Strategic Questions to Ask Senior Leaders
Questions to ask about corporate strategy when you get time with a senior leader inside your own organization: a skip-level, a mentoring half hour, five minutes after a town hall. The 53 questions are grouped by what you are trying to understand: direction, the market, where money and people are committed, execution, how decisions get made and your own part in the plan. Students interviewing an executive for a strategic management course can use the same groups as an outline. The wording throughout asks for an event, a name or a number, which is harder to answer with the line from the all-hands.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Direction
What's changed in your thinking since you last presented this strategy?
Why ask it
There is a prepared answer for what the strategy is, and none for what has moved. The updates show which parts of the plan are load bearing and which were aspiration written for an audience.
What is the one bet at the center of our corporate strategy?
Why ask it
Most strategies come down to a single wager: a customer group, a price point, a technology. If you hear a list of five, ask which one the other four depend on.
What are we choosing not to do this year?
Why ask it
Strategy is visible in the refusals. If nobody can name what was dropped, the plan is closer to a wish list, and teams usually discover that by being over-committed.
Of everything on your list, what actually has your attention this month?
Why ask it
Priority lists are long and attention is scarce. Wherever a leader is personally spending time is where decisions get made quickly, and everything else waits.
What does winning look like for us in three years, in terms a customer would notice?
Why ask it
Three years is far enough out to get past this year's targets and close enough to be held to. Framing it around the customer keeps the answer from being a revenue figure alone.
How much of this strategy was chosen, and how much was forced on us?
Why ask it
Some plans are a response to a lost account, a new rule or a rival's move, written up afterwards as intent. The forced parts are the least likely to change, so they are the ones to plan your own work around.
What from the previous strategy did we deliberately keep?
Why ask it
Continuity is a choice too. Whatever survived the change of plan is what leadership regards as the core of the business, whether or not anyone has said so.
What does each of our businesses get from being part of this company that it couldn't get on its own?
Why ask it
Corporate strategy in its plainest form is what the whole adds to the parts. Shared customers, a brand, a pool of managers and central funding are the usual answers, and a unit that gets none of them is one to ask about. In a single-business company, put it about the regions or functions.
Which part of the strategy do you find hardest to explain?
Why ask it
The piece that resists a plain explanation is often the piece still being argued over at the top. It also warns you which section of the next company update will be vague.
Market
What do you hear from customers that doesn't reach the rest of us?
Why ask it
Senior people sit in conversations most staff never see. Ask for the specific complaint or request rather than the theme, since the theme is already in the deck.
Why do customers pick us over the alternative, in their words and not ours?
Why ask it
The sales deck has one answer and customers have another. A leader who has heard it first hand will quote somebody, and it is fair to ask when they last sat in on that kind of call.
Which customer group will matter more to us in five years than it does today?
Why ask it
Growth plans often hide a shift in who the company is for. If your work serves the group that is losing importance, better to hear it in this conversation than to read it in a budget.
Which competitor are you watching most closely, and what would they have to do to worry you?
Why ask it
The second half turns a name into a threshold. You also find out whether the watching is systematic or rests on the last press release.
What advantage do we have that would be hardest for a rival to copy?
Why ask it
This is the classic strategic management question about competitive advantage, so push past the classic answer. Scale, a license, a data set and a web of relationships wear away at very different speeds; ask how long they think this one lasts.
What is changing in our industry that we have not responded to yet?
Why ask it
Many executives carry a private list of things they know the company is late on. One named item beats a tour of trends, so ask for the one that bothers them most.
What have you read or seen recently that changed your view of our industry?
Why ask it
Sources are more useful than opinions, and the answer shows whether this leader is still learning from outside the company or only from inside it.
Where are we exposed if the market turns?
Why ask it
The risk register exists somewhere; this asks for it in plain language. One large customer, one supplier, debt and a single product each call for a different kind of caution in your own planning, so ask which it is.
Resources
How much room is there on budget and headcount this year?
Why ask it
Blunt, so save it for a private conversation, where it can spare you months of proposals aimed at money that does not exist. The limit may be cash, sign-off or the ability to hire at all, and each one changes what is worth proposing.
Where is the next round of investment going, and what is it coming out of?
Why ask it
Budget is strategy with the adjectives taken out. The second half is the one that seldom makes it onto a slide, and it is where the real choice was made.
When you last had two good options and could fund only one, how did you choose?
Why ask it
The criteria they reach for, payback period, strategic fit, whose team it was, are the ones your own proposal will be judged against. If the example is a few years old, ask whether they would choose the same way now.
How long are you willing to wait for a new bet to pay off?
Why ask it
Patience is set by owners, lenders or a board as much as by the person you are talking to. A two-year limit rules out a different set of ideas than a five-year one, so it is worth knowing before you propose anything.
