Episode 51: Asking the Right Questions – Deb Calvert

Predictable Prospecting
Asking the Right Questions
00:00 / 00:00

Curiosity might have killed the cat, but it can save the sales rep! In this episode we’re joined by Deb Calvert, President of People First Productivity Solutions and an expert on asking the right questions to target buyers at the top of funnel.

Deb explains her innovative DISCOVER method for asking questions, why you shouldn’t be afraid of negative feedback, and how to build trust and rapport over email communication.

Episode Highlights:

  • How Deb Calvert began a career of questioning
  • The D.I.S.C.O.V.E.R model of asking questions
  • Asking questions that create value
  • Scripts to follow
  • Breaking down the acronym
  • Leveraging questions with non-voice communications
  • The data behind the movement
  • Stop selling and start leading


Want to chat with Deb? Email her at: deb.calvert@peoplefirstps.com


“Questions are one of the fastest ways to build bonds and create trust and rapport with people” – Deb

“You have to try some things and not be afraid that questions will get negative reactions. They really don’t, not nearly as often as we think they will” – Deb

Episode Transcript

Marylou: Hi, it’s Marylou Tyler. I have a wonderful guest today. I just met Deb not too long ago. I’ve been a part of her BrightTALK channel, she’ll tell you more about that. She is a person that we’re going to really love having on the show today because Deb is all about questions. She’s all about discovering the right questions, getting people out of their status quo, out of their stupor, out of the trans so that we can start having those conversations we need at top of funnel. She’s the president of People First xProductivity Solutions. Is that correct, Deb?

Deb: It is. It’s a mouthful.

Marylou: She’s also the author of twenty of the most highly rated sales books of all time according to Hubspot and Amazon. The book is called Discover Questions to Get You Connected. Welcome to the podcast Deb, it’s nice to have you.

Deb: Really nice to be here, Marylou. Thanks for the invitation.

Marylou: Tell us what got you interested in the realm of questioning? I mean, how did you get involved in that? What was is it that you decided that this is something that you’re going to be a master of?

Deb: I think it was my purpose in life. I’m one of those kids who did the same thing all two or three years old too asking why and why and why questions consistently. The problem is I never stopped. I remember my parents and my teacher when I went into school telling me, “Debby, you shouldn’t ask so many questions. It’s not polite to ask questions.” But I just did. I wanted to know.

I got this all worked out. By the time I was in high school, there were actually appropriate places, debates and journalism, to work on the school’s newspaper, becoming a debater. Those were places where questions were a good thing. I went on and got a journalism degree. I kept using questions and rediscovered sales which I’d done a little bit of. I was always the top CampFire Candy sales girl and that kind of thing.

Sales, because I wanted a job at a newspaper and I couldn’t get one on the news side express out of school. I took a sales job in the classified department and questions started serving me really well. When I moved in my first outside territory, I went to the library to find a book on selling. There was only one on the shelf, Spin Selling, of course that was all about questions. Then, I started my own research fast-forward 20 years later, buyer side research on questions and having put a framework together, I decided that there are only ever eight purposes that anybody asks for questions, and that’s the acronym of discover.

Marylou: Wow, okay. This is sounding really juicy. Let me just preface this by I did a webinar on your channel, the BrightTALK channel. It was about phone habits. One of the things I offered up was the calming questions that I ask and there were so many people who downloaded that little file. I’m sure it’s just a tip of the iceberg of what you’re going to share with us today with the discover model. Take it away and tell us all about it.

Deb: Sure. Discover is an acronym. Each of those letters stands for a purpose for asking a question. Sometimes, sellers think too narrowly about questions. We think of them in two ways, we think about using them to qualify a buyer and we think about using them in a discovery process, our sales process. Occasionally, the sellers think about them when they close to do an either or, or just ask kind of a close.

Questions can serve any conversation in a lot more ways. First of all, we know from buyer’s side research and other body support that questions are one of the fastest ways that we can build bond and create trust and rapport with people. Well, thinking about that, changes everything and I love your sales expert channel webinar because you did think about and offer up questions as the way to change things, to change the conversation between the relationship to open up. Really for opening a sale, let’s open a conversation. Let’s open people in a way that they’re thinking. As you said here at the top, that’s about disrupting what they expect from the sales person and creating value. Value makes them pause and think, questions do all that.

Marylou: Let me ask you, we are bombarded with the term creating value. I’m sure my audience is saying, “Okay, here’s that term again.” What does that mean in the questioning world, or how do you ask a question that is a creating value question?

Deb: I love that question. I’m going to break it down a little bit. First of all, let’s just take the term creating value. Here’s how I see it, it’s not the same as the value that’s inherent in your product. Your product, whatever it is, is delivering some kind of value to some people. That’s the bare bone price of admission to ever sell anything.

On top of that, there’s added value, that’s where your company layers in. It’s the deal sweetener, it’s the extras, it’s the differentiators driven by your company and maybe your marketing department. Created value is neither of those things. Created value happens in the moment, in the experience that you are inviting your buyer into with you.

Created value is for that reason never generic. Created value is always spontaneous and it’s always about what’s happening right now, in this moment. If you’re working on the phone, you have to be so present to understand what matters to this buyer, and what matters by the way, I’m not talking about the ultimate value that you’re going to deliver with your product and your company’s added value. I’m talking about why would they even spend 10 more seconds on the phone with you? Did you peak their interest, did your human self bring enough credibility and enough stimulating thoughts that in that moment there’s value for the remaining seconds that I can commit to you. And beyond that, that there is value that you’ve opened up so that I’ll take a full meeting with you and progress through that the process of buying with you, that’s what I mean when I say created value. That’s why questions are the number one way and this isn’t me saying this, these are buyers we’ve interviewed.

