Quick Question: How will we know we’ve made the right choice?

Quick Question

Here is today's quick question for you...How will we know we’ve made the right choice?

This question keeps many leaders up at night. Big decisions made with incomplete information are revisited and sometimes relitigated. The concept of ‘rightness’ is the topic of many debates in coaching sessions with my clients.

Ask it when you're...

  1. Second-guessing a decision - When that familiar doubt settles in, this question helps distinguish between healthy reflection and destructive rumination.

  2. Facing a high-stakes choice - Before you commit, getting clear on your success criteria prevents you from shifting the goalposts later when pressure increases.

  3. Leading through uncertainty - When your team is looking to you for confidence, acknowledging that "rightness" is often unattainable rather than predetermined can increase their trust in your leadership.

Listen for...

Try to listen for:

  • Perfectionism masquerading as standards - if you or your team are paralysed by the need for the "perfect" choice, you're likely missing the opportunity to progress.

  • Winner obsession - when all focus is on being "right" rather than adapting and progressing, you're creating a culture that may not serve your long-term interests.

  • Fear-based language - if conversations are dominated by what might go wrong rather than how you'll navigate challenges, your decision-making process may be unbalanced.

Follow up with...

Sometimes, the greatest value comes from the one extra question you take the time to ask.

In this situation, you could try…

  • What would we need to see in the first 90 days to feel confident we're on track?

  • How will we know when it's time to pivot rather than persevere?

  • What does "good enough" look like here, and how is that different from perfect?


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Quick Question: Why does this decision feel hard?

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Quick Question: What if we do nothing?