How do you decide a project has earned a second round of funding?
Why ask it
Some places fund on results so far, some on the size of the prize, some on who is asking. Ask about the last project that got more money and what it had shown by then.
Which skills does the strategy assume we have that we would struggle to hire for today?
Why ask it
A plan can be fully funded and still impossible to staff. Their answer points to where training money and outside hires will go, and which teams will be asked to stretch until then.
For the next capability we need, would we rather build it, buy it or partner for it?
Why ask it
Each route trades cost, speed and control differently, and companies tend to have a habit. The habit tells you whether the coming years hold acquisitions, a hiring push or a run of vendor contracts.
Which trade-off between this quarter and the long term is hardest right now?
Why ask it
Most senior leaders are holding a near-term number against a slower investment. A concrete case, such as delaying a hire to protect a margin, shows which side is winning this year.
Which product or business line would we not start today if we didn't already have it?
Why ask it
A gentle way of asking what is under review. Leaders seldom announce a wind-down early, so take a careful answer for what it is and do not press for a name.
Execution
How will we know in six months whether the strategy is working?
Why ask it
Six months is too soon for the annual result, so the answer has to be an early signal: orders in a pilot region, renewal conversations, time to ship. A plan without one tends to be judged only after the money is spent.
Which measure do you trust most to tell you the truth about the business?
Why ask it
Dashboards carry dozens of figures and a leader relies on two or three. Ask why that one: the reason usually includes a story about a number that once misled them.
Which assumption in the plan worries you most?
Why ask it
Every plan rests on a few numbers nobody controls. A leader who can name one has stress-tested the plan; a leader who names none is presenting it rather than thinking about it.
What risk are we taking on purpose?
Why ask it
Chosen risk and exposure nobody decided on are different things. Follow up with what was accepted in exchange, a thinner margin for a faster launch, say, because the trade is where the judgment shows.
Where do you think we're slower than we should be?
Why ask it
You already have a view on this from below, so compare the two. When the bottleneck they name is an approval step their own layer added, ask what it was put there to prevent.
Where does the strategy get lost between your level and the front line?
Why ask it
Translation loss is a known problem and most executives have a view on which layer it happens at. Tell them what the plan sounds like by the time it reaches your team, since that is something they rarely get to hear.
Which two teams most need to work better together for this to succeed?
Why ask it
Plans tend to fail at the joins between functions more than inside any one of them. If your team is one of the two named, you have been handed your most useful project.
What has gone better than you expected so far, and why?
Why ask it
A comfortable question to place straight after a hard one. The 'why' shows whether the success is understood well enough to repeat or was simply a kind quarter.
What did we learn from the last thing that didn't work?
Why ask it
The age of the example is the tell. When the only failure anyone will discuss is years old, or belongs to a team since reorganized, recent ones are not being talked about and their lessons are not travelling.
What would have to happen for us to stop a major initiative partway through?
Why ask it
Ask it about the biggest project now running and whether a stopping point was agreed before it began. Without one, the decision to stop tends to come late, from whoever runs out of budget first.
Decisions
Who outside your own team do you have to convince before a big change goes ahead?
Why ask it
Even a senior leader needs a peer in finance, a board member or a regulator to agree. Once you know who that is, a delay that looked like indecision reads as someone waiting on a yes.
What does the board ask you about most often?
Why ask it
Attention at the top is shaped from above it, and the recurring question explains much of what gets pushed down to you. Where there is no board, put it about whoever the leader answers to: owners, a parent company, trustees or a ministry.
How often does the leadership team revisit the strategy, and what would trigger a rethink between reviews?
Why ask it
You learn whether strategy is an annual document or a standing conversation. The trigger matters more than the calendar: a lost account, a missed quarter, a competitor's launch.
What was the last real disagreement about direction among the leadership team?
Why ask it
Because it asks for an event, it is hard to answer with a line about healthy debate. Expect discretion about colleagues; the subject of the argument is the useful part anyway.
What information do you wish you had before the big calls?
Why ask it
Executives decide on partial data all the time and know which gap hurts most. If your team sits near that gap, a short regular report could be worth more than your next project.
How do you tell a team that needs more time from a plan that is wrong?
Why ask it
There is no formula for this, which is what makes a specific answer worth having. Listen for the evidence they look at and for how long they waited the last time.
Which of our stated values has cost us something to keep?
Why ask it
A value that has never cost a deal, a hire or a deadline has not been tested yet. The decision where one was kept at a price tells you more about how the next hard call will go than the poster in reception does.
What's the part of your job that people at my level misunderstand?
Why ask it
From below, a slow or odd decision looks like dithering. This gives them room to describe the constraint behind it, a commitment already made or a timing they cannot share, without your having to challenge the decision itself.
