For nearly eighteen years, a scheduling system I built in Excel continued to do its job. When I first created it, there was no suitable programme available to us, so I made one. At the time, people thought it was excellent. It solved a genuine problem, gave the organisation something it had not had before and, importantly, worked. When I moved on, I handed it to my successor. She continued to use it. Later, it passed to her successor. Elements of it are still being used today. There is a small part of me that looks at that and thinks: not bad. I made something useful enough to survive three leaders and the better part of two decades. There is another part of me that thinks: what on earth are we still doing using Excel for this?
Both reactions are true, and I suspect the tension between them matters. Leaders quite rightly want to build things that last. We talk about sustainable systems, institutional memory and leaving an organisation stronger than we found it. Yet longevity can flatter us. Something surviving for years can feel like proof that we got it right, when sometimes it only proves that nobody has seriously asked whether it is still right. The scheduling system continued to perform its basic function for a long time because the organisation itself did not change very much. Once the demands placed upon it began changing more frequently, its limitations became increasingly obvious. It had not suddenly become badly designed. The organisation had simply moved beyond the problem it had originally been designed to solve.
That experience has made me wary of one of the easiest questions in leadership: does it work? Most things work, at least at some level. A meeting can work because everybody eventually leaves knowing what has been decided. A reporting process can work because a report appears at the end of it. A tradition can work because the event takes place every year. An old spreadsheet can work because it still produces the information people need. The harder questions are whether it works effectively, whether the value justifies the time and effort it consumes, whether it can adapt, whether it remains sustainable and, perhaps most importantly, whether it is still having the impact we think it is having. A process can be functional long after it has stopped being particularly valuable.
I saw something similar when I returned to an organisation after being away for many, many years. I had helped establish an annual community celebration. When it was new, it felt fresh and successful. When I returned thirteen or fourteen years later, much of the same approach was still there. Again, I had two reactions. A tiny part of me was pleased that something I had helped create had lasted. A much larger part was wondering why it had barely changed. People knew what was coming. They knew how the event would unfold and what would happen next. It still worked. People participated. But its impact had diminished because familiarity had taken away much of what had once made it engaging.
The uncomfortable question is whether I would have noticed that if I had never left. I would like to think I would. I am not convinced. That was my first organisation, and early in my career I probably saw much of what happened there as the natural way organisations worked. After working on two different continents, in very different settings, I came back with other reference points. I could see things I might once have accepted without noticing. Distance had given me fresh eyes. Had I stayed continuously, I might instead have refined the event, defended it and become increasingly skilled at maintaining something whose original impact was quietly fading.
This is one of the less comfortable consequences of experience. Experience can sharpen judgement, but familiarity can dull it. The longer we remain close to a system, tradition or organisation, the easier it becomes to confuse what is normal with what is necessary. We learn the reasons things are done. We understand the history. We know which compromises were made and why. All of that knowledge is valuable, but it can also make established practice remarkably difficult to see clearly. A newcomer may ask, “Why do you do it like that?” and the experienced leader can provide a perfectly coherent answer. The existence of an answer, however, does not mean the practice still deserves to exist.
I have seen the same tendency in myself in much smaller ways. Earlier in my career, I would send several emails about one subject, then follow them up in a meeting and expect everyone to know where we were. When people arrived without the information I thought they should have, it was tempting to see a preparation problem. Eventually I had to recognise that I had helped create the problem. The information might have been there, but it was scattered across messages and not always presented in a way that made the important action obvious. At times I was more concerned with how an email looked than with whether the person receiving it could use it effectively.
My response over time has been to move towards one comprehensive email: one central point of record containing what people need to know. That does not please everybody either. Some people find a long email overwhelming. There is no communication system that perfectly matches every individual’s preference. The lesson for me has therefore not been to discover the perfect email. It has been to make the way I communicate predictable enough that people know how to work with it, while remaining willing to question whether my preferred structure is actually helping the audience. Consistency has value, but consistency should not become an excuse for designing everything around the leader.
That distinction changes how I think about accountability. If one person repeatedly arrives at a meeting without completing reasonable preparation, I may need to have an accountability conversation with that person. If half the room arrives unprepared, I need to resist the satisfaction of concluding that half the room has suddenly become irresponsible. I should first look at the conditions I have created. Was the preparation reasonable? Was its purpose clear? Could people find what they needed? Did they understand what was expected of them? A pattern does not automatically prove that the system is wrong, but it should make the system part of the investigation.
