Ask ‘What,’ Not ‘How’

Engage in strategic thinking techniques at all levels of your organization.

By Jill Fowler, SPHR, and Jeanette Savage Aug 1, 2011
Reuse Permissions
April Cover

Thinking strategically is an elusive concept for many managers. Simply put, it is a high-level decision-making skill. It involves recognizing trends and challenging assumptions while maintaining a global view of situations and an affinity toward embracing change. It requires appreciating the organization’s or department’s current situation while looking for ways to capitalize on opportunities. Strategic thinkers ask what can and will be done to move forward, not how a project will be executed. “What” is strategic; “how” is tactical.


Whether you are working solo or as a member of a cross-functional workgroup, strategic thinking allows you to focus on what is truly important.

Organizations that systematically encourage strategic thinking are ready for the unexpected and have the ability to adapt more easily to unforeseen changes. At the managerial level, strategic thinking guarantees that focus and scope will become more targeted, allowing for more-purposeful activity. And, strategic thinking gives employees the ability to make decisions and understand how their decisions move the organization forward.

As a manager, strategic thinking will help you stand out to senior-level decision-makers and become more valuable. Your decisions and recommendations will be recognized and appreciated as the foundation for organizational efficiency. Strategic thinking also will help you make the most of your time at work.

Super Strategic Strength

Whether you’re an experienced strategic thinker or new to the idea, you must use the skill or risk losing it. The following are some exercises to assist in the development and maintenance of strategic thinking:

Think what, not how. If you find yourself thinking about how to accomplish a project, stop. Change your perspective and think about what must be done to meet your objective. Asking “how” or focusing on the minutia of basic needs and outputs is a tactical exercise. When a group devolves into how something will get done before thoroughly exploring what members want to accomplish, the discussion will lead to rehashing past history or worrying about potential obstacles, thus hindering strategic progress.

Ask the right questions. Generate strategic conversation by asking higher-level questions, such as “Where do we want to be in the next three years?” and “What must be done organizationally to accomplish this?” By focusing on the larger picture, group members’ thinking will automatically become more strategic.

Observe strategic thinkers, ideally in team environments. How do they approach challenges? What types of questions do they ask? How do group members respond? Once you have had the opportunity to observe a strategic thinker in action, emulate the behavior.

Learn from history. Examine a past situation where strategic thinking was required. Consider 10 ways it could have been approached differently and alternative outcomes that could have resulted. If you have difficulty coming up with 10 ways, ask what additional information is necessary, acquire this knowledge and start again. You will begin to think strategically and develop new, tangible ideas that may be put into action.

Look toward the future. Consider a future challenge where strategic thinking will be required. Repeat the exercises above.

Keep up with current trends.Subscribe to trade journals, join groups, attend conferences, or sign up to receive automatic e-mails on a topic. When you are informed about your external environment, you will be better-equipped to respond to your internal environment.

Become involved in planning activities. Join a strategic workgroup within your organization, serve as a board member in a nonprofit organization, or take on a leadership position in a professional association. By immersing yourself in situations that require strategic thinking, you are bound to develop these skills naturally.

Encourage Strategic Thinking

If members of your team or workgroup lack strategic thinking skills, it can be difficult to generate a strategic discussion or decision. It then becomes your duty to enhance their understanding of strategic thinking for everyone’s benefit. So how do you go about instilling these skills in others?

For a boss or management:

  • Ask leading questions to enhance the quality of decision-making.
  • When discussing a decision you have made, present the full scope of the process, including research methodology, background information, various alternatives, and desired and expected outcomes.
  • Model strategic thinking behavior.

For peers:

  • Increase knowledge by sharing relevant research findings and articles.
  • Ask leading questions to challenge conventional thinking, such as “Are there other options we haven’t considered?” or “What must we do to take this idea to the next level?” or “Why?”
  • Model strategic thinking behavior.

For staff:

  • Create opportunities for employees to become more involved in situations that require strategic thinking.
  • Make strategic thinking a valued part of departmental culture.
  • Measure strategic thinking behavior during the performance review process.
  • Model strategic thinking behavior.

By approaching situations in a strategic manner and inspiring others to do the same, you will create a culture of strategic thinkers, allowing you and your team to become critical players in the organization’s future success.

The authors are co-founders of Savage Fowler Consulting, a strategic planning consulting firm in Cleveland. They can be reached at

Reuse Permissions


The application deadline is November 11

Apply Today

Job Finder

Find an HR Job Near You


Find the Right Vendor for Your HR Needs

SHRM’s HR Vendor Directory contains over 3,200 companies

Search & Connect