Leadership is a craft: On leading strategy
The most common strategic problem I have encountered is the weight of too many good ideas. When every initiative makes sense in isolation, they pull the organisation in different directions. It rarely looks like dramatic failure. It's more often a slow, steady drain on energy and progress.
I have seen this in rooms where talented people work at capacity without ever reaching real momentum. Meetings end with high energy but no decisions. Everyone agrees on the vision, but diverges on almost everything required to reach it. People stay busy. Progress stays theoretical.
I have also seen the opposite. A team that moves together because it shares not just a goal, but a clear view of why that goal matters and the way there. Where the daily work and the larger direction are the same thing. Where saying no to something attractive creates space for something important. That version is not reserved for the lucky few. It is the result of choices made deliberately, and held over time.
That is what strategy, at its core, actually is. Every choice carries a consequence. So does every choice avoided.
Where strategy begins
Before any framework or competitor analysis, there is one question worth asking: does our ambition rest on an advantage that is genuinely ours?
Visions are inspiring. That does not automatically make them achievable. The space between the two rarely reveals itself in a workshop to find the gap. It tends to appear later, in targets that keep slipping, in yet another repositioning exercise, and in strategy decks that rewrite what was promised a year before.
Roger Martin's work is helpful here. Strategy, he argues, comes down to two questions: where will you play, and how will you win? Most organisations can answer the first and struggle with the second. If you cannot articulate a specific edge, you are simply hoping to be as good as the business already in your seat.
For leadership, that conversation is rarely comfortable, but it is valuable. It brings unspoken assumptions into the open and forces a clear view of what the organisation can and cannot credibly do. The expense of that work up front is small compared to the cost of learning, several years and many budgets later, that the ambition was built on conditions that were never there in the first place.
The cost of the mirror
A natural part of strategic development is to analyse competition. It feels responsible. It maps the landscape, studies the moves, and aims to reduce risk. Benchmarking has its place; used correctly, it offers a useful baseline.
The trouble starts when it becomes the dominant lens. A sustained focus on the field means the organisation starts answering the same questions as its close rivals. You work from the same data, reach similar conclusions, and produce strategies that appear distinctive but overlap in practice. Teams operate at full stretch while results remain modest. In many cases, the issue is simple: you did not build an original strategy, you built a mirror.
The work changes when you step outside the smaller frame. When the starting point is a problem that genuinely matters to your specific market, rather than a move that needs to be matched, a team will stop playing out the industry script. Legacy positions become less important than the outcomes you are actually trying to create. The link between daily effort and long-term direction becomes visible.
That difference runs deeper than aesthetics and storytelling. In my experience, it often separates organisations that meet their commitments from those that repeatedly have to mask a lack of delivery.
Strategic clarity in leadership
One illustration has stayed with me, as familiar as it might be. Roald Amundsen reached the South Pole in 1911, and beat Robert Falcon Scott. The gap between them was not courage or ambition. On those measures, they were peers.
The real difference was established long before they set out on their journeys. Amundsen's advantage did not lie in what he brought, but in what he refused to carry. He stripped away anything that did not serve his objective. The result was a coherent operation in which every team member understood the cost of the march. There was no second story underneath the official one, no hidden agendas or unaddressed risks.
Scott's expedition followed a different logic. His strategy was a set of hopes layered with compromises. He tried to hedge his bets with multiple transport methods and conflicting goals, creating a growing burden of complexity. In organisations, that logic often sounds reasonable: if you commit to one path and it fails, the accountability is personal. If you spread the bets and everything moves slowly, the blame diffuses. Options feel safe. Often, they are just insurance.
When the weather turned, Scott's team fought two battles at once: the environment in front of them and the weight of earlier decisions. The team arrived at the South Pole weeks after Amundsen's, and never returned.
In practice, strategic clarity is an exercise in making the real stakes explicit. Choices and their consequences have to be named, not left implied. This work is harder than it sounds. Many leaders are more comfortable keeping options open. Yet once the choices are clear and agreed, people begin to recognise the strategy in the small, everyday decisions they make. The direction becomes something they carry, not a slide they are shown. When conditions shift, as they do, the organisation can adapt without losing its line of march.
The point of strategic clarity is not a cleaner narrative, but an organisation that can keep moving when the ground changes.
What a decade of no can create
I thought of this recently while watching the new Devil Wears Prada, which was a nostalgic moment. In Nigel’s wardrobe scene, which echoes the original film, the rails that once displayed Dolce & Gabbana and Jimmy Choo now hold Fendi and Toteme. It is a brief, deliberate moment that also anchors a trailer viewed millions of times, and it signalled something worth paying attention to: Toteme had earned its place there.
In just over a decade, Elin Kling and Karl Lindman built Toteme into a global business with a nine-figure revenue. They did it without a traditional marketing campaign blitz, without chasing trends, and without flooding the market. Selective wholesale partners. Highly curated stores. Signature silhouettes repeated season after season. And, crucially, they declined opportunities that many brands, under pressure, would have taken.
From the outside, the story reads as focused. From the inside, it would have required restraint and patience beyond the usual metrics. A focused strategy can be more commercially effective, and it is definitely easier to communicate, easier to believe in, and easier to show up consistently. It demands the willingness to say no. The result of Toteme’s strategy has been a label that now sits naturally alongside Fendi in a scene designed to signal discernment. Toteme did not shout the loudest, yet it became the right reference in the right context.
Of course, subtraction only works if what remains is worth defending. Toteme had that. Not every brand that says no will end up in that wardrobe. But every brand that says yes to everything will end up somewhere else.
This is the cumulative effect of someone, over many years, sitting in a persuasive room and saying: not yet, not like that, and not at the expense of what we are building. It requires a person prepared to carry that tension.
Liberation
That tension between what we could do and what we should do is where strategy actually lives. Not in the deck. Not at an off-site. In the moment someone in the room is willing to give the harder answer.
I have always believed that the clearest thinking comes from the least noise, as a minimalist at heart. Subtraction is harder than addition. A real, specific ambition is rarer than it looks, and it is one of the most valuable things leadership can put on the table. Those aren't slogans. They are the questions to return to whenever the work starts to drag on.
Real strategy is not just a jargon word, although it is often treated as such. Many mistake it for concept development, business development, or simply having a plan. It is none of those things. Strategy is the leadership discipline of choosing the weight you are willing to carry, and having the restraint to leave everything else behind.
In the end, that discipline comes down to a simple choice that every leader meets, usually without naming it: will we carry a few things fully, or many things lightly? Am I leading like Amundsen, clear about what we are, deliberate about what we are not, and disciplined enough to hold that line? Or like Scott, ambitious, energetic, and gradually weighed down by complexity we never quite chose to leave behind?
These are the questions I bring with me. It has yet to fail as a starting point.
Cecilie Dobson
Founder, Dobson Advisory
Sources:Roger Martin & A.G. Lafley, Playing to Win: How Strategy Really Works, Harvard Business Review Press, 2013
hbr.org/books/playing-to-win Roland Huntford, The Last Place on Earth, Modern Library, 1999W Magazine, "The Devil Wears Prada 2: Every Fashion Easter Egg, Cameo, and Hidden Reference Explained", may 2026
wmagazine.com/culture/the-devil-wears-prada-2-fashion-easter-eggs-designers-cameos-references Business of Fashion, Toteme brand profile, may 2026
businessoffashion.com/organisations/toteme