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9 Powerful Questions to Ask CEOs

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Asking a tough question can be tough. What makes executive leaders? Insightful questions reach the core of a CEO’s values, discover their blind spots, and design strategies to transcend personal and business challenges. These questions as the beginning of a CEO’s journey toward stronger decision-making and more effective leadership development.

1. “Are you running your company or leading it?”

Ken can spot the CEOs who “run” their businesses — they are the ones racing from one tactical task to the next just to keep the company afloat.

“Leading is strategic,” says Ken. If CEOs are running their businesses, “they are forfeiting the opportunity to strategize about growth.”

Consider the example of a CEO who wants to grow revenue from $40 to $45 million. Ken wants the CEO to walk him through the steps it will take to get to the revenue target. The exercise will reveal if the CEO has spent adequate time developing an effective growth strategy.

2. “Are you doing more fire-fighting or fire prevention in your business?”

This question digs into whether or not process is on the CEO’s agenda. A CEO is a firefighter if she spends most of her day handling issues. This is a sign that the CEO needs to delegate process improvement to her direct reports.

Ken says one example of fire-fighting is if a business has had a vacancy in customer service for two weeks. If the CEO’s approach is to hire just anyone to fill the role, she’s fire-fighting. Fire prevention, he says, is when the CEO can say, “We have a hiring process, so we’re not going to shortcut.”

CEOs can move away from fire-fighting and into fire prevention by ensuring every department has clear, documented processes. “There’s a process to sell, a process to collect money, a process to send out invoices, even a process for how to onboard a new client,” says Ken.

3. “We don’t need to talk about the problem — we need to talk about why the problem hasn’t been solved yet. Why do you think it hasn’t?”

This question helps surface the reason why a CEO may be procrastinating about making a difficult decision.

“I’ve got a friend who calls it ‘the thing under the thing,’” says Wally, pointing out that it’s important to shift the focus away from the details of the issue and instead figure out why there is a lack of decisiveness around reaching a resolution.

CEOs who are part of Vistage peer advisory groups have the advantage of bringing a specific issue to the group so they can leverage the objective perspectives of their peers and Vistage Chair. “That’s where all these relationships really pay off,” Wally says.

4. “If you lump your employees into two categories, do you have more participants or contributors?”

Ken wants CEOs to think about the individuals who make up the company’s talent pool. Participants are those employees who show up to work and complete their function. Contributors are the employees who search for ways to add value to the company in addition to their typical responsibilities.

What is a tall-tale sign that a CEO employs mostly participants?

“At 4:59 p.m. the parking lot is empty,” says Ken. “You got a bunch of 4:50-niners. Those are participants.”

The next questions Ken wants the CEO to consider is, if the CEO is content with a company of participant employees, what does that say about him? What would be the value of moving participants to contributor status?

Whether an employee is a participant or a contributor has to do with both the individual’s choice and the company culture. CEOs have the responsibility to “set the expectation often and early of what a contributor looks like,” says Ken.

5. “Do you have any habits that hold you back from being the leader you’d like to be?”

“Habits multiplied by time end up being your outcomes,” says Wally, adding that habits “need to be scrutinized occasionally because they drive a lot of anticipated and unanticipated outcomes for leaders.”

Wally suggests a “habit audit” as an exercise to begin to pinpoint specific behaviors a leader may want to change. He encourages leaders to think about habits in objective categories: personal habits, relationship habits (how do you manage your relationship with your partner?), health habits (is there anything in your health habits that is not sustainable?) and leadership habits (how do you lead?).

Another way to approach rectifying habits is to create a “stop doing” list.

“Everybody has all these to-do’s and things they’re working on,” says Wally, “but every once in a while you’ve got to decide on what you’re going to stop doing — for example, things that don’t make sense in your current role.”

Wally has come across a habit that many high-performing leaders share in common: They often place their physical health last. “They would never neglect the financials of the business, their marketing or neglect doing reviews for people,” he says, pointing out that in prioritizing urgent business matters, CEOs let their physical well-being slip. When a CEO becomes aware he is neglecting his health he can begin to turn the tide in a better direction.

6. “Think about the last direct report who left the company. What percent of that employee’s departure are you willing to own?”

This question leads the CEO to ponder the importance of employee engagement. How exactly is the CEO engaging her employees? Does the CEO take steps to deepen engagement?

Communicating and connecting often is one path toward improving employee engagement. “CEOs need to meet with their direct reports every 30 or 60 days to ask how things are going,” says Ken.

Ken offers these questions for CEOs to ask their direct reports: Where are your challenges? What is the biggest knot in your rope? How can I support you more? Where do you think you need additional training? Open-ended questions “give people the opportunity to be heard,” he says.

When an employee does bring up a specific issue or need, engagement will only improve if the employee is provided the tools to resolve that need, and the CEO must follow-up to ensure it. Too often, a CEO’s busy schedule stymies ongoing conversations. They end up having ineffective once-per-year discussions with their direct reports. “That is a critique,” says Ken. “I don’t believe in critiques. I believe in engagement.”

7. “Why would someone want to work at your organization, and how do you attract the best and the brightest?”

This question gets the CEO thinking about his company’s culture and the specific reasons employees would desire to work at the business. Ken asks follow up questions, including, “If you were able to improve your culture, what do you think you would need to do differently? What do you think you would need to learn?”

“I’m asking questions like that to get CEOs to start thinking, ‘You know, that’s fair, I don’t really do a good job of understanding what our culture is.’”

8. “Describe You 3.0. What is the next version of you going to be like?”

Wally likes asking this question because it encourages CEOs to think about their leadership aspirations. “Thinking about the next version of themselves will nearly always give leaders needed objectivity,” he says.

In Wally’s eyes, the definition of great leadership is when people improve on your watch. If leaders notice that their people are not showing growth over time, it’s a sign that they have room to grow their leadership influence. Wally poses that CEOs ask self-reflective questions such as, “Do I need to get better at my communication? Do I need to set higher expectations or drive accountability?” The answers, says Wally, “is where self-awareness comes from.”

9. “It’s the last day of the year. What would have made this year truly meaningful for you — personally and professionally?”

Goal-setting can be a tricky task. Wally’s question is designed to take off the pressure of facing down an entire year and instead, asking the leader to imagine being in the future and looking back at a year well-lived.

“This way of fast-forwarding is a reliable way to get some fresh perspective,” says Wally.

The question ‘What are your goals for next year?’ is daunting for most people. Wally says it’s better to ask, “‘In retrospect, what would have made it a great year?’ CEOs can always come up with those things with no hesitation.”

This fresh take on the goal-setting question is especially effective for those who may be skeptical about goal-setting or New Year’s resolutions. As for stepping stones to attain the goal, Wally offers a simple roadmap: First develop awareness of your goal, narrow down your priority goals, be accountable and have something you can measure against to know you are on track to attain it.

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