20 Open-Ended Questions Sure To Increase Your Win Rate!

“We should not only master questions, but also act upon them, and act definitely.” – Woodrow Wilson

We’ve talked about Socratic sales in the past, but with our current focusing on the sales process, I thought we might have a look at one of my personal favorite sales techniques: open-ended questions.

What is an open-ended question?

According to mediacollege.com, “An open-ended question is designed to encourage a full, meaningful answer using the subject’s own knowledge and/or feelings,” thereby avoiding the dreaded word, “No.” An open-ended question is the opposite of a closed-ended question, which is meant to illicit a single-word response.

Asking the right question at the right time will often tell you everything you need to know to close the sale. All it takes is a little Dale Carnegie-style genuine interest and careful listening – along with knowing the best types of questions to ask, of course.

Fortunately for me, I had a great example to go by when learning the value of open-ended questions.

How I learned the value of open-ended questions

Like many people, one of my first jobs was at a supermarket. Through building a friendship with the store manager, I learned a great deal about what it means to “cultivate people skills” while working there.

The boss was named Joey and, to this day, he is the greatest “people person” I have ever met. Joey could smooth over any situation and could make friends with anyone, just by talking. The primary method that he used to accomplish this was through asking open-ended questions. So good at this was he that he hardly ever stopped asking questions. Yet it was all effortless and totally unforced.

After working for Joey for a while, I came to realize that Joey was employing some very advanced interpersonal skills on a (literally) constant basis. It was really amazing, now that I look back at it. No matter how urgent the day’s work was, Joey always greeted everyone – from the cashiers to the customers, to his own supervisors – with open-ended questions that were designed to engage. Joey strove to really know everyone around him.

While at first I dismissed this as some residual of having read How to Win Friends and Influence People, I eventually came to appreciate the fact that Joey was using open-ended questions in a much more integral way.

Socratic Selling

That guy’s got skills… people skills.

Joey would talk to everyone. If he saw a shopper come through with a shopping cart filled with meat, he would say, “Wow, that’s a lot of groceries! How many people are you cooking for this weekend?”

The shopper would take this as mere conversation. But Joey would look in the cart while they talked, taking a mental inventory of their purchases, and follow-up with things like “Hey, you’re going to need this seasoning, or that utensil,” using the same casual ease with which he conducted the rest of the conversation. Almost without fail, the shopper would take Joey’s advice, and his sales would nominally increase.

Joey’s knack for open-ended questions didn’t stop with the customers. If a worker seemed down or sullen in his or her duties, Joey would take the time to find out why. Joey knew people well enough to know that it was often a work-life balance getting out of whack, at the source of low performance. If the person’s home-life needed attention more than the store, Joey would tell that person to go home and take care of it, and it was never held against them. As you can imagine, this knack for listening and understanding inspired considerable loyalty among the ranks.

I’ve known Joey for years now, and I can tell you that he is proof of the value of asking the right open-ended questions. He hardly does anything else, yet he gets more done than anyone I have ever met. While the value of open-ended questions can readily be applied to management in a broad context, open-ended questions can be extremely valuable in any sales situation. The main lesson to learn from my friend Joey is “always ask questions” (and not just the ones that end in Yes or No.)

Let’s look at some of the best open-ended questions I’ve picked up along the way (with a few from Joey, of course). These questions are sure to aid in building rapport (greeting), qualifying, offering, and closing the sale, regardless of the type of business.

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Building Rapport

  1. How’s business?

  2. What have you been up to?

  3. How are you planning to spend your day off?

  4. How is the family?

  5. What’s on your mind?


  1. What did you want to talk about today?

  2. What don’t you like about your current service provider/product?

  3. What outcome/result are you looking for?

  4. What’s the biggest obstacle preventing you from reaching your goals?

  5. What will make this a successful meeting for you?


  1. Does this sound like what you have in mind? (repeat back to them what they’ve told you)

  2. What are your concerns?

  3. What are the restrictions on this project, from your side?

  4. Why do you feel now is not the time to change? Why do you feel like it is the time to change?

  5. What other factors have we not discussed? or Are there any other questions I should be asking you?


  1. Do you have any other questions for me while I start writing this up?

  2. Can any of our additional services assist you, besides what we talked about today?

  3. Would you like option A or option B?

  4. When would you like to meet again?

  5. Have I answered all of your questions today?

Bonus Tips:

  • Stay away from leading or prompting the customer. (Socratic questioning will lead them there naturally)

  • Assume nothing, question everything.

  • Listen carefully to the response.

  • Never interrupt.

  • Ask follow-up questions as needed.

  • Repeat back to them what they’re saying to be sure you’ve got it right.

You’ve got (open-ended) questions + they’ve got (meaningful) answers = a sale closer to closing

If you don’t ask, you won’t know. The thing is, you’ve got to ask the right kinds of questions to get the answers that will help you build a business relationship. The above list of questions is generally applicable to all sorts of businesses, though specific scenarios will dictate that you ask different questions. The important thing is to think on your feet, and keep on asking questions. In time, you’ll start seeing the benefit of all those open-ended questions. Who knows, you may even start using them without even thinking about it, just like my old friend Joey.

What types of questions are you asking your customers? Are those questions getting the right results?


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