The reverse matters just as much. Leadership can become so preoccupied with understanding people’s circumstances that accountability disappears. When someone says, “I don’t have the capacity to do this,” my instinct is to ask what we mean by capacity. Is the problem time, workload, confidence, skill, competing priorities or something else? But the conversation cannot end there, particularly when one person’s unfinished work prevents five other people from doing theirs. I might paraphrase the situation back: you have too much work to complete this task, and if it is not completed, these colleagues cannot complete theirs. Help me understand what we need to fix. That is not about catching somebody out. It is about recognising that in organisations, capacity and responsibility are rarely private matters. Our work creates conditions for other people’s work.
This is why I increasingly think leadership sits in an awkward space between enabling and controlling. We owe people clarity, context, workable systems and reasonable support. We should remove unnecessary obstacles and be prepared to change systems that no longer serve their purpose. But once those conditions are reasonably in place, people also owe something to one another: preparation, engagement, honest effort and a willingness to ask for support when they need it. Good leadership cannot mean taking responsibility away from everyone else. Nor can accountability mean ignoring the environment in which people are being asked to perform.
The same tension appears when leaders introduce something new. In one organisation, we introduced an online portfolio intended to make the work taking place with our students more visible to their families. The intention was sensible: create a richer connection between the organisation and the people it served. Some colleagues took to it extremely well. Then an unintended benchmark began to emerge. Families could see how much different teams were posting, and some started comparing staff on that basis: why can’t this group be more like that one? We had created visibility, but we had not sufficiently defined what good use of that visibility looked like. Posting activity risked becoming a proxy for professional quality, even though the real quality of the work lay in the difference people were making, not in how busy an online feed appeared.
We eventually introduced clearer expectations around the range and frequency of posting, but by then an important lesson had already been delivered. Systems do not merely organise work. They signal what matters. What we make visible, what we count and what we repeatedly ask people to produce can become a definition of quality whether we intended it to or not. This is hardly unique to education. Sales teams can confuse calls made with relationships built; organisations can confuse reports produced with decisions improved; leaders can confuse activity with progress. A system can be effective according to its own mechanics and still have the wrong impact.
I have been told in the past that I could be very good at the surface-level things while not always being as strong on what sat underneath them. I regard that as a historical criticism, but a useful one. Leadership makes surface activity seductive because it is visible. New branding, new programmes, polished communication, busy dashboards and well-attended events all provide evidence that something is happening. The foundations are harder to see. Yet the organisation beneath the organisation—the capacity, relationships, processes, expectations and assumptions that make the visible work possible—is often where the real health of the place resides.
Even the language of “strong foundations” can mislead us, though. We tend to speak as if the task is to build them once and then protect them. The scheduling system taught me otherwise. A foundation can be perfectly sound for the organisation that existed when it was built and still become unsuitable for the organisation that emerges later. If the structure above it changes, the foundations may need to change too. The challenge is knowing what should be protected and what has become an anchor. There is no single test that removes judgement from that decision, but repeated comments, recurring friction, disproportionate effort and difficulty adapting are all reasons to investigate. They are signals, not verdicts.
That last distinction matters. Repeated criticism does not automatically mean a process should be abandoned. Sometimes people object because they cannot yet see what a piece of organisational infrastructure is protecting. I have worked in situations where investment in functions such as HR attracted questions about why the money was not going more directly towards the organisation’s core purpose. Yet experience of other organisations had shown me what adequately resourced support functions looked like and what happened when one person was effectively expected to do the work of several. The frontline does not remain strong by starving everything behind it. Some of the most important organisational work is almost invisible when it is being done well.
Experience helped me make that judgement, but experience needs checking too. “I’ve seen this before” can be wisdom or bias. One of the safeguards is having enough contact with other organisations and other leaders to stop your own environment becoming your only definition of normal. I have found enormous value in asking colleagues elsewhere how they organise something, what staffing they use, what works and what does not. The point is not to copy them. Benchmarking becomes another form of laziness if we simply import somebody else’s answer. Multiple eyes are useful only when they are combined with a serious understanding of our own context.
