10 Questions to Ask Your AI Advisory Board This Week

Most people underuse advisory boards, AI or human, because they don't know what to ask. The default is either too general ("what should I be working on?") or too narrow ("give me a template for this thing"). The sweet spot is specific, strategic, and grounded in a real decision you're actually facing.

Here are 10 prompts worth using this week. Adapt them for your context.

1. Pricing

"My SaaS product has three tiers at $29, $79, and $199/month. My mid-tier has the highest churn. Based on what my expert sources say about pricing structure, what might be causing this and what would they recommend I test?"

This one is useful because pricing churn is almost always a positioning problem, not a price problem, but getting to that requires frameworks, not guesswork.

2. Hiring sequencing

"I'm at [ARR] with [team size]. I need to decide between hiring a sales rep or a growth marketer first. What have my board's sources said about early-stage GTM sequencing for a business like mine?"

3. Churn diagnosis

"My monthly churn is [X]%. Based on what my expert sources have written about churn root causes, what are the most likely explanations at my stage, and what should I investigate first?"

4. Market positioning

"I'm trying to decide whether to position [product] as an AI tool, a productivity tool, or a knowledge management tool. What have my sources said about positioning in crowded categories?"

5. Fundraising timing

"I'm considering raising a Seed round in the next 12 months. Based on what my board's sources say about fundraising timing and investor appetite right now, what should I be tracking before I go out?"

6. Content strategy

"What do my expert sources recommend for early-stage B2B content strategy when you have limited resources and need to prioritize?"

7. Customer discovery

"I have 50 customers and want to do a round of discovery interviews to understand my ICP better. What frameworks have my sources recommended for conducting useful customer discovery?"

8. Co-founder dynamics

"My co-founder and I are starting to diverge on product vision. What have my sources said about managing co-founder tension productively without letting it derail the company?"

9. Board/advisor relationships

"I'm about to bring on my first formal advisor. Based on what my expert sources recommend, how should I structure the relationship, the equity, and the expectations?"

10. The meta question

"Given everything you know about my business right now, what's the most important question I should be asking that I'm probably not asking?"

That last one usually surprises people. Ask it once a quarter. The answer changes as your business changes, and it's often uncomfortably good.

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