Harvey Mackay Academy's Blog

A grandfather was alone at home, so one of his young grandsons came to spend the night with him. The next morning grandpa prepared two big bowls of oatmeal, his own favorite breakfast.

He asked the young boy, “Do you like sugar?”

The grandson nodded yes.

“How about some butter, too?”

Again, yes.

“Of course, you like milk?”

“Sure,” the boy replied.

When grandpa placed the steaming bowl of oatmeal with sugar, butter and milk before his grandson, he refused to eat it. The exasperated grandfather said, “But when I asked you, didn’t you say you liked sugar, butter and milk?”

“Yes,” replied the youngster, “but you didn’t ask me if I liked oatmeal.”

Ask the right kind of question, and not only will you get good information, you’ll get it sooner and tailored to your needs.

I ask a lot of questions. A whole lot. There’s so much information out there, and I want only the good stuff. I want information that will help me make the right decisions and at the same time, won’t waste my time or my money. Is that asking too much?

There’s an art to asking questions and discovering what is central to your success. Here’s the secret: What is it that you really need to know?

The ability to get information when you need it and then act on it is what gets things done.

Before you start any project, ask questions to clarify objectives and expectations. This is the time to ask, “Why are we doing this?” and “What is our goal?”

Ask open-ended questions that need more than a simple yes or no answer. These are the bread and butter of productive conversations. They encourage a full, meaningful answer using the respondent’s own knowledge and feelings, which can help build rapport and trust.

Open-ended questions lead to a deeper understanding of the topic at hand. They help the conversation flow more naturally and avoid making the other person feel like they are being interrogated. Start with questions like this:

 How questions help you understand the process or method. For example, “How do you recommend we proceed?”

• What questions help you explore ideas and possibilities, such as “What will be our biggest advantages as we work on this project?”

• When questions are great for understanding timelines and deadlines, like “When do we need to have this completed?”

• Who and Where questions help identify people and places involved in a situation or project, such as “Who will be responsible for this task?” or “Where do we see the most potential for growth?”

Then during a project, regularly ask questions to monitor progress and make adjustments. After completion, reflect on the project with questions like “What did we learn?” and “How can we improve next time?”

The key is to listen carefully to the answers before asking the next question, so you can build on the information you’ve received and not waste any opportunity to learn more.

When I was just starting out in the envelope manufacturing business, I had a meeting with a potential client who was a key player in the industry. I knew that this meeting could be a turning point for my company, so I prepared meticulously. Instead of going in with a list of yes-or-no questions, I crafted a series of open-ended questions designed to get the client talking about their needs, concerns and goals.

During the meeting, I started with questions like, “What challenges are you currently facing with your envelope suppliers? and “How do you see the ideal partnership with an envelope provider?” These questions opened a rich dialogue and allowed the client to share insights that I would never have uncovered with closed questions.

The client spoke at length about their struggles with timely deliveries and the need for custom envelope designs that could set them apart in the market. Listening carefully, I was able to tailor my responses and highlight how my company could address those specific issues.

As a result of asking open-ended questions, I not only gained a deep understanding of the client’s needs but also built a strong rapport. The meeting ended with a handshake on a deal that became one of the most significant contracts for my company at the time. This experience taught me the power of open-ended questions in business and in life. They can transform conversations, deepen relationships and often lead to outcomes that exceed expectations.

Mackay’s Moral: Great questions are the keys that unlock the most valuable answers.

About the Author

Seven-time, New York Times best-selling author of "Swim With The Sharks Without Being Eaten Alive," with two books among the top 15 inspirational business books of all time, according to the New York Times. He is one of America’s most popular and entertaining business speakers, and currently serves as Chairman at the MackayMitchell Envelope Company, one of the nation’s major envelope manufacturers, producing 25 million envelopes a day.