This is also why succession is more complicated than handing over a folder and explaining the processes. When I leave a role, I want the next person to benefit from what I have learned. They should not have to rediscover every piece of context, every reason behind a decision or every practical lesson accumulated over years. But I am increasingly conscious that a thorough handover can carry a hidden message: this is how I did it, therefore this is how the job is done. That is not succession. That is replication.
If I could go back to the point at which I handed over that Excel system, I would still explain it. I would still show why it existed and how it worked. But I would add something much more explicit: this is not the be-all and end-all. It solves the problem we have now. If you can find something better—particularly something that can adapt as the organisation changes—use it. Hindsight makes that easy to say, of course. The point is not that I should somehow have predicted eighteen years of technological and organisational change. It is that perhaps we should design our handovers, and our systems, for future questioning rather than future certainty.
That requires a subtle change in what we mean by sustainability. A sustainable system is not necessarily one that lasts unchanged. Sometimes the most sustainable thing about a system should be its capacity to be reviewed, adapted or replaced. Organisations need deliberate opportunities to ask whether a process remains effective, whether the effort still matches the value, whether its impact is what was intended and whether the conditions that originally justified it still exist. Crucially, that review should not depend entirely on the person who created the system. A healthy organisation should not require the inventor to announce that their invention has expired.
There is an emotional difficulty in this that leadership writing sometimes skips over. We become attached to things we create. When something survives us, it can feel like legacy. Seeing an event I had helped establish still taking place years later gave me a small flash of pride. So did the scheduling system. That reaction is understandable, but it is also dangerous. Legacy can flatter a leader at exactly the moment it should concern them. Perhaps the better legacy is not a process that everybody continues to use. Perhaps it is an organisation confident enough to understand why the process existed, retain what remains valuable and discard the rest without feeling that it is somehow betraying the person who built it.
None of this means organisations should pursue permanent reinvention. Change has costs. A better scheduling programme may require a considerable initial investment of time from someone whose workload is already full. The sensible leadership response is not simply to announce that modernisation is strategically important and add it to the pile. “We don’t have capacity” should prompt a real conversation about what capacity means and what would need to move, stop or be supported for the change to happen. Nor should leaders assume that complaints disappearing means a change has succeeded. Silence is not agreement. People may stop objecting because they have been convinced, but they may also stop because they have become resigned.
Equally, not everything valuable can be reduced to efficiency. Organisations contain traditions, relationships and ways of working that carry identity and belonging. Something can look inefficient and still preserve something worth protecting. That is why judgement cannot rest only on what is easiest to measure. We need to understand both what a practice produces and what it preserves. We also need to recognise that the two can change over time. A tradition that once created connection can become routine. A system that once saved time can become cumbersome. A process that once provided necessary consistency can begin restricting judgement. Yesterday’s solution does not become today’s mistake simply because time has passed, but neither does yesterday’s success earn permanent protection.
Perhaps that is the thread connecting meetings, communication, technology, succession and the systems we inherit. Leadership is partly the work of creating conditions in which other people can do good work. That means giving enough clarity without scripting every move, enough structure without creating dependency, enough continuity without turning history into obligation, and enough accountability without pretending that context does not matter. Those balances are never settled permanently because the organisation itself does not stand still.
The question I now find more useful than “Does this work?” is not especially complicated. It is simply harder to answer: “What is this helping us do now?” The word now matters. It forces us to separate the reason a system was created from the value it currently provides. It invites the people experiencing the system to contribute to the judgement. It makes room for evidence, context and unintended consequences. And it leaves open the possibility that something we are proud of, something familiar, even something we once built ourselves, may have completed its useful life.
There is no shame in that. The spreadsheet did its job. The annual celebration had its moment. The early systems and habits I developed were responses to the leader I was and the organisations I was working with at the time. The mistake would be to demand that today’s people keep living inside yesterday’s solutions simply because those solutions carry our fingerprints. A leader should leave knowledge behind, certainly. Context too. But perhaps one of the most generous things we can also leave is permission: permission to question what we built, to adapt what still has value and, when the time comes, to make something better.
If you enjoyed this article, you can continue exploring these ideas through the growing collection of short leadership videos published across TikTok, Instagram, YouTube, Facebook and LinkedIn. Wherever you choose to follow, I hope the reflections encourage you to think a little differently about the quieter moments that shape leadership every day.