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Five of My Favourite Questions to Address During Strategic Planning Exercises

By Tom Brady posted 08-23-2022 15:50




The ol’ strategic planning exercise. That time of the year when everyone is in a room fighting for their priorities for the next 12 months.

Or is it?

Many strategic planning exercises tend to be no more than creating a plan in time to comply with the policy that says we need a plan. As such, they follow a template (often the last strategic plan) which can lead to a box-ticking approach.

Instead, a strategic planning exercise should be where governance and leadership get together to determine a common understanding of who they are, where they’re going, each groups’ role in getting there, what it will look like when they do, and how they’ll communicate and respond with each other.

Action and Motivation
Although it is important to follow structure, planning must result in action if it is to be effective. Action needs motivation, and motivation is all about inspiring people.

Over years of being involved in strategic planning exercises, I have witnessed many wise participants who focussed the process with well-timed and insightful questions.

Most are variations on the following five examples. By introducing them into discussion, I find they maintain the engagement that is so crucial.

1) Think of your strategy as a journey. Like any journey, it must have a point. The destination is not just a place; it is an experience at that place.

Arriving tired, hungry, and broke will probably defeat the purpose of the journey. A useful question is, “How would we describe our destination?”

Spend ample time describing the vision and purpose of your organization in terms of how you will know when you get there. Focus on what life will be like instead of just facts and figures.

By creating a clear common “picture” of the destination, many of the routes and objectives needed to get there (that is, your strategy) will become clear.


2) Sometimes the budget dominates proceedings during planning exercises. The everyday reality of making ends meet reaches the point where the “strategy” becomes no more than trying to live within one’s means.

Bold ideas are trimmed back to “more realistic” ambitions. The simple closed question, “Is our work important?” can help pause the discussion and allow you to refocus from, “What can we afford to do?” to “What must we find the means to do?”

Strategy needs to be aspirational if an organization is going to change the world.


3) One word overused in the sector is “competition.” Charitable organizations shouldn’t be in competition with each other. They each have a job and, although they might collaborate, they must stay true to the purpose for which they were created.

If progress seems hampered by the success of another organization, reinvestigate your niche. By asking, “What do we do that nobody else does?” groups can rediscover their unique proposition and build their strategy on their own strengths, rather than be dictated to by the actions of others.


4) Strategy is big picture stuff. Stay high level and don’t get too deep into the day-to-day of the journey.

However, a strategy document is useless if not put into action. Planning the strategy’s implementation must be a key part of any exercise. Although the detail should be delegated, it is important to outline the main steps of action.

A question like, “What do we need to do in the next five years to continue the journey?” keeps planning at the appropriate level while ensuring implementation is fully considered.


5) I was once involved in a new medical research charity. They had been relatively successful raising money and funding researchers in their area of work.

The strategic planning exercise was based on the idea that if they kept funding more research, they would one day meet their goal. They just needed to raise more money. It all seemed a bit pedestrian to me.

I asked them, “If money were no object, what is one thing you would do right now to move your mission forward?” The answer was immediate—a clinical trial—the cost of which was twice their total annual research budget.

Suddenly the exercise morphed and refocussed on their destination. They had no choice but to step up to the next level. We had a new strategy. As a result, within two years they had doubled the research budget AND funded the trial.

It's Time to Start Asking
Any of these questions could be used in any kind of strategic planning. I never use them all in one exercise but pick those that challenge any ruts I see being fallen into.

Remember, strategy and planning are not dirty words. Done well they motivate and add focus, unleashing the can-do innovation that makes our sector so powerful.