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Our theme this week is judgment. When AI can execute almost anything in seconds, the scarce skill becomes deciding what is actually worth doing.

In this newsletter, Eric Nehrlich, former Chief of Staff for Google Search Ads, on why AI is a productivity boost and not a compass. Our partner think-cell on using AI to turn Excel data into boardroom-ready PowerPoint slides without ever leaving the app. Plus the Chief of Staff Network chapters and cohorts gathering over the next few weeks.

When code costs nothing, judgment becomes the job.

Eric Nehrlich spent six years as Chief of Staff for Google Search Ads before becoming an executive coach. He has a theory about what AI quietly makes more valuable.

"Code is cheap now." That is how one of Eric Nehrlich's clients summed up the shift, and it reframes almost everything. When you can vibe-code away a tedious monthly task and rebuild it tomorrow if it breaks, the question stops being can we do this and becomes should we. The cost of execution is collapsing. What stays expensive is knowing what is worth executing in the first place.

Eric, who ran Google's five-month annual planning cycle before that cycle became obsolete, puts the distinction plainly:

It's a boost in productivity. It helps you get things done faster... But it doesn't tell you what to do. That's the thing that matters. Like, where are you going? What's worth doing? Who are you serving? Those are questions AI doesn't answer because they're value questions. They're mission questions. They're purpose questions.

AI handles the how. The what, the why, and the who stay stubbornly human. That is where Eric lands the Chief of Staff: as the owner of alignment, getting the engineer vibe-coding on the front lines pointed in the same direction as the principal at the top, so all that cheap, fast effort is not wasted pulling against itself.

The second job is harder to name. Eric describes working with AI as a slot machine, the kind of intermittent reward that keeps founders up until 2 or 3 AM chasing one more pull request. So he tells clients to ask their AI a question: is this next thing more valuable than showing up as a calm, present leader tomorrow? Someone has to be the brake on the system. His bet is the Chief of Staff.

That instinct to pause is the heart of the book Eric wrote, You Have a Choice: Beyond Hard Work to Meaningful Impact. The premise is that you control only one thing, your next action, and you have more choices than you think once you are willing to accept the consequences. It is a quietly radical idea in a moment that rewards speed above everything: the way to make the right call, personally and professionally, is often to slow down long enough to make it on purpose. Faster is not the same as better, and in an age of constant change, knowing the difference might be the most valuable thing a Chief of Staff brings to the table.

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📆 Upcoming Events

Where we're gathering

In person and online, around the world.

Next 2 Weeks

JUN
23
TUE
Chief of Staff Launchpad (June to July)
VIRTUALCohort program

The cohort that helps you build the role from the ground up. Free for PRO members.

JUN
24
WED
Detroit CoS Meet Up
DETROITIn person

Detroit operators, grab a seat and meet the people doing the work nearby.

JUN
25
THU
Workflow Thinking: The Skill Behind Every Automation
VIRTUALWebinar

Before you automate anything, you have to think in workflows. A practical session on how.

JUN
30
TUE
From Reactive to Regulated: Energy Management for Chiefs of Staff
VIRTUALWebinar

Managing your energy, not just your calendar. Tools to move from reactive to regulated.

June & July

JUL
9
THU
Sydney CoS Networking Event
SYDNEYIn person

Sydney operators are getting together. Save the date and come meet the local network.

JUL
15
WED
Boston CoS Meetup
BOSTONIn person

The Boston crew is meeting up. Bring a question worth trading for an answer.

Stop Surviving the Role. Start Leading It.

Most Chiefs of Staff learn the role by surviving it. There's a better way.

The CoS Launchpad is a 6-week certification program built for people who want to operate at the highest level from day one. You'll learn the frameworks, build the instincts, and get the credentials that signal you're serious about the role.

Whether you're stepping into your first CoS position or looking to sharpen what you've built over years in the seat, Launchpad gives you the structure most CoS never get.

Not ready for a cohort-led program? Try Chief of Staff Fundamentals first!

Thanks for tuning in this week, let us know where you are on your AI journey!

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