Ten decisions that
define a decade
The executives who build lasting organisations don’t make better decisions every day. They make a small number of genuinely important ones — and get those right.
A sk a chief executive to name the decision that defined their organisation and almost none will cite a product launch, a marketing campaign, or a quarterly earnings beat. The answers are almost always structural: a hiring decision, an exit, a refusal to take outside capital, a market they chose not to enter.
In reviewing the career arcs of thirty leaders profiled in The Victory Magazine over seven years, a consistent pattern emerged. The executives whose organisations compounded most reliably over time did not make better decisions every day. They made a small number of genuinely consequential decisions — and they got those right.
The first hire after yourself
The first person a founder brings into an organisation shapes everything that follows. Not because of what they do directly, but because of the culture they establish by example. Every leader we spoke to who had hired for aptitude over attitude at this stage described paying for it over years. Those who hired for character first — and taught skills second — described the opposite effect.
“I made every possible mistake in the first year,” said one founder of a healthcare technology firm whose company has now operated profitably for eleven consecutive years. “The one thing I got right was the second person I hired. She is still with us. So is the culture she set.”
When to stop doing everything yourself
Every founder is, at some point, the bottleneck in their own organisation. The decision to recognise this — and to genuinely delegate rather than nominally delegate — is harder than it sounds and more consequential than almost any other a leader will make.
The executives who made this transition well described a common trait: they had hired people they were slightly afraid of. People who were demonstrably better than them in specific domains. “The day I stopped being the smartest person in the room on any given topic,” one managing director told us, “was the day the company started growing properly.”
The executives who built the most lasting organisations did not make better decisions every day. They made a small number of genuinely important ones — and got those right.”
— The Victory Magazine Editorial Analysis, 2026
Which customer to walk away from
Every growing business eventually encounters a customer whose revenue is significant but whose relationship is corrosive — to the team, the culture, or the product roadmap. The decision to end that relationship, which feels financially reckless in the moment, is one that virtually every leader we interviewed described as among the most liberating they had ever made.
The pattern is consistent: within twelve months of walking away from a damaging key account, the gap was filled — usually by a better customer, often by two or three.
Whether to take outside capital
This is not a decision with a universal right answer. But it is a decision that is made too quickly, too often, with too little examination of what it actually means to have external shareholders with their own return timelines, their own portfolio pressures, and their own definition of success.
Several leaders in our research described taking capital they did not need because it felt validating — and spending years managing the consequences. Several others described refusing capital at moments of apparent vulnerability and building the constraint into a competitive advantage.
The market you choose not to enter
Expansion feels like progress. Restraint feels like timidity. This is one of the most persistent and damaging illusions in business. The leaders in our research who had expanded into adjacent markets or geographies without genuine conviction described — almost without exception — a period of painful retrenchment, usually within two to three years.
The leaders whose organisations grew most durably had, at some point, made a conscious and explicit decision about what they would not do. They had named it, committed to it, and returned to it when the temptation of new opportunities arose.
How you communicate in difficult times
The way a leader communicates — with their team, their board, their clients, and the public — during periods of difficulty defines how they are remembered and whether trust survives the difficulty itself.
The most effective communicators in our research shared a common trait: they communicated more than felt comfortable, more directly than felt safe, and more personally than their advisers recommended. They stayed visible and accountable, and their organisations reflected that back to them in loyalty and resilience.
What you decide your legacy is before you need to
The leaders whose organisations proved most enduring had thought about their legacy not as a retrospective question but as an active operating principle. They had asked themselves: what do I want to be true about this organisation in twenty years? And they had used the answer to make decisions in the present.
This is not nostalgia or vanity. It is a practical tool. When the answer to that question is clear, a large number of everyday decisions become easier — because they can be tested against a long-horizon standard rather than a short-term optimisation. The executives who built the most lasting organisations were those who made the right decisions when the stakes were highest — and who knew, with some clarity, which decisions those were.
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THE VICTORY MAGAZINE EST, 2018
Your leadership story belongs
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