How Can Asking Better Questions Change the Trajectory of My Business

Every business owner knows the feeling of standing at a crossroads, wondering which path leads to success and which to failure. 

What if the key to choosing the right path was as simple as asking the right questions? 

Keith Cunningham’s "The Road Less Stupid" illuminates the transformative power of questioning in navigating the business landscape. 

Through insightful reflections and practical advice, Cunningham demonstrates how strategic inquiries can steer businesses towards unprecedented growth and away from costly mistakes. 

Let’s explore how cultivating a practice of asking better questions can fundamentally alter the trajectory of your business, drawing directly from Cunningham’s profound wisdom.

This article is based on our highlights from the book,The Road Less Stupid by Keith Cunningham. Check out the overview here >>

The Catalyst of Inquiry

The Foundation of Better Questions

Asking the right questions acts as a catalyst for business innovation and problem-solving. 

Cunningham emphasizes that "Thinking Time," dedicated to formulating high-value questions, is crucial for uncovering actionable insights and strategies. 

This process begins with recognizing that many business challenges stem from asking inferior or incorrect questions, leading to tactical rather than strategic solutions.

Techniques for Crafting Powerful Questions

Crafting powerful questions involves focusing on clarity, solvability, and expanding possibilities. 

Cunningham suggests framing problems as “How might I…” questions to open up a broader range of solutions and perspectives. 

This approach encourages looking beyond symptoms to identify the core issues impacting your business’s growth and efficiency.

Transforming Business Through Strategic Inquiry

Identifying Core Obstacles

By asking targeted and strategic questions, leaders can identify the real obstacles blocking progress, distinguishing between symptoms and the actual problem. 

This differentiation is key to developing effective strategies and avoiding the waste of resources on solutions that fail to address the root issue.

Leveraging the Power of 3 Questions

Cunningham’s "Power of 3" questions serve as a litmus test for decision-making:

1. What is the upside? 

2. What is the downside? 

3. Can I live with the downside?

This framework ensures a balanced evaluation of potential actions, highlighting the importance of considering both positive and negative outcomes.

By embracing the practice of asking better questions, as Keith Cunningham outlines, businesses can unlock new avenues for growth, efficiency, and resilience. 

This approach not only changes the trajectory of your business but also embeds a high performance culture of strategic thinking and continuous improvement.