Insights

Every chief executive now wants a chief of staff. The title has gone, in about five years, from White House exotica to standard-issue kit for any ambitious leader, and the reason is not hard to find. We are all drowning. 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, working at an unrelenting pace in fragments. Now multiply that by a hundred channels and put a generative AI on every desk, producing yet more to read, weigh, and act on. Faced with that deluge, the instinct is to 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 fires 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. In an age that fetishises speed, the most valuable person in the building is often the one prepared to apply the brake.

There is a subtler trap, and it is the one the current vogue for 'systems' and 'operating rhythms' walks straight into. Technical command of process is necessary but nowhere near sufficient. I met a great many candidates who could design an immaculate framework, map a decision cycle, and install an accountability rhythm with real elegance, and a number of them would still have failed. The reason is that their instinct was to impose the structure from above, as though an organisation were a machine waiting to be correctly configured. In a flat, collegial body working across very different cultures, that instinct is fatal. Process has to be built with people rather than done to them, and the difference between the two is not technical at all. It is human.

This is the part the field tends to undersell. The candidates who genuinely impressed me were not the ones with the cleverest operating models, though several had those too. They were the ones who combined that structural intelligence with something much harder to find and almost impossible to teach: a deep, genuine interest in people. They wanted to know what motivated a colleague who was quietly disengaging, what a nervous team actually needed to hear during a period of change, where the unspoken resistance to a new idea was really coming from. They read emotion as fluently as they read a spreadsheet. 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 high emotional intelligence is rare precisely because the three qualities so seldom sit comfortably in the same person. The systems thinkers are often impatient with feelings; the empathetic are often vague about delivery. The candidate who can do both, and who actively enjoys the human part rather than tolerating it, is worth holding out for.

Machiavelli, who understood the politics of proximity to power better than any management theorist since, 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 acquire a bottleneck with good intentions. Get it right and you acquire a multiplier, someone who makes the whole leadership team perceptibly better at its job.

Here is the part that should give the AI-will-fix-everything crowd pause. The function exploding in popularity 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. If anything, the more our working lives are mediated by machines, the more valuable the people who can do the irreducibly human parts become.

The candidate eventually appointed had all of this, and the empathy is what swung it. Strong operators were not in short supply. Strong operators who genuinely cared about the people the strategy would land on were. For a job this idiosyncratic, that combination beats raw brilliance more often than search committees dare admit.

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.

“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.