Working with leadership teams to validate direction is one of the more enjoyable parts of what I do. Looking at market dynamics, competitive activity, adjacent opportunities and commercial priorities. Trying to answer one deceptively simple question: where are we trying to get to?

It’s creative and analytical all at the same time.

An interesting part of writing the strategy, however, comes after. All in imagining how people will read and react to it.

Over the past couple of weeks, while working on a three-year strategic roadmap, I found myself mentally sitting in the room with the people who would review it.

The question that popped into my head: “sure … but how?”

It isn’t a bad question. In fact, it is an entirely reasonable one.

Yet, I have found that one of the quickest ways to derail a conversation about strategy is to ask the right question at the wrong time.

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The cost of asking “how” too quickly

A business term I never fully appreciated until recently is the “helicopter view”.

I always understood it to mean taking a step back to look at the bigger picture. When you are high above the landscape (with the birds), patterns become obvious. You can see how everything connects, where the obstacles are and which direction makes the most sense.

What I had appreciated even less was that seeing the bigger picture was only half the challenge. It is rather difficult to stay at that altitude.

Give a room full of intelligent people a strategic discussion, and before long, someone will ask a reasonable question that essentially shifts the helicopter to descent mode. Before anyone has agreed where they are landing, the discussion has moved to the size of the landing pad, the materials it should be built from, and who is responsible for the maintenance of it once it has been built.

Strategy, fundamentally, is abstract. It is about exploring the possibilities, choices and setting direction through uncertainty.

Implementation, on the other hand, is tangible. It gives something that teams can get their teeth stuck into. Something that can be built, measured and improved upon.

No wonder, therefore, people naturally gravitate towards the latter conversation.

Choosing the destination at high altitude

Strategy deliberately operates in the space before certainty. At high altitude. Exploring the possibilities rather than prescribing actions.

This is where we discuss what we are trying to achieve, and what the possible directions for getting there are. Weighing evidence, discussing the trade-offs and gradually narrowing down the endless set of possibilities into a clear direction, always aligned and guided by our purpose. Our why.

Where we ask ourselves:

What is the objective?

What options exist?

What are the trade-offs?

Which direction are we choosing?

Designing the journey during the descent

This is often where the strategy ends, and the operational design can begin. Shifting the conversation from possibilities to practicalities.

We are no longer deciding where we are going, but how we will organise ourselves to get there. The ‘how’ is important. Necessary. It gives shape to the strategy, translating that direction into capabilities, governance and ways of working that will help make success more likely.

What capabilities do we need?

How should we structure the work?

Which processes will support this strategy?

What needs to change?

Taking the first steps on the ground

Now we can talk about the implementation itself. The nitty-gritty and practical steps that become the day-to-day once we’ve landed.

Plans become projects, responsibilities can be assigned, and progress can be measured. None of this provides meaningful traction, however, if the earlier conversations haven’t happened well.

Who owns it?

What happens first?

How do we deliver it?

When does it happen?

How will progress (and success) be measured?

Every single one of these questions is 100% valid and of equal importance. Every one deserves an answer. But they need to be asked at the right time, and in the right order.

That is the challenge.

Otherwise, we risk becoming consumed by detail and implementation before we have fully explored the possibilities, solving problems that may not even truly exist.

Simply put, for me, the strategy should leave people with a clear view on where they are going and why. Not what is the next step that I do on Monday morning. That belongs to the implementation plan.

Leading the conversation

Through this, I’ve been pondering whether that is one of the core reasons that strategies struggle. Because we often ask the implementation questions before we’ve concluded the strategic conversation.

Even experienced leadership teams have a tendency to jump into the detail before the strategic possibilities have been fully explored.

Ultimately, though, we need to be aware enough as leaders to pause when strategic conversations begin to deviate. To ask whether we want to allow the implementation to shape the strategy rather than the strategy shaping the implementation.

One of the hardest parts of strategy then is not deciding where to go. It’s resisting that temptation to descend into implementation too quickly and before everyone has agreed on the destination.

Photo by Austin Neill on Unsplash

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