Get strategic challenge from board papers

The problem

You've written board papers for an important decision but you're stuck in the details. You can't see the forest for the trees. What questions aren't you asking? What perspectives are missing? What assumptions have you baked in? You need someone to challenge your thinking, but you wrote the paper so you can't see your own blind spots.

The solution

Use Claude or ChatGPT to act as a critical board member who asks awkward questions. Feed it your board paper and ask: what questions should we be asking that we're not? What perspectives are absent? What are the counter-arguments? What assumptions are we making? What could go wrong that we haven't considered? The AI spots gaps in your thinking that you're too close to notice.

What you get

A list of challenging questions your board should consider: questions you haven't addressed, perspectives that are missing (service users, staff, funders), assumptions you've made without realizing, risks you've understated, alternative approaches not considered, and metrics you're not measuring. You strengthen your paper by addressing these gaps.

Before you start

• A draft board paper or strategic proposal
• Willingness to have your logic challenged
• A Claude or ChatGPT account (paid tier recommended for longer documents)
• Openness to considering perspectives you hadn't thought about
• IMPORTANT: Board papers often contain highly sensitive data (salaries, legal disputes, serious incident reports). Redact specific names, financial figures, and identifiable details before pasting into AI tools

When to use this

• You're making a significant strategic decision and need challenge
• Your board tends to agree with management too readily
• You're too close to the issue to see alternative viewpoints
• You want to stress-test your thinking before presenting to trustees

When not to use this

• You haven't thought through the basics yet - do that first
• You're not willing to genuinely reconsider your approach
• The decision is already made and you're just seeking validation
• The paper contains highly sensitive strategic information you can't share externally (consider paid AI tiers with data protection rather than free tiers)

Steps

1. 1

   Write your board paper first

   Don't use AI to write your board paper. You know the context, the history, the stakes. Write it yourself. Get it to the point where you think it's solid and you're ready to present. That's when you need strategic challenge.

2. 2

   Ask for missing questions

   Paste your paper into Claude or ChatGPT. Ask: 'Act as a challenging board member. What important questions does this paper not address? What would a sceptical trustee ask that I haven't answered? Be specific about gaps in my analysis.' The AI will spot questions you've assumed away.

3. 3

   Identify absent perspectives

   Ask: 'Whose perspectives are missing from this analysis? Have I considered: service user impact, staff workload and morale, funder expectations, community reaction, volunteer implications, partner organisations, Trustees and their legal duties? Am I considering compliance with our charitable objects and Charity Commission guidance? Which stakeholders aren't represented in my thinking?' You can't see all angles alone.

4. 4

   Challenge your assumptions

   Ask: 'What assumptions am I making without stating them? What am I treating as given that might not be true? Where am I being optimistic about timelines, costs, or outcomes? What could go wrong that I've understated or ignored?' Assumptions are dangerous because they're invisible to you.

5. 5

   Get counter-arguments

   Ask: 'Make the strongest case against this proposal. What are the reasons we shouldn't do this? What are the risks I'm downplaying? What alternatives might be better?' A good board needs to hear the case against, not just the case for.

6. 6

   Question your metrics

   Ask: 'What am I not measuring? What outcomes matter that I haven't included? What unintended consequences might this have that I should track? Are my success metrics comprehensive or are they just the easy things to measure?' What gets measured gets done - but what matters that you're not measuring?

7. 7

   Identify decision criteria gaps

   Ask: 'What criteria should inform this decision that I haven't explicitly considered? Am I balancing short-term vs long-term impact? Mission vs financial sustainability? Service quality vs reach? What trade-offs am I not acknowledging?' Strategic decisions involve trade-offs you need to make explicit.

8. 8

   Strengthen your paper

   Now revise your board paper. Address the valid challenges, acknowledge the absent perspectives, state your assumptions, present counter-arguments fairly, add missing metrics. Your paper should be stronger and your board discussion more robust. You're not changing your recommendation based on AI, you're improving your thinking.

Tools

Resources