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Healthy Habits for High-Performing Leaders: Ask Great Questions

You don’t have to work for the CIA to know that effective questioning is more than just a skill—it’s a fundamental competency influencing various aspects of an organization. Asking good questions is important when you need to solve a problem, when you are dealing with a challenging situation, or when you are coaching someone and want them to think about coming up with the answer.

Many of us, myself included, fall into the trap of addressing problems by providing answers due to our familiarity with the solution or the efficiency of resolving it independently. While there are instances where this approach is necessary, in most cases, it deprives others of the opportunity to learn through trial and error or problem-solving.

Robert Anthony, American organizational theorist and professor of management control at Harvard Business School, is credited with saying, “If you do something for someone, they will let you.”

Consequently, people become reliant on you as the go-to problem solver.

Why don’t business leaders ask good questions? It’s your parents’ fault.

business leaders ask good questions

“Dad, will you change my tire for me?” Most of us grew up with parents used to simply answering the question. Parents are used to taking care of children. Eventually, your kids grow up, so the answers (and the questions) may become more complex. But if you think about it, instead of saying, “Of course, I’ll take care of that for you,” what if you asked them, “What if we do this together so you will know how to do this next time?” or even “What do you think needs to be done to get that tire changed?”

It’s not really your parent’s fault (even if your therapist tells you differently).

Applying this perspective to a business context unveils similarities. The root cause could lie in the ingrained habits from upbringing or in a fixed mindset that prioritizes personal ideas over the ideas of others. Additionally, organizational cultures that discourage questioning may exacerbate the issue. Time constraints also play a role; leaders are inundated with questions, prompting an instinctive response rather than inquiry. Asking questions only sometimes comes naturally to leaders, who more often default to giving directives instead.

While executive coaches, therapists, and select professionals are trained in effective questioning, others rarely receive such training or may even be discouraged from asking questions altogether. An organization’s cultural norms may further compound the issue, where questioning is not tolerated. Furthermore, leaders may feel compelled to have all the answers, underestimating the potential contributions of their team members.

We talk more about asking effective questions in a previous blog entitled “Four Reasons Great Leaders Ask More Questions,” which may provide further insight into how you can become a better coach and listener.

Asking questions costs you nothing

Encouraging leaders to ask questions fosters collaboration, critical thinking, and ownership among team members, leading to more innovative solutions, better decision-making, and a more inclusive and adaptive organizational culture.

Effective questions are asked with a sense of sincere curiosity. They get people to think and are powerful because they ask the person to engage their brain. Telling doesn’t require people to think.

Great leaders are not authorities; they are adept listeners, mentors, and educators for those who will follow in their footsteps. Their leadership isn’t just about making decisions; it’s about fostering growth in others. They understand that true leadership involves imparting knowledge, offering guidance and creating an environment that empowers others to succeed and future leaders can flourish. By actively listening and posing insightful questions, they guide their team members toward finding their own solutions and honing their skills.

When leaders ask effective questions, productivity, trust, profitability, creativity, and problem-solving skills are enhanced. 

Organizations invest millions or billions annually in activities such as pizza parties or paintball games to boost engagement. While these activities offer benefits, they do not fully address the outcomes companies desire. Effective questioning, however, helps individuals feel heard and can contribute significantly to enhancing overall results.

In my experience, very few leaders ask questions effectively. They do more telling than asking. And if they do ask, they don’t do so effectively.

All questions are not created equal, and here’s why.

When leaders ask questions, how they do so can inadvertently strain rather than strengthen relationships. This may occur unintentionally, driven by a belief that such questioning is the norm. Examples include asking pointed or “gotcha” questions designed to undermine individuals, queries aimed at testing someone’s knowledge when the leader already knows the answer, or veiled suggestions presented as questions. Questions laden with judgment, often beginning with “why,” also contribute to this dynamic. Ineffective questions tend to be closed-ended, eliciting only yes or no responses or one-word responses such as asking, “What color is the sky?”

asking questions

Conversely, effective questions are characterized by genuine curiosity, prompting individuals to engage in deeper thought. Their power lies in stimulating the brain and encouraging critical thinking. Unlike yes-no questions, effective inquiries allow leaders to test hypotheses and challenge assumptions, preventing misguided actions based on unfounded beliefs. For instance, if an employee’s performance declines, one might assume they are disengaged or seeking alternative employment. However, by refraining from jumping to conclusions and instead asking questions, leaders can uncover underlying factors such as personal challenges or family issues that may impact the situation. This approach fosters a more understanding and supportive environment, promoting trust and collaboration within the team.

Effective questions are follow-up questions. This requires listening. It makes people feel heard. They uncover assumptions and beliefs. Underlying assumptions and beliefs uncover the perceptions that can help change behavior. They are open-ended questions and generally start with what and how. Turn why questions into what questions, ie, “Why did you make that decision?” Change it to “What thought process did you go through to make that decision?”

How to develop the habit of asking effective questions

For the next week, observe your communication patterns with your team. Embrace moments of silence and practice active listening, focusing not on your response but on truly understanding the person’s perspective. 

What is your ask-to-tell ratio?

Take note of how often you’re asking questions versus simply providing instructions. 

Pay attention to the type of questions you’re asking—are they open-ended or closed? Do they begin with ”what” and “how” or “why”? Cultivate a sense of curiosity in your questioning approach.

Over the following few weeks, when someone asks you a question, resist the urge to respond with an answer immediately. Instead, consider if posing a question in return is more effective. While the natural inclination may be to provide solutions as a leader, embracing the power of questions can lead to more insightful conversations.

Encouraging questions among team members fosters a sense of engagement, empowerment, and value, ultimately resulting in enhanced productivity and superior outcomes.

A great resource that dives deeper into the subject is a book by Michael J. Marquardt and Bob Tiede, authors of Leading With Questions: How Leaders Discover Powerful Answers by Knowing How and What to Ask.

We also offer a complimentary e-book titled “Leader Language,” which delves deeper into the art of asking impactful questions. I invite you to explore this resource to gain further insights into various leadership strategies, including the potency of effective questioning, and to discover practical techniques for seamlessly integrating them into your everyday communication. Download “Leader Language” here.

Next Steps in Becoming a Better Leader

For those seeking a comprehensive and rigorous program for themselves or their team, we encourage you to  contact us regarding our tailored leadership development program. This program encompasses hands-on practice, role-playing, insightful discussions, peer learning, and engaging activities focused on the art of asking impactful questions.

Additionally, it features a dedicated section on coaching for managers, providing guidance on navigating challenging conversations, managing conflicts, and delivering constructive yet candid feedback.

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