40 Questions You Can Ask at Your Board Meetings

Business owners who take advantage of the August Rule by hosting board meetings at their personal residences or vacation homes often ask us a common question: What needs to be discussed in these meetings?

Here’s the truth—board meetings don’t have to feel overwhelming.

To help you, here are 40 questions you can ask in your board meetings.

They are grouped into two categories: Tactical and Strategic.

Tactical questions focus on the next 6 - 12 months. They try to solve today’s problems.

Strategic questions focus on the next few years. They are looking into the future.

Tactical Questions

Operations & Finance

1. What metrics should I track monthly to make faster decisions?

2. How can we strengthen cash flow management in the next 6–12 months?

3. Are there inefficiencies in our current operations we can clean up now?

4. Where are we losing margin or leaving money on the table?

5. Which growth initiatives should we double down on this year?

Leadership & Team

1. Am I delegating effectively, or am I holding too much myself?

2. Do we have the right people in the right seats on the team today?

3. Where should I hire next, and where should I hold off?

4. What weaknesses in my leadership style are limiting day-to-day execution?

Sales & Customers

1. Are we targeting the right customers right now, or should we refine?

2. Are our current prices aligned with the value we deliver?

3. What would keep customers around longer this year (increase retention)?

4. What quick wins could improve the customer experience in the next 90 days?

Execution & Risk

1. Which projects or ideas should we kill so we can focus better?

2. Are there short-term risks (supply, compliance, cash flow) we need to get ahead of?

3. What’s the fastest path to hitting our revenue target this year?

4. What small operational tweaks would give us the biggest payoff?

Reflection

1. If you were me, what tough decision would you make right now?

2. What should I stop doing immediately that’s slowing us down?

3. What’s one tactical move I’m overlooking that could have outsized results?

Strategic Questions

Vision & Positioning

1. Are we clear enough on our long-term vision, or does it need refinement?

2. Where do you see the biggest growth opportunities in our industry over the next 3–5 years?

3. How well are we positioned against competitors—do we need to differentiate further?

4. What blind spots in our current business model could limit long-term success?

5. What external forces (technology, regulation, customer behavior) could disrupt us?

Financial Health & Structure

1. Are our margins sustainable compared to industry norms long-term?

2. Do we have the right balance of debt vs equity for resilience and growth?

3. What would make our business more attractive to a future acquirer or investor?

Leadership & People

1. Do we have the right leadership structure to support long-term growth?

2. How do I need to evolve as a leader for the business we’re building (not just today’s business)?

3. What talent gaps do you see that could hold us back?

Market & Customers

1. Are we pursuing the right customer segments for the future, or should we pivot?

2. How do you see customer expectations shifting in the next 3–5 years?

3. What would make our offering more indispensable (“sticky”) to customers long-term?

Growth & Risk

1. Which strategic initiatives should we prioritize in the next 3–5 years?

2. Are we spreading ourselves too thin across too many directions?

3. What’s the single biggest existential risk we face that we must prepare for?

4. If you were in my shoes, what bold move would you make today for the long term?

5. Are we building a company that could thrive without me?

Reflection

1. What’s one strategic question I haven’t asked but should?

Book Your Free Tax Advisory Call Today