Hi, it's Will here.

Strategy, at its heart, is a human process. A conversation about what matters, what’s possible, and what’s next.

But too often we treat it like a logic puzzle; linear, objective, neat. We apply frameworks, chase clarity, and focus on outputs while ignoring the undercurrents that shape how decisions are really made.

Coaching, too, is a conversation. One that makes space. Surfaces unspoken tensions. Invites depth, reflection, and the kind of insight that can’t be forced.

I’ve always been uncomfortable with the idea of the strategist having all the answers, as though strategy is akin to Moses descending from the mountain bearing The Truth. That just never rang true. Strategy has always felt, to me, like a messy, live, collaborative process. So, having spent 20 years developing brand strategy, when I subsequently trained as an Executive Coach, something clicked. It turned out I’d been blending the two all along. I just hadn’t had the language for it.

Coaching helped me name the discomfort I felt with traditional strategy work. And it gave me new tools to lean into the discomfort rather than paper over it. Coaching breeds an obsessive focus on defining the real problem, and great strategy demands that. The easy thing is to take the presenting problem at face value. The real work is sitting in the ambiguity and getting under the surface. I can’t count the number of times I’ve been brought in to solve a ‘comms problem’ that turned out to be a product issue. Or a ‘growth challenge’ that was really about team dynamics. The presenting problem is rarely the problem.

To surface the real issue, great coaches use words sparingly but powerfully. They ask questions that stop you in your tracks. The kind of question that makes you pause, sigh, and say, "That's a good question." As a Coach Strategist, I try to do the same. I want my questions to reframe the conversation, to make people look at their business- and themselves- differently. A favourite of mine: "What are we pretending not to know?" Simple. But it shifts something.

This kind of depth doesn’t happen by accident. A coach works hard to create the space for it. A space of trust, psychological safety, and focused attention. As a Coach Strategist, I bring that same intent to strategy work. Because there is vulnerability in confronting the real problem. And that requires a container where honest thinking can emerge. One of the most valuable things a coach learns is how to actually see when someone is thinking. And then not interrupt. Silence is not the enemy. Sometimes it’s where the strategy lives.

Listening is an underestimated skill in strategy. In the early stages of strategy work- the discovery phase- we need to really hear context, perspective, and lived experience. And that means listening in a way most strategists were never taught. I remember the first time I experienced Nancy Kline’s Time To Think methodology. It blew me away. Her Ten Components of a Thinking Environment is a cheat sheet for how strategists can show up in workshops and client conversations. If you want to hear something new, you have to stop filling the silence.

Another lesson coaching teaches is that it's not about you. The best coaches don't show up to be the smartest person in the room. They show up to help the other person think better. That can be humbling for strategists, especially early in your career when you feel pressure to perform and have the answers. But over time, I’ve learned to trust the process. And I’ve become more comfortable "staying in the fire"; holding space without rushing to a solution. That’s when real insight arrives.

Coaching also helps you become more conscious of the dynamic between you and your client. Are we meeting as equals? Or is there a hidden power play at work? What assumptions are shaping this interaction? Training in Transactional Analysis (TA) has been invaluable here. It helps you spot parent-child dynamics and shift back into adult-adult mode, where true collaboration happens.

But coaching goes beyond the one-to-one. It’s increasingly systemic. A rapidly emerging modality is Systemic Coaching and Constellations. Rather than zooming in on the individual, it looks at the whole system: the team, the culture, the interdependencies, the energy. The Coach Strategist maps the business in its full complexity: the people, the processes, the unspoken dynamics. They don’t treat strategy as a fixed blueprint. They treat it as something emergent and alive. Change one part of the system, and everything else shifts.

When a coaching approach is integrated into strategy development, something powerful happens. We surface the real problem, not just the presenting one. We ask bolder questions. We work with systems, not silos. And we allow complexity, emotion and emergence to have a seat at the table. Not as distractions, but as vital ingredients in meaningful, adaptive strategy.

I don’t arrive with a rigid playbook. I bring presence, curiosity, and a mindset that invites emergence, not just execution. In a world that prizes speed, certainty and linear logic, this work offers something different: a way to go deeper, listen harder, and think more intelligently about the human dynamics that shape strategy.

Because strategy doesn’t live in a slide deck. It lives in people. And if we want better strategies, we need to become better at working with the people who create them.

Will Worsdell
Founder, Growth Perspective