Questions Directors Should Ask When Reviewing a Strategic Plan
When the board reviews a new strategic plan, there is often a mix of optimism and unease. The plan may look impressive, but soon someone is wondering “Are we sure this is actually the right strategy?”
That question, simple as it sounds, is where the director’s greatest contribution begins.
When The Board That Looked Past the Surface
A few years ago, a colleague on a large non-profit board told me a story about receiving a detailed plan promising to “modernize” the organization through a suite of new digital tools. It checked every box - forward-looking, innovative, measurable.
But when the board stepped back to ask a few simple questions - What’s driving this? What are we solving for? - they realized the underlying issue wasn’t digital tools at all.
The real problem was relevance: their core clients’ needs had shifted faster than the organization had evolved. The programs hadn’t evolved and they hadn’t been listening to their clients.
That short conversation changed the direction of the plan entirely. The strategy moved from “digital modernization” to “client reconnection”. This involved investing in feedback loops, partnerships, and thoughtful service design.
It wasn’t glamorous, but it was what the organization needed.
Role of the Board In Strategic Planning
Management often views the role of the board as endorsing or tweaking the strategic plan they developed. Directors sometimes see their role as adding their ideas to the mix. But effective directors know their role is to test its foundations.
Even when the board is involved in the strategy brainstorming stage, directors should step back afterwards and assume the testing role.
In my work with boards, I’ve found that the most valuable contribution directors make is better questions – curious questions that surface assumptions, expose gaps, and sharpen priorities.
The Five Prongs to a Strategic Plan – Director Questions
1. Diagnose the Challenges & Opportunities
Seek to identify: “Are we sure we’re solving the right problem?”
Boards add the most value here by testing management’s diagnosis and the depth of their insight.
Questions directors can ask:
Does the diagnosis consider both internal performance issues and external change pressures?
What important issues or opportunities might be missing from this diagnosis?
Do the challenges and opportunities identified feel like symptoms or root causes?
Is there evidence that stakeholder needs and expectations are clearly understood, or are they assumed?
This is where good directors gently slow the conversation down to consider, “What’s really going on underneath this?”
2. Make Choices on Direction
Seek to identify: “Have we made real choices, or just listed everything we could do?”
Strategic plans sometimes look like Thanksgiving dinner – multiple dishes of every category. The board’s role is to bring clarity and courage of strategic choices.
Questions directors can ask:
Do the strategic choices flow logically out of the problem / opportunity diagnosis?
Do the choices reflect the organization’s risk tolerance and capabilities?
Are the objectives bold enough to matter, yet realistic enough to deliver?
Is the strategy specific enough to visualize what success could look and feel like in three years?
Strong boards don’t let “strategy” blur into the regular operating plan.
3. Identify the Initiatives That Matter
Seek to identify: “Which of these actions will actually change our trajectory?”
Boards can help test whether initiatives align with the strategy - or whether they’re legacy projects carried forward by habit. If the list feels too long, it probably is.
Questions directors can ask:
Do the proposed initiatives clearly advance the strategic direction, or are some legacy or opportunistic add-ons?
Are there too many initiatives for the organization’s capacity?
Where the right solution is still uncertain, are “learning” or pilot initiatives included?
The best directors focus the organization on achieving the strategies through targeted initiatives.
4. Align Resources and Budget
Seek to identify: “Do we have the money and capacity to deliver on this strategy?”
A plan is only credible if it’s resourced. Directors should look for evidence that people and funds are part of the plan.
Questions directors can ask:
What will we need to stop funding and doing to make room for these new priorities?
Are the financial and human-capital assumptions credible and evidence-based?
Do we have the right leadership, expertise, systems, and culture to deliver the plan?
And when funding assumptions are optimistic, directors can steer the discussion toward realism: “If this revenue doesn’t materialize, which parts of the plan are still viable?”
5. Define Evidence and Metrics
Seek to identify: “How will we know if it’s working - and what will we learn along the way?”
Boards should push for metrics that measure real impact and test assumptions.
Questions directors can ask:
Do the metrics measure outcomes or merely effort?
Are metrics tied to organizational purpose and stakeholder value creation, not only efficiency or growth?
Do the metrics enable the board to see whether assumptions in the strategy are proving valid?
Are guardrails in place to prevent gaming or unintended consequences?
It’s not about micro-monitoring. It’s about ensuring the organization stays focused on its strategic objectives rather than the planned activities.
The Board’s True Value: Clarity and Courage
Strategic planning isn’t about predicting the future. It’s about being ready for it.
When boards engage strategically, they don’t just approve plans - they sharpen them. They ensure the organization is tackling the right problems, with the right focus, at the right pace.
So next time you’re handed a polished strategy deck, ask one value-adding clarifying question. You might just change the direction of the whole plan.