Experience is supposed to make leadership easier. The longer we lead, the more situations we encounter, the more patterns we recognise and the more evidence we accumulate about what works. Yet there is a contradiction hidden inside that experience: the more often something has worked for us, the easier it becomes to stop asking why it worked in the first place. An approach succeeds in one organisation, then another, perhaps even a third, and eventually it stops feeling like an approach at all. It becomes part of how we lead. We have seen the results, we have evidence and we have earned some confidence in our judgement. Then we move somewhere new, apply much the same thinking and discover that the response is completely different. The tempting conclusion is that the new organisation is the problem. Sometimes it might be. Organisations can become stale, established practices can cease to serve their purpose and people who have worked together for years can become just as attached to their assumptions as an incoming leader is to theirs. Being established does not make something right any more than being new makes something better. The harder leadership task is resisting either conclusion until we understand enough to make it responsibly. Experience should make us more capable, but it should also give us better questions rather than simply greater confidence in our old answers.
Nobody enters a new organisation empty handed. We carry experience, habits, expectations and assumptions about what competent leadership looks like. Some are obvious to us, while others have become so normal that we no longer recognise them as choices. How much should a leader consult? How quickly should decisions be made? How visible should hierarchy be? How directly should people challenge one another? How much authority should individuals have? Work in one environment for long enough and our answers can stop looking contextual. They simply become how things are done. I have experienced this in surprisingly trivial ways. I remember moving somewhere and wondering where the free tea and coffee was because I had become accustomed to workplaces providing it. It is hardly a profound leadership problem, but that is precisely why I find the example useful. If we can absorb an expectation about something so insignificant without noticing, imagine how many assumptions we can absorb about leadership, authority and relationships. Looking back, I can see the same process in my own development. There was a time when I associated effective leadership much more strongly with having answers. Making a decision myself could feel like good leadership because I was not wasting everybody else’s time by involving them unnecessarily. There was also something reassuring about looking like a leader who knew what he was doing. I was not trying to exclude people; I genuinely thought I was being efficient.
Experience has changed that view considerably, but the lesson has not been that consultation is always better. That would simply replace one unquestioned rule with another. I am much more interested now in asking which is more beneficial in a particular situation: making the decision myself or involving the people it might affect? Sometimes involvement brings information I do not have, exposes consequences I have not considered or creates greater understanding of what follows. At other times, involving people in a decision adds little beyond consuming their time. Leadership judgement sits in recognising the difference. That is one reason I have become increasingly wary of describing practices as simply good or bad leadership without understanding the circumstances around them. A practice can be effective without being universally effective, and a leader can learn the right lesson from an experience only to make the mistake of applying it in the wrong place.
Moving between countries made these assumptions much more visible to me. I remember arriving in Germany after years of leading in very different environments and discovering fairly quickly that some ways of operating that had become normal to me did not fit the context I had entered. Working with the Works Council was part of that learning. I had not consciously decided to import a particular leadership philosophy; I had simply spent long enough elsewhere for certain behaviours to feel normal. The same behaviour can carry very different meanings in different environments. Decisiveness might reassure one group and feel unnecessarily controlling to another. Extensive consultation might demonstrate respect and inclusion in one context while another group experiences it as frustrating hesitation. Neither interpretation can be understood properly by examining the leader’s intention alone. Context also exists in layers. We sometimes talk about national or organisational culture as though a leader operates inside one neat set of expectations, when someone might simultaneously be working within the legal and social expectations of one country, the norms of a profession, the culture of an organisation, the established practices of a team and the expectations within individual relationships. Those layers do not necessarily point in the same direction. Understanding context therefore cannot mean simply learning how things are done somewhere and copying them. Some requirements are not negotiable, professional expectations may differ from wider social conventions, and an organisation can have established practices that genuinely need challenging. Understanding context is not the same as surrendering to it.
There is another version of the problem that I find particularly interesting: returning to somewhere we think we already understand. When I returned to Europe, I had been away for sixteen years. I am British and had worked in Europe before, so there was a danger in thinking I was returning to something familiar. Yet some of what I remembered about working and leading there was no longer the reality I encountered. When we enter somewhere obviously unfamiliar, we expect to learn. We observe carefully because we know there are things we do not understand. Familiarity can remove that instinct, even though contexts do not stand still while we are somewhere else. Professional expectations change, workplace relationships change and behaviours once considered completely ordinary may be interpreted differently years later. Even our memory of the old context may be unreliable because it was formed through one particular organisation or experience. My earlier European leadership experience, for example, had itself been shaped by a relatively top-down environment. What I remembered as familiar was therefore not only old; it had always been partial. The same problem exists without crossing national borders. People return to former organisations, move back into sectors they once knew or take responsibility for areas in which they once had expertise. Familiarity can give them a head start, but it can also convince them that the learning stage is unnecessary. Sometimes the context we are most confident we understand is precisely the one we need to rediscover.
