Questions to Ask Stakeholders for Strategic Planning
The strategic questions to ask in strategic planning are the ones put to stakeholders before anything is drafted, whether the interviewer is a consultant, a chief executive, a board chair or a planning committee. These 54 run in the order an interview tends to go: where the organisation stands, what is changing outside it, direction, trade-offs, delivery and the stakeholder's own stake. The wording speaks of the people you serve and leaves the sector to you, so one list covers a charity, a school or a public body as well as an owner working out a business strategy.
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The questions
Each question, and why to ask it
Where we stand
How would you describe where we are right now, in a sentence or two?
Why ask it
A broad opener lets the person pick their own starting point, and the pick is information: money, morale, reputation or the people served. Write down the exact words, because the distance between one stakeholder's sentence and the next is the first thing the plan has to reconcile.
What did the last plan promise, and what actually happened?
Why ask it
How the last plan fared is the nearest thing to a forecast for this one. If nobody can recall its goals, that is your first finding about how plans get used here.
What has changed in the last two years that our current plan does not account for?
Why ask it
A plan is written against conditions that keep moving after it is signed off. The gap tells you how much of the old plan can be carried over, and the fullest answer tends to come from whoever is closest to the work.
What are we best at, judged by results rather than by effort?
Why ask it
Organisations tend to rate themselves on how hard something was, which is why the question insists on results. Ask for the evidence behind each strength named, and note which ones only insiders can see.
What do we keep getting wrong, however many times we try to fix it?
Why ask it
A problem that returns after every fix is rarely about the people involved. It usually points to a structure, an incentive or a missing owner, and those are things a strategic plan can change where a memo cannot.
Where do we genuinely do something others would find hard to copy?
Why ask it
Hard to copy is a tougher test than good, and it sets aside the strengths every rival shares. Answers about people or relationships are common, so follow up on what would happen if two of those people left.
Which part of the organisation is carrying more than its share right now?
Why ask it
Strain is easier for stakeholders to name than weakness, and it lands in the same place. A team already stretched is the one a new plan tends to load first, so mark it before the priorities are drafted.
What do you rely on us for that you could not easily get somewhere else?
Why ask it
Put this to customers, members, partners and funders rather than to staff. Their answer is often narrower and more practical than the organisation's own account of its value, which makes it a firmer base for strategy.
What are we proudest of from the last few years, and would the people we serve pick the same thing?
Why ask it
Pride shows what the culture rewards. When the internal choice and the outside one differ, the plan has to decide which of the two it is built around.
Which numbers do you look at to judge how we are doing, and what do they say?
Why ask it
Stakeholders who watch different figures will disagree about the plan for reasons unrelated to strategy. Collect the list across interviews and you have a head start on a shared scorecard, plus a record of which figures nobody watches.
Outside
What is changing for the people we serve that we have been slow to respond to?
Why ask it
Frontline staff and long-standing customers tend to answer this fastest, because they hear the requests that do not fit the current offer. Ask when they first noticed the shift, as the date shows how long the lag has been.
What are we assuming about the people we serve that nobody has checked recently?
Why ask it
Beliefs about customers or members get repeated until they are treated as facts. Each one named becomes something you can go and verify before the plan is signed off, which is worth more than debating it in the interview.
Who competes with us for attention, not just for customers or funding?
Why ask it
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.
What is a competitor or peer organisation doing that you wish we had done first?
Why ask it
Envy is a more honest guide than a competitor grid. Follow up by asking why it did not happen here, since the reason, whether money, nerve or permission, is likely to still be in place.
Which outside change, in regulation, technology, funding or the economy, could hurt us most in the next three years?
Why ask it
Naming four areas stops everyone giving the same headline answer. Where a stakeholder cites a rule or a funding condition, record it as something to confirm with whoever handles compliance or grants for your country and sector before it shapes the plan.
What opportunity is open now that will not be open in two years?
Why ask it
A time limit forces a choice between openings instead of a list of them. Ask what makes the window close, because a deadline nobody can explain is often enthusiasm in disguise.
Who should we be working with that we are not working with yet?
Why ask it
Partners, suppliers, referrers and neighbouring organisations rarely appear in a plan until someone is asked for names. Ask what each side would bring, because a partnership where only one party gains tends to stay on paper.
What do people outside say about us that we would not say about ourselves?
Why ask it
Reputation runs behind reality in both directions, so the answer may be praise the organisation has stopped noticing or a complaint it has stopped hearing. Either one is cheaper to learn in an interview than from a lost contract or a lapsed donor.
