Insights
PerformAdaptationLeading Difficult People Is Easier When You're One of Them
9 October 2026
Most leadership advice about difficult people starts from the assumption that they’re a problem to be managed: set expectations, establish boundaries, address the behaviour and, if necessary, manage them out. There’s nothing particularly wrong with that advice, it’s just incomplete.
I’ve spent most of my career leading people, including some extraordinarily talented and occasionally difficult individuals, and I’ve been the difficult one myself often enough to recognise the behaviour. Some of the people who make a leader’s life harder are precisely the people who can make the biggest difference to a business. The trick is knowing when their difficulty is creating value, when it’s getting in the way, and when the environment simply isn’t right for them.
The issue with following instructions
Years ago, I got involved in a performance problem that had kept a couple of consultants busy for weeks. An overnight process was taking 36 hours to run. I questioned the architecture rather than continuing to tune the application, suggested a fairly simple change, and got it down to 14 minutes. I wasn’t doing what I’d been asked to do, I was questioning whether what we’d been asked to do made sense in the first place. That approach has served me well throughout my career, and it’s also occasionally made me difficult to manage.
The point isn’t that ignoring instructions makes you clever. Plenty of people ignore instructions and achieve absolutely nothing useful. It’s that sometimes the most valuable thing you can do is challenge the assumptions behind the work rather than diligently execute the work itself, and that creates an interesting problem for leaders.
From the outside, someone exercising independent judgement and someone simply going off-script can look remarkably similar. Both question decisions, both push boundaries, both can be frustrating to manage. One might be about to deliver something extraordinary; the other might be creating a mess that everyone else will have to clean up. How do you tell the difference?
Two people I’ve known for a long time
Two people I’ve known for an awfully long time have recently written articles that got me thinking about this. Phil worked for me earlier in his career, and I’ve known his independence, curiosity and occasional difficulty firsthand. His recent piece, Difficult to Lead, Impossible to Drive, describes a lifelong habit of being hired to do one thing and ending up doing something else because he’d discovered a problem that wasn’t being properly addressed. He recounts being hired by a founder specifically to shake things up, only for the founder’s brother to conclude that he couldn’t be managed, same person, same behaviour, two quite different interpretations. His preferred arrangement is straightforward: give him a problem space, challenge his judgement, expect transparency and accountability, but don’t prescribe every step. I recognise a great deal of myself in that.
Ian Johnson was once a customer of mine; these days we work together at Mio. His recent article, The Solo AI Phenomenon, approaches a related problem from another direction. He describes the increasingly familiar situation where one capable, self-directed individual gets hold of modern AI tools and starts clearing years of accumulated technology backlog, things that previously required teams and substantial budgets suddenly achievable by one person. Wonderful, until that person leaves. The organisation has become dependent on an individual whose knowledge, decisions and solutions may exist largely in their own head, and Ian argues for putting the right foundations and governance around that capability so the business can retain the benefits without becoming hostage to the individual.
Phil writes about the person, Ian writes about the organisation. I’ve spent much of my career standing between those two perspectives, responsible for getting results while creating an environment in which talented, independent people can do their best work, and it’s rarely as simple as either giving them complete freedom or making them follow the rules.
Difficult or just inconvenient?
I sometimes wonder how many people labelled difficult are genuinely difficult, and how many are simply inconvenient to someone who prefers predictability. Organisations need people who make things work reliably: consistency, processes, standards and accountability. Without those things, businesses become chaotic and exhausting places to work. But they also need people who question whether things should work that way at all, and the problem arises when we confuse compliance with competence, or independence with insubordination.
I’ve seen organisations hire people precisely because they’re creative, independent and willing to challenge conventional thinking, then become uncomfortable when those people do exactly what they were hired to do. Of course, the reverse is also true. Not every difficult person is a misunderstood genius. Some are simply difficult: they resist accountability, pursue their own interests, ignore the consequences for colleagues, or mistake being contrary for being insightful.
Having been difficult yourself doesn’t automatically make you a better leader. You can be too sympathetic to behaviour that resembles your own, and you can excuse poor discipline because you recognise the curiosity behind it. That’s where judgement comes in.
