This week we're going behind the high hedges. Donald J. Cunningham has spent 12 years running single family offices in New York and London, and today he's Head of Family Office for a senior member of the Qatari royal family. He joins me on the podcast to talk about what the Chief of Staff job becomes when your principal can say yes to almost anything.
Chief of Staff Connect London is six weeks out and the agenda is live on our site. And Sentience is sponsoring this week with a free month of Sentience Max for our readers.
🎙️ Inside the family office
Most Chiefs of Staff spend a lot of energy on resourcing. Is there budget? Is there headcount? Is this the right investment right now? Donald J. Cunningham works for a principal where the answer to all three is almost always yes. That changes the job. When anything is possible, the Chief of Staff becomes the person who makes the cost visible.
THE CHIEF OF STAFF PODCAST
Inside the Family Office: The Chief of Staff Role with Donald J Cunningham
Donald calls this the trade-off realization. Yes, we can do this, but it comes at the expense of that other thing over here. A principal's homes, investments, board seats, family and succession plans are all connected, and 12 years across four families is what lets him see those connections before they surprise anyone. When naming the trade-off isn't enough, he borrows a rule from a friend in a similar seat: say it three times.
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I think this is a bad idea. I think this is a bad idea. I think this is a bad idea. Now after three iterations, if the answer is still, I want to go and do this thing, the job is to execute on that wish.
Donald J Cunningham, Head of Family Office
The rule of three gives the principal room to change course and puts your judgment on the record, which is where credibility gets built over years. The rest of the episode is the job itself: a 2am Indeed application with a cover letter from a "recovering investment banker," why there's no room for ego when you work out of a principal's home, how to interview the principal as hard as they interview you, and what corporate Chiefs of Staff should make of getting pulled into an executive's personal life.
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🤝 Chief of Staff Connect: London, November 13. Explore the full Agenda!
On November 13 we're bringing senior Chiefs of Staff from across the UK and Europe together for one day on the same theme as New York: From Force Multiplier to Builder, the shift from amplifying leaders behind the scenes to owning the systems and operating models that move the business.
The day covers building operating systems that scale, shipping projects that move real metrics, owning AI strategy as the person who makes it work, and designing an organization that stops solving the same problems twice.
Bundle your ticket with PRO+ membership and save up to 24%.
📅 Upcoming events
📍 This week
Next two weeks
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OCT
15
THU |
Chief of Staff AI Buildathon
Berlin · In person
Bring the workflow that eats your week and build the fix with peers at Ojin AIxHaus. |
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OCT
17
SAT |
Mumbai Chief of Staff Meetup
Mumbai · In person
The India chapter meets again, this time on how to make strategy travel across a complex organization. |
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Coming up
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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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If Donald's episode has you thinking about what you protect for your principal, COSC New York is three weeks out on Oct 22-23 and London follows on November 13.
I hope to see you in one of those rooms!
