Peter Drucker and the Art of Strategic Questioning

In today’s environment of ultra-uncertainty, it's tempting for managers and leaders to reach for elusive easy answers. Instead, it would be wise to first turn to one of Peter Drucker’s most trusted tactics, regularly searching for and asking strategic questions.

Drucker is justly famous for his ‘five most important questions,’ codified and extended in his bestselling book with Frances Hesselbein and Joan Snyder Kuhl, Peter Drucker’s Five Most Important Questions: Enduring Wisdom for Today’s Leaders.

It pays to think deeply about his questions, and to begin to formulate answers specific to your professional role, as well as to the organization you serve:

  1. What is our mission?
  2. Who is our customer?
  3. What does the customer value?
  4. What are our results?
  5. What is our plan?

When the most recent edition of this book was published in 2015, I interviewed Frances Hesselbein, whom I have the honor of working with in my role as managing editor of the quarterly journal, Leader to Leader, where Frances is editor-in-chief.

“Leadership is a journey–not a destination,” Frances said. “The power of the old hierarchy is gone. Instead the leader of the future understands:

  • The power of language
  • The power of example
  • The power of persuasion
  • The power of dispersed leadership
  • The power of circular management
  • The power of a mission focused, values-based, demographic-driven organization.”

Questioning was a major part of Drucker’s approach as a consultant, and he also practiced self-questioning in his own multifaceted career as a consultant, writer and professor. He advocated that people regularly ask questions of themselves that drilled down to the core of their being, as a person and as a professional.

For instance, consider the questions he explored in a fascinating 1966 essay, “The Romantic Generation,” in Harper’s Magazine. (The article was later included in the 1971 collection Men, Ideas & Politics, a book that Harvard Business Review Press is reissuing under the title Business and Society.)

He wondered how, in a “society of big organizations,” an individual could “maintain his integrity and privacy,” certainly a valid concern more than 50 years later, though perhaps for somewhat different circumstances in today’s hyper-connected society. Those questions were, “In such a society of big organizations, the need becomes more urgent for new answers to the old questions, Who am I? What am I? What should I be?”

Drucker explored similar themes in his classic 1969 book The Age of Discontinuity. He pointed out that people should think beyond a career to “a demand that the individual take responsibility for society and its institutions.” The questions now became: “The society of organizations forces the individual to ask of himself: “Who am I?” “What do I want to be?” “What do I want to put into life and what do I want to get out of it?”

Sometimes Drucker recommended purely operational questions, such as this string on productivity: "What is the task? What are we trying to accomplish? Why do it at all?"

And these, related to his concept of systematic abandonment: “Which of our present businesses should we abandon? Which should we play down? Which should we push and supply new resources to?”

Consider these prescient questions from 1992: “But the organization, too, has to become information-literate. It, too, needs to learn to ask, What information do we need in this company? When do we need it? In what form? And where do we get it?”

The art of questioning resonates in today’s business/organizational world through such powerful books as Hal Gregersen’s Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life; Warren Berger’s The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect and Lead; Alexandra Carter’s Ask for More: 10 Questions to Negotiate Anything; Frank Sesno’s Ask More: The Power of Questions to Open Doors, Uncover Solutions and Spark Change; Andrew Sobel and Jerold Panas’ Power Questions: Build Relationships, Win New Business and Influence Others; and Marilee Adams’ Change Your Questions, Change Your Life: 12 Powerful Tools for Leadership, Coaching and Life.

Returning to my interview with Frances Hesselbein, I remarked upon her mentioning of the importance of ‘commitment to the future,’ and asked if there was one Drucker question that was particularly future-oriented.

She replied, “Question 5 'What is our plan?' " is totally future-oriented. Peter taught us to consider what we’re going to do on Monday that is different from the past, and that if you don't conclude with a plan, “a good time was had by all, but that is all.”