How Successful Leaders Ask Successful Questions

Technology leadership demands critical thinking above all, and the bedrock foundation of critical thought is a well-formed question. If you only add one skill to your leadership portfolio in 2021, make it the skill of strategic questioning.‍

Innovation Insights
 Min read
March 4, 2021

How Successful Leaders Ask Successful Questions


Socrates may not be a typical model for technology executives—after all, he drank hemlock to avoid being banished from the city he loved. But historians can draw a bright line from most of the educational and civic traditions we value to the questioning techniques Socrates used as he developed leaders and improved Athenian society. He got so good at pointing out fallacies and revealing truths that Socrates' nickname was "the gadfly," and he ultimately fell out of favor because the Athenian elites couldn't handle his queries.

Successful CXOs in 2021 probably don’t wear a chiton or wander through public forums. Still, we stand in the sandals of tradition every time we troubleshoot a network, debug a program or optimize our department's configuration. Technology leadership demands critical thinking above all, and the bedrock foundation of critical thought is a well-formed question. If you only add one skill to your leadership portfolio in 2021, make it the skill of strategic questioning.

Cue a Questioning Culture

Every culture has an unspoken "permission meter" that sets the acceptable level of challenge and innovation. Although it may not be explicit, it is always known and usually obeyed. In a top-down culture with insular leaders, questions flow one way only, and the expected response bounces back from a reliable cohort of "yes-men/women." That stereotype is the antithesis of a productive, questioning culture. At the other end of the spectrum is a culture where every topic is fodder for dialogue and debate. Creative professions and collaborative teams are highly tolerant of a high-question approach, but many industries require a calibrated balance of deference and challenge depending on the task. After crash investigators analyzed a series of international airliner disasters, they discovered that cockpit teams with high copilot deference were more likely to suffer avoidable accidents. The more critical the decision, the more important it is to cultivate open inquiry and welcome productive conflict.

Because hierarchical authority tends to inhibit the openness required for a questioning culture, senior leaders must overcompensate by inviting and modeling respectful questioning. In one organization celebrated as the top-performing health-care system in North America, senior leaders are required to delegate one colleague to play the designated "gadfly" for every major decision. They call that role "the opposer," and they depend on questions to identify gaps or surface defects in the consensus of the group. Leaders who follow that model's wisdom must reinforce colleagues—especially subordinates—when they ask strong questions or invite divergent perspectives. Normalizing a questioning culture through roles, routines, and reinforcement can transform a low-permission organization into a team model where questions lift performance and activate deep collaboration.

We previously discussed the importance of leading with a sense of humanity and humility. Embracing this mindset as a leader can help you normalize the acceptance of a questioning culture.

Innovate With Provocative, Creative Questions

Most leadership programs spend more time preparing executives to analyze and answer questions than they do teaching how to ask effective questions. One of the keys to crafting excellent questions is understanding the purpose and timing. Leaders who are managing early implementation or expanding their influence should focus on creative questions that provoke lateral thinking and divergent solutions. Often, imposing artificial constraints on established processes can serve that purpose well. Consider questions like:

➢ If we had to sustain productivity with one facility offline, could we pull that off?

➢ If ten years from now our top service line is a new business venture, what might that be?

➢ A competitor plans to cripple one part of our system. What will they choose and why?

➢ If you had to take over an existing division tomorrow, which one would you choose?

Questions that challenge assumptions or introduce new configurations can "loosen up" the dialogue and demonstrate value for alternative ideas. Leaders who employ creative questioning to stimulate thought and provoke innovation access the totality of their team's insights and gain a competitive advantage over more rigid and linear rivals.

Sequence with Tactical, Critical Questions

Identifying innovation opportunities and alternative approaches is necessary but not sufficient. An executive who employs Socratic questioning will follow up the creative phase with a sequence of purposeful, tactical queries. Leading with "why" will help the leaders and team articulate the purpose and probable deliverables of any new project. "Why?" isn't always the most important question, but it must come first. Asking why defines the launch point, and it also describes what success will look like. “Why” also sets priorities and justifies selecting one course of action over the alternatives.

Knowing "Why?" leads naturally into "How?" A growing enterprise that needs to secure customer orders might understand that the purpose is growing revenue, but there are many ways to accomplish that objective. Should you increase sales staff to cold call prospects? Would it be better to invest in marketing and sales assets? Perhaps a discount campaign or referral bonus would cultivate new clients. Even with a clear strategic purpose, determining tactical approaches requires ongoing, iterative inquiry and monitoring to improve effectiveness.

Often, the question of "How?" will push directly into "Who?" Selecting tactics to serve strategy means picking colleagues or contracting specialists who have the necessary skills. Even with identified skills and experience, the colleagues who implement a strategy need clarity about roles, authority, and reporting relationships. A leader who builds a pattern of dispassionate but purposeful critical questions will find themselves leading more thoughtful and purposeful teams.


We might think that Socrates would flounder if asked to lead a modern technology team, but we have more faith in him than that. He was adept at using the most powerful technology of his day—dialogue and analysis—to clarify issues and solve problems. Once he got over the jet lag of time travel, we’re convinced that Socrates' skill with questioning would serve him well, even in our most technical and complex environments. We can't drag him through the centuries, but we can draw on his approach and techniques to become the questioning leaders our organizations need.

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