A leader’s dilemma: Expected to lead strategy but without the know how to do so effectively

The gap between leadership expectations and support simply blows my mind.

Most leaders rise to their positions through deep subject matter expertise. If their organizations are forward-thinking, they may also invest in leadership development to help them grow into their roles.

But when it comes to strategy, arguably one of the most critical leadership skills, leaders are often feel left alone. Organizations rarely provide consistent, practical strategy education. Instead, leaders are sent to high-profile business school programs that, while impressive, often fall short of delivering actionable insights.

The expectation is clear, though rarely spoken: leaders are simply supposed to know how strategy works.

Here’s the reality: Strategy is not something you can master overnight or learn in a moment of crisis. It’s a skill built intentionally over time, through guidance, practice, and real-world application.

This leaves leaders in a dilemma. Expected to lead with strategic clarity but without the tools or training to do so effectively.

It’s what many of my clients experience. This isn’t just unfair—it’s unsustainable.

How are you experiencing this gap between expectation and support? How has it shaped your ability to develop and execute strategy?

Send me an email to [email protected] and let me know so that I can provide you with resources that help you immediately.

Main image by Towfiqu Barbhuiya

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