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Ask Questions That Enhance Strategic Thinking

Oct. 1, 2019
Asking challenging questions makes you more effective and more influential

The foundation of effective strategic thinking and strategy development is knowing how to ask the right questions. Learning to ask the right questions can be difficult because most people only know how to ask superficial questions that have easy answers. Asking challenging questions allows you to be more impactful in critical situations, have a greater influence on outcomes and help your organization achieve greater results.

The level of uncertainty in today’s business climate is driving major challenges for most leaders.

To be an effective leader, you have to understand fully the overall strategic goals of your enterprise and its leadership. Use these goals as the framework to align your thinking.

Understand the critical market forces impacting your business strategies so you can determine the questions to be answered. What critical market forces are at play in your industry? Are there forces evolving around you which have the potential to impact your survival or growth opportunities? Consider what it will take to grow revenue, expand profitability, improve job satisfaction, enhance productivity, or increase customer retention. How does each of these areas impact the questions you should to consider?  Structure your questions to challenge the critical issues impacting your ability to achieve these goals.

Three critical categories — There are three categories of questions to evaluate when you are focusing on your strategic thinking. These questions allow to you to scan the various elements impacting your enterprise. These include reviewing what is going on internally in your oranization, exploring external market forces creating new challenges or opportunities, and a review of your organizational relationships. Here are some samples of the types of questions you can consider for each level of your scan.
  Internal scan: Ask detailed questions about your customers and their evolving needs. What is the impact of your ownership, culture, stage of your business lifecycle? Where are the sources of your profitability and capital resources? What are your leadership capabilities? How deep is the expertise of your team? Make sure you fully undertand the key strategies of your organization and the opportunities you have to implement them.
•  External scan: Consider the impact of various market forces on your target market and opportunities. What is happening demographically? How is your competition influencing your target market’s expectations on services, costs, and quality? What generational influences impact your ability to compete for your customers? What are the risks of remaining status quo?
•  Relationship scan: Consider the status of the strategic relationships and partnerships you and your enterprise have developed. How do they impact your opportunties and create new challenges? Can you tap into other resources they offer or leverage them to achieve your goals? What are your internal relationships and how can you use them to impact success?

Constructing your questions — Focus your consideration of the questions on the key components impacting your enterprise growth or survival. Your questions should follow the who-what-where-when- why-how format. They should be action-oriented. As you answer them, they should provide clarity to your strategic direction and focus. This will provide guidance on areas needing more research.

Align your questions to answer critical business questions. Your questions should help you clarify the most critical priorities for your organization. These should be organized by level of importance: top, short-term, and on-going.

Also consider the time-horizon for the impact: short-term, mid-term or long-term. By understanding the time priorities, you can categorize your strategic questions to align them with the external market forces impacting your ability to achieve your goals. Aligning your questions with the external market forces provides you with a deeper level of critical thinking. As you elevate your critical thinking, you can begin to link your questions to impact your overall enterprise strategies.

Make sure your questions are challenging enough so they cannot be answered without some research or reflection. Questions that can be answered with a “yes” or “no” are not strategic questions. Ask provocative questions to encourage deeper thinking. This will bring higher-level thinking to your planning effort. If your team cannot ask tough enough questions, find an advisor who can provide insight.

Answers that improve insight — Often you will have to research before you can develop your questions. Think of this as “homework”: preparation ensures you will ask better questions. Look to your major industry associations as a starting source for insight about emerging issues and challenges. Study how your competitors tackle challenging market forces.

Consider your options for obtaining the information which will allow you to confidently address your questions. Outside resources can be an objective source of obtaining information. If you keep this research role internal, work carefully to minimize any bias you might inject into the research.

Identify the key metrics you should be monitoring by carefully analyzing industry data. Tie your questions to what improves or impacts each of these metrics. Your questions should consider what impacts your profit margin, return on capital employed, return on investment, and return on assets. If you don’t understand these terms, learn more about them.

You will never have all of the available data to answer all of your questions. The goal is to obtain enough to make reasonable judgments or to clarify the next layer of questions to ask.

Asking the questions that matter will build your confidence and others will be more confident in working with you. Learning to ask challenging questions allows you to be more impactful in critical situations, have an influence on outcomes, and help achieve greater results. Thinking strategically is a skill you must actively work at to improve. Find resources to help you learn and practice your critical thinking skills. Building your strategic mindset takes time, discipline, and focus.
Jill Johnson is the president and founder of Johnson Consulting services, a management consultant, and author of "Compounding Your Confidence.". Contact her at LinkedIn, or visit

About the Author

Jill Johnson | President

Jill J. Johnson is the President and Founder of Johnson Consulting Services, a management consultant, and author of “Compounding Your Confidence.”