The 5 Questions Every Founder Should Ask Before Writing a Strategy

Suze Dowling
The 5 Questions Every Founder Should Ask Before Writing a Strategy

There’s nothing more intimidating than staring at a blank page labeled “Strategy.” Do you write a 20-page plan? A few bullet points? Something visionary or something tactical?

Most founders overcomplicate strategy. The truth is, you don’t need to start with a masterpiece. You just need to start with the right questions.

The Core Five

Every effective strategy–whether for your business overall, a product launch, or a marketing campaign–should be guided by five simple questions:

1. What is our aspiration?
What's the long-term outcome you're working toward? This becomes your North Star.

2. Where will we play?
Who are you serving, what markets will you enter, and what will you not do? Focus beats expansion.

3. How will we win?
What makes your approach different? It's not enough to show up–you need to stand out.

4. What capabilities are required?
What resources, skills, or partners do you need to actually pull this off?

5. How will we sequence our efforts?
Strategy isn't about doing everything at once. What's the order of operations that will build momentum without overwhelming you?

Why This Matters for DTC Founders

When you’re in the $0–5M stage, you don’t have endless time, people, or capital. Answering these questions forces you to:

  • Prioritize what moves the needle.

  • Identify gaps before they become costly mistakes.

  • Build clarity that aligns your team and guide decisions.

A Common Mistake

Many founders confuse “strategy” with “goals.” Goals are what you want to achieve. Strategy is how you’re going to get there, and in what order. Without clarity on the “how,” goals are just wishful thinking.

Takeaway

You don’t need a 50-page strategy doc. You need thoughtful answers to five questions—and the discipline to revisit them as your business grows.

For the full playbook—including sub-questions, practical examples, and a framework to apply these questions across business, product, and marketing strategy—check out Strategy: The Complete Toolkit inside The DTC Operator.