How AI-ready are you as a Chief of Staff?

Hey {{first_name|there}},

How AI-ready are you as a Chief of Staff?

‍If you haven’t yet realized that the way companies work has changed, it’s time to face reality. Off-the-shelf AI systems can now do a substantial portion of tasks that white collar workers do today, and the improvement curve is steep. Chiefs of Staff are not immune to that change. ‍

At Chief of Staff Network, we view it as our responsibility to help Chiefs of Staff around the world connect and grow. Historically, that has been around skills like managing OKRs, running effective offsites, improving corporate culture, and optimizing internal communications. Some of these skills will still be important in a year or two.

Other skills will be entirely taken over, or made obsolete, by AI. Today - as in right now - it can generate a good first draft of your next board deck and write your next investor update. It can provide (good) advice on tough personnel issues with a little bit of context. It can create an internal web app to track and update OKRs and suggest new ones.

It can generate a full plan for an executive offsite, gather venue options, and email those venues for quotes. It can create and update a financial model in Excel. It can take product usage data, qualitative input from your sales team, and customer feedback and create a PRD for a new feature, then build that feature and push it to production. And these are just a few examples.‍

You’re likely already thinking: if these tasks are taken off your plate, what will your role be? Your answer might be: “Well, I’ll work with our Exec team to move our strategic priorities along faster.” But, large parts of their jobs (and their teams’ jobs) will be done by AI, too. It will take longer for Chiefs of Staff in government and highly-regulated industries to feel the impacts (fax machines are still widely used in healthcare, after all). At larger companies, these changes will take a longer time to take hold, too, whether because of organizational inertia, employment law, time to get leadership buy-in, or data privacy and security concerns. Still, technological changes of this magnitude don’t leave any organizations untouched.

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AI Readiness Diagnostic

Take the AI Readiness Diagnostic to find out where you stand and what to do next.

‍Observer: You're aware AI exists, but it's not part of how you work yet and the window to start is closing.‍
Experimenter: You're using AI for individual tasks, but you haven't rewired how you actually operate.‍
Practitioner: AI is part of your workflow. Now the question is whether you'll lead your organization's transformation or just your own.‍
AI Native: You're not just using AI, you're rebuilding the role around it, and the community needs what you've learned.

Take the Diagnostic

🎧 LISTEN: The Career Accelerant

Bryan Silverman joined Suzy as an SDR and nearly 11 years later is the company's COO, and the Chief of Staff role is what made that trajectory possible. In this episode, Bryan gets into how he navigated the tension of leading without authority, why he chose to leave the CoS seat by raising his hand for a problem nobody else was solving, and how he thinks about the two glass ceilings that cap most Chiefs of Staff: P&L ownership and managing people.

As Bryan put it: "I view the Chief of Staff role as the ultimate career accelerant, exposing me to all parts of the business, learning new things, getting new opportunities, meeting new people. I definitely would not be in the role I am today if I hadn't taken that leap."

Listen to the episode

🚀 March Cohort Now Open — Chief of Staff Launchpad

The next cohort of the Chief of Staff Launchpad kicks off March 10, and spots are filling fast. Enrollment closes March 5.

This 6-week, cohort-based certification is built for aspiring and first-time Chiefs of Staff who want to hit the ground running — with proven frameworks, live expert sessions, and a tight-knit peer community to support you along the way.

What you'll get:

6 live expert-led sessions covering role clarity, strategic planning, comms, exec alignment, and your job search
Group coaching & office hours with practitioners who've been in the role
A digital certification badge to showcase on LinkedIn
Join the Cohort