Small Wins Add Up
# The Project I Almost Killed, And What Five Years of Hindsight Taught Me About Momentum I still remember sitting across from my programme manager in month three, watching her make a genuinely reasonable case for why we should stop. She was not wrong on the facts: the project had no visible wins, the team was tired, and the internal stakeholders who had commissioned the work had already moved on to three other priorities. We were rebuilding a regulatory reporting framework for a business unit that had been quietly non-compliant for years, not dramatically, not dangerously, but consistently enough that someone senior had eventually noticed and handed me the problem, the kind of problem that arrives without fanfare and leaves without applause. She laid out the argument for pausing clearly, professionally, with a slide deck that made stopping look almost responsible. I nearly said yes, not because I believed it was the right call, but because I was tired too, and tired people find well-reasoned arguments more persuasive than they should. The Situation I was working on this project in 2019. The business unit had been operating on a patchwork of manual processes and institutional memory for the better part of a decade. Nobody had deliberately built a broken system: it had simply grown in the way most broken systems grow, one pragmatic workaround at a time, until the workarounds became the system. My job was to replace it with something that would actually hold under regulatory scrutiny. The challenge was that progress, in this kind of work, does not look like progress for a long time. I was not building features, I was excavating. Every week we found another process that existed only inside someone’s head, another data feed that connected to a spreadsheet no one had updated since 2016, another exception that had been handled manually so long it had stopped being seen as an exception at all. To anyone watching from outside the room, we appeared to be standing still. My programme manager’s case for pausing was rational: a pause, she argued, would give us time to regroup, re-engage stakeholders, and come back with a cleaner plan. The logic was sound, and that is precisely why it was dangerous. In complex rebuilds, “coming back with a cleaner plan” is usually a polite way of describing the moment a team loses its nerve and never quite recovers it. I had seen it before, the pause that becomes a pivot that becomes a quiet cancellation eighteen months later. What I said instead was this: we are not pausing, but we are going to do one thing differently. Every week, I would identify one thing that is measurably better than it was seven days ago, not a milestone, not a formal deliverable, just one thing, documented, visible, shared with the team. It sounds almost embarrassingly simple, that is, I suppose, the point. What the Next Five Years Taught Me The first insight is that momentum is not a feeling, it is a record. What changed from month three onwards was not the pace of work, it was the existence of evidence. Every Friday, there was something concrete to point to: a data feed validated, a manual step eliminated, a process documented for the first time. Individually, each item was unremarkable, collectively, they became the proof that the project was alive. And that proof did something I had not fully anticipated, it made the team stop measuring progress against the original plan and start measuring it against last week, that is a much more honest comparison, and a far more sustainable one. I have since watched organisations spend enormous energy on formal programme governance, traffic-light reports, steering committees, milestone reviews, while neglecting the simpler practice of recording what actually improved. The bureaucracy of progress is not the same as progress itself. The second insight is that stopping teaches something you cannot easily unteach. Had we paused in month three, the framework would probably have resumed eventually, projects like this rarely die entirely, they get restarted, rebranded, handed to someone new. But the team would have carried a piece of learning that I think is genuinely corrosive in professional environments: that when progress is hard to see, stopping is the appropriate response. That lesson travels, it shows up in the next project, and the one after that, as a lowered threshold for retreat. The damage of an unnecessary pause is rarely visible in the project itself, it is visible in the people. The third insight is the one that took longest to articulate clearly: consistency is not the slow path. Most senior people I know, and I include myself in this, with some embarrassment, are instinctively drawn to the bold intervention, the restructure, the strategic pivot, the announcement that signals decisive leadership. These things have their place, but I have watched more value created by sustained, unglamorous consistency than by any single bold move, and I have watched more value destroyed by the instinct to reach for drama when patience was actually what the situation required. The regulatory framework that is now running across three regions was not born from a brilliant insight in month three, it was built one documented improvement at a time, over two years, by a team that had decided to stay in the room. What This Means in Practice If I am leading a complex programme right now, a technology rebuild, a regulatory change, a cultural shift, and progress is invisible, the question worth asking is not whether to pause, it is whether I have created the conditions for small progress to be seen at all. Most organisations are reasonably good at celebrating the launch and catastrophically bad at recognising the incremental work that makes launches possible. The team that ships quietly, week after week, without a milestone in sight, is doing the most important work in the building, they are also the most likely to be told to pause. I build the record, I show
Bright and Early: Leadership Insights from London
What 5:51am Taught Me That No Meeting Ever Could At 5:51am in London, the sky is genuinely undecided, not dark, not light, something in between that has not yet chosen a direction. I find that oddly reassuring. The city has not started demanding anything from me yet. The inbox is technically open but morally closed. The coffee in my hand is still hot enough to count. I used to treat this hour as a competitive advantage. Up before the market, ahead of the inbox, winning the day before it started, that kind of framing. The problem with that framing, I have since learned, is that it turns the one quiet hour I have into another form of performance. I am still running. I am just running earlier. That distinction matters more than I thought it did. The Situation That Corrected Me I was three months into a regulatory restructure that covered two jurisdictions simultaneously in early 2021. I will spare the details, partly for confidentiality and partly because the details were less interesting than the chaos they produced. What I can say is this: the number of stakeholders involved was significantly higher than the number of clear answers available. Everyone had a perspective. Everyone had a risk appetite, a reporting line, a political consideration. The meetings were long and the clarity was short. I was running on the assumption that volume equals progress. More sessions, more calls, more documentation. If I kept moving, I would eventually arrive somewhere useful. I did not. I circled. The moment I remember most clearly was a Tuesday morning in February. I was up before six, not out of discipline but because I had woken up at four with something unresolved and could not get back to sleep, which, if anyone is quietly selling this as a glamorous executive habit, I should know the origin story is usually just low-grade insomnia. I