What’s the tempo?
What surprised you, and how will you ensure not to be surprised again?
If you had to blow up this project, where is the critical point to place the explosives?
Where have you underestimated?
Where are people bored, and where are they frightened?
How do we measure progress?
What do we want to be able to say, to whom, and when?
Where is complacency or lethargy limiting progress?
Dreaming about the future:
What’s our big Why?
What could we learn from XYZ industry that’s different than ours?
What’s our biggest problem, and how do we bypass it?
What strengths do we have that our competition does not have?
Who is a small competitor now that is growing quickly?
What will we/our customer/our investors feel like when we/they reach this future?
How can we work backwards to chart a path for the desired future?
Who do we need?
What signals us that we’re getting off-track?
To a direct report:
What’s something new I can do to help you?
Where do you need someone else to come in and help out?
What have you learned in the past 2 days?
Who have you met recently that you didn’t know before?
What would you do if you couldn’t fail?
What should we stop doing because it’s just not valuable anymore?
What are the most critical 10% of your activities which you’re uniquely positioned/qualified for?
Gut check: how is your heart?
What is the 1% thing which is so valuable I should invest more time/energy in it?
Do I have the right rhythms of taking information in, and creating?
Am I building on the strengths of the people in my organization, and preparing for future growth/turnover/change?
Where are opportunities to communicate more/better – up to customers, senior leaders, investors; sideways to peers and my broad network; down to people in my particular organization?
Where do I need to exercise better self-control and self-leadership?
What other questions would you add?