Direction
If this plan works, what is different around here in three years?
Why ask it
A picture is harder to fill with jargon than a goal is. Answers that describe the organisation itself, and leave out the people it serves, tell you where attention currently sits.
Who are we for, and just as importantly, who are we not for?
Why ask it
Plans get vague when nobody wants to exclude anyone. If the person cannot name a group you are not for, the strategy is likely to end up as a list of everything the organisation already does.
What is the single most important thing for us to get right in this planning period?
Why ask it
Limiting the answer to one thing is the point, so do not accept a list. Tally the answers across interviews: a spread of ten different priorities is itself a finding to bring to the first planning session.
How far ahead should this plan look, and why that far?
Why ask it
Three years is a habit more than a rule, and the right horizon may be set by a lease, a funding cycle, a contract renewal or an owner's retirement. Whatever period people settle on, swap it into the questions here that say three years.
Where should we grow, where should we hold steady, and where should we shrink?
Why ask it
Three verbs in one question make it normal to name something for the third. People who fill in only the first are describing ambition without a way to pay for it.
What should stay exactly as it is, whatever else the plan changes?
Why ask it
Planning talk leans toward change, and this gives the cautious stakeholder a legitimate turn. The things named here are where a new direction will meet its firmest resistance, so it helps to know them before the draft.
Is the mission as written still the right one, or has the work moved past it?
Why ask it
Many planning processes treat the mission statement as fixed and plan around it. If several people describe work that the statement does not cover, raise that with the board or owners first, since rewording it is usually their decision. For a registered charity it can also need a formal step, so ask how that works in your country.
What would you want us to be known for that we are not known for yet?
Why ask it
The word yet makes this a target instead of a grievance about reputation. Compare the answer with what the organisation actually spends on, because a wish with no budget line behind it is unlikely to survive the first year.
How much risk should this plan take: a steady improvement or a real bet?
Why ask it
Appetite for risk is rarely discussed and varies widely between a founder, a finance lead and a trustee. Getting each person's answer separately shows whether a bold plan would be backed or merely tolerated.
Where will the money come from in three years that it does not come from today?
Why ask it
This ties direction to income, whether that means revenue lines in a business or funding sources in a charity. If the answer is that nothing will change, that is a strategy too, and it ought to be chosen on purpose.
Trade-offs
What are we doing today that you would stop?
Why ask it
Stopping things is the part of planning most often skipped, so ask about it before anyone is invested in the new list. Watch for people who can only name activities owned by other departments.
What are we going to say no to, even though it would be good work?
Why ask it
The stop question covers what already exists, and this one covers the offers, grants and requests that have not arrived yet. Ask for a real example the person would have turned down, since a refusal agreed in principle seldom holds when the invitation comes.
If the budget dropped by a fifth, what would you protect?
Why ask it
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.
If an unexpected sum arrived tomorrow, what would you spend it on?
Why ask it
Paired with the cut question, this shows whether people want to do more of what exists or something different. A stakeholder who only names extensions of current work may be telling you there is little appetite for change.
What is the real constraint: money, people, time, or attention?
Why ask it
Organisations tend to have one binding constraint and several imagined ones. Naming the wrong one produces a plan that solves a problem you do not have, such as raising money when nobody has the time to spend it well.
When two priorities collide, which one wins, and who gets to say so?
Why ask it
Ask for a recent example instead of a principle, such as the last time a deadline and a quality standard pulled apart. How that was settled shows the rule people already follow, and the plan either confirms it or has to overturn it.
Which of our current priorities is a priority only in name?
Why ask it
Plenty of organisations carry a goal that appears in every document and on nobody's calendar. Naming it lets the plan either fund it properly or retire it, both of which beat another cycle of pretending.
What would be worth going slower for?
Why ask it
Speed is the trade nobody volunteers. Answers such as quality, keeping experienced staff or building reserves reveal the values a growth target would quietly override.
Which decisions do you want this plan to settle so we stop reopening them?
Why ask it
Some arguments restart every quarter: whether to open a second site, whether to keep a service that loses money, who the main customer is. A plan that closes even two of them gives people a reason to read it.
Delivery
Who would have to change how they work for the direction you have described to happen?
Why ask it
Plans are usually written as things the organisation will do, with nobody in particular doing anything differently. Ask for roles or names, and whether those people know yet.
Do we have the people and skills this direction needs, or are we planning for a team we do not have?