There is a danger, however, in placing all the responsibility for contextual humility on the incoming leader. Organisations carry their own suitcases. I have worked in and observed environments where people have been there for a very long time and things have become stale. “This is how we do things here” can be every bit as limiting as “This is how we did it in my last organisation.” Longevity provides knowledge, and people who have lived through an organisation’s history understand things that a newcomer cannot possibly know on arrival. Dismissing that experience would be foolish. But longevity can also normalise practices whose original purpose has disappeared. A system may have made perfect sense years ago, or a behaviour may have developed in response to circumstances that no longer exist. This creates a more useful conversation than simply telling new leaders to listen. The incoming leader brings outside experience but incomplete local understanding; the established organisation brings deep contextual knowledge but potentially entrenched assumptions. Neither side automatically owns the better answer. The more productive relationship is one in which experience and context are allowed to interrogate one another: the newcomer remains willing to ask what they might not yet be seeing, while the established organisation remains willing to ask whether something is being defended because it still works or simply because it is familiar.
The distinction that has become increasingly important to me is between the principles behind my leadership and the practices through which I express them. I do not believe leaders need one fixed leadership style. People, circumstances and organisations differ, so what is needed from a leader changes. But that does not mean everything changes. The principles I try to lead through are to inspire, understand, trust, clarify, develop and improve. Those provide continuity for me, while how they appear in practice can vary considerably. A principle is something deeper that we believe leadership should protect, enable or achieve. A practice is one way of putting that principle into action. An assumption begins to emerge when a practice works so consistently in one context that we forget it was ever contextual. Consultation is a good example for me. Working in more participative environments made me much better at involving people, and I came to value consultation far more strongly, but I did not eventually conclude that every decision should be democratic. There are times when a leader needs to gather information, listen carefully, consider different perspectives and then make a decision. If I turned consultation into an absolute rule, I would risk making exactly the same mistake I had made before, just from the opposite direction. Adaptability therefore need not mean inconsistency. A leader can remain consistent about what they are trying to achieve while being flexible about how they achieve it. The more useful question may not be, “What is my leadership style?” but, “What do I stand for, and what does leading according to those principles require here?”
A striking example of what can happen when successful experience travels without enough contextual challenge is Ron Johnson’s move from Apple to J.C. Penney. Johnson arrived in 2011 with an exceptional retail reputation, having previously worked at Target and helped develop Apple’s highly successful retail operation. J.C. Penney had genuine reasons to pursue change, which is important: this was not a healthy organisation being disrupted merely for the sake of an executive’s ego. Yet Johnson pursued a dramatic transformation that included abandoning the coupons and continual discounting familiar to many J.C. Penney customers, while introducing major changes quickly and with limited testing. Harvard Business School later examined how Johnson’s experiences at Target and Apple shaped the strategies he introduced at J.C. Penney, while Harvard Business Review criticised the assumption that practices associated with a Silicon Valley and Apple context could simply transfer to a retailer serving very different customers.
It would be simplistic to say that Johnson failed because he copied Apple, just as it would be simplistic to attribute the fortunes of an organisation of that size to one person or one decision. The more useful lesson is about confidence and context. Contemporary accounts reported that when testing aspects of the new approach was suggested, Johnson referred to not testing at Apple; he later acknowledged underestimating how much J.C. Penney’s core customers valued coupons. The transformation was followed by a severe deterioration in sales, and Johnson left after approximately seventeen months. What makes the case valuable is not that an experienced leader tried to change an organisation and got it wrong. Leaders are sometimes recruited precisely because an organisation needs to change. It is that previous success can provide both the confidence necessary to challenge an established context and the confidence to underestimate how much that context needs to be understood first. The methods associated with our greatest successes may therefore deserve more scrutiny when we move, not less.
That risk becomes more consequential as leaders become more senior. The more authority a leader has, the greater their ability to turn an assumption into organisational practice. At the same time, people may become less willing to challenge them, particularly when the leader arrives with a formidable reputation. The person with the greatest power to import an approach may therefore also be the person least likely to hear that what worked elsewhere may not belong here. There is a responsibility on organisations to create enough openness for that challenge to happen, but there is an equal responsibility on senior leaders not merely to say they welcome challenge but to behave in ways that make challenging them realistic. For me, that includes being transparent when I do not know something. I have sometimes wondered whether I am too honest about situations, but I have little appetite for a version of leadership where uncertainty has to be disguised as authority. If I genuinely do not know an answer, I would rather say so than perform certainty. Imagine an organisation where people could routinely say what they know, what they do not know and what they genuinely think without constantly calculating the politics of doing so. There is considerable power in that simplicity, particularly when a leader is new enough to the context that pretending to understand everything would be absurd.
