Strategic Questions to Ask a Board of Directors
Questions for a chief executive, chair or executive taking a strategy session to the board, and for directors who want to raise the level of the discussion. They are written to get judgement out of the room rather than approval, and most of them work equally well asked of the board or by it.
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 we only get one thing right over the next three years, what is it?
A deliberately narrow opener that surfaces disagreement quickly. When directors give five different answers, you have learned that the board has never agreed the priority, only the plan document, and that is the session's real subject.
- 2
What business do you think we are actually in, and has that changed?
Boards often carry a definition from the era in which each member joined. Hearing them say it out loud exposes the gap between the company on the deck and the company in their heads.
- 3
Where are we strongest, and is that still true or is it something we used to be?
Advantages decay quietly while the language describing them persists. Ask for the current evidence, and treat any answer that rests on a customer story more than two years old as unverified.
- 4
What would a well funded competitor do to us first?
Directors will engage with this when they will not engage with a threat assessment, because it invites them to be the aggressor. The first thing they name is usually the weakness management has been managing rather than fixing.
- 5
Which of our assumptions would be most expensive to be wrong about?
This gets at model risk rather than list risk. Push for the assumptions buried in the plan, such as pricing holding, a channel staying available, or a key customer renewing, and ask what would tell us early.
- 6
What are we spending on because we always have?
Budgets accumulate history that no single review catches, since every line was justified once. Boards are better placed to ask this than management, because they carry less loyalty to individual programmes.
- 7
If we were founding this company today, what would we not build?
The answers name the products, offices and processes that survive on inertia. It is a softer route to the same place as a closure discussion, and people speak more freely on the way in.
- 8
Which customers do we not want, and are we still serving them?
Most organisations know their unprofitable or distracting segments and keep them for the revenue optics. Ask what it would cost to exit and what capacity it would free.
- 9
What do you see in the numbers that management does not present?
Directors read the pack differently and often notice something they assume is already known. Asking directly gets it into the room instead of into a side conversation after the meeting.
- 10
Are we resourced for the strategy we approved, or for the one we used to have?
Strategy changes at a board meeting and headcount, budget and incentives change over years, if at all. This question tends to produce the most actionable answer of any on the list.
- 11
What is the single point of failure in this organisation?
Expect answers about a person, a supplier, a system or a regulator. If everyone names the same one and nothing has been done about it, that is a governance finding rather than an operational one.
- 12
What happens if the chief executive leaves in ninety days?
Succession planning is routinely deferred because raising it feels like a vote of no confidence. Asking it as a scenario, ideally with the chief executive in the room, removes most of the awkwardness.
- 13
What capability will we need in two years that we have no pipeline for?
Hiring plans usually extend to the next twelve months and the next org chart. The two year horizon is where boards can add something management is too busy to think about.
- 14
Which risk on the register keeps you awake, and which ones are there for form?
Registers flatten everything to the same visual weight. Asking directors to rank by personal concern separates live risk from compliance decoration, and the two lists rarely match.
- 15
What would have to happen for us to walk away from this market?
Exit criteria set in advance are far cheaper than exit decisions made under pressure. If the board cannot state one, the company will keep funding the position until the funding runs out.
- 16
What would have to be true for us to double, and what would that cost?
Forces the growth conversation past ambition and into inputs: capital, people, capacity, time. A board that cannot describe the cost of its own growth target has approved a number rather than a plan.
- 17
Where is our capital earning the least, and why have we not moved it?
The second half is the question. There is usually a reason, and it is often a relationship, a legacy commitment or a fear of the write-down, none of which appear in the papers.
- 18
What is the board not asking management, and why not?
Ask it in the room and then wait through the silence. The unasked questions are typically about a founder, a large customer, a failing programme or a director's own area, and naming the reason matters as much as naming the question.
- 19
If someone acquired us tomorrow, what would they change in the first month?
An outside view that directors can give without criticising anyone directly. The changes they name are usually available to the company today, which is the uncomfortable and useful part.
- 20
Twelve months from now, what number tells us this strategy worked?
Close on a commitment. If the board cannot agree a small number of measures and a date, the strategy has been discussed rather than adopted, and the same conversation will recur next year.
Running a strategy session with the board
Practical guidance for the conversation itself.
Before the session
Before the session
- Send the material a week ahead, and send analysis rather than a recap of performance. Directors who read numbers for the first time in the room will spend the session asking about numbers.
- Tell the board what decision you want from them, and what you do not. Sessions drift when the purpose is left as a discussion.
- Send two or three questions in advance so directors can think. The best answers on this list are not first-draft answers.
- Ask the chair which topics have history. Every board has a subject that reliably consumes an hour, and you can plan for it or be surprised by it.
- Prepare the uncomfortable slide yourself. If the board finds the problem before management raises it, the rest of the session is about trust rather than strategy.
In the room
In the room
- Ask the least senior or newest director first on any question where you expect consensus. Anchoring happens within about ninety seconds.
- Ask for disagreement explicitly, by name, and give it a slot. Boards default to unanimity in the absence of an invitation not to.
- Separate the discussion of what is true from the discussion of what to do. Merging them turns a factual dispute into a factional one.
- Write down what was actually decided before anyone leaves, and read it back. Recollections of board decisions diverge within a fortnight.
- Give management a chance to answer without the chief executive speaking first, at least once per session.
After
After
- Circulate the decisions, the owners and the dates within a few days, separate from the formal minutes.
- Put the two or three questions that were left unresolved on the next agenda by name rather than letting them dissolve.
- Follow up individually with any director who went quiet. Silence in a board meeting is information and it is rarely agreement.
- Revisit the measures you agreed at the next full session, even briefly. A strategy nobody checks becomes a document.
- If the same question comes back a third time unresolved, treat that as the issue itself and give it a session of its own.