How To Ask Better Questions

Hitting a creative wall, or getting nowhere with a colleague? Think differently about how you ask questions.

How To Ask Better Questions
[Photo: Flickr user db Photography | Demi-Brooke]

“Effective leaders ask questions instead of giving orders,” wrote Dale Carnegie nearly 80 years ago in his iconic book How to Win Friends and Influence People, but too few of today’s bosses are following his advice.


“Leaders are expected to be decisive, bold, charismatic and visionary–they’re expected to know all the answers before others have thought of the questions,” writes Michael J. Marquardt in his book Leading with Questions: How Leaders Find the Right Solutions by Knowing What to Ask .

Instead of thinking of questions as a sign of weakness, Krista Brookman, vice president of the Inclusive Leadership Initiative at Catalyst, a nonprofit organization that seeks to expand opportunities for women and business, says leaders should consider questions to be a way to open doors and start important conversations.

“Good questions create good dialogue,” she says. “Questions allow leaders to connect with employees and better understand what’s going on with that individual. Ultimately asking questions makes you a better leader.”

But there’s a right way and a wrong way to ask. Here are five things to consider when phrasing your questions:

1. Questions Should Empower

Too often questions sound like accusations, putting the emphasis on the reasons why the person did not succeed. This form of inquiry puts the person in defensive mode and can change their answers.

“By asking disempowering questions, the leader closes the gateway to identifying paths to success,” writes Marquardt. In comparison, empowering questions draw out optimum performance and create high-energy, high-trust environments.


Instead of asking “Why are you behind schedule?” Marquardt suggests asking, “How do you feel about the project thus far?” This allows the person a safer space to share information without feeling directly at fault.

2. Questions Should Create Inclusiveness

Some situations result from biased perspectives, and Brookman says leaders can expand everyone’s thinking by first asking a question that seeks a connection.

“’Have you ever’ questions can be effective,” she says. “For example, ’Have you ever been the only person in the room of a particular race or gender?’ Asking this question creates awareness and helps the person reconsider how they perceive the actions of others.”

3. Questions Should Challenge Assumptions

The most common mistake leaders can make is not asking a question because they think they already know the answer, says Brookman, but it’s important to first get behind the assumptions you’re making about individuals.

“A leader might think that if an employee has children, he or she won’t be willing to take an international assignment,” she says. “Good leaders go in with an open mind and ask questions to gain better understanding, otherwise they’re unintentionally holding someone back.”

4. Questions Should Cause The Person To Stretch

Open-ended questions encourage the person being asked to expand on ideas and explore what is important to them or what is comfortable to reveal, writes Marquardt. For example, instead of asking “Do you agree with this decision?” ask “What do you think about …?” or “What do you want to do next?”


Open-ended questions show respect for the views of others because they don’t lead people to a certain type of answer. Marquardt says some leaders are uncomfortable asking open-ended questions because control goes to the person being asked, but the technique goes a long way to building rapport and increasing understanding.

5. Questions Should Encourage Breakthrough Thinking

If your company keeps rubbing up against the same kinds of problems, you need to rethink your questions, says Brookman.

“Asking the same questions in the same way will get you the same answers,” she says. “Instead of asking ‘What can women do at our company to get ahead?’ for example, rephrase it and ask ‘What are we going to do to make it possible?’”

“Why” questions will also challenge the status quo, says Marquardt. To be effective, “why” needs to be asked at least three times because the first answer won’t dig deep enough. The process is a variant of cause-and-effect thinking, and through a series of “whys” the questioner can drill down to a specific level.


“As organizations think about what they need to do to make changes, they need to look for the questions that will make the big difference,” says Brookman. “The right questions will empower everyone to think in new ways.”