Why Is Strategy So Difficult to Sell?

It's a question that's been bothering me for a while.

Not because I don't believe strategy matters. Quite the opposite. After more than twenty years working in digital transformation, leadership and organisational change, I'd argue that strategy is one of the most important things a business can have.

So why is it so difficult to sell?

Recently, I had the opportunity to put that question to an ai version of Keith Cunningham, author of The Road Less Stupid. If you've read his work, you'll know he's obsessed with thinking time, asking better questions and helping business owners avoid expensive mistakes.

I expected to spend the conversation talking about AI. Instead, we spent most of it talking about strategy. Or perhaps more accurately, why so many business owners don't buy it.

His argument was simple.

Founders don't wake up in the morning thinking they need strategy.

They wake up wondering whether they'll hit their sales target this month. They worry about cash flow, competitors, recruitment, customer retention and whether they're making the right decisions. They're thinking about today's problems, not tomorrow's framework.

The more I reflected on that conversation, the more I realised he was right.

Nobody buys strategy for the sake of having strategy.

But I also came away thinking there was something missing from the discussion.

We've all heard the old business analogy that people don't buy a drill because they want a drill. They buy it because they need a hole. Personally, I don't think that's the end of the story. They don't really want the hole either. They want the picture hanging on the wall. The drill is just a tool.

The hole is just a step.

The picture represents the outcome they were trying to achieve all along. Business strategy is exactly the same. Very few people want a strategic plan.

They want a business that's growing. They want confidence that they're making the right decisions. They want a team pulling in the same direction. They want to avoid costly mistakes and seize opportunities before someone else does.

In other words, they want the picture on the wall. That conversation forced me to separate three ideas that I'd previously bundled together.

The first is the category.

For us, that's Strategic Navigation.

The second is the product.

That's Syncity AI.

The third is the value proposition.

That's different depending on who you're talking to. A business coach wants to deliver more value to clients and retain them for longer. A founder wants to identify opportunities earlier and avoid expensive mistakes. A leadership team wants confidence that today's decisions are moving the organisation towards tomorrow's goals.

The destination changes. The method doesn't. That distinction changed the way I think about our own business.

For years we've talked about strategy as though it were a document. Something you create at the beginning of the year before putting it in a drawer until the next planning session.

But businesses don't operate like that. Markets change. Competitors launch new products. Technology evolves. Customers behave differently. The destination may remain exactly the same, but the route almost never does.

That's why the idea of Strategic Navigation resonates with me so strongly. Imagine setting off on a long journey with a satellite navigation system.

You don't spend weeks trying to predict every diversion, traffic jam or road closure before you leave the driveway. You simply decide where you want to go.

From that point onwards, the sat nav continually helps you adapt to changing conditions while keeping you focused on the same destination.

Business should feel exactly the same.

One of the interesting things is that we've experienced this ourselves while building Syncity AI.

Our original route to market was straightforward. We planned to sell directly to founders and business owners. That was the route.

The destination, however, was always much bigger. We wanted to build a scalable software company that genuinely helped organisations make better decisions.

Then our own AI Scouts started surfacing something we hadn't expected. Business coaches. Advisers. Consultants. White-label partnerships.

The evidence kept pointing in the same direction. We didn't change our destination. We changed the route.

Looking back, that's probably the best example of Strategic Navigation I can give. The strategy remained intact. The navigation evolved.

Ironically, the conversation I'd expected to be about AI turned out to be about something much more fundamental. Clarity.

Businesses don't need more complicated strategies. They need a clear destination and better visibility of the road ahead.

That's what allows leaders to adapt with confidence instead of reacting with panic every time the landscape changes.

So why is strategy so difficult to sell?

I don't think it's because business owners don't value it. I think it's because they're buying the wrong thing. They don't want another strategy document. They want the picture on the wall.

They want to know where they're going. And once they've chosen that destination, they need something that helps them navigate the journey. That's the category we're trying to build.

Not because strategy is boring. But because reaching your destination has always been far more important than writing the map.