Why Asking the Right Questions is the Secret Weapon of Successful CEOs

October 19, 2024
Leadership Questions

The CEO of a large professional services firm called me the other day. Leadership challenges in economic uncertainty are on everyone’s minds. “I need to restructure my business,” he said. “I’m thinking of eliminating my acquisitions team.”

Like many of the CEOs I coach, he was anxious about the current economic uncertainty and had a hard time thinking beyond the pressing question of the moment: “How do I cut costs?” This is a key consideration in cost reduction strategies for leaders.

The complexity of today’s environment is clearly overwhelming many leaders who haven’t adjusted to strategic leadership in uncertain times. Instead, they’re habituated to asking the same types of questions over and over again—’since revenues are dropping, how do we reduce unnecessary costs?’—and they find it difficult to reframe the present situation through a new lens.

As I probed deeper into my client’s context, I asked, “What’s another way to do acquisitions given the current environment?”

He paused for a moment and then said, “Oh, we could buy at the bottom—we can take over debt from people who don’t want to keep working for another ten years.”

And just like that, the direction of our conversation shifted, and my client began excitedly discussing new possibilities. The right question made all the difference.

How do we look at a situation from a new perspective and ask different questions? It doesn’t come naturally to most of us. Even outside of crises, most people only ask about 25% of the questions available to them—we get lodged in a particular mental mold. But before we discuss how to break out of that mold and tap into the 75% of questions we aren’t asking, let’s first start with the basics: As a leader, are you sure you’re asking enough questions in the first place?

Why Great Leaders Ask More Questions Than They Answer

The paradox of leadership is that the reasons why people get promoted into leadership roles are different from the reasons that they succeed as leaders. People get promoted for having good answers. But once they take the helm, what distinguishes good from bad leaders is not whether they have the answers, but how often they ask questions. In fact, I would go so far as to say that there is never a situation in which leaders shouldn’t ask questions.

Ineffective leaders assume they know the answers. They bulldoze their plans through, and others, who weren’t consulted, wind up resisting them—no surprise there. Successful leaders spend 70 to 80 percent of their time asking questions, not answering them. This approach fosters engagement strategies for leaders and cultivates widespread accountability.

This was my conclusion after I conducted around 170 formal and informal interviews with world-renowned leaders—from Walter Isaacson, the former head of CNN, to four-star U.S. General Jack Chain, who was responsible for the country’s nuclear arsenals, to Jack Welch, former CEO of G.E. When Chain’s 10-year-old daughter asked him what he did when he served as a staff officer in the Pentagon, he said, “I answer questions.” When, after he was made commander, she asked how his new role would be different, he responded, “Now I ask the questions.”

And although Welch has been tagged as a “hard-nosed” leader, those close to him speak of Welch’s “insatiable curiosity” and his trademark of asking more questions than anyone else in the room.

Good leaders are able to relinquish their egos and give others the chance to flourish—that was the premise of my book, Just Ask Leadership, in 2015. Since then, I’ve expanded upon that conclusion. Yes, what distinguishes bad leaders from good ones is how frequently they ask questions, but what distinguishes good leaders from truly great ones is the ability to ask different types of questions and to help others do so as well.

Types of Questions Great Leaders Ask

If you’re hoping for a formula that spells out, ‘All great leaders ask this question…’—you might be a bit disappointed with this article. It’s far more effective for you to reflect on the kinds of questions you’re prone to asking and why that is the case. Effective leadership questions can make all the difference.

In working with others, do you tend to…

  • Try new ways of taking action immediately and ask, “Where should we go from here? How can we do it better?” (Innovator)
  • Assess alternative methods of taking action, such as, “Will this help us reach our goal? What will we measure?” (Director)
  • Gather information to evaluate a situation, such as, “Is this in alignment with our values, strategy, and goals?” (Judge)
  • Explore new ideas to frame a situation, such as, “What should be our goal? How else could we think about this?” (Professor)
Leadership Questions

Each of these leadership styles can be mapped onto two axes—Perspective to Evaluative, and Knowledge to Action—which stems from a leadership model that my company, CO2 Coaching, built and tested among a few hundred organizational leaders and HR professionals to ensure it was psychographically valid. We did this because we know that leadership questions are the answer. We call this model PEAK Leadership.

There is no single style of leading that is best, although some styles are more suited to certain situations than others (e.g., in building strategy, the “professor” style works well; in motivating people to action, the “innovator” style is effective). The key is to expand your and your team’s repertoire in order to tap into the questions from each style so you’re not locked into one or two styles.

Let’s say you’re facing a big decision or challenge. To ensure you’re covering your bases, try going in a ‘Z’ pattern across the grid:

  • Start by asking Professor-style questions (‘Who else do we need to talk to?’) in the top-left quadrant to broaden thinking and get divergent opinions to form a perspective.
  • Once you have an informed perspective, move across to the top-right quadrant, Innovator (‘What’s stopping us from taking action, and how can we overcome that?’), to translate ideas into actionable steps.
  • Before you get going, cross diagonally toward Judge to carefully evaluate and refine the plan (‘What is the best option out of everything?’).
  • Finally, move into action by thinking as a Director (‘Whose decision is it?’).