made coffee. I sat down. I had no agenda and nobody needed anything from me for at least another two hours. And in that space, without anyone asking me a question or handing me a problem to react to, the answer I had been looking for arrived. Not the whole answer. But the structural insight that had been obscured by the noise, the thing I had been unable to see because I had been too busy generating activity to allow any actual thinking. I decided to shift the restructure after that morning. Not because of a meeting. Because I had finally been quiet long enough to hear what I already knew. What That Morning Actually Demonstrated The first thing it demonstrated is that thinking and doing occupy different mental states, and most organisations are structurally committed to the second at the expense of the first. Calendars fill with rooms full of people producing outputs. The outputs are real. But the underlying thinking, the kind that questions whether those outputs are the right ones, has no scheduled slot. I do this thinking in margins. If I have no margins, it does not happen. The second thing it demonstrated is something I now believe fairly firmly after two decades across regulated industries: the quality of a decision is often inversely related to how many people were in the room when it was made. That is not an argument for isolation. It is an argument for protecting the phase of thinking that precedes the room. I should arrive at the meeting with a considered view, not form my view inside it. The meeting should test my thinking, not replace it. The third thing, and this is the one that took me longest to accept, is that stillness is not a reward. For years I treated quiet mornings as something I had earned by being productive the day before. If I had had a hard week, I deserved a slow Saturday morning. That framing is backwards. Stillness is not a reward for finishing the work. It is, structurally, where the useful work happens. It belongs at the front of the day, not as compensation at the end of it. That shift in sequencing changes everything about how I design my time. What This Means in Practice None of this is an argument for becoming a morning person. Some of the sharpest leaders I have worked with do their best thinking late at night, or on long walks, or in the car. The format is not the point. The point is that every leader I respect has some version of unstructured, undemanded time that they protect with the same seriousness they bring to a board meeting. They do not treat it as a luxury or a preference. They treat it as infrastructure. If I am currently running a team, or navigating something complex, or managing more stakeholders than I have clear answers for, my instinct will be to add more sessions, more touchpoints, more movement. I will resist that instinct occasionally. The breakthrough I am looking for is probably not hiding in the next meeting. It is more likely waiting in the next quiet morning I have not yet cancelled. Later Has People In It The sky over London has made its decision now. The city is loud and the inbox has opinions. Whatever I was going to think clearly about, I thought it an hour ago. The most useful thinking I do today will probably not happen between nine and five. It will happen in the margins I was disciplined enough to protect, not because I won the morning, but because I was finally still enough to hear myself. Later has people in it. Earlier, for a while, is just mine.
Night Owl Leadership: Why Not Everyone Peaks at 9am
I recall the moment it arrived at 11:47pm, the timestamp was right there in the commit log, precise and unapologetic. A complete architectural solution to a problem we had been circling in morning standups for three weeks. No preamble, no draft, no “just thinking out loud.” Ready for production review. My first reaction, I will admit, was not admiration. It was something closer to mild institutional irritation. I had spent eighteen months building a programme governance model that ran on calendar discipline and visibility. And here was one of our best architects producing the clearest thinking of the entire quarter at a time when I was firmly, unambiguously, asleep. That moment did not immediately feel like a lesson. It felt like a scheduling problem, which is precisely the kind of wrong answer that looks sensible at scale. The Situation I was deep into an enterprise data infrastructure overhaul – four regions, nineteen legacy systems, somewhere north of forty stakeholders depending on the week and the mood of the steering committee. The programme was running. Milestones were being met. By every external measure, I was in good shape. However, something kept slipping. Not deliverables – those were landing. It was the quality of the decisions inside the deliverables. The morning syncs felt sharp. The design reviews were engaged. And then, consistently, inexplicably, the decisions made in those rooms would begin to unravel within days. Not because the people were wrong. Because the thinking was incomplete. In late 2023, I pulled the contribution logs. I did this not to catch anyone out – the programme was not in crisis – but because I had a nagging suspicion that what I was measuring (attendance, responsiveness, meeting participation) had quietly drifted away from what I actually needed to track (thinking quality, architectural coherence, decision durability). What I found was uncomfortable in the specific way that useful findings tend to be. Two of my strongest architects – people whose judgement I trusted more than most governance frameworks I have ever read – were doing their clearest, most structurally complete thinking between nine and midnight. Not occasionally. Consistently. The contribution logs made it embarrassingly obvious in retrospect: the commits that unblocked other people’s work, the design notes that reoriented entire workstreams, the quiet corrections that prevented expensive rework. Almost all of it after hours. I had built a programme governance model around availability windows. The work was happening around them, not inside them. The thinking was occurring anyway – just invisibly, uncredited, at midnight, outside the architecture of the programme itself. What I Got Wrong The first thing I got wrong was conflating presence with production. I found comfort in a full calendar. It signaled momentum. It signaled alignment. It signaled that I was, at a minimum, in the same room as the people who were supposed to be solving the problem. What it did not signal – and this is the thing governance models consistently fail to encode – is when the actual thinking happens. I had optimised for observable effort and was quietly surprised when that turned out not to be the same thing as best effort. Chronotype is not a wellness concept. It is a cognitive variable. The research on this is not new – circadian rhythms, ultradian cycles, the neuroscience of alertness and decision-making under fatigue – but in enterprise transformation, it remains almost entirely absent from how I structure work. I talk about agility, about flow states, about psychological safety. And then I schedule the most cognitively demanding decisions at 9am on a Monday following a cross-regional steering committee. The second thing I got wrong was the word I kept using. When I began discussing how to respond to what I had found, the language in the room defaulted to flexibility and async policy. Both reasonable words. Both slightly beside the point. The word I kept avoiding – the one that actually described what my architects needed – was permission. Not a formal policy change. Not a new HR framework. The quiet organisational signal that your best thinking does not have to be witnessed to count. That is a harder thing to give than a flexible working policy, because it requires something institutions are structurally