For me leadership involves a constant willingness to be asking the questions. One of the challenges though that comes with this is figuring out what the questions are that need to be asked.

You can always start with the standard questions that shape and form any story: who, what, where, why, and how? But after those starters, I have a few that I have found work well in many contexts.

Why do we do what we do? 

This gets to the ideas and questions related to mission, purpose, and values. If this question cannot be unpacked easily it might suggest that there has been either some sort of mission drift, or most definitely a lack of focus. Some time for reflection and evaluation is needed.

What do we want to do, and why? 

This is a question that gets to the values of the organization and the values of those involved with it. It is also a future oriented question. What is our purpose? What need or needs are we responding to? What service(s) do we provide in response to that need or needs? Do we need to pivot from what we are currently doing in order to more closely do what it is we want to be doing? (See: Ries, 149ff).

What do we need to learn and discover to make this possible? 

By asking this question you are admitting that you aren't the expert at everything. Not only is this a good thing, it enables collaboration. It also allows one or one's organization to play to its strengths. Where are we lacking in knowledge that is important for us to be successful at doing the work we want to do? How can we go about either gaining that knowledge or reaching out to those who have that knowledge? How can we collaborate with others with other expertise?

Who is our customer and what do they value?  

For congregations or nonprofits perhaps a better way to phrase this might be, "Who do we serve, or who participates with us, and what do they value?" It is important to recognize that an organization is not solely about those who work for it. It is also (in fact probably more so) about the people it serves and intends to serve. However these questions are phrased, I need to note that I take them directly from Peter Drucker. I highly recommend that if you have not read, or do not own his book The Five Most Important Questions You Will Ever Ask Your Organization, that you quickly lay your hands on that book. It is so simple and succinctly lays out the importance of the questions in constantly evaluating your work, mission, purpose, values, and organization. (See: Drucker, 23ff).

What is our plan? 

Again this is a Drucker question. But any one who wants to tackle something whether a small term challenge or a long term vision must do so with a form or an idea of a plan. What is your approach? What is your strategy? Admittedly, this will change over time and need to be reevaluated based on  learning and experience. But the need for a plan persists. (See:  Drucker, 63ff).

What other questions come to mind as go to questions for leadership?  Are there others that you would add to the list of imperatives?

This is adapted from a previous post on Timothy's blog, timothysiburg.wordpress.com

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Sources and reading recommendations (more information under Related Products)

Peter F. Drucker, The Five Most Important Questions You Will Ever Ask About Your Organization, (San Francisco, CA:  Jossey-Bass, 2008).

Tom Rath & Barry Conchie, Strengths Based Leadership:  Great Leaders, Teams, and Why People Follow, (New York, NY;  Gallup Press, 2008).

Eric Ries, The Lean Startup:  How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, (New York, NY:  Crown Business, 2011).