A Leader’s Guide to Asking Better Open-Ended Questions of Employees

In the fast-paced world of work we all live in now, one of the most understandable and common mistakes all employees make is simply not asking the right kinds of questions.

To get the work done on deadline or to exceed deadlines to impress a client or colleague, we dive into the work, spending minimal time on clarifying questions. Yet in many cases, being curious and asking better questions about the work from the start can make all the difference in the quality of the results. Asking better questions also builds better relationships and leads to more innovative solutions.

And when it comes down to it, the key to asking better questions is simple: ask a well-crafted, open-ended question rather than a closed-ended one. Naturally, this applies to leaders and employees. No matter your role, everyone needs to get better at asking questions to be better communicators.

What is an Open-Ended vs. a Closed-Ended Question?

Open-ended questions give respondents the chance to provide more detailed and expansive answers in their own words. Closed-ended questions often require a simple “yes/no” response or provide respondents with a set of listed choices, like the kind you’d see on a standardized test.

By nature, open-ended questions encourage deeper exploration and reflection on a topic, while closed-ended questions prompt quick, quantifiable data points.

Benefits of Open-Ended Questions

A big part of my work is coaching leaders on strategic presentation skills. One leader I was helping struggled with talking without pausing. He needed help connecting with employees in the room. We talked about the importance of pausing during the presentation and asking a question to engage the audience.

During our coaching session, when he first paused for emphasis, I was happy he had listened to my recommendation, yet then he made the mistake of stating, “Does anyone have any questions?” A closed-ended question like that is a surefire way of shutting down an audience rather than truly opening them up. 

On the other hand, leaders can create an energizing dialogue if they use a few common open-ended questions, such as:

• “What lingering questions do you have regarding what I just shared?”
• “What more would you like to know about our next steps to succeed?”
• “What kinds of support do you need from the leadership team to get started on this work?”  

As you can see, there are a number of critical benefits of the open-ended question, including:

1. Enhances Dialogue

Open-ended questions spark better dialogue, which leads to increased engagement. When employees or colleagues can weigh in with added thoughts and questions, rather than just “yes/no” responses, quality communication and increased understanding flourish.

2. Builds Trust

When leaders or colleagues ask open-ended questions, they demonstrate a genuine interest in the respondent’s perspective.

Think about a time when you’ve been in a meeting and heard a leader quickly say, “Any questions?” The tone and body language may signal the leader hopes no one speaks up so he or she can move on.

By contrast, asking a more provocative or detailed open-ended question demonstrates empathy and authenticity. That builds trust, which has a positive effect on the overall employee culture.

3. Encourages Creativity and Innovation

Open-ended questions challenge others to expand their perspectives, which can spark new and innovative ideas and approaches. When there’s no invitation to add a thought, audiences presume innovation or collaborative thoughts aren’t welcome.

4. Breaks Down Perceived Barriers

Open-ended questions invite the audience to ask questions they might otherwise feel they can’t ask, either in the interest of time or out of fear that probing questions aren’t actually encouraged.

5. Deepens Understanding

Open-ended questions allow for a more sophisticated discussion. For example, employees can share background on what they’ve already learned, such as: “I read in our investor report that we are expanding offices in Singapore because of growing demand for our products in the area. What kind of interest are we seeing in Singapore and what other details can you provide about our expansion there?”

6. Fosters Employee Growth and Development

In work cultures where asking good questions is encouraged, employees learn how to be more curious and grow their skills, which is a win-win for the employees and the company.

7. Avoids Mistakes and Re-Work on Important Projects

When employees fail to ask the right questions and make assumptions about what’s needed, they can make critical mistakes.

Projects can be set back months when employees go down the wrong path, and often the costly detours could have been avoided if employees simply asked better open-ended questions upfront.

Examples of Open-Ended vs. Closed-Ended Questions

The following chart offers examples of how questions might be asked in a closed-ended versus open-ended format.

As you can see from the examples, open-ended questions often lead to higher-level thinking, which can enhance the way people work together, lead to better understanding, and improve business results.

In many cases below, the closed-ended questions might invite the employee to respond with a simple yes/no answer or a very short reply.

Why is it important to ask more Open-Ended Questions?

One of the biggest problems with business communication today is the tendency of leaders to fall into a predictable routine. For example, the perfunctory town hall or team meeting that feature “talking heads” with leaders simply taking turns at the PowerPoints with little back-and-forth discussion with employees or time set aside for questions and genuine conversation.

The power of open-ended questions is that they are a natural way to more critical thinking. When you invite employees to share more, inevitably new insights will surface.

Hal Gregersen, the former director of the MIT Leadership Center, has written extensively on the topic of asking better questions, and authored the book, “Questions are the Answer.”

In an article for The Wall Street Journal, Gregersen said there’s a simple truth he believes firmly in: “If you want a dramatically different answer, the key is to ask a better question.” 

Gregersen said the kinds of questions that spark creative thinking share five main traits. The questions tend to achieve the following:

• Reframes the problem
• Intrigues the imagination
• Invites others’ perspectives
• Opens up space for different answers
• Is nonaggressive, not posed to embarrass, humiliate, or assert power over the other person

I also appreciate another tip Gregersen offers that I’ve found to be particularly effective. Whenever there’s a problem or opportunity in the business, leaders can spend some time with their teams, quickly coming up with 15 open-ended questions regarding the problem. Frequently, the questions lead to fresh perspectives.

“Eighty percent of the time, I find the exercise yields some new angle of attack on the problem, and it virtually always re-energizes people to go at it with renewed gusto,” Gregersen said.

Clearly, well-crafted, open-ended questions are the natural vehicle to achieve those kinds of breakthroughs.

Open-Ended Questions as Tools for Personal Growth of Employees and Teams

Another area where open-ended questions are particularly effective is personal growth and development check-ins between leaders and employees. These can take place as part of a formal annual evaluation, or during a more informal one-on-one meeting to discuss how employees are feeling about their work.

In these situations, well-constructed open-ended questions are a great chance to promote self-reflection, personal goals, and growth opportunities. The following are some effective open-ended questions we’ve found helpful in promoting great dialogue between leaders and employees.

Personal Growth and Team Development Open-Ended Questions

• What do you like most about your job today?
• Thinking back on your work over the last year, what are you most proud of and why?
• What’s one thing many people might not realize that you do very well?
• What are your top priorities and goals for your work today?
• If there’s one thing you could change about your work today, what would it be?
• Thinking about your future here, what’s one role you’d like to take on if given the opportunity and why do you think it would be a good fit for you?
• What are some things I could do to better support your growth and development?
• Thinking about your team, what are the two biggest things getting in the way of the team’s ongoing success?
• What other ideas do you have to improve the work life of employees here?
• What feedback do you have for the leadership team in general? What’s working and not working in the way people are managed?