I’ve been thinking again about the future of work and AI. This time after a conversation with my brother, who works in fashion. We were talking about how parts of the industry are responding to AI. They're not trying to compete with it on perfection, but by leaning into what AI can’t do. He mentioned how luxury brands are increasingly embracing the imperfect, with things like creases and asymmetry. Things that look lived in rather than pristine. He talked about a recent Chanel moment that really stayed with me. It originated in haute couture, which is where fashion houses tend to experiment and push boundaries, a kind of innovation melting pot for the industry. Models walked with their handbags open. Notes appeared to be falling out. Not literally, of course, but exquisitely rendered, embroidered onto silk. Mess, but elevated. Imperfection, but intentional.
What struck me was that this isn’t nostalgia or rebellion. It’s adaptive. When a new technology enters a system, value shifts. The things that were once rare become easier and cheaper to produce. The things the technology cannot replicate become more valuable.
AI is exceptionally good at polish, pattern and at optimisation. It can produce clean, coherent outputs at speed so polish starts to matter less. In effect, it becomes less distinctive and, as that happens, value migrates elsewhere. In parts of fashion, it’s migrating towards imperfection and towards signs of real life. The value is in texture, irregularity and evidence of a human behind the product.
Let’s translate this to leadership. For a long time, many organisations rewarded leaders who looked polished and certain. We've learnt to be (or attempt to be) always in control and always have an answer. That made sense when leaders were expected to be the primary source of expertise and clarity.
But AI changes that context. When machines can generate answers, summaries and scenarios faster than any human, the value of leadership no longer sits in having the most polished response. Perhaps instead it sits in deep and global awareness and sense-making. Or the ability to hold complexity without rushing to simplify it. Perhaps it’s noticing what is not being said and understanding the emotional and relational data that never makes it into a spreadsheet.
For now at least, AI cannot feel the room. It doesn’t seem to be able to hold contradiction and, ChatGPT for one, has an irritating tendency to make stuff up when it doesn’t know. It cannot tell when the system needs containment rather than direction. It cannot work with shame, fear or unspoken power dynamics. So value migrates again - away from perfection and towards presence.
What teams increasingly need from leaders is not certainty, but credibility. They don’t need flawless delivery, but trust. Rather than constant answers, the value is in the ability to stay steady when the answers are not yet clear. This is where imperfection matters and, having been banging that drum for a while now (without the AI lens), it is often misunderstood. This is not about lowering standards or about being messy for effect. It is also not about oversharing. (Let’s remember the Chanel “scrappy notes” were beautifully embroidered on silk).
It is about allowing some of the reality of leadership to be visible. For example, the uncertainty and trade-offs. The fact that you are working with incomplete information and human complexity. (My brother, in his design work, is being encouraged to be less perfect in his presentation and to show the sketch book documented workings). The open handbag works as a metaphor because it signals a real life behind the image. It says this hasn’t been overly curated (I mean it clearly has, because it’s couture! But let’s stick with the metaphor). This belongs to someone who is living, not posing.
Leadership works in much the same way. When leaders allow some of the mess to show - not chaos, but reality - it sends a quiet signal that you don’t have to perform here. You don’t have to pretend to be tidier than you are. In an AI-shaped workplace, that signal becomes more important, not less. Because the more automated and optimised work becomes, the more people need environments where nuance is allowed and where emotion is not treated as a problem to be fixed. We need to try not to flatten complexity for the sake of speed.
AI will continue to raise the bar on technical excellence. Human leadership will increasingly be judged on something different, in my opinion.
Can you create enough safety for people to think?
Can you stay connected when things are uncomfortable?
Can you resist the pull towards over-control?
Can you hold the mess long enough for something better to emerge?
Fashion often shows us what culture is working out before organisational language catches up. From that conversation with my brother, one thing feels clear. As perfection becomes easier to produce, it becomes less valuable. And what becomes rarer, and therefore more precious, is visible humanity.
The leaders who matter most in the future of work won’t be the most flawless ones - they’ll be the ones who know when to open the bag and let the truth be seen.
Rox x