reluctant to offer: trust in the output over trust in the process. It means accepting that I will not always see the work happening. I will see what the work produces. The third thing I got wrong was treating this as an edge case. Two architects doing their best work at night sounds like a curiosity. An anecdote. A nice story for a team retrospective. What the contribution logs actually showed was a systemic misalignment between when my programme demanded cognitive energy and when my people had it to give. That is not an individual quirk. That is an organisational design problem. I restructured two workstreams around output quality, not presence. No midnight standups. No requirement to be online at any particular time. Clear deliverable expectations, clear quality standards, genuine latitude on when the work happened. Six weeks later: the same people, the same problems, measurably sharper decisions. Not marginally sharper. Structurally different. What This Means for Your Organisation Most high-performing organisations are already benefiting from their night-thinkers. They simply are not doing it intentionally, which means they are also not doing it efficiently, and they are almost certainly losing some of those people to organisations that make them feel less like they are working around the system. The competitive edge here is not in discovering that chronotype exists – your best people already know this about themselves. It is in building an operating model that makes their best thinking visible and valued, rather than something they contribute quietly, on their own time, hoping someone notices the timestamp. The organisations that figure this out will not just retain better people. They will extract the thinking those people were already doing anyway – just uncredited, in the margins, at 11:47pm – and bring it properly into
Small Steps, Big Progress: A Personal Leadership Story
The Particular Silence of a Programme That Has Learned to Perform Momentum I recall a specific kind of organisational stillness that does not announce itself, no alarm, no escalation call, no red flag on the RAG status. Just the quiet hum of meetings that end with actions nobody completes, decks that get refined rather than decided upon, and governance forums that produce minutes instead of movement. If you have ever sat inside this silence, you will recognise it immediately. If you have not yet encountered it, you will, and you will almost certainly mistake it for progress, because it has learned to dress that way. Stalled is not stopped. Stopped is visible. Stopped has a reason, a postmortem, a recovery plan. Stalled is insidious precisely because it looks, from a distance, like careful deliberation. The calendar is full. The stakeholders are engaged. The strategy deck has been updated to version fourteen. And yet the organisation has not moved, not really, in months. I spent the better part of a year inside exactly this situation, and the most uncomfortable thing I can tell you is that I did not see it clearly until much later. Not because I was not paying attention. Because the absence of crisis can be its own kind of blindfold. Eighteen Months In I was mid-programme, the dangerous middle, where the initial energy has long since dissipated and the end is still too far away to generate any fresh urgency, when I finally sat with the numbers and let them tell me something I had been avoiding. We were eighteen months into a cross-regional data transformation. The kind of programme that involves multiple geographies, legacy infrastructure that predates most of the team, regulatory considerations across jurisdictions, and the careful, painstaking work of getting organisations that have operated independently to agree on something as fundamental as how data should be classified. I had the governance forums. I had the steering committee. I had a transformation office and a methodology and a set of principles that had been workshopped, reviewed, socialised and signed off. What I did not have, when I sat down and looked at it honestly, was a single team that had completed a full migration and was operating differently as a result. I remember the specific meeting where this registered. Not a crisis point, there was no shouting, no failed deadline, no public moment of reckoning. Just a quiet conversation with two of my leads in which we tried to articulate what had actually changed in the last quarter, and found ourselves talking mainly about what we had prepared rather than what we had done. The decks were excellent. The readiness assessments were thorough. The roadmaps were beautifully structured. I had spent months building a perfect runway and had not yet taken off. The dry version of this is: I had optimised for planning and confused it with progress. The honest version is: I had let the programme learn to perform momentum, and I had not noticed quickly enough. What Actually Shifted The first insight sounds almost embarrassingly simple in retrospect, which is usually a sign that it is genuine. I stopped measuring against the destination and started measuring against last Thursday. Not last quarter. Not the original programme plan. Last week. The question I began asking in every team check-in was not “where are we relative to where we need to be?” but “what is different today that was not true seven days ago?” This change in reference point sounds minor. It is not. Measuring against a distant destination in a multi-year enterprise programme is a near-perfect mechanism for generating demoralisation, because the gap never closes fast enough to feel real. Measuring against last week creates a completely different relationship with forward motion, because even the smallest genuine movement becomes visible, and visible movement compounds. The second shift came from a single word, and I want to be precise about this because the word itself matters. The word was adjacent. Not “forward.” Not “progress”, a word so large it had become meaningless in our conversations. Adjacent: the next thing that is close enough to reach without requiring the organisation to believe again in the entirety of the vision. In practical terms, this meant I stopped trying to create conditions for the whole programme to move simultaneously and started identifying one data domain, one team, one geography where the conditions were already nearly right. I migrated that domain. I made it real, visible, and unremarkable, not a pilot, not an experiment, just the way that team now worked. Then I waited. Within a few weeks, the team running that domain had begun talking informally to the next team along. A regional lead asked to replicate the approach. The conversation changed from “why should we do this” to “how did you do that.” This is not a new insight about change management. But experiencing it at enterprise scale, after months of stalled momentum, makes it feel like a discovery every time. The third insight is the most counter-intuitive, and it is the one I am most confident about after everything I have seen in large institutions: small steps are not a compromise. They are not what I do when I cannot get organisational permission for the real approach. They are the only mechanism that actually works at enterprise scale, because enterprise scale means I cannot ask the entire organisation to believe in something it has not yet experienced. I can only ask a small part of it to take a step small enough to be genuinely reversible, and then let the evidence of that step do the work that no vision document ever could. What This Means for Your Programme If any of this is familiar, the full calendar, the unremarkable governance forums, the strategy deck on its fourteenth iteration, the question worth sitting with is not “what is wrong with our approach?” but “what is the one thing that could be different by next Thursday?”
