The Best Can Lose, The Worst Can Win: Leadership Lessons in Strategy

SHARE

Not just about talent—a question of preparation and adaptability.

There are football matches where the star player seems invisible. Neutralised. We even ask if they were on the field. I remember the 2007 UEFA Champions League semi-final between Manchester United and AC Milan. Carlo Ancelotti ‘used’ Gattuso to completely neutralise Ronaldo. The game ended 3–0, and AC Milan went on to win the cup.

Or think of James “Buster” Douglas—the underdog who ended Mike Tyson’s undefeated reign. How? He studied his opponent, trained relentlessly, strategised, turned personal pain into motivation, and most importantly, adapted his style mid-fight.

In law, the best lawyers sometimes lose—not because they lack skill, but because the other side studied, prepared, and adjusted their approach.

Even in ancient times, when scouts returned from Canaan, most saw giants and gave up—except Caleb and Joshua, who believed and acted differently.

Here’s the real question: 

Who or what are we up against? The best? Will we throw in the towel—or study, train, strategise, and adapt? The worst? Will we stay complacent—or innovate to maintain our edge?

Because one truth remains: winning isn’t guaranteed by being the best or facing the weakest. It’s secured by having a strategy—a well-thought-out, adaptable strategy. (Ref: Joshua 6, Luke 14:28)

Call to Action: 

Take a moment today. Review one area—your team, your project, your approach—and ask: Do we have a strategy that anticipates change? Share this insight with your team. Because leadership isn’t just about talent; it’s about modelling strategic thinking that turns challenges into wins.