The Strategy Game
Playing to Win
“From the backyard to the world stage, dream big and play even bigger.”
— Brendon McCullum
Picture the mist of dawn clinging to the ground, the sharp bite of cold on your skin, the cloud of breath hanging in the chill morning air. The smell of fresh-cut grass, sweat and adrenaline in the air. Hear the thud of a purposeful pass, the clang of a weight being racked. Feel the elation of victory, the emptiness of defeat.
Strategy is sport.
It’s a living, breathing game plan, adjusting as the conditions change, as the crowd roars, as your opponent shifts their stance.
Choose the Game You want to Play
Before the first whistle blows, before they take to the field, before they even put on their training kit, a team needs to know exactly what game they’re in. Are you sprinting 100 metres or playing five-day test cricket? Are you building to dominate a season, or chasing glory in a single knockout tie?
Your purpose is that core vision: the kind of win you want to create. It’s the shape of the season. The atmosphere in the locker room. The feeling in your bones when the plan works and the crowd surges behind you.
“Your strategy is about creating the conditions you want to play in, on a playing field of your choosing, in a way that sets you aside from the rest… to win. It is a coherent, logical theory of your game.”
Purpose gets shaped by the people on your team, your fans, your stakeholders. Ask around. Listen closely. Strategy lives in these shared ambitions.
Ask yourself:
What do I want to make possible?
What needs to change - for me, for the business, for customers - to feel like we’ve played our best game?
Define What Success Looks Like on the Scoreboard
Once you're clear on the game, it’s time to pick the right scoreboard. How will you measure what success looks like for you? Winning the league? An incremental improvement on last season? Or something completely different - how happy your supporters are, how many attend your games? How many new grassroots players you attract to your academy?
Outcomes are your big wins. Maybe it’s becoming the go-to brand in your space. Maybe it’s building something so valuable customers queue up to be part of it. When I worked at Aha!, we tracked lovability as a key indicator of success.
Be mindful. You control the plan, the effort, the training. But the outcome? That’s felt on the field, not guaranteed in the playbook. At Aha! we could not control whether customers told us they loved our product or service.
“If you create outcomes you control then you’re planning, not creating strategy… And this creates tension and anxiety for many leaders.”
Critically, you don’t control your outcomes but you must track them.
Strategy is laying down the coherent theory of what you want to accomplish and how you think you can accomplish it - with no guarantees. Performance measures are your match stats: passes completed, distance covered, tackles won. You can see if you’re moving in the right direction. They’re the sweat and data behind the glory. And the work - the drills, the daily training, the team briefings - that’s the heartbeat of it all.
Stay uncomfortable. Real outcomes are never things you can guarantee. You don’t control if fans turn up or if they cheer or jeer. But you track, you learn, you keep playing.
Choose Your Plays… and Your Bench
You can’t play every shot at once. You can’t put every player on the pitch. And you definitely can’t chase every ball that moves. Understanding what you will do is just as much about being clear on what you won’t do. Strategy demands choice. Keep it simple, sharp, and visible, so your whole team can see the goal and run toward it.
“Choosing is the training ground for clarity.”
Decide how many outcomes and goals you want to focus on. Five? Then pick five. If number six is fighting to get in, hold firm. There’s power in knowing what’s off the field. Say yes with your whole self and no with the same confidence and clarity. That’s how you protect your energy, your resources, your team.
Prioritise Like a Pro Coach
In every match, every moment is high-stakes. Every second presents the opportunity to seize the momentum or give it away. Pressure builds and nerves fray. Knowing your strategy eases that pressure, provides confidence and clarity in the decisions to make. A well-drilled team instinctively knows the right choice because they are free from the indecision that stems from a lack of clarity.
“The art of strategy is taking calculated risks and being unafraid of failure.”
The crowd is watching. What do they care about? What keeps them glued to the edge of their seat? Build your game around that. Review past performances, monitor your wins, and prioritise the moves that carry you closer to your purpose. Until it doesn’t.
Stay lean. Avoid strategy bloat. A solid formation, a few practiced moves, and a team that knows where it’s heading and what’s most important to get them there. That’s where magic happens.
Know Your Plan B
No coach walks away once the first whistle blows. The best teams listen, scan, shift. A head nod from the captain. A switch from defence to attack. A gutsy substitution when something’s not working.
Your strategy needs space for this. Call it your Emerging Strategy - the place where new ideas, fresh angles and game-day instincts live. What seemed smart in the boardroom might need tweaking under stadium lights.
“Probe the limits of your potential with every swing of a bat or kick of a ball.”
Build in time to notice. Ask yourself: What did we miss when we made the plan that now feels obvious? What’s happening on the field that opens a new opportunity? Keep asking: And what else? Again. And again. That’s where insight lives.
Capture those insights. Evaluate how they align with your purpose. Consider what can be folded into your game with minimal disruption and maximum gain. And most critical of all - be sensitive and decisive about the right time to make a change.
Final Whistle – Wrapping It Up
When the final whistle blows, whatever the result, however buoyant or broken you feel, there will always be fresh opportunity. How will you find it?
Strategy is movement, rhythm, teamwork and focus. It's the sound of boots on turf. The feel of sweat on your back and the crowd in your chest. It’s saying, “This is the game we’re playing. These are the rules we’ve chosen. Let’s give it everything.”
At Your Roadmap Coaching & Consulting, we help teams design strategies that can flex, flow, and win - whatever the conditions - with everyone on the field knowing why they’re playing and how they’ll know they’re winning.
Now lace up. The field is waiting. Play to win.
Steve Dagless
I am the Founder of Your Roadmap - Coaching & Consulting.
Life, work and business can be so simple. Let me help quieten the noise.
Helping leaders find
Balance - working in harmony with the world
Fulfilment - by doing what matters most
Process - to be at their best
Helping business deliver
Strategy - purposefully connecting with ‘why’
Operations - what, when and how; smoothly and simply
Roadmapping - alignment around a compelling visual
