After nearly thirty years in the same career, it becomes difficult to identify exactly when you learnt something. Leadership development is often presented as though people move neatly from one lesson to the next, gradually collecting wisdom until they become the finished article. My experience has been considerably less organised. I have learnt things, forgotten them, repeated mistakes, changed my mind, overcorrected, and occasionally discovered that something I believed for years was not entirely wrong, but simply incomplete. Some of the things I regret most about my earlier leadership were not caused by bad intentions or a lack of commitment. Quite the opposite. They often began with instincts that seemed perfectly reasonable at the time. I wanted to support people, so I checked in too often. I wanted to trust people, so sometimes I did not check in enough. I wanted to help, so I solved problems that other people needed the opportunity to solve themselves. I wanted to be prepared, so I spent too much time imagining everything that could go wrong. Experience has not taught me that these instincts were wrong. It has taught me that almost every useful leadership instinct becomes unhelpful when taken too far.
Trust is probably the clearest example. Earlier in my career, there were times when I checked delegated work far too frequently. Responsibility made me nervous, and checking provided reassurance that things were moving in the right direction. I do not think I consciously distrusted the people involved, but I can understand now that my behaviour may have communicated something different. If someone has been given responsibility for a piece of work and the leader repeatedly asks for updates, checks progress and remains closely involved in every detail, eventually the person begins to wonder whether they were ever genuinely trusted with the responsibility in the first place. Ownership is difficult to develop when somebody is constantly standing over your shoulder. Over time, I learnt to step back, give people more space and resist the temptation to involve myself simply because I remained accountable for the outcome. Like many leadership lessons, however, I managed to learn this one well enough to create a different problem.
There have also been times when I checked in far too little. I have a naturally trusting approach to people, and I have occasionally assumed that if someone has accepted responsibility for something, they will either complete it or tell me if they are struggling. That has not always happened. Work has remained unfinished, deadlines have passed and other people have experienced the consequences. On at least one occasion, my own line manager was understandably unhappy with me because something under my responsibility had not been completed. I took responsibility for it because I have always believed that complaints go up, not down. If I am accountable for a team, I do not protect myself by blaming the people I lead when speaking to those above me. Problems with my own leadership should be discussed upwards, and concerns about performance should be addressed directly with the person involved. But taking responsibility does not remove the lesson. I had trusted someone, failed to follow up appropriately and allowed a preventable problem to affect others. The answer was not to stop trusting people or to begin monitoring everything they did. One incident should not completely change how we see someone. Patterns matter. If something happens again, we reassess. What I gradually learnt was that trust and follow-up are not opposites. People can be trusted and still need support, encouragement, challenge and appropriate accountability.
That tension appears in many of the things I wish I had understood earlier. I expected people to be more consistent than human beings can reasonably be. If someone was usually productive, positive and reliable but suddenly seemed distracted, impatient or less effective, I could be too quick to wonder whether their commitment had changed. Experience taught me that performance and commitment are not the same thing. Becoming a parent helped me understand this differently too. People arrive at work carrying lives that leaders often know very little about. Children have been awake during the night. Relationships are difficult. Parents are ill. Money is worrying them. Confidence has disappeared. Someone may be exhausted, anxious or simply having a bad day. None of this means that standards disappear or that accountability no longer matters, but it should affect how quickly we decide what someone’s behaviour means. One of the most useful phrases I have learnt to use is simply, “Help me understand.” I use it constantly because it creates space between noticing something and deciding what it means. It can be supportive, curious or quite challenging depending on how it is used, but it begins with inquiry rather than accusation. I wish I had learnt earlier that understanding a situation before judging it does not make a leader weak. It usually makes the eventual response more accurate.
I also misunderstood recognition for a long time. I thought encouraging people meant praising them, and that if people heard enough positive feedback they would know that their contribution was valued. Encouragement still matters to me, but I have learnt that praise and recognition are not the same thing. Generic praise is pleasant and quickly forgotten. Specific recognition tells someone that their effort was actually noticed. There is a difference between telling someone they have done a great job and acknowledging the patience they showed with a difficult colleague, the consistency they maintained during a demanding period or the work they completed when nobody was watching. People do not necessarily need louder applause. Often, they need someone to pay attention. Looking back, I suspect there were people whose work I appreciated but did not recognise specifically enough because I assumed they already knew. Leadership contains many assumptions like this. We assume people know they are valued. We assume they understand what we meant. We assume agreement means commitment. We assume silence means clarity. Then we are surprised when reality turns out to be more complicated.
