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Powerful Questions for Leadership Challenges

Guidelines for people shaping a leadership challenge 

. . . from Anne Topping, leadership consultant, Breaking the Rules


  • How will your identified leadership challenge help you develop as a leader?
  • How will your organisation benefit from you engaging in your identified challenge?
  • By the end of March what indicators will there be to demonstrate that both you and your organisation have benefitted?

The activity below may help you to dig deeper into what truly needs to be addressed and may help you hone your focus and process. 

A powerful question . . . 

  • is thought provoking
  • challenges assumptions
  • generates energy
  • focuses inquiry and reflection
  • touches a deeper meaning
  • evokes related questions

Assessing the landscape

Get a feel for the larger context in which you are operating. Scan the horizon as well as the contours of the current business and organisational landscape; whatever level of systems or project you are working with.

Like trackers in the mountains, look for obvious and subtle signals. Notice indicators that point to storms as well as to sunny skies. Allow your curiosity and imagination to take the lead as you begin to identify the many questions that the landscape reveals. It will be tough, but important, to frame your findings as questions, rather than concerns or problems.

To help frame those questions, ask yourself:

”How does A relate to C and what questions does that suggest?"

"If X were at play here . . . .what would we be asking? What is the real question underneath all this data?”

Discovering the core questions

A question is only as good as the answer it elicits.

Once you think you’ve posed most of the relevant questions (and there may be many of them), look for patterns. This is not a mechanical process, even though it can be disciplined and systematic. You are on a treasure hunt, seeking the core questions - usually three to five - which, if answered, would make the most difference to the future of your work. Cluster the questions and consider relationships among them. Notice what ‘pops up” in order to discover the deeper themes that the initial questions reveal.

Section Strategy and Purpose from

The Dance of Change

The Challenges of Sustaining Momentum in Learning Organisations

Peter Senge et al