Strategy & Leadership

The hard part isn't
the strategy.

A strategy is a way through a difficulty, an approach to overcoming an obstacle, a response to a challenge. A plan for getting from where you are to where you want to be.

I've worked on the strategic direction of around 134 businesses over the past 15 years. Here's what I've noticed about what getting there actually requires.

What people think
strategy's about:

  • ·Coming up with a direction.

What getting there actually requires:

It starts with people. The right ones in the room — and that's rarely just the board.

  • 01Being honest about where you actually are — not where you'd like to be.
  • 02Understanding why the last strategy didn't move. That answer is usually already in the room.
  • 03Naming the obstacle nobody's said out loud yet.
  • 04Knowing the difference between the stated obstacle and the real one.
  • 05Getting a leadership team honest about what they're afraid of.
  • 06Accepting there is no digital strategy. No AI strategy. There is only a business strategy — and it requires understanding the business deeply.
  • 07Building a clear path — connected through every layer of the business, with real measurement, not vanity metrics.
  • 08Accepting the path requires experimentation — and that culture will block it if the business isn't ready to face that.
  • 09Investing in the capabilities the journey requires — not just the plan.
  • 10Holding the room when the real difficulty finally surfaces.
  • 11Designing for culture change, not around it. It is the obstacle.
  • 12Making room for the next generation of leadership before the current one is ready to let go.
  • 13Knowing when to kill the comfortable answer — it is usually what's keeping you where you are.
  • 14Knowing the strategy is only as good as the execution — and the willingness to adapt as the path changes.
  • ·...and yes, coming up with a direction.

If this resonates, I write about strategy, AI, leadership, and the human side of change in my newsletter — Creative Value Builders.