Perhaps one of my most persistent habits has been assuming the worst too quickly. If an unexpected meeting appears in my calendar, particularly one that sounds serious, my mind is remarkably capable of constructing possibilities before I have any useful information. On balance, I have probably spent far too much time and energy preparing emotionally for situations that never happened. There is a strange comfort in imagining the worst. If you have considered the most difficult outcome, you feel less likely to be surprised by it, and anything better can feel like a relief. The problem is that the body and mind can begin responding to possibilities as though they are already real. Hours or days are spent carrying anxiety about conversations that turn out to be routine. Eventually, I started asking people what they wanted to discuss when meetings appeared unexpectedly, partly because clarity is healthier than speculation.
And yet I cannot dismiss worst-case thinking completely, because it has sometimes served me well. I have been involved in difficult conversations that deteriorated quickly, where the person opposite appeared to expect that I would be unprepared, unfamiliar with the detail or unable to defend a position under pressure. On those occasions, considering what might go wrong beforehand meant that I had already thought through the arguments, anticipated the questions and understood the position I needed to explain. Preparation gave me confidence when the conversation became difficult. The regret, therefore, is not that I prepare for the worst. It is that I have sometimes given every uncertain situation the emotional weight of a genuine crisis. Leadership requires judgement not only about what might happen, but about which possibilities deserve our attention. There is little value in being exceptionally prepared for every disaster if the process of preparation exhausts us before ordinary life has even happened.
I have also regretted how easily agreement can be mistaken for progress. Earlier in my leadership journey, I sometimes left meetings feeling enormously positive because everyone appeared to support a proposal. People nodded, contributed ideas and agreed that something needed to change. I assumed momentum would follow. Often it did not. People returned to busy roles, priorities competed for attention, interpretations differed and good intentions gradually disappeared into daily pressure. I learnt that people can genuinely agree with something and still not implement it. Agreement is emotional and intellectual; implementation is practical. It requires clarity about who is doing what, by when, with what support and how anyone will know whether it has happened. I wish I had understood earlier that gaining agreement is often the easier part of leadership. The less exciting work comes afterwards: following up, repeating expectations, checking understanding and maintaining attention when the initial enthusiasm has disappeared.
Communication created a similar regret. I used to believe that if I had explained something clearly, answered questions and watched people leave a meeting apparently satisfied, the communication had been successful. Experience repeatedly proved otherwise. People hear the same message differently. They connect it to different priorities, remember different parts and fill gaps with their own assumptions. Some people will nod because they understand. Others will nod because everyone else is nodding. Some will remain silent because they do not want to admit confusion in front of colleagues. I have left meetings convinced that everyone was aligned, only to discover later that several versions of the same decision were now circulating. Eventually, I learnt that communication cannot be measured by how clearly I believe I have spoken. It has to be measured by what other people understood and what happens afterwards. Important messages usually need repeating, reinforcing and checking over time. I wish leadership communication were as simple as saying the right thing once. It rarely is.
Another regret is that I sometimes solved problems too quickly. Earlier in my career, if someone brought me an issue, I often moved rapidly towards a solution. Helping felt useful, and solving something efficiently appeared to be good leadership. Over time, I realised that repeatedly providing answers can quietly teach people to stop searching for their own. Some people began bringing problems before they had fully thought them through because they knew I would help resolve them. That was not necessarily their failure. I had helped create the pattern. My approach now is different. I ask questions. I want to know what they think, what they have considered, what they would do if I were not available and what support they actually need from me. More often than not, people already have an answer. Sometimes they need challenge. Sometimes they need reassurance. Sometimes they simply need someone to listen while they organise their own thinking. Helping people develop judgement takes longer than giving them instructions, but it is far less likely to create dependency. Leadership is not demonstrated by becoming indispensable. In many ways, the opposite is true.
