Insights
Why your next chief of staff shouldn't think like you
Every chief executive now wants a chief of staff, and most of them want the wrong one.
The title has travelled a long way in about five years, from White House exotica to standard-issue kit for any ambitious leader. The reason is not hard to find: we are all working in fragments now. Half a century ago Henry Mintzberg sat and watched what managers actually did all day, and found not the calm, systematic planner of the textbooks but someone lurching from interruption to interruption at an unrelenting pace. Multiply that by a hundred channels, put a generative AI on every desk producing yet more to read and weigh and act on, and the instinct is obvious: hire someone who will help you go faster. That instinct is usually wrong, and I have just spent several months proving it.
I recently ran a search for a chief of staff at a global philanthropy, working with a brilliant, fast-moving first-time chief executive who, by her own cheerful admission, generates ideas like one of those machines that fire tennis balls. The obvious hire for such a person is a mirror: someone equally quick, equally clever, equally relentless. It is almost always a mistake. What a fast principal needs is not an accelerant but a counterweight, someone with the composure to slow things down without appearing to obstruct, and the judgement to know which ideas to midwife and which to let quietly die. This also means there is no such thing as a good chief of staff in the abstract. The same person who steadies one principal will suffocate another, so the thing being assessed is never the candidate alone but the pairing, and you cannot judge a pairing without first taking a close, honest measure of the principal. In an age that fetishises speed, the most valuable person in the building is often the one prepared to apply the brake.
But composure alone is not the thing, and this is where the search became instructive. The counterweight is the necessary condition; it is not the whole of it. The most analytically gifted candidate I met came from the upper reaches of management consulting, and her command of analysis was close to flawless. On any competency framework she would have scored at or near the top of every box; a process run against a scorecard would have advanced her without a second thought. She spoke, when asked, about being interested in how decisions affect other people. I believed her, and it was still not enough. What she never convinced me of was that she was interested in how those decisions were experienced: how they felt, what they cost, why a team might resist something that made perfect sense on paper. She grasped the human dimension intellectually and remained, in manner, a little cool, a little remote. The tell was nowhere in her answers, which were excellent. It showed across the table, and later in conversations with people who had worked for her, once the question was no longer whether she delivered but how her teams felt about her afterwards. She did not lack empathy in any sentimental sense; the trouble was that understanding people and reaching them are different capacities, and a chief of staff who has only the first will align an organisation on the whiteboard and lose it in the room.
This is the part the field tends to undersell. The candidates who impressed me most were not the ones with the cleverest operating models, though several had those too. They were the ones who combined that structural intelligence with a deep and genuine interest in people: who wanted to know what was really behind a colleague's quiet disengagement, what a nervous team actually needed to hear during a period of change, where the unspoken resistance to a new idea was coming from. They understood that alignment is not won in the meeting where the decision is announced, but in the dozens of small, careful conversations that precede it. That blend of process architecture, strategic judgement, and real emotional intelligence is rare, though I suspect less because the three qualities cannot coexist than because search committees so seldom think to look for all three at once (in my experience they reward the first two and are faintly embarrassed by the third). The candidate who does both, and actively enjoys the human part rather than tolerating it, has to be looked for deliberately, and held out for.
Machiavelli understood the politics of proximity to power better than any management theorist since, and he put it plainly five centuries ago. The first way to judge a ruler's intelligence, he wrote, is to look at the people around him. The chief of staff is the most revealing of those choices, because it is the one made not for show but for how the leader actually thinks and works. Get it wrong and you have hired a bottleneck with good intentions. Get it right and the whole leadership team becomes perceptibly better at its job, which is a strange sort of leverage for a role with no formal power of its own.
Here is what should give the Panglossians of AI pause. The function now so much in vogue is precisely the one that resists automation. Judgement, trust, the reading of a room, the absorption of complexity so that someone else can think clearly, the patient and unglamorous work of bringing people along: none of it can be prompted into existence. The more our working lives are mediated by machines, the more the irreducibly human parts are worth, and the more a leader should be willing to spend real effort finding the person who can do them. That, in the end, is the case for taking this one appointment more seriously than almost any other on the chart. The age is busy making most kinds of help cheap. This kind is going the other way.
If you are contemplating making an appointment of this kind, I would be glad to talk. Assessing the nuances of 'fit' as well as hard skills is exactly the sort of challenge my practice exists to solve.
The interview questions a clever candidate can't game
Boards interviewing for a chief of staff tend to hire the wrong quality, and they do it for an understandable reason: the interview rewards the thing that is easiest to see. A candidate who is articulate, quick, and visibly accomplished will always read as the strong appointment, because those qualities announce themselves in the room. The qualities that decide whether the role actually works do not announce themselves at all. They surface only under a particular principal, in the particular pressure of a particular organisation, and none of that is legible across a conference table in an hour. So the polished candidate wins the interview and, often enough, loses the job a year later, by which point the cost has landed somewhere the board no longer connects to the decision it made.
