September 14

2 comments

#395: When Is the Best Time for A Leader to Ask Questions?


By Ron

September 14, 2020

minute read time

Ask Questions

When I was growing up, I loved a TV show called Perry Mason. Mason was a trial attorney who would expertly ask questions guiding some hapless witness right where Mason wanted him to go, which was usually a full confession and off to jail!

Another expert questioner from the small screen was Columbo. Columbo was a detective who, like Mason, would ask questions in a series that cornered his unsuspecting victim. With nowhere to go, they finally confessed to their crimes.

Television attorneys and detectives are experts at asking questions!

As a salesperson and later, as a sales manager, I learned that asking questions was often the fastest and best way to learn what I needed to learn and make decisions.

One of my co-workers, Mark, was even better at asking questions than I was. Often, after work hours, I would tell Mark about a situation I was trying to resolve. Whenever I posed a business problem I had been wrestling with, Mark started by asking questions. Some questions guided the conversation, while some questions probed deep and made me think about my situation in new and different ways.

When Should Leaders Ask Questions?

Combining my insights from Perry, Columbo, and Mark, I realized there are two times when leaders need to ask questions.

  • Leaders should ask questions when they know the answer but need to guide the respondent’s thinking.
  • Leaders should ask questions when they don’t know the answer and need to gain information.

In other words, leaders should ask questions when they know the answer, and when they don’t know the answer! So, there is no wrong time for leaders to ask questions.

Now that we know leaders should be asking questions, the question you should be asking yourself right now is, “What types of questions should I be asking?”

Great question! I’m glad you asked.

There Are Two Types of Questions

There are two primary types of questions, and each type has a specific purpose.

Closed-Ended Questions

Closed-ended questions are those that can be answered with one or two words, often “yes” or “no.” Closed-ended questions are best used to guide a discussion where you need it to go.

  • “Did you finish the accounting project due today?”
  • “Have you called all the customers on your call sheet?”
  • “Are you sick?”

The limitation of closed-ended questions is they supply little information. The advantage is they can expertly guide a conversation.

Open-Ended Questions

Open-ended questions are those with a wide range of possible responses. Often, open-ended questions begin with “how,” “what,” or “why.

  • “What are the key benefits we should build into this new product?”
  • “Why do you think Jane should be the new team leader?”
  • “How should we deploy the new product to market?”

The advantage of an open-ended question is it can supply a lot of new information. The disadvantage of an open-ended question is the answer can easily go off-track and not be helpful.

Asking Questions Is A Learned Skill

Asking questions to guide a conversation or to uncover information to solve problems is a learned skill.

From the time we are little, we are programmed to answer questions. First, it’s our parent’s questions, then our teacher’s, and eventually our boss’s. But for most of us along the way, no one teaches us the power of asking questions! As a result, most of us ask questions rather haphazardly without a plan or strategy.

Someone counted and found Jesus asked 308 questions. Check out the types of questions Jesus asked.

  • “What are you looking for” (John 1:38)? An open-ended question about longing.
  • “Where is your faith” (Luke 8:25? An open-ended question about individual faith.
  • “Do you want to get well (John 5:6)? A closed-ended question about his desire to be healed.
  • “Who do you say I am” (Mark 8:29)? A closed-ended question about who Jesus is.

You can see from these questions. Jesus asked all kinds of questions. Some were short answer closed-ended questions, while some were complex theological open-ended questions.

Of course, Jesus wasn’t asking questions to get information. He already knew the answers to every question He asked! What is important is Jesus asked the questions needed to get the respondent to understand a greater truth.

The ability to ask questions like this is a skill leaders need to develop. We need to learn to ask a series of questions, so the respondent understands a situation better, so they see a greater truth, or so they see the answer to their question!

Learning to ask questions is a skill you can learn, but you must work at it. You have to be intentional about improving your questioning skills. Perry Mason and Columbo had the advantage of having scriptwriters helping them out. My friend Mark became an expert at asking questions by honing this skill over many years.

If you need to hone your question asking skillset, I suggest starting small. Try talking less and asking more questions the next time you have coffee with someone. The next time a co-worker asks you how to solve a problem, see if you can guide them to answer their own question and discover a solution by asking a series of questions.

Asking questions is fun. However, it is a critical skill set for a leader who needs to gather information.

More Articles

I have written other articles on communication skills. You can find them by typing “communication skills” in the search bar. In the meantime, here are two of my favorites.

·        #162: How Distrust, Conjecture, and Hasty Actions Lead to Disaster

·        #040: What Did You Say? I Wasn’t Listening!

Join the Conversation

As always, questions and comments are welcome. Was there anyone in your career who stands out as an expert at asking questions? How did this skill impact you/your organization?

I’d love your help. This blog is read primarily because of people like you who share it with friends. Would you be kind enough to share it by pressing the share button?

Category: Skills | Communication Skills

Ron Kelleher round small
About the author

Ron spent 36-years in Sales and Marketing with Procter & Gamble before heading off to Talbot Seminary. Now Ron spends all his time writing, volunteering at church, and loving his beautiful family!
Read More>>

  • As a police detective I was sent to many schools, including interview/interrogation school, which taught me a great deal about asking questions and getting answers. And one very important part of this is silence. After you ask a question, you stay silent. People don’t like silence in conversations, often rushing to jump in with a comment. But by remaining silent after asking a question, and staying quiet while the other person answers, often learn more.

    • Silence is a powerful weapon in any conversation. We are generally so uncomfortable with those dead spaces in a conversation that we rush to fill them. Yes, the best tool ever to use after asking a question is simple silence. Wait them out, it may take a second but it works nearly every time,

  • {"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}

    Never Miss A New Post!
    Receive This FREE E-Book When You Subscribe

    Optimized by Optimole
    >