I also underestimated the effect of my own mood. I am generally a happy person, and throughout my career I have tried to be approachable and available to people. But when I have been in a mood, particularly earlier in my career, it could be quite a big mood. Leaders sometimes believe their emotions are private because they have not explicitly discussed them. They are not. People notice changes in tone, patience, body language and energy. They become more cautious, wonder whether they have done something wrong or simply find the atmosphere more difficult than it needed to be. I have become better at recognising this over time. If I know I am not in the best frame of mind, I will tell the people closest to me rather than expecting them to interpret my behaviour. If I respond in a way that is unprofessional, I apologise. I do not believe leadership requires pretending to be cheerful every day. Leaders are human beings, and people usually recognise artificial positivity anyway. But there is a difference between having emotions and making everyone else responsible for experiencing them. Part of professional maturity is recognising when our internal state is beginning to become somebody else’s working environment.
The final regret may be the least dramatic and perhaps the most important. I underestimated exhaustion. Tiredness does not simply reduce energy. It changes judgement. Patience becomes shorter, perspective narrows and the easiest option begins to look like the best one. I have sent emails because having a proper conversation felt like too much effort. I have responded more quickly than I should have because I wanted something finished rather than resolved properly. Small issues have felt disproportionately important because I did not have enough emotional capacity to see them clearly. Exhaustion does not excuse poor leadership, but ignoring its effect is equally irresponsible. Sometimes the most professional decision is to wait. Do not send the email. Do not have the conversation when you know you are too tired to listen properly. Do not make an important judgement simply because postponing it feels inconvenient. Rest does not guarantee wisdom, but exhaustion has contributed to enough poor decisions for me to know that leaders should take it seriously.
Looking back across these regrets, I do not think experience has given me a set of perfect answers. It has given me better questions. Am I checking in because someone needs support, or because I need reassurance? Am I stepping back because I trust someone, or because I am avoiding a difficult conversation about progress? Am I recognising a pattern in someone’s performance, or reacting to one difficult day? Have I genuinely recognised someone’s contribution, or simply offered praise because praise is easy? Am I preparing for a realistic possibility, or spending emotional energy on an imagined disaster? Do people agree with the direction, or do they actually know what happens next? Have I communicated clearly, or have I simply spoken clearly? Am I helping someone think, or making myself responsible for solving another problem? Is my mood mine to manage, or have I quietly made it everyone else’s problem? Am I making this decision because it is right, or because I am too tired to do something more difficult?
Nearly thirty years in a career teaches you a great deal, but not in the orderly way leadership books sometimes suggest. You pick things up gradually. You notice that a conversation went better when you asked one more question. You realise that somebody needed support when you thought they needed space. You discover that the thing you were worrying about never happened, while the problem you did not anticipate was developing quietly somewhere else. You become more comfortable admitting that an approach which worked brilliantly with one person may fail completely with another. Perhaps experience is less about accumulating certainty and more about becoming slower to assume that your first instinct is automatically the right one.
I still check in too much sometimes, and occasionally not enough. I still prepare for conversations that never become difficult. I still have moments when solving a problem myself would feel considerably easier than helping someone work through it. I still become tired, frustrated and impatient. The difference is that I recognise more of these patterns now. Recognition creates the possibility of choice. Not always, and certainly not perfectly, but more often than before. That may be one of the quieter benefits of experience. We do not necessarily stop making mistakes. We become better at noticing the moment when an old mistake is about to happen again.
If I could speak to the leader I was earlier in my career, I would not give him ten instructions. I am not sure he would listen anyway. I would probably tell him that many of the things he believes about leadership are not wrong, but they are incomplete. Trust people, but remain present. Support people, but do not take away their ownership. Maintain standards, but remember that people have lives you cannot always see. Prepare carefully, but do not live through every disaster before it happens. Communicate clearly, then check what people actually understood. Take responsibility when things go wrong, because complaints go up, not down. Ask “Help me understand” before deciding that you already do. Pay attention to your mood. Take exhaustion seriously. And perhaps most importantly, accept that becoming a better leader is not a destination you eventually reach. It is the continuing, sometimes uncomfortable process of noticing where your instincts, habits and assumptions still need work.
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.