What the pink Cadillac taught me about strategic thinking.

No-one expected the pink Cadillac.

I was working with the leadership team of a high-volume temporary staffing business. We were thinking about what a worker of the year might look like; voted for by clients and colleagues, meaningful to the people it was meant to recognise.

I asked: in an ideal world, with no restraints, what wild idea could make this genuinely mean something?

The pink Cadillac suggestion was outrageous by design. Most of those workers would absolutely not want to be seen in one. It was amusing, then debated, then thought through properly. And it became a real prize: a prestige car of their choice, for a week.

It was never pink. But the thinking that produced it was, and that’s my point. 

Giving people permission to think without constraints, even briefly, produces ideas that careful and cautious thinking never would. And those ideas, when they’re taken seriously and worked through, often become something genuinely useful. 

This isn’t a one-off observation. It’s based on what I’ve seen consistently across twenty years of working with founder-led businesses.

Watch the video below for an overview, or read on for the full story.

The consultant who thought business development was not for him.

A consultant in a professional services recruitment firm: experienced, highly regarded, and not quite making the numbers. He resisted business development, found it transactional, felt it was beneath the kind of work he did.

Rather than challenge that directly, I asked him what he knew about the external factors affecting his market that he had no control over, but could absolutely control his response to. Then: “What percentage of your work is actually bringing results? And which clients are those coming from?”

He worked it out himself. The clients he thought of as genuine partnerships, where there was real alignment and mutual respect, he was placing virtually everyone he put forward. For the rest, the fill rate was close to two percent. He was spending the vast majority of his time on work that was producing almost nothing.

It was just arithmetic, and it clicked.

Finding more clients like his favourites wasn’t cold or uncomfortable. It was reaching out to organisations that shared his values, where existing clients could offer referrals or at least credibility. That he could do; it was his kind of work.

He aimed for three meetings a week. In a deep recession, he ended up complaining, happily, that he was exhausted with more than that.

He was promoted three months later.

The high performer with no sales, who wasn’t actually failing.

A technical recruiter, international market, had been outstanding. Hard-working, well-connected, real expertise. And then the results stopped coming, gradually at first and then more completely. 

The business told her to keep doing what had always worked. Exactly the wrong advice, because it was the doing that had stopped working.

The clients who had needed so much of her attention had been in fast-growing markets that were now maturing. Their own businesses were maturing too; their need to hire in volume was no longer there. And a whole other closely related market existed that she hadn’t been looking at.

The problem was never performance. The world had moved and nobody had helped her see it.

The situation changed from “I’m failing” to “I’ve never needed to think this way before.”

The tools that make this possible.

Both of those stories share something important. The people involved weren’t lacking ability or effort. What they were missing was a way of looking outward; a framework for understanding what had changed around them and where the real opportunity was.

Two tools I come back to consistently, because they work and they always have, are PESTLE and the Boston Matrix.

I’ll be honest: I learned both in my HND and, in my own business, felt completely invincible at points where I should have been paying closer attention. The markets were changing and I didn’t look up soon enough. That’s a lesson I’ve carried into every conversation since.

PESTLE, which maps the political, economic, social, technological, legal, and environmental factors affecting a business, is often dismissed as academic.

In practice, it’s simply a structured way of asking: what’s happening outside this business that we’re not directly in control of, but we can definitely control our reaction to? The IT recruiter’s situation is a textbook illustration. Her market had matured. The economic and market context had shifted. Nobody had thought to sit with her and helped her see that for herself.

The Boston Matrix is equally practical. It maps where products, services, or in this case client relationships sit in terms of market growth and market share. The insight it gives is that not all revenue is equal; some of it is in growing markets worth investing in, some of it is in declining markets where defending position can cost more than it returns. When markets mature, the instinct is often to protect what’s there. The matrix gives people a way to see that dynamic clearly and unemotionally. It’s not failure. It’s a natural cycle; and knowing that changes the conversation entirely.

Neither tool requires a strategy consultant. They require a few honest questions, the willingness to look at the answers, and act on them.

Why this isn’t just for leaders.

The assumption in most businesses is that strategic thinking is a leadership function. Something that happens at the top, in the boardroom, at the annual away-day.

I’ve never found that to be true in practice. The pink Cadillac came from someone on a leadership team who felt safe enough to suggest something ridiculous and have it taken seriously. The consultant’s transformation happened because he was given a framework for thinking about his own market, not just his own activity. The recruiter’s results changed because someone helped her look outward rather than inward.

None of those were board-level conversations. All of them were strategic.

The research confirms what I’ve seen consistently: a strategic (mixed with coaching) approach to leadership works best when it’s embedded throughout an organisation, not reserved for isolated interventions at the top.

The businesses that perform most consistently are those where this kind of thinking isn’t reserved for the few. Where people at every level are given the questions, the frameworks, and the space to find their own answers.

That’s what good frameworks and good questions do. They don’t give people answers. They give people the conditions to find their own.

Where to start.

If these questions feel familiar and relevant to where you are right now, the strategic thinking content in the Growth Framework® is where this kind of thinking becomes embedded. Not as a one-off exercise, but as the way your business operates.

Your vision, your strategic plan, your strategic KPIs; built by your people, owned by your business.

The Growth Benchmark is where that process begins. A structured hour your whole leadership team works through together, looking honestly at where the business is aligned and where it isn’t. It’s free, and strategically, it’s the right place to start.