Deep Focus as a Leadership Discipline
The Hedge Is the Trap I was running four workstreams across two geographies in late 2022. Each one had a legitimate case. I could have defended any of them in front of a board. There was a regulatory thread in one, a commercial opportunity in another, a partnership that had been eighteen months in the making, and a technology build that we had already sunk real money into. Individually, each made sense. Together, they made a very convincing picture of a senior executive who was across everything. By Thursday each week, I had touched all four and completed none. I told myself this was diligence. I told myself that senior work is inherently non-linear, that complexity requires parallel thinking, that running multiple streams simultaneously was evidence of capability, not avoidance. I was, as it turns out, an excellent storyteller, primarily to myself. Dubai, A Tuesday, A Question I Was Not Ready For. A colleague I have known for fifteen years sat across from me in Dubai. We were not in a formal review. We were between meetings, the kind of half-hour that exists because one meeting ran short and the next has not started. He did not ask what I was working on. He had seen the update decks. He already knew. He asked: “Which one would actually hurt to lose?” I answered in three seconds. Without pausing. One workstream. Immediately. No deliberation. He did not say anything for a moment. Then: “So what are the other three for?” I did not have a clean answer. What I had, sitting in that room, was the slow recognition that I had known for months, probably longer, which workstream actually mattered. The other three were not really about value. They were about optionality. They were insurance against being definitively, visibly, unambiguously wrong about the one that counted. The activity had felt like diligence. It was hedging dressed up as a work ethic. And I had been thorough enough about it that I had almost convinced myself otherwise. Three Things That Became Clear After That Conversation Focus is not a time management problem. Every article written about focus eventually slides into calendar hygiene, time-blocking, single-tasking, the Pomodoro technique. None of that is wrong, exactly, but it diagnoses the wrong condition. The reason most senior professionals scatter their attention is not that they have poor scheduling habits. It is that committing fully to one thing, before the outcome is certain, is genuinely uncomfortable. Spreading effort across four workstreams means that when something fails, you were not really betting on it. You were merely involved. Focus requires a different kind of exposure, the kind where, if the thing does not work, you cannot point to the three other things you were also doing. That discomfort is real. Managing it with busyness is entirely human. It is also, over time, professionally corrosive. The hedge is not neutral, it has a cost most people do not account for. When I was giving partial attention to four workstreams, I was not giving 25% to each. I was giving fragmented, context-switching, half-loaded attention to all of them, which meant none of them were getting the quality of thinking they needed. The one workstream that actually mattered was being shortchanged precisely because it mattered most. That is the cruel arithmetic of hedging: you protect yourself from the feeling of risk while simultaneously ensuring that your most important work is never fully resourced. The protection is real. The trade-off is invisible until it is not. Most senior people are not lazy. They are protecting themselves from being definitively wrong. I have seen this pattern in enough organisations now, across regulated industries, across geographies, across leadership levels, that I am comfortable saying it is structural rather than personal. The more visible your role, the more costly a clear, public failure feels. So the incentive is to stay in motion across many things rather than commit to one. This looks like productivity. It functions as risk mitigation. The organisations that break this pattern are the ones where leaders are genuinely supported when they commit and fail, not just when they succeed. That is a culture question, not an individual discipline question. Though waiting for the culture to change before you change is also a hedge. What This Means in Practice If you are leading a team or a function right now, the question worth asking is not “are we busy?” Almost certainly, yes. The question is whether the things consuming your week are the things that will matter when you look back in eighteen months. In my experience, the workstreams that get described as “important but not urgent” are often neither. They are placeholders, things that justify the feeling of motion without requiring the commitment that real priorities demand. Strategy fails when priorities are vague, which I wrote about separately when working through how we communicate decisions inside organisations. The same logic applies here: when everything is a priority, the word loses its operational meaning entirely. One of the clearest signs of leadership maturity I have seen, and this connects to the kind of continuous, embedded readiness we talk about in the context of operational resilience, is the ability to say “we are not doing that” and mean it, rather than “we will get to that” and not mean it. The work of focus is not scheduling. It is the act of committing to one thing before you know how it ends, and being willing to be wrong about it in public if it comes to that. The Close Most people are not scattered because they lack discipline. They are scattered because they have not yet decided that being wrong about one important thing is less costly than being irrelevant across many.
