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  • Writer's pictureSimon Zryd

Mastering the Art of Questions for Small Business Owners

When it comes to navigating the challenges of a small business, the ability to ask the right questions is as crucial as finding the right answers. For small business owners or solo entrepreneurs, who often navigate their business journeys independently, developing a robust questioning strategy can be the key to unlocking innovation and making informed decisions. By shifting from a traditional leadership style that focuses on answers to one that values questions, solo entrepreneurs can gain deeper insights into their operations and market opportunities.

The Evolution of Leadership to Inquiry

Leadership styles have transformed significantly in recent decades, with a notable shift towards inquiry-based approaches. This change is not just relevant for organizations with large teams but is especially pertinent for small business owners. The benefits of this approach include fostering innovation, improving adaptability, and making more informed decisions—all critical elements for business owners facing the complexities of today's business environment.

Why Effective Questioning Matters

"Question-storming," or the practice of brainstorming through questions rather than answers, is becoming an essential technique in business. For entrepreneurs, who might not have formal training in strategic questioning, learning to craft and utilize effective questions is vital. These skills can help uncover hidden challenges and opportunities, ensuring that every business decision is well-informed and thoroughly considered.

Types of Questions for Strategic Insight

  • Investigative Questions: These help you understand the root causes of business issues. For instance, instead of merely identifying a decline in sales, ask, "What specific changes in the market or customer preferences have contributed to this decline?"

  • Speculative Questions: Encourage you to think broadly and creatively, such as, "What new markets or untapped demographics could I explore for expansion?"

  • Productive Questions: Focus on logistics and resources, like, "What steps must I take to scale my business, and do I have the necessary resources?"

  • Interpretive Questions: Help synthesize information and redefine problems or solutions, such as, "What does this data tell me about changing customer behaviors, and how can I adapt my marketing strategy accordingly?"

  • Subjective Questions: Address personal biases and emotional factors, important for understanding your own decision-making process, like, "What assumptions am I making about my customers or products that could be challenged or reassessed?"

Applying Questioning to Solo Ventures

For entrepreneurs, applying these types of questions can transform daily operations and strategic planning. Whether you’re considering a new service, facing a challenging client relationship, or planning your next big move, thoughtful questions can pave the way for success. For example, before launching a new product, a speculative question like “What if I targeted a different customer segment with this product?” could open up new avenues for revenue that you hadn’t considered.

Cultivating a Personal Culture of Inquiry

Developing a mindset that values continuous inquiry involves more than just asking questions; it involves reflecting on the answers and being ready to adapt based on new insights. Regularly schedule time to review your business operations through these lenses, perhaps through a monthly review where you ask and answer these critical types of questions about different aspects of your business.

Balancing and Enhancing Your Questioning Techniques

It’s easy to rely on the types of questions that have worked in the past, but a balanced questioning approach can expose you to new ideas and prevent oversight. To enhance your questioning skills, try to identify which types of questions you use least often and make a conscious effort to incorporate them into your strategic planning.


For business owners, mastering the art of questioning isn't just about problem-solving—it's about proactively shaping the future of your business. By embedding strategic questioning into your decision-making processes, you can enhance your business's adaptability, drive growth, and remain competitive in a dynamic market environment.

Call to Action

Reflect on your current questioning habits: Which types of questions do you often use, and which do you avoid? Try integrating a new type of question into your next business challenge and share your experiences. How did a different approach to questioning impact your business decision?

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