What Are Your Great Questions?

man and woman talking

Interesting and valuable conversations are often easily created with family, friends and colleagues. Can we create this same level of communication with prospects and clients? How do we inspire conversations that build trust and relationships, and deliver value to everyone?

The answer is in the questions. Great conversations come from great questions. Preparing and practicing our questions – and continually experimenting with new questions – is the foundation of both a great sales process and excellent customer service.

What questions should you ask?  How can you create the best possible questions?

This summer, with thanks to both Chris Spurvey and MyRevenueRoom, I was introduced to The One Thing by Gary Keller. While I’ve always been an advocate of asking good questions, Gary’s book has me thinking in new ways.

Here’s the excerpt that really stood out for me:

“Answers come from questions, and the quality of any answer is directly determined by the quality of the question. Ask the wrong question, get the wrong answer. Ask the right question, get the right answer. Ask the most powerful question possible, and the answer can be life-altering.” 

When I am connecting with new prospects, introducing them to my work, I will often begin with a question that simply gets the conversation started, which puts us on a path to discover if my expertise is truly of value. Here’s my question:

“How do you make decisions about trainers that work with your team?”

I receive one of three answers to this question:

1) “We don’t make those decisions. You’d have to connect with someone at our head office in … Toronto, Vancouver, New York,” etc. At this point, I’ll ask for the contact information at head office and add that call to my leads list.

2) “We make those decisions in November each year.” I might ask a follow-up question relating to their training priorities for 2021 and then get their agreement that I can follow up in October with additional information.

3) “Tell me more about what you do?” This is the response that opens the door for the longer, more detailed conversation. It allows both of us to learn if there is an opportunity for us to work together.

But is this the most powerful question I can ask? And does it lead to the best possible conversation I could inspire? This is what Keller’s words have me wondering. So my next step is to craft some new questions and try them out.

When we are crafting questions, we want to make sure they are open-ended, i.e. don’t result in a simple “yes” or “no”. When we’re in the early stages of building trust and relationships, we don’t want questions that can be perceived as too aggressive or rude. We are looking for a question that gets the conversation started and allows both parties to get to know each other.

And the way to know if you’ve created the best possible questions is … to try them out. You can start with role plays with colleagues or friends. But the ultimate test is when you are speaking with a potential new customer. While it feels risky and uncomfortable to keep trying new things … it’s the only way to improve our results and find our most powerful questions.

What do you think? Do you already have a powerful question you rely on? Share your thoughts and experience in the comment section below.


Closing a sale is the natural outcome of inspiring great conversations and listening intently to our potential customers.

This natural approach still involves a process – a plan that moves potential customers through a journey of discovery with you. So ... what's your process? And am I the right sales coach for you? Let's find out.

4 thoughts on “What Are Your Great Questions?”

  1. You’ve pinpointed exactly my biggest challenge with calling a “stranger”. I really appreciate the coaching discussions you and I have had about this. It’s so much easier when it comes to questions for inbound conversations – got that down pat.

    • Hmmm … I think you’ve given me a future blog post, Linda. I’m curious as to why the questions would be easier on an inbound call than an outbound call. Definitely not something I’ve considered before. Thanks for taking the time to send this to me.

      • Oh, I have some thoughts on that! If a potential clients is referred to me and calls me, it’s easy to talk—I know what I want to ask about their project, their past experiences with editors, their budget, etc. They have come to me, they want to talk to me, and it’s… easy. Calling in seach of potential clients means initiating the call and then, as you say, knowing what you want to ask.

        • This is great, Dimitra. I’m definitely going to do a post about this now that you and Linda have written about it. I’m guessing that, with the inbound call, the person is open to conversation already. You don’t have to dissolve their defensiveness or “organize” the conversation, so it is easier. Hmmm. Lots for me to think about. Thanks!


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