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10 Takeaways from the Chief of Staff Podcast

No new episode this week, so we went back through the archive and pulled the 10 insights that stuck with us most. Let us know which of these or other episodes have resonated most with you!

  • Measure your impact by decisions removed, not tasks completed. "One of the KPIs that I try to measure myself against is how many decisions I took off the plate of my CEO. How many decisions I made instead of him, for him." Your principal's calendar is also a cheat code. It tells you where their energy actually goes, which is often more honest than what they say their priorities are.

  • Bryan went from SDR to CoS to COO at the same company over 11 years. His take: the CoS role is the ultimate career accelerant — but only if you use it to learn leverage, not just output. "You're kind of in this awesome strong position, but at the same time you want to figure out how you can leverage the people in your organization." Going go-go-go without building that muscle is the most common mistake.

  • The Builder's Mindset: How Chiefs of Staff Create Real Ownership — Elyse Levine, Executive Director, Capital Campus, USC (former CoS, FBI & Disney)

    The CoS sweet spot is cross-functional projects that don't fit neatly into anyone else's remit. "Every time an interesting opportunity has come up that there's no immediate answer for — like, who do we give it to? — I'm like, I want to do it." Before saying yes, run it through three questions: Does it fit your skill set? Is it a real priority for your principal? Does it move the needle for the organization?

  • The Hidden Power of Saying It Well — Rachel Peck, former Chief of Staff, Harry's; Founder, Metronome

    Internal comms is far bigger than all-hands and board decks — think Slack channels, office walls, even how your CEO ends a company-wide email. Rachel's rule: maintain a 3:1 positive-to-constructive ratio across all communications. And in a crisis, resist the urge to explain. "A very helpful reminder in moments of crisis is to just find ways to listen instead of talk."

  • Strategy Is a Choice: Aarti Bhatnagar on Leading with Intention — Aarti Bhatnagar, former Chief of Staff, Change.org & Guild

    "Strategy to me is really about making a deliberate choice — the things you're choosing to do and also not going to do." The CoS owns the process of getting there: keep the core planning window to two weeks per quarter, make sure key voices are heard, and wire the outcome into the operating rhythm.

  • Building the CEO Operating System: Lessons on Scale, Conflict, and the People Side of Growth — Dora Nagy, Executive Coach (former Google, SoftBank Vision Fund)

    Dora's three-pillar operating system — People, Execution (OKRs), Operating Model — functions as a flywheel. Weaken any one pillar and the others fall apart. The most overlooked? People. "99% of business problems are people problems at the end of the day." That includes the CEO. Recognizing when someone has hit the ceiling of their current role is one of the most valuable things a CoS can do.

  • Humans, Fear, and AI: Leading Transformations with Dominique Lear — Dominique Lear, Chief of Staff, Incandescent

    Most transformation efforts address the technical and structural layers, but fail on the adaptive one: changing how people think. The SCARF model (Status, Certainty, Autonomy, Relatedness, Fairness) explains why: humans react to social threats the same way they react to physical danger. "The amount of times I've been in a client setting where people hear a colleague say 'I feel that too' — and there's kind of a magic of that moment." The fix is simple; make the fear discussable. That's where transformation actually begins.

  • Context Into Action: Systems Thinking as a Chief of Staff — Jamie White, Chief of Staff (CMO), Notion (prev. Grammarly)

    A mentor at Slalom reframed Jamie's entire leadership style with one piece of feedback: "You can't connect dots if you're the only person that has the context. Information is what's going to empower your team." Her habit now: after any meeting where she's spotted something important, she debriefs her team live, turning her pattern recognition into a shared muscle, not a personal superpower.

  • Storytelling That Sticks: Andrea Mayendia on Driving Change at Dow Jones — Andrea Mayendia, Chief of Staff (CPO/CTO), Dow Jones

    Andrea uses the DMAIC framework (Define, Measure, Analyze, Improve, Control) (originally from Lean Six Sigma) as a mental model for almost any process problem. But her real edge is pairing it with data-driven storytelling: "I find I'm constantly reminded of this in my role, using data, even in my storytelling, to rally a team to make my argument or to make meaningful change within the organization." When you're trying to drive alignment in a legacy organization, showing the data helps create alignment.

  • Positioning Yourself as a Chief of Staff — Scott Amenta, Tom Guthrie, Rahul Desai & Lauren Werner, Chief of Staff Network

    The thing that separates standout CoS candidates from the rest? Commercial rigor — the ability to tie every bullet on your resume to a business outcome. "The thing that really stands out to me is the person can tie whatever it is they're doing to commercial outcomes." — Rahul Desai. Tom's pre-interview move: write a reverse job description for yourself. And always ask the principal to walk you through the 90-day plan.

Building with AI: A Non-Technical Guide to Shipping Real Software

Wednesday, March 18 | Virtual
Perfect for Chiefs of Staff looking to bridge the technical-business divide. This session demystifies AI implementation without requiring a technical background.
Register here

🌍 Global Chapter Launches & Regional Events

The Chief of Staff community continues its worldwide expansion with new chapters and meetups:

  • Sydney Chapter Launch — March 25 | Details

  • San Francisco Mixer — March 25 | Register

  • Singapore Meet Up — April 9 | Join

  • Paris Meetup — April 14 | Sign up

  • Dubai Forum — April 20 | Learn more

  • Austin Meetup — April 21 | RSVP

  • Detroit Meet Up — April 29 | Join

🤖 AI-Focused Programming

How AI Agents Actually Get Work Done

Thursday, March 26 | Virtual
Go beyond the hype. Learn practical applications of AI agents in organizational workflows.
Register

Chief of AI Fellowship

Thursday, April 2 | Virtual
An intensive program for Chiefs of Staff navigating AI transformation within their organizations.
Apply here

Building an Organization Equipped for the AI Age

Thursday, April 2 | Virtual
Strategic frameworks for organizational readiness in the age of AI.
Details

📚 Professional Development

Chief of Staff Launchpad

May 5 - June | Multi-session program
A comprehensive program for those stepping into or leveling up in CoS roles.
Learn more

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