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🎙️ Chief of Staff to the CEO, or to the business?
Ryan Kelly pitched the Chief of Staff role to his founder CEO, then had to beat more than 1,000 applicants for it. A few weeks in, his CTO asked him a question every Chief of Staff eventually has to answer.
"Are you the Chief of Staff to Daniel, or are you the Chief of Staff to the business?"
That's what Veremark's CTO asked Ryan Kelly not long after he became the company's first Chief of Staff. Ryan's gut said the business. The honest answer is both, and the tension between the two is where most Chiefs of Staff quietly lose their quarter.
THE CHIEF OF STAFF PODCAST
Chief of Staff to the CEO, or to the Business? with Ryan Kelly
The CEO's asks are real and they're urgent. Clear them fast and your principal is happy this week. But Ryan, talking with host Tristan Lim, puts the trap plainly:
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"If you only keep the CEO happy day-to-day, they'll not be happy at the end of the quarter."
Ryan Kelly, Chief of Staff, Veremark
So once a month he runs a check on himself. Has he only been putting out fires, or is he still moving the big cross-functional pieces? Ask any CEO which mattered more, the fire or the three-month objective, and the answer is obvious in hindsight. It rarely feels obvious on a Tuesday afternoon.
Ryan protects that longer horizon in two ways. In quarterly planning he puts himself last in the review order, so he's heard every function's problems before he picks his own. Then he takes the work no single team will own: the multi-quarter problems that only make sense when someone can see across the whole business. He calls it clearing the fog of war.
The second habit is listening for quiet noise. New starters at Veremark were occasionally arriving to no laptop. Two in ten wasn't loud enough for the CEO or the CTO, but it was grinding down HR. Ryan mapped the process end to end, and the fix removed a step nobody had questioned.
None of it works without trust, and Ryan front-loaded that in a way most new hires wouldn't dare: a week in Dubai, 500 questions, and a request to have dinner with his CEO's family.
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"Be a human Chief of Staff and you'll add more value."
Ryan Kelly, Chief of Staff, Veremark
What that dinner taught him about supporting a founder is the part of the conversation worth hearing in his own words.
🇬🇧 Chief of Staff Connect London is three weeks out
November 13 at the Hyatt Regency London Blackfriars, built with Operations Nation for 75+ senior Chiefs of Staff and operations leaders.
One day, on the same theme as New York: From Force Multiplier to Builder.
The agenda gets specific. Farah Cohen and Dora Nagy take on why you'd need a Chief of Staff if you already have a COO. Libby Dangoor talks through the path from Chief of Staff to COO and beyond. And Alex and Jamie from Portswigger run a hands-on AI workshop where you leave with one of your own workflows rebuilt.
November 13 · Hyatt Regency London Blackfriars
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NOV
13
FRI |
Chief of Staff Connect: London
London · In person
A full day with senior Chiefs of Staff and operations leaders at the Hyatt Regency London Blackfriars. |
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NOV
19
THU |
Leading Without Authority
Virtual
Theresa Friend on building the influence to move work forward when nobody reports to you. |
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Ryan's monthly check is simple enough to try this week. Look back at the last month and ask whether the work that mattered most to the quarter actually moved, or whether the fires took it.