The questions I find useful aren’t whether someone followed the instructions or stayed within their job description. They’re whether they understood the outcome we were trying to achieve, whether their challenge was grounded in evidence, whether they understood the consequences, and whether they were prepared to take responsibility for what happened next. I don’t mind someone telling me I’m wrong, in fact I’d be concerned if nobody ever did, but I expect them to have thought about why, to be willing to explain their reasoning, and to understand that challenging a decision doesn’t automatically give them the authority to make a different one.
There’s a difference between initiative and entitlement. Good leadership means making room for the former without inadvertently encouraging the latter.
Sometimes the kindest thing is to let someone go
There’s another side to this that doesn’t get enough attention. Sometimes a talented, capable person simply doesn’t fit the organisation they’re in. It doesn’t necessarily mean the person is wrong, the leader is wrong or the organisation is dysfunctional, it can just be the wrong environment.
I’ve had that conversation with people who’ve worked for me, sometimes trying to make things work and eventually recognising that we weren’t going to get there. I’ve always tried to make those conversations as constructive as possible: be kind, make the move easy, help them on their way, and then sit back and admire their future success. That’s not a consolation prize for failing to make the relationship work, it’s recognising that someone’s ability to contribute depends partly on the environment they’re working in. Some days I love being old enough to mean that without gritting my teeth.
I’ve been on the receiving end too. A leader I respected once told me, quite plainly, that he didn’t really get me. He wasn’t being unkind, he was being honest, and I appreciated it. We agreed that it was time for me to move on, and he treated me with exactly the kindness I’ve tried to show others. Neither of us was wrong. I’d found myself in a large, mature, successful organisation that was genuinely difficult to change; there was nothing inherently wrong with that organisation, it had become successful for good reasons, but it wasn’t an environment particularly suited to my temperament or the way I liked to work. The experience reinforced something I’ve come to believe quite strongly.
Leadership isn’t about making everyone fit. Sometimes it’s about recognising when they won’t, and helping them succeed somewhere they will.
The capability multiplier
All of this becomes more interesting as AI changes what individuals can accomplish. The person who questions the brief, sees an alternative and decides to build it no longer necessarily needs a development team, a substantial budget or months of elapsed time, one capable individual can now do things that would have been almost unimaginable a few years ago. That’s exciting, particularly for smaller businesses, and also challenging for leaders who are accustomed to controlling work through budgets, project plans, reporting structures and formal approvals. The distance between having an idea and implementing it is shrinking dramatically.
Ian’s concern about the solo AI phenomenon is therefore well founded. Individual capability is becoming an extraordinary asset, but it can also create dependency and risk if the organisation doesn’t provide the right foundations. Phil’s perspective is equally important: if we respond by wrapping every capable person in layers of approval and control, we’ll lose much of the benefit we’re trying to capture.
And there’s another twist. AI agents themselves are starting to exhibit some of the behaviours we’ve traditionally associated with independent, difficult people. They can take a brief as a starting point, explore alternatives, challenge assumptions and pursue approaches nobody explicitly instructed them to take, but unlike experienced colleagues, they don’t bring the same personal accountability, professional judgement or understanding of organisational consequences. That makes the distinction between capability and authority even more important: just because someone, or something, can do something doesn’t mean they should be authorised to do it. The answer isn’t simply a tighter leash, nor is it unlimited freedom. It’s developing the judgement to know where independence creates value, where boundaries are necessary and when those boundaries should change.
Knowing when to get out of the way
Looking back, some of the most valuable people I’ve worked with have also been among the most challenging. They’ve questioned my decisions, pushed beyond their briefs, found problems I hadn’t seen and occasionally driven me up the wall, and I’ve also had to recognise when that independence wasn’t producing value, when the consequences were becoming unacceptable, or when we simply weren’t going to make the relationship work.
Being the difficult one myself from time to time has helped, not because it gives me some special insight into every independent thinker, but because I understand the impulse to question the instructions when the instructions don’t make sense. I also understand that the impulse isn’t always right.
Ultimately, I don’t think the job of a leader is to eliminate difficulty. It’s to distinguish the difficulty that moves the business forward from the difficulty that holds it back, and sometimes the most important leadership decision is recognising that the person making your life difficult is actually the one asking the right question.