This decision-making framework for leaders helps ensure you are not locked into just one style of leadership.

The client I mentioned at the beginning of this article was trapped in Director (Evaluate + Action) mode, evaluating options to take action by cutting costs. Only when his mindset shifted to Professor (Perspective + Knowledge) and he took a moment to broaden his horizons to get divergent views—”Given the changing environment, is there a different way of doing acquisitions?”—did he start to see the opportunity in this challenge.

Questions Leaders Should Ask to Overcome Challenges

If you find your team or yourself bogged down in a discussion over a decision, here are three questions to ask to get unstuck:

1. Are all our “different” questions… essentially the same?

Questions that sound stylistically dissimilar can, at their core, be the same type of question.

Towards the end of a multi-day strategic planning session for our leadership team last year, our facilitator asked, “Can we really do all of this?” The question was well-taken, as people had voiced feeling overwhelmed by the plans. Still, people were reluctant to jettison any of the ideas they had laboriously crafted over the past few days. The facilitator interjected again at a later point, “Isn’t this a lot? How can we accomplish this?”

People tried to answer the question, but soon the conversation drifted back. The energy in the room started to feel sluggish and heavy. I sensed what our facilitator was trying to do, so I offered my question, “What is the biggest challenge we will face in getting this done?” That didn’t move the conversation either. The real breakthrough occurred when someone asked, “How would things change if this was a two-year and not a one-year plan?”

The question sliced through the building tension like a hot knife through butter. Everyone exhaled, and we decided to recalibrate the plan for an expanded timeline.

Although the facilitator and I thought we were asking different questions, we were ultimately asking questions from the same quadrant: Judge (Evaluate + Knowledge). We were evaluating “how labor-intensive” or “how difficult” our strategy was. It was only when we shifted the parameters of our discussion to view our plans in an alternative lens (Innovator) that we were able to finally dissolve the tension in the room.

2. What types of questions are not being asked in this conversation?

Draw the axes and quadrants.

I draw out the quadrants for myself all the time. When I’m pondering a decision with a team or by myself, I take out a notepad, sketch the four quadrants, and ask, “Where would the questions we are asking fall in this map? What quadrants are we missing?” Seeing the graph forces me to think through, “What would this style ask in this scenario? How about that style?” and helps me realize what angles have been missing.

This approach paid off for a leader at a software consulting company. She was working with a junior teammate on a months-long project, for whom she was responsible for developing and improving how he showed up in calls with stakeholders. But no matter how many times she tried to get him to see that he came off as over-confident and needed to ask more questions, his behavior indicated that she wasn’t getting through to him.

After going through a role-playing exercise with other leaders in which she had to ask questions from all four quadrants, she reflected to the larger group her realization that she was only asking this teammate questions from the Judge style (“How did you think you did on that call? Did your approach work?”).

“If I’m really going to serve this person as a leader, I need to ask questions that will expand his perspective, not shrink it,” she said.

The easiest way to switch up one’s dominant style is to move diagonally to the opposite quadrant, which meant, for her, moving to the Innovator style—which is about exploring divergent ways of acting—and asking her teammate, “What could you do differently to try something new out? What would you need to change to become wildly successful at this?” If she wanted to take it a step further, she could even ask him directly, “It’s clear my feedback isn’t coming through. What do I need to do differently to help you?”

What was at stake in her shift was not just changing up some questions, but fundamentally shifting how she understood leadership: from evaluating performance as a judge, to helping someone look for new opportunities to grow and innovate.

3. Do the people in my team each have unique dominant styles?

Yes, you can train yourself to expand your repertoire for questions, but the fastest way to work past your blind spots is to collaborate with someone who has a different set of blind spots.

If you know you’re dominant in a particular style or two, surround yourself with people who do not share your dominant style and who will ask questions that don’t come naturally to you. If you’re in a leadership position, then know that it’s one thing to assemble a team with diverse styles, and another thing altogether to create a safe psychological space for people to voice alternative questions.

People may not feel comfortable “derailing” the conversation onto a different set of tracks than the ones you’ve laid, which is why it is incumbent upon the leader to proactively encourage people to do so. Be explicit and ask: “What is a different question we could be asking? What am I missing?”

Ultimately, the point of asking different types of questions is not just to make better decisions, but to facilitate leadership growth by empowering teams to make decisions. The only person truly qualified to make a decision is the person who lives in the situation every day, not the person with the biggest title in the room.

So what can leaders do to help others make decisions? Encourage different types of questions—not as a fanciful Socratic exercise, but as a way to help people get ‘unblocked’ and see a situation from a new perspective. Shrinking your ego and conferring power to your employees through asking different types of questions is truly what distinguishes great leaders from the rest.

At CO2 Coaching, we specialize in helping leaders unlock the questions that drive transformation. Our approach isn’t one-size-fits-all; it’s built on a deep understanding of your unique challenges. Let us help you—and your team—reach your next peak.

Are you ready to elevate your leadership? Schedule a complimentary consultation today, and let’s explore the questions that will unlock your organization’s full potential.

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