The difficulty is that the qualities that matter are precisely the ones a competent candidate can produce on demand. Anyone can call themselves a strategic thinker with sound judgement and strong relationships; the words cost nothing and disprove nothing. Useful questions, then, are the ones that are hard to game: where the revealing thing is not the fluency of the answer but its substance, and where a weak candidate walks into a trap they cannot see well enough to avoid. Three of these I would never skip.
The first: tell me about a time you talked your principal out of something they badly wanted to do. A fast, clever leader has no shortage of people willing to agree with them faster and more cleverly; what they lack, and what they need, is someone with the nerve to apply the brake and the judgement to know which occasions warrant it. The trap is the candidate who cannot find an example, or who quietly reframes every story as the loyal execution of someone else's wishes. That is a courtier, and a courtier will watch a principal walk into a poor decision rather than spend relationship capital to stop it. What you want is specific: a real disagreement, genuinely pressed, and, crucially, handled in a way that left the principal's authority intact. Picking a fight is easy and tells you nothing. The skill is calibrated dissent, the kind that holds trust rather than spending it, because that is the only kind that survives a real working relationship past its first month.
The second question separates the people who can build a system from the people who can lead one into a proud, dispersed, mission-driven organisation, which is a different and rarer competence: walk me through a new way of working you introduced against real resistance. Plenty of candidates will describe an immaculate operating rhythm, a decision log, an accountability framework, and offer it as evidence of rigour. But process imposed from above dies on contact with people who did not ask for it, and the candidate who narrates a frictionless rollout is telling you, without meaning to, that they have never actually done this to anyone who could push back. The tell is someone who reaches for people before systems: whose buy-in they secured before launching, where they bent the design in response to a sharp objection, how they arranged for colleagues to feel like the authors of the change rather than its subjects. A candidate who understands that in their bones mentions the politics before the architecture, every time, because they know that is where the work actually is.
The third is the one most often skipped, and the one that decides the appointment: describe a colleague you found genuinely difficult, and what you eventually came to understand about what was driving them. Here the trap is seductive, because there are two comfortable ways to fail it. One is to stay at the level of the other person's shortcomings, cataloguing what was wrong with them; the other is to reach too quickly for the tidy resolution, the "and then we communicated better" that closes the story without ever having opened the person. What you are listening for is insight into someone else's fears and incentives, offered without contempt: a difficult colleague described with curiosity rather than grievance. This is the rarest disposition of the three, and the most decisive, because so much of the role is reading a room, sensing the resistance nobody has voiced, and knowing what a nervous team needs to hear before anyone thinks to say it. A candidate who reads a person as fluently as a spreadsheet has the one thing no framework supplies.
These are, of course, one question asked three ways. Each is a route to the same judgement: what is this person actually for. Between them they test whether a candidate can hold a principal to account, move an organisation without bruising it, and read the people inside it, which are the three faculties that no operating model, and no amount of artificial intelligence, can manufacture. They are also, not by coincidence, the faculties hardest to fake under sustained and specific questioning, which is the whole reason to ask them slowly.
There is a real tension buried in the first two, worth naming because the best candidates feel it themselves. The nerve to brake a principal and the instinct to make colleagues feel like authors do not always sit in the same person: the temperament that will risk a relationship to stop a bad call is not obviously the temperament that spends weeks courting quiet buy-in. A candidate who is plainly strong on one and evasive on the other is telling you which half of the job they will actually do, and which half you will have to cover elsewhere. The rare appointment holds both, and holds them without the two collapsing into either timidity or force.
Which points at where the real risk of the process lies. The candidate who handles the first two questions with ease and then falters on the third is the one to weigh most carefully, precisely because they are usually the most impressive person you will meet all week, and the most easily mistaken for the right one. The genuinely rare candidate answers all three well, and is worth holding the search open for. In my experience the shortlist rarely offers them up on the first pass; that is ordinarily the point at which it is worth being slow.
Lofty ends, earthly means: the role of the COO in global philanthropies
“What do we live for, if not to make life less difficult for each other?” — George Eliot, Middlemarch
The modern philanthropist speaks fondly of systems change. Somewhat less celebrated is the plumbing that keeps those systems moving. In grant-making foundations, that task falls to the chief operating officer: a role once caricatured as the keeper of forms and cheques, but now closer to a chief strategist with a spanner. COOs sit at the point where lofty moral purpose meets the gritty realities of cash flow, compliance, and human behaviour. Their challenges can be as prosaic as database fields, and as consequential as reputational risk.
Strategy, because operations without strategy is mere housework. Many foundations accumulate programmes like a Victorian museum: earnest collections begun with purpose, responsive to need and opportunity, but seldom retired with ceremony. The COO’s first duty is to advance the concept of focus and combat portfolio sprawl. That means forcing choices: asking which grants truly advance the theory of change, and which are sentimental holdovers. It also means deciding when to follow the field and when to lead it, particularly in areas such as climate, public health, or criminal justice, where bandwagons are as common as breakthroughs.
