I believe that an essential leadership skills is the practice of asking more and better questions, and asking them in a professionally-skilled manner.  It is important because:

Leaders lead by asking questions.

Many of my clients and students have asked for a single list of good questions.  So here are over 80 questions, organized into three categories.

I grouped those questions that are part of a more sophisticated probe into a string.  In most cases, the questions are contextual; I selectively inserted “Read More” links to lead you to articles that would help you understand the why and how for the question.

A Do and Don’t recommendation:

• Do use this list to improve your skills at inquiry and strategic thinking. The best questions are “informed questions” that are asked in a specific context.
• Don’t use this list as a checklist.

Greg’s Master List – Questions for Setting Strategic Path Finding

If we are successful, how do we appear to our investors/owners? To achieve our vision, how must we appear to customers? To satisfy our customers, at which processes must we excel? To achieve our vision, how must our organization learn and improve?  Read more.
Why are we doing this? Who needs to be involved? What exactly are we going to do? When are we going to do it? Read more.
What is the impact you want to have? Considering the competition, what change in direction is needed to realize the impact? How will we need to change the thinking in our organization?
What are you deeply passionate about? What can you be best at? What drives your economic engine?
What is portfolio management?
What category of innovation is this (superficial, feature enhancement, solution enhancement, breakthrough, or disruptive)?
What are the strategic pillars that support the vision? Read more.
What are your leading and lagging performance indicators?
Are the statements in the strategy document coupled to either a problem or an opportunity?
Where does the money come from? What are the revenue streams? Where does the money go? What is the cost structure? Read more.

Greg’s Master List – Questions for Betterment of Risks, Issues, and Decisions

What type of decision is this? Read more.
What is the crux of the matter?
What do I want to achieve, preserve, and avoid?
If this is the strategy, what does it imply for implementation?  What are the opportunities for synergy?
What are the strategic assumptions?
What are you concerned about?
Are we facing ambiguity or uncertainty? What kind of ambiguity is present (outcomes, priorities, metrics, and methods)? Read more.
What happened to cause this {disaster or delight} scenario?
How important is it to get the decision right? If wrong, what are the consequences? Are we considering the long-term and systematic consequences? Are we considering our stakeholders? Is the decision reversible?
Is this a problem or an opportunity? Of what is this a part of? Where does it sit on the ladder of abstraction? What are the boundaries between these and other related concepts?
What are the likely consequences of this decision? How likely is the given consequence of a risk event? Can I manage the adverse consequences [for risk events that I have chosen to accept]?
Why didn’t I know? Why didn’t my team know? Why wasn’t I told? Why didn’t I ask?
What are the mistakes I must not make? What are the mistakes that others must not make? What resources do I have to deal with the unexpected? Read more.
Are we asking the right questions?

Greg’s Master List – Questions for Elaborating Requirements, Solution Designs, and Value Propositions

Who are the stakeholders?
What is your pain? Who else has the pain?
What are the seven most important things to know about your job?
What is the future state? Is it to maintain a function, add a function, or increase performance of a function?
What is the customer experience? What is a bad experience? What do we do that annoys important stakeholders? What is a good experience? What do we do – or could we do – to delight people?
What is being bought and what is being offered?
What is distinctive about the offering?
What does the user need to be able to do? How well do they need to be able to do it? How will you verify it?
Are we measuring the right things?” What are the right things to focus on? What are the right actions to focus on?
Where have others found similar problems, opportunities and solutions?
What barrier, if removed, would allow us to make amazing progress?
Which of your many duties is most essential to your organization’s performance? How do you know if you are doing a good job? Compared to today, what do you need to be able to do better tomorrow? What do you want to be different a year from now? Read more.
How does the stakeholder interact with elements of the business model that drive revenue streams or the cost structure?  Where do they spend most of their time?
What are the actions that inhibit vision development and problem solving?
Is there any question that I should have asked you that I haven’t asked?  Read more.

Greg’s Master List – Strategy-as-Story Questions

What is the Strategic Initiative Backstory?
Can you walk me through the background and your thought process?” Read more.
Given this set of activities, what is the most likely outcome?
What’s Scary, Weird, Stupid, or Hard? Read more.
What do we know? What don’t we know? How do we find out?
How do you feel about ______?
What happened? What am I feeling? Who am I?

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Disclaimer: I am not the author of many (perhaps most) of these questions. I often hear good things from others and make a mental note, so my apologies to those who are not cited as references.

What are some other good questions for leading strategic initiatives?

Related articles

• Use the As-Is-&-To-Be Table to Clarify Strategic Initiative Vision (leadingstrategicinitiatives.wordpress.com)
• Three Templates: Strategic Initiative Benefit Propositions (Part 2) (leadingstrategicinitiatives.wordpress.com)
• How to Improve Strategic-Operational Collaboration (leadingstrategicinitiatives.wordpress.com)