Momentum Through Small Progress
Momentum Is a Lie You Tell Yourself in Retrospect I was rebuilding in 2021, not the kind of rebuilding that makes for a clean narrative at a conference: I sat in my home office at 7am with cold coffee and genuinely wondered whether the version of myself I was trying to recover was actually worth recovering. The business pivot I had made the previous year had cost me more than I was prepared to admit publicly, or privately, for some time. The financial exposure was real but survivable. What surprised me, and I say this with the full awareness that I should have known better, was what the failure took from me that I had not put a value on: my confidence in my own judgment, time I will not get back, and a kind of professional identity I had worn for so long that I had mistaken it for my actual self. I had spent two decades advising organisations on transformation, risk strategy, and resilience. Apparently, the curriculum did not include a module on what to do when my own plan unravels on schedule. The Rule I Set Because I Had Nothing Else Somewhere in early 2021, I made a decision that felt embarrassingly small at the time. I gave myself one rule: do one visible thing each day, not a strategy review, not a restructuring plan, not the ambitious Q2 roadmap I kept drafting and abandoning. One thing: an email sent, a conversation completed, a document closed and filed, something that existed in the world after I did it, that had not existed before. I want to be honest about how that rule felt in practice. Some days, sending a single email was a genuine achievement. I would look at the rule, one visible thing, and think: this is a standard set for someone recovering from surgery, not someone who has run teams of several hundred people across multiple geographies. The bar was, objectively, on the floor. I kept the rule anyway, partly because I had nothing better, partly because the alternative was producing nothing, and I had enough experience with organisations in freefall to know that zero output days compound in the wrong direction just as fast as progress days compound in the right one. Ninety days in, I reviewed what I had produced, not to feel good about myself, I was not expecting to feel good about myself, but because I needed an honest read on whether the approach was working or whether I was simply managing a slow decline with better optics. What I found genuinely surprised me. The volume of work was not the surprise. What stopped me was that I could not draw a straight line from where I had been to where I was. The distance had appeared gradually enough that I had not registered it. Momentum, it turned out, does not announce itself. Three Things That Pivot Taught Me That No Strategy Course Ever Did Progress made quietly does not feel like progress. This is the trap most capable people fall into when they are behind. They have succeeded visibly before, they know what it feels like when things are working, the energy in the room, the metrics ticking up, the sense of forward motion that others can see. When none of that is present, my instinct is to conclude that nothing is working. That instinct is usually wrong. The compound effect of consistent small action is not a motivational phrase, it is arithmetic. But arithmetic does not feel like anything while it is happening. The ledger is invisible until I run the numbers. Waiting for readiness is a strategy for staying still. There is a version of professional discipline that looks like patience but is actually avoidance in good clothing. I have watched senior leaders wait for the right conditions, the right quarter, the right team configuration, and I have watched them wait themselves into irrelevance. In 2021, I was at risk of doing exactly that. The energy to do something significant does not precede action, it follows it. That sequencing matters. Getting it backwards is one of the most common and most expensive mistakes I have seen in executive careers, including my own. Consistency is a decision, not a character trait. I used to believe, and I hear this belief echoed constantly in leadership conversation, that some people are naturally consistent and some are not. That consistency is something you either have or you develop through habit. I do not think that is right anymore. What I experienced in that ninety-day period was not the emergence of a new habit, it was a daily decision, made again every morning, often against my own inclination. Some mornings the decision took five minutes of sitting at the desk and arguing with myself. Consistency is not a trait I possess, it is a choice I make when nothing feels worth doing. That distinction matters because traits are fixed and choices are not. What This Means If You Are Running Something Right Now If I lead an organisation, a team, or a professional practice that is currently behind where it should be, and most are, in some dimension, at any given time, my instinct is to wait for the moment when I can make a significant move. Restructure properly, relaunch with conviction, come back strong. I understand that instinct, I have acted on it, and I have watched others act on it, and I have seen what it produces. What it produces, mostly, is a longer period of stagnation with a more elaborate justification. The organisations I have seen recover fastest from genuine difficulty were not the ones that waited for the transformational moment. They were the ones that kept producing output, imperfect, incremental, sometimes undistinguished output, on the days when producing nothing would have been entirely forgivable. The compound effect is not selective, it does not care whether I am in a good quarter or a difficult one. It runs in
Asia changed my perspective
What Six Months in Asia Taught Me About the Limits of My Own Experience I stepped off a plane in Hong Kong in early 2025, carrying twenty years of assumptions about how regulated industries work, how risk is managed, how governance frameworks are built, and, if I am honest, about where the serious thinking in financial services actually happens. I had built a career in London, operated across EMEA, navigated Basel frameworks, sat in front of regulators in three time zones. I thought I had a reasonably accurate map of the global landscape. By the time I landed back at Heathrow six months later, that map was in pieces on the floor. This is not a story about being humbled by the exotic East. That framing is its own form of condescension, and it is not what happened. What happened was more specific, and more uncomfortable: I discovered that some of the hardest problems I had spent years advising organisations to manage had already been solved – operationally, not theoretically – in places I had been too comfortable to spend serious time in. The Moment I Stopped Being Certain The jolt came in Singapore, about six weeks into the trip. I was in a working session with a team running AI governance infrastructure for a major financial institution. Not a pilot, not a roadmap: live infrastructure, being stress-tested against real regulatory requirements in real time. The team lead was explaining their model validation approach – the controls architecture, the feedback loops, the way they had structured human oversight into the decision chain – and I was taking notes like a junior analyst. She was thirty-two, maybe thirty-three. In London, the person with that responsibility is usually someone with grey hair, institutional scar tissue from a crisis or two, and a carefully curated network of regulators they can call. Experience is used as a credential. Here, the credential was demonstrated capability. The question the organisation had asked was not “who has done this before?” It was “who can actually do this