Capital allocation is the second lever. Endowments rise and fall; commitments do not. A prudent COO balances multi-year obligations with liquidity, smoothing payout rates while keeping dry powder for moments when philanthropy can be unusually catalytic: disasters, political crises, legislative windows, or technological inflections. The question is not merely how much to give, but when, to whom, and on what terms. The trend for trust-based approaches offering flexible, multi-year support has real merits, but it shifts diligence and monitoring burdens onto the foundation; someone must recalibrate the machinery so that generosity does not become evidence-free.
Risk. Philanthropy imagines itself as risk-taking, and sometimes it is. More often the risk in question is reputational: support for a grantee who later attracts scrutiny; cross-border transfers that fall foul of controls; advocacy that edges towards politics. The COO’s craft is to express values as thresholds. What level of uncertainty is tolerable for a £30,000 pilot versus a £3m flagship grant? Which exceptions merit escalation to trustees, and on what timetable? Formal risk appetites, long beloved by banks, are making their way into board packs; the wise COO ensures they are substantive rather than decorative.
Impact measurement. Funders want decision-grade evidence; grantees want to deliver programmes rather than fill in forms. The art lies in right-sizing monitoring, evaluation, and learning: few indicators, collected consistently, analysed in time to change decisions. Too often data are gathered because they are collectible rather than useful. A competent COO builds a learning agenda — two or three questions the foundation will actually answer this year — and refuses to inflict reporting requests that serve neither party.
If strategy sets direction, operations determine speed. The grant-making lifecycle is the place to look: intake, due diligence, decision, agreement, disbursement, reporting, closeout. In many foundations this sequence resembles a relay race in which every runner edits the baton. Cycle times stretch; applicants wait; trustees wonder why “approved” does not mean “paid.” The remedy is standard work: clearly defined decision rights, templated agreements, fast-track lanes for low-risk grants, and service-level expectations for each step. The goal is not automation for its own sake, but the elimination of friction that adds cost without adding value.
Grantee experience is not merely kindness; it is strategy. Foundations with opaque criteria and baroque application portals filter for organisations skilled at grant-seeking, not those best at solving problems. The COO can measure the burden — hours spent applying, revising, reporting — and remove steps that never change outcomes. If two reviewers reach the same decision 95% of the time, one will do. If a £20,000 grant must clear a £200,000 hurdle, the hurdle is wrong. Payment timeliness, routinely ignored, is a moral choice: cash-constrained charities should not be forced into involuntary credit provision because a foundation’s finance cycle is glacial.
Compliance is less glamorous, but no less consequential. Cross-border giving requires sanctions checks and expenditure responsibility; domestic work still involves conflicts of interest, safeguarding, and data protection. The point is controls proportionate to risk, not a forensic audit for every grant. Technology helps (the better grants management systems now integrate due diligence, document workflows, and payment rails) but it will never rescue confused governance. Decision rights, escalation paths, and trustee delegations must be crisp enough to survive hurried exceptions in a crisis.
Data are the COO’s silent ally and frequent nemesis. Foundations love narratives but need taxonomies. Without a disciplined data model covering issues, geographies, populations, and mechanisms, portfolio analysis becomes anecdote. The answer is dull and powerful: a canonical set of fields enforced across programmes, clear ownership for data quality, and the humility to publish what is known alongside what is not. Dashboards should privilege signals over vanity: payout pacing against target; median days from application to decision; share of unrestricted and multi-year grants; concentration among the top grantees; equity indicators; grantee satisfaction; audit and incident trends.
Culture, too, falls into the COO’s remit, whether invited or not. Foundations compete for talent with NGOs on mission and with the private sector on pay; hybrid working has muddled expectations on both sides. The operational leader sets norms: reviewer training to reduce bias; common templates so knowledge outlives staff turnover; realistic workloads in request-for-proposal season. Communications must be an accomplice, not a saboteur. Nothing undermines credibility faster than a press line that outruns programme commitments, or a cautious legal view revealed only at the eleventh hour.
What, then, distinguishes the foundations that hum from those that grind? They practise deliberate simplicity. They close obsolete programmes as readily as they open new ones. They publish just enough to be accountable, without turning transparency into theatre. They invest in intermediaries when reach or proximity is needed, and govern those relationships through service-level agreements and shared metrics rather than goodwill alone. They rehearse for volatility — market drawdowns, regulatory shifts, public controversies — so that muscle memory exists before adrenaline does.
The COO’s job is neither heroic nor clerical. It is architectural. Done well, it turns grand strategy into reliable practice, swaps performative complexity for purposeful flow, and makes the organisation kinder to grantees and tougher on its own bad habits. Philanthropy cannot buy progress; it can, however, waste remarkably little of it. The operating model is where that choice is made.
If you are wrestling with an appointment of this kind, I would be glad to talk. I have worked with numerous organisations who have appointed COOs - all presented different challenges and required a thoughtful, bespoke approach.
