Five Questions to Stress Test Your Strategy: Will Yours Survive?

You’ve probably spent a lot of time crafting your strategy. It looks good on paper, it’s been signed off by the board, and you might even have a neat one-page version for presentations. That is excellent progress.

But how do you know that it will actually help your business succeed? Will it stand up to pressure when things get messy, fast, or uncertain?

A strategy that only holds good in calm conditions can damage reputations, teams and businesses.

I would love to help you test the fortitude of your strategy. If you want to know whether yours is genuinely fit for purpose, these five questions are a great start.

1. Does your strategy chunk up to a vision?

A vision should be inspirational. A strategy should be deliverable.

Your vision sits alongside your strategy, not inside it.

Vision is part of the cultural narrative, alongside your mission, purpose, and values. A great vision gives people something to believe in and align around. But it’s not measurable, and it’s not supposed to be.

Your strategy, on the other hand, has to be measurable.

Every objective should be clear, specific, and SMART.

If your strategy “chunks up” to a vision, you’re blurring the line between inspiration and execution.

That makes it almost impossible to drive real accountability, ownership, or results.

A strong vision unites the organisation. A strong strategy drives performance. You need both, but they do very different jobs.

2. Does every senior leader share the same view of what strategy actually is?

Here’s a quick test: ask each member of your senior team to define “strategy” in one sentence.

If you get more than one answer, you’ve got work to do.

Clarity on what strategy means comes before clarity on what the strategy is.

Without that alignment, you’ll always be talking at cross-purposes.

3. Was your strategy created in silos?

I find it amazing how often the strategy is really six separate departmental plans glued together in a PowerPoint.

A real strategy integrates those plans into something cohesive and directional, where each enabling objective combines to deliver the overall strategic objective.

If your business functions can’t see how their objectives depend on and reinforce each other, your strategy will crumble the moment it’s tested.

4. Are your strategic objectives actually SMART?

Leaders often tell me their objectives are clear, but when we dig into them, some are vague, some overlap, and many are completely unmeasurable.

If your objectives aren’t specific, measurable, achievable, relevant, and time-bound, they’re not objectives; they’re statements of hope.

SMART doesn’t have to mean complex. It does mean that everyone knows what success looks like and how you’ll know when you’ve got there.

5. Does your strategy clearly articulate the organisation’s priorities?

A good strategy doesn’t try to do everything. It deliberately leaves things out. In fact, my favourite thing about a good strategy is that it tells you what not to do.

If your strategy doesn’t clearly and unequivocally say what matters most, your people will fill the gaps with their own assumptions, and your resources will scatter instead of focus.

As Roger Martin says, “strategy is about making choices and trade-offs. ”If you haven’t made any, you don’t have a strategy.

Our call to action

A good strategy doesn’t just sit neatly on paper. It shapes decisions, priorities, and focus across the business.

If you’re not sure whether yours does that or if it will stand up to real pressure, I would love to help you assess it.

Let’s have a call to test your strategy together. You’ll walk away with practical insights and a clear view of where to focus next.

Email me now at richard@twentyoneleadership.com, or set up a call by clicking here.