now?” I have spent two decades in rooms where seniority determines credibility. That session in Singapore was the first time in a long while that I felt the distance between my assumptions and reality as a physical thing. Three Things That Refused to Fit My Existing Model I started in Hong Kong, because it was where the dissonance started. The regulatory environment there operates at a pace I was not prepared for. In London, the gap between regulatory intent and enforcement action can stretch across years – consultations, industry responses, phased implementation, guidance notes on the guidance notes. In Hong Kong, that gap is measured in weeks. The senior executives I met were doing something I found genuinely rare: they were holding two entirely different regulatory worldviews simultaneously – mainland and international – without it visibly destabilising their decision-making. That is not a skill most frameworks teach. It is the product of operating under sustained complexity for long enough that ambiguity becomes a normal working condition rather than a problem to be resolved before you proceed. Singapore was infrastructure where I expected aspiration. AI governance in that market is not a strategy document. It is funded, staffed, and running. The Model Risk Management frameworks had been adapted specifically for generative AI contexts – not retrofitted from credit risk models from 2009, which is what I see most often in European institutions. The regulatory bodies had developed technical capacity in parallel with the private sector, not after it. That sequencing matters more than most governance discussions acknowledge. Tokyo took longer to read, but it had the most to say about execution. The pace was slower. Consensus takes the time it takes, and there is no shortcut that does not eventually cost you. But the data governance practices I observed had a quality I had genuinely not expected: they were operational, not decorative. There was no gap between policy and practice, no shelf full of frameworks that the business quietly ignores. The controls were embedded in how work actually happened. In my experience across UK and European financial institutions, that gap – between the governance document and the governed reality – is one of the most persistent and expensive problems in the industry. In the organisations I visited in Tokyo, it had been closed. They were not debating data quality. They had built systems that made low-quality data structurally difficult to introduce. The Thought That Arrived Somewhere Over the Gulf On the third return leg – somewhere between Dubai and London, around 2am – something settled. Asia is not catching up to Western regulatory and governance thinking. That framing assumes the West defined the destination and everyone else is navigating toward it. What I had actually witnessed was a set of jurisdictions solving problems that the West has not yet named clearly enough to begin solving. The West is good at frameworks. I write them, export them, consult on them, and convene conferences about them. The frameworks are often genuinely rigorous. But a framework without the infrastructure to run it is a very expensive piece of intellectual comfort. What I saw in those six months was the infrastructure – built with urgency, staffed for capability rather than seniority, and designed to adapt rather than to endure. What This Means for Anyone Leading in Risk, Compliance, or AI If my organisation is building AI governance, updating its model risk framework, or trying to understand how regulatory expectations are shifting globally – the most useful thing I can do is not commission another benchmarking report from a global consultancy. Those reports will tell me what was true eighteen months ago, filtered through a lens that probably originated in Western financial centres. I will go. I will sit in the actual rooms. My education begins the moment I clear customs and starts to compound when I realise how many of my own assumptions were doing work I never asked them to do. The competence
Managing Energy, Not Just Time: A Leadership Reality
You Are Not The Same Person You Were Eight Hours Ago I once missed a critical concession during a high-stakes regulatory negotiation at 4:15pm. A concession I would have caught in seconds at 9am. Not because the issue was buried in the documentation. Not because the counterparty had been particularly clever about it. Because I was not the same person I had been when I sat down that morning, and I had convinced myself otherwise. That cost six weeks of rework. Six weeks of calls, revised positions, internal re-briefings, and the particular exhaustion that comes not from hard work but from correctable mistakes. The kind that follows you home. What I remember most clearly is not the moment I spotted the error – that came later, in the debrief. What I remember is the certainty I felt getting on that call. Tired, yes. But experienced. Seasoned. Twenty years in the room for situations exactly like this. I had done harder things on less sleep. I would be fine. I was not fine. The Situation This was 2021. I was in a regulatory settlement negotiation – the kind where the stakes are measured not just in money but in precedent, in relationship, in what I would have to explain to a board that trusted my judgment. The counterparty’s team had pushed for a late afternoon slot. I knew this was not an accident when it happens in negotiations. Scheduling is a tactic. I knew that. I agreed anyway. By the time the call started, I had already been in five hours of prior meetings. The morning had been sharp – I had gone into an early session and caught two inconsistencies in the counterparty’s position before the first coffee had gone cold. That version of me was good. That version of me was not on the 4:15pm call. The concession slipped through in the language of an indemnity clause, framed as a minor administrative provision. In the context of the full document, in the state I was in, it read like standard boilerplate. At full capacity, the phrasing would have stopped me cold. Instead, I moved on. We concluded the call. I noted it as a productive session. This was not a productive session. The error surfaced forty-eight hours later during a legal review. What followed was not a crisis – we recovered, we corrected, we rebuilt the position. But the cost was real. Six weeks. And the harder cost: I had to sit with the knowledge that I had known, at some level, that I was not sharp enough for that call. I had chosen to get on it anyway, because the alternative felt like an admission I was not ready to make. What I Got Wrong – And Had Been Getting Wrong For Twenty Years The first thing I got wrong was the assumption that experience is a substitute for condition. For most of my career I had treated my own cognitive state as essentially stable. Adjustable by caffeine, by willpower, by the professional obligation to perform. My logic ran something like: I have navigated complex situations before, therefore I can navigate this one now, regardless of timing. This logic is seductive and it is false. Experience sharpens my tools. It does not mean I am holding them the same way at 4pm as I was at 9am. Neuroscience has been clear on this for decades – decision quality, working memory, and the ability to detect subtle inconsistencies all degrade across the day for most people, particularly after sustained cognitive load. Knowing this intellectually and actually scheduling around it are two entirely different things. The second thing I got wrong was conflating busyness with prioritisation. For years I had scheduled my hardest thinking into whatever slot remained after everything else was placed. Board preparation at 6pm. Critical document reviews at end of