misalignment that Chiefs of Staff face. Participants work through scenarios like navigating changes AI is having on a given team/process then debrief with peers who've faced similar challenges.
As Dara Chen, Chief of Staff to CEO at Rad AI, put it: "Attending the Chief of Staff Connect conference was a highly valuable way to connect with others in the role. It was a practical, engaging way to learn from and connect with the best. I not only left with a treasure trove of best practices but also gained a network of like-minded peers."
We create moments where you can test your thinking against peers from other industries, hear how others would approach your challenges, and refine your ideas in real time. The best part of in-person learning is the person you meet at your table, not just the person holding the mic.
Workshops Over Panels
Panels and keynotes rarely leave a lasting impression. One of my mentors used to say that if the speakers failed to deliver “tweetable moments”, then the whole session was a bust. That puts a lot of pressure on the panelists to deliver those memorable snippets.
Instead, what you usually remember is when you worked through a tough problem with a small group. When you were challenged to think in a new way. When you saw your situation reflected in someone else’s experience.
This year’s "Storytelling for Operators" session will start with a CEO keynote on setting the right goals, then immediately shift into hands-on work. You'll write, refine, and share actual memos on organizational change, practicing how to influence up, down, and across without endless meetings. Participants leave with frameworks they can use the next day.
We’re designing COSC to prioritize hands-on workshops. You’ll bring your current challenges into the room and apply new frameworks, mental models, and tools to them on the spot. You’ll hear real-life stories from CEO’s founders, and Chiefs of Staff and take action on those case studies. It’s not theoretical. It’s not filler. It’s a chance to do the work together with others who get it.
Hands-On Skill Building
The future of Chief of Staff work sits at the intersection of aligning humans and adopting technology. You need to know how to lead through complexity and how to harness the best of AI and new workflows.
"Taste, Judgment, and Power: Honing Executive Sensibility in the Age of AI" is an interactive session where you'll evaluate real scenarios and discuss in pairs: What's good? What's off? Would you ship it or stop it? As AI scales outputs, developing exceptional taste becomes your competitive advantage.
At COSC, you’ll get to test tools, build workflows, and learn by doing. You won’t just hear about AI adoption. You’ll sit down with peers and work through building AI-powered workflows together, while reflecting on the areas where humans still excel at the job. You’ll learn the nuances of quality and taste when it comes to judging the difference between good and great AI output. You’ll see what others are trying and where it’s working. It’s the fastest way to get over the learning curve.
We’re Building What This Community Deserves
As the leading community for Chiefs of Staff, we’ve hosted hundreds of events and attended the best conferences ourselves. We’ve seen what works and what falls flat. COSC NY and EU are built to deliver what you actually need: connection with peers at your level, practical learning you can apply immediately, and a clear-eyed look at what’s coming next for the role.
Beyond the formal sessions, we design for organic connection. We spend ample time designing the "Collective Experience" helping you find your cohort naturally through conversation rather than forced networking.
We’re not trying to pack the room with as many people as possible. We care about who is in the room and the experience they have. You deserve a conference that respects your time and helps you leave sharper, more connected, and ready to take on what’s next.
Ready to Join Us?
The agendas for COSC NY and EU are now live on our website. If you’ve been looking for a professional development experience that matches the caliber of your work, we’ve built these gatherings for you. You'll leave with practical tools, refined judgment, and connections that accelerate your impact.
We hope you’ll join us.
Scott
Founder | Chief of Staff Network
Explore the conferences here: COSC NY and COSC EU
