Purpose and preparation

The Strategy Deep Dive is the second working session when a new Operator Board is established.

The purpose is to help the Operators understand the company’s strategic direction directly from the founder. Where the company is going, why that direction has been chosen, what assumptions it depends on, what trade-offs have been made, and which strategic questions are still open.

This is not a strategy workshop yet. It is not the moment for Operators to suggest a new strategy, challenge every assumption, or bring in their own playbooks. The first job is to understand the founder’s logic and the company’s current reality.

The session should be honest. Strategy is rarely perfect, especially in a scaling company. Some things are proven. Some are assumptions. Some choices have been made deliberately. Some are still open. Some constraints are real. The value of the session comes from making this clear.

Good strategic advice later depends on understanding the actual strategy first.

Before the session

The founder should share relevant strategic materials in advance. This can be existing material - there is no need to produce something new unless it makes the session better.

Relevant materials may include:

• Company deck

• Strategy memo

• Business plan

• Financial model

• Market overview

• Competitive landscape

• Customer segmentation

• Go-to-market plan

• Fundraising materials

• Board materials

• Key metrics or milestones

Operators should read through the material before the session and send their questions back to the founder in advance. This helps the founder prepare and keeps the discussion focused on what needs to be understood.

What to cover in the session

The founder should walk the Operators through the company’s strategy and cover the following points:

1. Company ambition
   What the company is trying to become, and what success looks like over time.

2. Current position
   Where the company stands today across product, market, customers, team, capital, traction, and competitive position.

3. Market and timing
   Which market the company is operating in, what is changing, why the opportunity matters, and why now is the right time.

4. Customer focus
   Which customer segments the company is prioritising, why they matter, and where the strongest demand is expected to come from.

5. Business model
   How the company creates value, captures value, prices its product or service, and expects the economics to develop.

6. Go-to-market direction
   How the company plans to reach customers, sell, scale commercially, use partners, enter markets, or expand geographically.

7. Competitive landscape
   The main alternatives, competitors, substitutes, and incumbents - and why the company believes it can win.

8. Strategic assumptions
   The most important assumptions behind the strategy, including demand, willingness to pay, adoption, scalability, differentiation, regulation, technology, capital needs, or market development.

9. Choices and trade-offs
   What the company has chosen to focus on, what has been deprioritised, and what strategic choices are still open.

10. Risks and constraints
    The biggest risks, bottlenecks, dependencies, and limitations that could affect execution.

11. Milestones
    The most important strategic priorities, milestones, and proof points for the next 6, 12, and 24 months.

12. Open questions
    The strategic questions the founder is currently working through.

Good Outcome

After the session, the Operators should understand the company’s strategy well enough to engage with it properly later.

They should understand the ambition, the logic, the assumptions, the trade-offs, and the real constraints. The goal is not to pressure-test or redesign the strategy in the session. The goal is to create a shared understanding of where the company is going, why, and what still needs to be figured out.