day. Strategic planning sessions wedged between operational calls. My reasoning was efficient: get the administrative and relational work done first, then tackle the substantive. In practice, I had it entirely backwards. I was giving the work that required the least of me my best hours, and giving the work that required everything I had the hours when I had nothing left. My calendar looked productive. My output suffered in ways I had not tracked carefully enough to notice the pattern. The third thing I got wrong was making this a personal failing rather than a structural one. After 2021, I did not immediately change how I operated. What I did first – and I say this without pride – was file the mistake under “lessons learned” and quietly resolve to be more careful next time. As if vigilance was the missing ingredient. What I actually needed was a different architecture. The sharpest executives I have worked alongside do not rely on willpower to protect their cognitive peak. They protect it structurally. They decline late afternoon calls for high-stakes decisions. They build buffers before complex work. They are, in this specific sense, harder to schedule than their less experienced peers – and that difficulty is not arrogance. It is professionalism. I have written before about the conditions under which teams perform at their genuine best – and the same principle applies at the individual level. The environment and the timing are not irrelevant context. They are part of the result. What This Means In Practice This is not an argument for becoming precious about my calendar. Most senior roles do not afford the luxury of perfect scheduling, and the executives who refuse any meeting after noon are usually protecting mediocrity more than sharpness. But there is a meaningful difference between unavoidable scheduling constraints and the habit of treating my cognitive peak as a flexible resource I can deploy wherever the day demands. The question worth asking is a simple one: do I know which hour of my day I am genuinely dangerous – the hour when my pattern recognition is fastest, my judgment is cleanest, my read
AI won’t replace wisdom
I first met her when she called market turns that saved the bank millions. She could read a balance sheet the way most people read a menu, instinctively, with taste, the numbers arranging themselves into meaning before anyone else in the room had found the right page. Thirty-one years of credit risk experience. The kind of institutional knowledge that doesn’t live in documentation, can’t be onboarded in a fortnight, and walks out the door when people like her retire, leaving quiet devastation in its wake. When we introduced AI-assisted risk tooling last year, she went quiet in every session. Not disruptive. Not vocal in her resistance. Quiet in a way that, if you weren’t paying attention, read as disengagement. I was paying attention, eventually, and what I saw wasn’t a woman failing to keep up. It was a woman calculating, with thirty-one years of precision, exactly how much it would cost her to be seen not-knowing., – Standing in the lift at Canary Wharf on a Tuesday morning in Q3, I kept returning to the session where she sat in the second row. We were running the third onboarding cohort for the new tooling, a mixed group, analysts through to senior directors. I had told myself we were being inclusive by putting everyone in the same room. When the facilitator asked participants to navigate the model interface live, I watched her pause at the screen for slightly longer than everyone else. Not long enough for anyone to notice. Long enough for me to notice. She recovered, clicked through, and said nothing for the rest of the session. Afterwards, I asked her how she found it. She said, *Fine.* And then, after a deliberate beat: *I just need to practice the file saving. The cloud thing.* The file saving. The cloud thing. This was a woman who had built risk frameworks from first principles, who had sat on credit committees shaping the bank’s exposure through two financial crises. She wasn’t struggling with the AI. She was struggling with the visibility of struggling, in front of people she had mentored, whose careers she had shaped, who still sent her questions they couldn’t answer. We had designed the onboarding for capability. We hadn’t designed it for dignity., – We got two things wrong initially. First, we assumed resistance and silence meant the same thing. They don’t. Resistance is a position. Silence is a calculation. When a senior expert goes quiet in a learning environment, they aren’t refusing to learn, they’re refusing to be seen as a beginner in a culture that has spent decades rewarding them for being advanced. These are different problems with different solutions, and conflating them wastes months. Second, we got the architecture of the room wrong. Mixed-cohort onboarding feels democratic. In practice, it creates a quiet social tax on senior participants, who must weigh the cost of every question against the impression it makes on people whose careers they influence. The learning environment we built was technically open and psychologically closed. Openness isn’t the absence of barriers; it’s the deliberate removal of the specific barriers that apply to the specific people in the room. The third thing I didn’t expect was that capability and confidence decouple under observation. She could navigate the tool. What she couldn’t do, not yet, was navigate it in public without the fluency she’d spent thirty years building in every other domain. There’s a particular kind of competence that only exists when no one is watching. Good learning design has to account for that gap, the gap between private ability and public performance, because that’s where most senior professionals quietly give up., – We rebuilt the onboarding from the structure outward. Smaller cohorts. Senior peers paired with senior peers, not because they needed protection, but because psychological safety isn’t an abstract value; it’s a specific condition created by specific design choices. We removed performance metrics for the first sixty days entirely. Progress was measured in questions asked, not tasks completed, because questions are evidence of engagement, and tasks completed can simply be evidence of avoidance. Ninety days after that Tuesday morning, she was running the internal AI literacy sessions herself. Not because we fixed her, but because we fixed the room. The capability was always there. The environment had been charging her too much to use it., – If your AI adoption numbers are disappointing, look at your learning architecture before you look at your people. The dominant assumption, that resistance to AI is about fear of replacement, technophobia, or generational lag, is wrong often enough to be dangerous. In financial services especially, where authority is built on the appearance of knowing, the real barrier is frequently the psychological cost of public inexperience. Your most experienced people are also your most exposed. They have the most to lose from being seen as a beginner, and they will quietly disengage before they’ll let that happen. The organisations that get this right don’t build learning environments that are merely open. They build environments that are specifically safe for expertise, where asking a question is evidence of intellectual seriousness, not a signal of inadequacy. That’s a design problem, not a culture problem. And design problems are solvable. AI won’t replace the woman who can read a balance sheet like a menu. But a poorly designed onboarding session will teach her that learning your tools isn’t worth what it costs, and that’s a loss no model can recover. Wisdom doesn’t need to be replaced. It needs a room where it’s safe to be new.