Your part
How does my team's work connect to the strategy you've just described?
Why ask it
Ask it late, once they have laid out the plan in their own words, so the link has to be made on the spot. A long pause means your team's work needs a clearer story, and now you know to write it.
How can someone outside the leadership team contribute to strategy here?
Why ask it
Some companies have a planning cycle with a way in, and others rely on leaders picking things up informally. Ask for the practical route: a document, a forum, a person, a time of year.
Which decisions would you like made at my level without waiting for yours?
Why ask it
Strategy slows down when calls travel further up than they need to. A leader who has thought about it will give a boundary, a spending limit or a type of customer commitment, and that boundary is permission you can use the next day.
How do you want to hear that something is going wrong?
Why ask it
Better settled before you need it. Some leaders want a rough early signal in a message and others want the problem diagnosed with an option attached, and guessing wrong costs you the first time it matters.
What does someone have to demonstrate to be trusted with more here?
Why ask it
The word 'demonstrate' asks for something that was seen, not a quality. If you get 'impact' or 'ownership', ask about the last person who was given more and what they had done by then.
What should someone at my level be learning now to be useful to this strategy in three years?
Why ask it
A career question in strategic clothing, and a fair one. Check the reply against what they said about where the investment is going; if the two do not match, trust the money.
When did you start thinking about the whole business and not only your own function?
Why ask it
Most executives can date the shift: a general management job, a turnaround, a boss who made them present to the board. It gives you a picture of the experience to go looking for.
What could I do that would make your job easier?
Why ask it
What they ask for is often smaller than you expect: a clearer weekly number, an earlier warning, one meeting fewer. Do it within the month, since visible follow-through is what earns the next conversation.
What should I come back and ask you about in six months?
Why ask it
It sets up a second conversation and makes them name what they expect to have moved by then. Put the date in your own calendar and open that meeting with their answer.
How to use these questions
Practical guidance for the conversation itself
Choosing from 53 questions
A skip-level or a mentoring half hour
Open with one question from Direction, usually the one about what has changed since the strategy was last presented, then go where your own work sits: Resources if you are about to propose something, Execution if you are delivering part of the plan. Keep the last five minutes for Your part, because that group turns the conversation into something you can act on.
Five minutes after a town hall
One question, and it should build on what was just said from the stage. The one about what the company is choosing not to do and the one about the assumption that worries them most can both be asked in a sentence and answered standing up. Leave budget, headcount and anything from Decisions for a room with a door.
Interviewing an executive for a strategic management course
If you need sample strategic management questions to ask an executive for an assignment, the groups sit close enough to a course outline to use as a spine: Direction for intent and choices, Market for the competitive position, Resources for allocation, Execution for measurement and control, Decisions for governance. Change 'we' and 'our' to 'you' and 'your company', take two from each group, and ask the executive beforehand what can be quoted and what is confidential.
When the subject is corporate strategy and not one business unit
Corporate strategy is the question of which businesses the company should be in and what the center adds to them, a level above how one product competes. The questions about the bet at the center, what each business gets from being part of the company, building versus buying, the business line that would not be started today and where the next round of investment goes are aimed at that level. Put them to someone who sits in those discussions; a divisional leader may only be able to tell you how the decisions arrived.
Getting and using the time
Ask for twenty-five minutes and name the decision you want explained
A request to understand how one specific decision was made is easier to say yes to than a request to pick someone's brain, and it means you both arrive knowing what the conversation is for.
Bring three questions and abandon two
One question answered properly, with two follow-ups, beats six answered at surface level. Choose the one whose answer would change what you do on Monday.
Say what you are seeing from your level
Senior leaders are short of unfiltered detail. Offering one concrete observation before you ask makes the exchange mutual and generally gets you a fuller answer.
What the answers tend to tell you
- A named assumption or risk means the plan has been examined. A confident answer with no caveats means you are hearing the external version.
- If a leader can tell you exactly what was dropped this year, the strategy has real constraints behind it.
- Answers about decisions that mention specific people usually reflect how things actually get approved here.
- Any hesitation on budget and headcount tells you where the ceiling is more accurately than the plan does.
- If they cannot name a recent failure, do not expect your own setbacks to be discussed openly either.
Common pitfalls
Using the meeting to lobby
Arriving with a proposal turns a rare conversation into a pitch that a senior leader will politely route back to your manager. Ask about the criteria instead and use them later.
Asking questions that have public answers
Anything in the last all-hands deck wastes the slot. Ask about what has changed since it was written.
Going around your manager
Skip-levels create problems when the manager finds out afterwards. Mention it beforehand and share anything useful that came out of it.
Treating candor as an invitation to complain
If a leader names a weakness in the organization, adding a list of grievances closes the conversation. Ask what would have to change and who would need to agree.