Questions to Ask Stakeholders for Strategic Planning
Questions for interviewing stakeholders while a strategic plan is being shaped, covering what has changed, what to stop doing, where the real constraint sits, what the organisation will say no to, and what would make the plan fail.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
If this plan works, what is different around here in three years?
Opening with a picture rather than a goal keeps people out of jargon for a few minutes. Answers that describe the organisation itself, rather than the people it serves, tell you where attention currently sits.
- 2
What has changed in the last two years that our current plan does not account for?
Most strategic plans fail because they were written against conditions that have since moved. This question surfaces the gap early, and the person who answers it best is usually closest to the work.
- 3
What are we doing today that you would stop?
Stopping things is the part of planning that never happens, so ask about it before anyone is invested in the new list. Watch for people who can only name activities owned by other departments.
- 4
Who are we for, and just as importantly, who are we not for?
Plans get vague because nobody wants to exclude anyone. If the second half of the answer is empty, the strategy will end up as a list of everything the organisation already does.
- 5
What did the last plan promise, and what actually happened?
Institutional memory about previous plans is the best available data on how this one will go. If nobody can recall the last set of goals, that is your first finding about how plans are used here.
- 6
Where do we genuinely do something others would find hard to copy?
Asking about difficulty of imitation rather than strength filters out things that are merely good. Answers about people or relationships are common, so follow up on what would happen if two of those people left.
- 7
What is the real constraint: money, people, time, or attention?
Every organisation has one binding constraint and several imagined ones. Naming the wrong one produces a plan that solves a problem you do not have, usually by raising money you cannot spend well.
- 8
What are we assuming about the people we serve that nobody has checked recently?
Assumptions harden into facts inside organisations over about five years. The value here is in the list, not the answers, because each item becomes something you can go and verify before the plan is signed off.
- 9
If the budget dropped by a fifth, what would you protect?
This gets a priority ranking from people who would refuse to give one directly. What survives a cut is the actual strategy, whatever the plan document ends up saying.
- 10
If an unexpected sum arrived tomorrow, what would you spend it on?
Paired with the cut question, this shows whether people want to do more of what exists or something different. A room that only names extensions of current work is telling you it has no appetite for change.
- 11
Who competes with us for attention, not just for customers or funding?
Most organisations name the obvious rival and stop. The threat is more often something that takes the same hour or the same budget line without appearing on any competitor list.
- 12
What would have to be true for this plan to fail?
Inverting the question gets past the optimism that planning sessions produce. The failure conditions people name are usually more specific than the success conditions, and they make better things to monitor.
- 13
Which decisions do you want this plan to settle so we stop reopening them?
A great deal of organisational time goes into arguments that restart every quarter. Asking which ones to close turns the plan from a wish list into something that saves people work.
- 14
What is the thing everyone knows and nobody says in these meetings?
Ask this one to one, never in a group, and be prepared to sit in silence for a while. If several people independently name the same thing, the plan is not credible until it is addressed.
- 15
Which goals should carry a number, and which would be damaged by one?
Some work is measurable and some becomes distorted the moment it is measured. Letting stakeholders sort them prevents the familiar outcome where the easy metric quietly becomes the strategy.
- 16
Who has to change how they work for this to happen?
Plans are usually written as things the organisation will do rather than things specific people will do differently. Named change is the difference between a plan and a document.
- 17
What are we going to say no to?
This is the question that separates a strategy from a budget. Expect resistance, expect the room to go quiet, and expect the answer to be the most argued line in the final draft.
- 18
Where do you disagree with the direction this conversation is heading?
Dissent expressed during planning is cheap. The same dissent expressed six months into implementation is expensive and arrives as slow compliance rather than as an objection.
- 19
Twelve months from now, what would tell us this is working?
Early indicators are more useful than three year targets because they arrive while you can still act. Push for something observable rather than a milestone that is simply the plan restated.
- 20
What would make you personally stop backing this plan?
Every stakeholder has a condition under which their support ends, and it is almost never mentioned unprompted. Knowing it lets you see withdrawal coming instead of interpreting it as a scheduling problem.
Using these questions in a planning process
Practical guidance for the conversation itself.
Who to ask, and separately
Who to ask, and separately
- Interview one to one before any group session. The same person gives a different answer in front of their boss, and the private answer is the one you need.
- Include people who deliver the work daily, not only those who fund or oversee it. Frontline answers are where the constraint question gets answered honestly.
- Ask at least a few people outside the organisation: customers, members, partners, funders. Internal stakeholders agree with each other more than the outside world agrees with them.
- Note who says nothing new. A stakeholder who repeats the mission statement back to you is usually not close enough to the work to be a useful input.
Running the conversation
Running the conversation
- Say up front whether you are gathering input or seeking approval. Confusing the two produces defensive answers and later resentment.
- Keep the session under an hour and cover fewer questions well rather than all twenty badly.
- When someone gives an abstraction, ask for the last time it happened. Examples travel into the plan, adjectives do not.
- Record contradictions instead of resolving them in the room. The pattern of disagreement is one of the most useful things a planning process produces.
Turning answers into a plan
Turning answers into a plan
- Group answers into three piles: things everyone agrees on, things people disagree on, and things only one person raised. The middle pile needs a decision maker, not another workshop.
- Anything that survived the budget cut question belongs near the top of the plan. Anything that only appeared in the windfall question probably does not belong in it at all.
- Write the stop list before the start list, and put a name and a date against each item on it.
- Send stakeholders back what you heard before the plan is drafted. Being visibly misheard early is how people disengage from a process they were invited into.