What Happens to Teams When You Force Them Outside Their Comfort Zone
When I Put My Team Somewhere They Had No Business Being 2021 was the year my best team almost quit. Not because the work was too hard. Because the work was the wrong kind of hard, and I had put them there deliberately, despite being told twice that I was making a mistake. That detail matters. This wasn’t a miscalculation born of ignorance. Their manager came to me with specific concerns. I listened, acknowledged his point, and changed nothing. Which is either evidence of considered leadership or a fairly confident act of institutional recklessness, depending on which week you ask me about. What happened next is the part I return to. Not the outcome, it went better than anyone, including me, expected, but the mechanics of what changed in those eight weeks, and why no training program I’ve ever seen could have produced the same result., – The Situation The context was a cross-border regulatory implementation. Five jurisdictions, compressed timelines, the usual chaos that attends anything involving multiple regulators who technically harmonized their frameworks but practically agree on very little. I made the call in the commercial negotiation. Two compliance leads, genuinely excellent at their work, technically rigorous, professionally credible, were assigned to a room where the currency wasn’t regulatory precision but commercial positioning. Different instincts required. Different language spoken. Their manager’s concern wasn’t unfounded. These were professionals whose careers had been built on structured frameworks, defined parameters, and the confidence that comes from knowing exactly what the rules say. I was handing them a situation where the rules were being written in real time by the people across the table. By week four, they were struggling. Not failing, there’s an important difference, but clearly operating in a way that cost them more energy than the same effort would have in a familiar environment. They were translating. Converting commercial signals into regulatory logic and back again, in every meeting, in every conversation. By week eight, they had stopped translating. They were reading the room directly., – What Actually Happened The first thing I noticed was how they handled ambiguity. In a regulatory environment, ambiguity is a problem to be resolved, you find the rule, apply the rule, document the application. In a commercial negotiation, ambiguity is often a tool. The other side uses it deliberately. Learning to recognize that distinction, and then to use it yourself, isn’t something you develop from a course on negotiation frameworks. They developed it by being in the room without a script long enough that improvising became the only option. The second thing, and this is the part that stayed with me, was how it changed the way they thought about risk. Compliance professionals are trained to see risk as something to be mitigated, disclosed, or avoided. Commercial negotiators see risk as something to be priced. Neither view is wrong. But someone who can hold both simultaneously is genuinely rare, genuinely valuable, and almost impossible to hire for because most hiring processes sort for one or the other. These two had been forced to carry both, in the same meeting, across eight weeks. The cross-wiring that produced wasn’t visible on any CV. But I watched it happen. The third observation, the one I keep coming back to in conversations about team development, is what happened to their confidence. Not the surface-level kind that comes from positive feedback, but the structural kind: the understanding that they could be wrong, correct in real time, and still keep moving. That specific resilience is what I mean when I say discomfort builds range rather than confidence. Confidence is a feeling. Range is a capability. You can fake the first. The second only exists if it has been tested., – What This Means I’ve written before about the connection between strategic clarity and team ownership, the idea that people move with more precision when they understand the *why* behind a decision, not just the *what*. What 2021 added to that is a harder truth: sometimes the *why* can’t be shared in advance, because the person receiving it isn’t yet equipped to trust it. You have to earn their retrospective agreement by being right. And that means accepting that you might be wrong, and that the cost of being wrong lands on them first. That’s an uncomfortable position for any leader who takes responsibility seriously. It was uncomfortable for me. The reflection I offer in *Final Reflections from the Front Lines of Finance* is that the decisions I most regret aren’t the bold ones, they’re the ones where I defaulted to safety on behalf of people who, given the choice, would have chosen the climb. The ceiling on familiar territory is real. Most people can’t see it from where they stand because they’ve never been high enough in unfamiliar territory to look back and notice the difference in the view. The implication for any organization trying to develop the next layer of leadership is this: your internal talent pipeline is being constrained not by ability but by assignment. The people who will surprise you most are probably sitting in rooms where they’re too comfortable being excellent at the thing they already know. Put them somewhere they don’t yet belong. Stay close enough to catch a fall. Far enough that the climb is genuinely theirs., – Comfort produces competence. Only discomfort produces people who eventually stop needing the net, and quietly start building one for someone else.