10 Questions to Ask Your AI Advisory Board This Week
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?"
[Image suggestion: A founder at a whiteboard with a list of business questions — each one connected to a glowing advisory board interface that provides a researched, sourced answer. The questions feel real, not hypothetical. Warm, slightly editorial illustration.]
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.
Keep Reading:
- How to Cross-Reference Advice From Multiple Experts — getting synthesized perspectives on your questions
- How I Use Adviserry to Get Personalized Pricing Advice From Hormozi's Content — a real pricing question in action
- How to Set Up Your First Adviserry panel in 5 Minutes — start asking your board today
Image Prompts:
- A clean visual list of 10 question cards, each with a topic label (Pricing, Hiring, Churn, etc.) and a small icon — displayed as if they're physical cards or sticky notes on a board. Organized but not sterile. Warm, tactile-feeling illustration.
- A founder typing a specific business question into an AI advisory interface, with expert source icons visible in the sidebar and a thoughtful response beginning to appear. Real-feeling product illustration, modern and editorial.