There is, though, an obvious danger in taking adaptability too far. If leadership should respond to context, does that mean a good leader should be capable of adapting to almost any organisational culture? I do not think so. At some point, adaptability meets personal values. I have seen or heard about environments characterised by behaviours I would find extremely difficult to work within: cliques, conversations behind closed doors, destructive organisational politics and people feeling as though they are constantly treading on eggshells. I have very little appetite for working that way. Yet there is an important qualification. My interpretation is still an interpretation. What I might describe as cliquey, somebody else might experience as a close-knit community; behaviour I regard as unhealthy organisational politics might be interpreted differently by somebody else. Contextual humility requires me to acknowledge that my judgement does not become objectively correct simply because I feel strongly about it, but that does not require me to abandon the judgement either. Every leader has boundaries, whether they articulate them explicitly or not. There will be behaviours we are willing to adapt, practices we are willing to reconsider and compromises that are simply part of working with other human beings. There may also be a point beyond which adaptation begins to mean becoming somebody we do not want to be. Understanding the context properly helps us distinguish between the two.
My instinct in an environment I believed was unhealthy would probably be to try to influence it. We see something that concerns us and believe we might be able to improve it, and sometimes we can. But no individual is bigger than an organisation. There may come a point when we understand the environment, have tried appropriately to influence it and recognise that meaningful change is unlikely. If remaining then requires us continually to behave in ways that conflict with our values, leaving may be a more honest decision than learning how to survive it. This is not an argument for walking away whenever an organisation makes us uncomfortable. Leadership inevitably involves compromise, disagreement and working alongside people whose views differ from our own, and our personal preferences do not provide the objective definition of a healthy organisation. The question becomes more serious when the conflict is sustained and fundamental. At that point, asking whether we can succeed in the organisation may not be enough. We may also need to ask what succeeding there would require us to become.
Ideally, some of this thinking begins before we enter the organisation at all. We are usually quite good at noticing the newcomer who repeatedly says, “In my last organisation, we did it this way.” It can become irritating remarkably quickly. Yet leaders can import exactly the same attitude without ever speaking those words. If I were considering a significant leadership role now, I would want to understand far more about the environment before deciding whether to enter it. I would walk around if I could, observe how people interact, seek genuine conversations rather than relying entirely on formal interview exchanges, ask my own questions of HR and listen carefully to the language people use when describing the organisation. An interview is not only about whether an organisation wants you; you are making a decision about them as well. That matters particularly when the commitment extends beyond changing jobs. Moving country, relocating a family or making another significant personal investment increases the consequences of discovering too late that the context is fundamentally wrong for you. None of this guarantees foresight. Organisations cannot reveal themselves completely during recruitment, and candidates cannot anticipate every difficulty. I know that if I found myself somewhere fundamentally incompatible with my values, part of my reaction would probably be to wonder how I had failed to see it beforehand. The objective is not to eliminate uncertainty but to approach opportunity with more curiosity. If I could give my younger self one warning, it would not be to avoid unfamiliar environments; working across very different contexts has taught me an enormous amount. It would be not to take an opportunity simply because it is there if accepting it requires you to bend or break the morals and values that matter to you. A bigger role is not automatically a better fit.
Perhaps this leaves experienced leaders with a more demanding set of questions than a simple instruction to adapt. What do I genuinely know about this environment, and what am I assuming? Which parts of my judgement are supported by evidence, and which simply feel obvious because of where I have worked before? What is genuinely ineffective here, and what is merely different from my preference? Which parts of my approach express principles I want to retain, which are practices that worked because particular conditions existed, and which have been repeated for so long that I have stopped recognising them as choices? The questions also need to work in the other direction. What might this organisation be taking for granted? Where could an outside perspective genuinely help? What deserves challenging rather than accommodating? Finally, there are the questions we perhaps ask too late: where are my boundaries, what am I willing to adapt, what am I unwilling to normalise, am I right for this environment, and is this environment right for me? There will rarely be neat answers, because contextual leadership is an exercise in judgement rather than a formula for getting every decision right. We should carry our experience with us; starting again from nothing every time we change context would waste much of what leadership experience gives us. But perhaps mature leadership means becoming more willing to unpack that experience before assuming everything in the suitcase still belongs in the room. Some things will deserve to stay exactly where they are, some will need adapting, some assumptions may have outlived the context that created them, and occasionally understanding the environment properly may lead us to a more uncomfortable conclusion about whether we belong there at all. Experience should make us more capable. Perhaps one of the clearest signs that it has is not the confidence with which we carry our old answers, but the quality of the questions we are still willing to ask.
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.