Hi {{first_name|there}},
At Chief of Staff Connect in London last year, sixty-odd Chiefs of Staff were asked to submit one word describing their role. The word that surfaced most? Lonely.
Not "strategic." Not "impactful." Lonely.
"You hold the complete picture and the only person you can share it with is yourself."
Lissa Sorgenfrei, who spent eight years at Capmo, a German construction software company, ultimately as its first Chief of Staff knows exactly why. As she explained to Tristan Lim on this week’s CoS Podcast, the role puts you in what she calls a "sandwich situation": trusted completely by leadership, trusted completely by employees, never able to fully confide in either. You hold the complete picture of a company, and the only person you can share it with is yourself.
That structural loneliness is the first idea this conversation keeps circling back to. The second is Lissa's instinct to follow the learning curve, a habit so reliable it functioned like a career GPS for her. She left customer success when the curve flattened. Left product management. Left the CoS role itself. Each exit came at a time where she was looking for new opportunities to learn and create impact.
And the CoS role, she argues, was the best possible training for what came next. It didn’t prepare her for any specific domain, but it taught her to learn anything fast, ask the right people the right questions, and hold an entire business in her head at once.
The third idea is the one nobody talks about: the grief of giving all that up. When Lissa transitioned out of CoS into a go-to-market role, she described losing full company transparency as the hardest part - "the sweet taste of nectar," she called it. That breadth was, she eventually realized, the thing she was actually chasing. And the only place to fully reclaim it was to start something of her own.
She tried a women's retreat concept. Researched buying an HVAC business. Ran fake Meta ads to test landing pages. None of it clicked, until one Friday she went to a pottery studio to clear her head and noticed they weren't doing anything to connect the people in the room. She wrote the business plan that weekend.
It's a satisfying ending to the story, but it raises a harder question underneath it: Lisa had spent eight years learning to hold a whole company in her head, filtering every piece of information through a sandwich of competing loyalties, following her learning curve from role to role. All of that built something in her. But none of it told her what it would actually feel like to stop serving someone else's vision and start risking her own.
That part she had to figure out alone. And she talks through it in a way that's worth hearing for yourself!
The rooms where it happens. Are you in?
Chief of Staff Connect is coming to three cities and seats are going fast. These aren't passive conferences. They're curated gatherings of sharp, senior operators who come to think out loud, trade hard-won lessons, and build real relationships.
Don't just take our word for it:
"Energizing and inspiring… I left feeling less intimidated and re-energized about the possibilities of using AI more intelligently and intentionally in my organization."
"Being in a room with people who truly understood the role, could relate to the challenges, and openly shared their perspectives. The connections were meaningful and impactful."
"For the first time, I was able to sit in a room with other Chiefs of Staff. Most impactful was realising there are others out there who are owning this role and excelling in it."
🌁 San Francisco — May 15 Coming up fast. Grab your spot before it's gone.
🤠 Austin — June 4 Deep in the heart of Frontier Tech. Come ready to connect.
📆 Upcoming Events
We've got an incredible lineup of events coming up across the globe from local chapter meetups to deep-dive workshops on AI, legal risk, and automation. Whether you're looking to connect with other Chiefs of Staff in your city or level up your technical skills, there's something here for you.
This Week
Kicking things off today, our Boston CoS Meetup brings together local operators for conversation and connection. On Thursday, we're doubling up with the Berlin Chief of Staff Meetup and The CoS AI Build-A-Thon — a hands-on session where you'll actually build something with AI tools.
Mid-May Highlights
The following week, we head to Amsterdam for a CoS Borrel on May 13, followed by our San Diego Meetup on May 14. On May 15, join us for Chief of Staff Connect in San Francisco — one of our signature forums for strategic conversation and community building.
On May 19, we're hosting the first of a new AI series: AI & The Law: An Operator's Guide to AI Risk, Governance, & Contracts. If you're navigating AI implementation in your org, this practical legal guidance will be invaluable.
Late May
Wrapping up the month on May 28, we're diving into Building an AI Champions Program That Actually Works — perfect for CoS leaders looking to scale AI adoption across their teams.
June Events
June 4 is a big day: we're launching our Austin Forum, kicking off the Chief of AI Fellowship, and celebrating the Zurich Chief of Staff Chapter Launch. Three different ways to engage with the community, all on the same day.
Later in the month, our next Chief of Staff Launchpad cohort begins on June 23, running through July. On June 25, join us for Workflow Thinking: The Skill Behind Every Automation — a workshop focused on the foundational thinking that makes automation successful.
Browse the full calendar and RSVP to the sessions that fit your schedule and interests. We hope to see you there.
best,
Scott
Founder, Chief of Staff Network & BizOps Network