Why ask it
Capability gaps are easy to wave through in a planning room and slow to close afterwards. Ask which roles would need to exist within the first year, and whether anyone has priced them.
Who should own each priority, by name rather than by department?
Why ask it
A department cannot be asked how something is going, but a person can. If stakeholders hesitate to name anyone, the priority may be one that everybody supports and nobody intends to carry.
How should the budget change to match this plan, and what happens if it does not?
Why ask it
Spending is where a strategy becomes visible. A new plan laid over an unchanged budget tends to become last year's activity with new headings, and finance leads will usually tell you so if asked directly.
What has to be decided in the first ninety days for everything else to be possible?
Why ask it
Long plans often stall on a few early decisions, such as a hire, a budget shift or a partner. With those listed, a multi-year document has a first quarter.
Which goals should carry a number, and which would be damaged by one?
Why ask it
Some work is measurable and some becomes distorted the moment it is measured. Letting stakeholders sort them guards against the familiar outcome where the easy metric quietly becomes the strategy.
Twelve months from now, what would tell us this is working?
Why ask it
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.
What would have to be true for this plan to fail?
Why ask it
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.
At what point does a plan here usually lose momentum?
Why ask it
People who have lived through earlier plans can often name the moment: the budget round, a change of leader, the first busy season. That is where to schedule a review before the plan is even approved.
How often should we look at this plan again, and what result would make us change it?
Why ask it
Agreeing the review rhythm while the plan is still a draft removes the stigma from revising it later. Press hardest on the trigger, since a result named in advance is far harder to explain away.
Your stake
What do you need from this plan for your own area or your own work?
Why ask it
Everyone in a planning process has an interest, and it is easier to weigh once it is spoken. Asking outright also separates the people arguing for the organisation from those arguing for their own department, without accusing either.
Where do you disagree with the direction this planning seems to be heading?
Why ask it
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.
What is the thing everyone knows and nobody says in these meetings?
Why ask it
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.
What would make you personally stop backing this plan?
Why ask it
Most stakeholders have a condition under which their support ends, and few mention it unprompted. Knowing it lets you see withdrawal coming instead of mistaking it for a scheduling problem.
How do you want to be involved from here: consulted, kept informed, or asked to decide?
Why ask it
The three options carry very different expectations, and a mismatch can cause more resentment than anything the plan says. Say honestly which of them is on offer, especially to anyone who expects a vote and will not have one.
Who else should I talk to, and who is likely to see this differently from you?
Why ask it
The first half extends your interview list, and the second protects you from hearing one circle's view five times. Stakeholders are usually generous about pointing to their critics when asked plainly.
What did you come in wanting to say that none of my questions gave you room for?
Why ask it
People prepare for these interviews, sometimes with a point they have been waiting months to make. Ending here means it gets heard, and it often turns out to be the most useful ten minutes of the hour.
Using these questions in a planning process
Practical guidance for the conversation itself
Choosing from 54 questions
Eight or ten for a one-hour interview
Nobody answers 54 questions in an hour. Take the opener and the last-plan question from Where we stand, one from Outside, the three-year picture and the who-are-we-for question from Direction, the stop and the say-no questions from Trade-offs, one from Delivery, and finish on two from Your stake. That gives every stakeholder the same spine, so the answers can be laid side by side afterwards.
Match the group to the person
Board members and owners are strongest on Direction and Trade-offs, because those are the choices they will be asked to approve. Staff who deliver the work answer Where we stand and Delivery with examples nobody else has. Customers, members, partners and funders should get the Outside group and the question about what they rely on you for, and should not be asked to settle internal trade-offs they cannot see.
Questions to ask to determine business strategy
In a company the interviews are often with the owner, the leadership team and a handful of customers, and the result is a business strategy more than a formal planning document. Lean on three questions: who the business is for and not for, where the money will come from in three years, and what it will say no to. If those three get the same answer from everyone, the strategy largely exists already and needs writing down. If they do not, that disagreement is the agenda for the planning day.
Strategic questions for the planning session itself
Some of these work better in a room than one to one. The grow, hold and shrink question, the budget cut question and the one about which decisions the plan should settle all gain from people hearing each other's answers. Keep the question about what nobody says, and the one about withdrawing support, for private interviews, where a candid answer costs the person nothing.
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 may be too far from the work to add detail, so add someone closer to it to the interview list.
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 let a good answer run. A stakeholder who is still talking about the third question after twenty minutes is giving you more than the next five would.
- 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
- 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.