Six Strategic Questions

Every Founder Should Ask

As founders, we’re often so immersed in the day-to-day grind that we forget to pause and reflect. But carving out time for strategic planning isn’t a luxury; it’s the secret weapon of successful businesses. Whether you’re sitting down for an annual operating plan or taking 15 minutes to sketch out next month’s goals, the questions you ask yourself can shape the trajectory of your business.

Here are six strategic questions every founder should ask—and revisit regularly:

1. Where Are We Headed?

Start with the basics. What’s your vision for the next 12 months? Outline specific goals for revenue, customer growth, and profitability. Use these targets as your North Star.

2. What Risks Are Looming?

Every business faces risks—from market shifts to new competitors. Take stock of what could derail your progress and create plans to mitigate those threats.

3. What Are Our Strengths and Weaknesses?

A SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) is a powerful tool. It provides clarity on where you shine and where you need to improve. Collaboration tools like Miro make it easy to involve your team in this process.

4. Do We Have the Right Team?

Whether it’s hiring a strategic partner or leveraging contract workers, your team is critical to your success. Ask yourself: Who’s missing from the table? How can I align my team with my goals?

5. What Opportunities Should We Explore?

Business moves fast, and opportunities can pass you by if you’re not looking. Consider diversification or experimentation—whether it’s launching a new product, entering a new market, or even exploring passive income streams like Airbnb investments.

6. How Strong Is Our Brand?

Your brand isn’t just a logo; it’s your reputation. Reflect on what your brand stands for, how well it’s recognized, and how you can amplify its presence in your market.

Making Time for Strategy

Strategic planning doesn’t have to be overwhelming. Start small. Dedicate an hour each month to reflect on these questions. Better yet, involve your team or a trusted advisor. Tools like annual operating plans or SWOT analyses can guide your efforts.

Remember, the best businesses don’t succeed by accident—they succeed because their founders take the time to ask the right questions. So, take a breath, carve out the time, and give your business the clarity it deserves.