To Develop Critical Thinkers, Leaders Must Shift from Giving All the Answers to Asking Insightful Questions.

I vividly recall when a Vice President approached me for advice on improving her team’s critical thinking skills. With great urgency, she declared, “I need my team to think more critically! They have to get better at critical thinking!” The irony was clear: every time I observed her in team meetings, she dominated the conversation—doing most of the talking and telling, seldom inviting input or opinions. Her approach was to rush through decisions, issue directives, and then wonder why her team wasn’t generating ideas on their own.

The challenge for leaders like her is that they’re often rewarded for making quick decisions and executing efficiently. Involving the team and seeking their input on problem-solving takes time—a luxury many leaders feel they can’t afford. Additionally, there’s a common belief among leaders that decision-making is precisely what they’re paid to do. In reality, this leader had only herself to blame for not fostering critical thinking within her team.

The term "critical thinking" originates from ancient Greek philosophers like Socrates, Plato, and Aristotle. The Socratic Method, still widely used today, involves posing a series of questions to challenge assumptions and promote deeper thinking.

Leaders don’t need to be law professors or ancient philosophers to harness the power of effective questioning. The most successful leaders understand that handing out answers through directives alone deprives their teams of the opportunity to engage, analyze, and tap into their natural problem-solving abilities.

Below are some questioning techniques and tips designed to help your team develop independent thinking skills. They may seem straightforward but can be challenging to implement.

Emphasize “What” and “How” Questions—Reserve “Why” for Uncovering Root Causes: Although Simon Sinek’s book Start with Why and the “5 Whys” technique are influential, seasoned coaches recognize that “Why” questions can unintentionally put employees on the defensive. To encourage a more open and solution-oriented conversation, opt for “What” and “How” questions, which are more likely to prompt thoughtful and non-defensive responses. Use “Why” questions deliberately when you need to explore the underlying reasons behind an issue, focusing on root cause analysis.

Ask One Question at a Time (Avoid Stacking Questions): If you listen to a podcast or watch a television interview, you’ll often notice that interviewers can take a couple of minutes just to get a question out. Trust your initial question. When we stack questions—asking multiple ones in succession—we end up confusing the person we're speaking to. They’ll likely only respond to the last question they heard.

Foster Strategic Thinking by Asking Insightful Questions: How does this decision align with our long-term goals and objectives? What impact will it have on other areas of the business or team? If our initial solution doesn’t work, what’s our backup plan? What additional information do we need to fully understand the situation? What alternative approaches could we explore? Which aspect of this problem should we prioritize first? Which tasks will most significantly impact our goals? What feedback should we collect to refine our process?

Embrace Awkward Silence: In my experience with consulting leaders, I often advise them to “make friends with the crickets.” This means waiting at least 10-12 seconds before asking another question. We tend to feel uneasy with silence and rush to fill it with our own voice. But we don’t need to—the other person (or group) is simply processing the question. Allow them ample time to respond.

Trust Your Instincts and Seek Clarification: As a professional coach, I was trained to silently reflect on the underlying reasons behind a person's words by asking myself, “Why are they sharing this?” There's often more beneath the surface. When a team member expresses concerns like, “We can’t get help from that other department,” or “We have so many priorities we don’t know where to start,” it's crucial to explore further. Engage them by asking questions that encourage deeper reflection, such as: “What challenges are you encountering with that department?” “What is the real challenge?” “What would successful collaboration look like?” “Which priority do you believe is most critical?” or “How would you recognize if the priorities were clear?”

Closing Thoughts

Cultivating critical thinkers on your team doesn’t require a radical overhaul of your leadership style—it simply calls for a shift in approach. By asking insightful questions, embracing silence, and trusting your instincts, you empower your team to think more deeply and independently. Remember, the goal isn’t to provide all the answers, but to guide your team in discovering them on their own. When you create a culture of inquiry and reflection, you not only enhance critical thinking but also foster a more engaged and innovative team.

Start with these techniques, and watch as your team’s problem-solving abilities—and confidence—grow stronger with each conversation.

Ready to take your managers' coaching skills to the next level? Contact me today to schedule a customized workshop designed to equip your leaders with advanced coaching techniques that drive performance and engagement - linda@lindapandey.com or click on Book a Consultation below.