Ask Better Questions

09-03-2025 11:05 AM By Jacqui
Female executive asking a question
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Great leaders don't just have answers – they ask better questions. As a leader, the questions you pose will shape your organization’s conversations about the future and unlock the innovative potential of your leadership team.

Ready to move beyond mediocrity? Here are 10 strategic questions that can transform your next leadership meeting.

Questions That Drive Innovation

1. What are your leaders’ unrealized aspirations for the company?

Often, the best ideas are hiding in plain sight during leadership retreats and casual conversations.

2. What seemingly crazy ideas could double your profitability in three years?

Sometimes the most outlandish suggestions contain kernels of breakthrough thinking.

3. Which company departments or industry niches offer disproportionate revenue opportunities?

Not all areas are created equal. Identify your hidden goldmines.

4. How can you transform status-quo-loving leaders into creative innovators?

Even your most traditional colleagues have untapped creative potential.

5. What past successes do you need to unlearn or discard?

Yesterday's winning strategies might be tomorrow's limitations.

Client-Centred Strategic Thinking

6. If your most demanding clients ran your company, what experiments would they launch?

Your toughest clients often see opportunities you've missed.

7. How can you gain breakthrough insights by truly seeing through your clients' eyes?

Empathy isn't just good service – it's strategic intelligence.

8. What new ways can you facilitate client collaboration to identify bigger challenges?

Your clients' networks might reveal your next big opportunity.

9. How can you anticipate client needs they don't even know they have yet?

The most valuable advisors solve problems before clients realize they exist.

10. What unique, missing feature can you create that competitors don't offer?

Differentiation is everything in a crowded market.

The Implementation Challenge

Here's the hard truth: even brilliant strategies fail during execution. Before you get excited about your next big idea, ask yourself two crucial questions:

  • What are the key reasons our best strategic ideas fall apart during implementation?

  • How will we absolutely ensure we stop allowing that to happen?

Remember, procrastination is where strategic dreams go to die. The difference between organizations that innovate and those that stagnate isn't the quality of their ideas; it's their commitment to turning questions into action.

The strategic mind is a questioning mind. Start your next leadership meeting with one of these questions and watch how it changes the conversation.

Jacqui