In fact, we very recently completed a B2B buyer survey, a panel study through Sta. Clara University with 530 B2B buyers. Among the top behaviors that they told us they want more from sellers are the different kind of questions, dialogues, this rich, stop, make me think, stimulate my brain cells and that’s where buyers are missing something from sellers.

Marylou: That’s great information. Okay, our audience here are process people, we’re prospectors, we’re closers. You mentioned the word model and discover. Is there a way that we can start, I don’t know if mapping is the right word but taking an idea of a question and correlating it to the actual conversation, or are we training ourselves when you say, “To react to the response of the buyer,” is there a script anywhere in here that we can start with to practice to get better at this? What is the normal way for us to start along that path of mastery of asking the right questions?

Deb: Yes, it’s a very delicate balance. You don’t want to become so process driven that your questions get in the way of you relationship. Your questions shouldn’t facilitate the relationship. This is a big mess in the part of some other program that have been in the past or maybe more fairly it would be the misinterpretation of some other program in the past including SPIN.

If you look at SPIN as four questions, 1, 2, 3, 4, I’m done, you’ve missed the real conversation, the connection and the value you could have created. You don’t need to put that caveat out first. And then, there is a process for learning and mastering the art of questioning and the connections and the trust that you can build with questions.

Step one is to first become a question detective to observe what’s happening when people on interviews that you might listen to or watch on TV, to pay attention in conversations. What happens when you ask to three to four close ended questions in a row? What happens when you’re asking questions because you’re fishing to get the answer you already thought of? Versus, what happens when you ask broader questions that push pause and make people think?

Just observing, that’s step one. Having the tool of an idea, of what are some of these higher purpose question. What are the eight purposes, in fact, because most sellers only ask three out of those eight. There’s a lot more space to play if you know all eight. Knowing that, as you are playing the role of question detective, it can certainly help. We have a free tool we’re going to give your listeners so that they’ll have contacts and then they can go out and do a little detective work. And very quickly, they’re going to see the impact of stronger questions.

Marylou: You’ve mentioned three of eight that we all know or at least that’s the baseline. What are the three that we know and what are the eight that we should know?

Deb: I’ll break it down that way. This is an acronym, the three that all sellers already asked. All sellers should say in selling that is, they [00:10:24] a question. They have data questions, you often do those as you’re qualifying. A data question is a question that simply goes after the fact. It’s not about opinion. It’s not about anything subjective. You just want the facts, the data.

The C and the O are the other two in the acronym of discover. I just skipped the I and S but we’ll come back to them. C and the O in the word discover are the other two that most sellers routinely ask. C, I’m calling it consequence. O, that’s outcome. Outcome is anything that’s about your hopes, dreams, plans, goals, visions of the future, what do you want to have. Consequence is of course the flip side of that. What if you don’t reach those outcomes? What are the risks if you don’t take action, they’re sometimes called pain questions. When we ask data, outcome and consequence questions in sales, we then simply have what we need to create a solution and that it should be sufficient to give us the information that will be compelling to the buyer.

The problem is it doesn’t work so well anymore. It used to work just fine but buyers have caught on and buyers have become empowered. Buyers are wanting more including this experience, this value that’s created. Data, consequence and outcome questions, they do serve a purpose, but they no longer stand alone. They don’t create value because everybody else is doing the same thing.

The other five have more opportunity for you to create value. I’ll continue going out of order just for the interest of time and being able to go quickly. The next one is my favorite, is the value question. We need to ask more value questions. They’re simple, there’s rich information within them. They help you avoid leaving money or opportunity on the table for someone else. Value question is getting the prioritization that the hierarchy of needs from your buyer. Your buyer says, “We need to do X, Y and Z as an outcome.” You might ask what happens if you don’t do X, Y and Z. They’ll give you an answer, “We still need to know out of X, Y and Z, which one matters most and why is that that it matters most?” That’s the need we want a response to, not the one that we might otherwise be counting on because it’s easier, we call it low hanging fruit.

Marylou: Correct, yes.

Deb: That’s a great question. We need that one. Another one that sometimes gets asked but not often enough is the R, that’s a rational question. I want to know the things related to your decision, the decision you’re going to make. What are the criteria, who’s involved, and so on. Sometimes, those flip in as qualifying questions.

I also want to know about decisions that you’ve made in the past. Walk me through your process for how you decided on that vendor? And the reason I want to know that is that the next time that there’s an opportunity, I want to get into your process, I wanna know those steps, I want to get into your head and know how you made those decisions earlier so that I can intercept sooner. We need to get a little bit more fine-tuned on that.

The D and the R, I put those in because I see them about a third of the time from sellers when I’m out field coaching. And then it’s the next three, we have left the I, the S and the E. Those are the ones that virtually no sellers are asking. Here’s the opportunity to immediately differentiate yourself. The E is an example question. It is the equivalent of putting your buyer behind the wheel of a car and asking them to take it for a test drive so that they can begin to experience something about your product. That’s why when you go to buy a car, they put you behind the wheel so that you can never imagine yourself without that car again. We don’t always get to do that because we sell intangibles or we’re working with people over the phone. Instead, we have to ask them a question that gets them living something out, gets them talking about example, gets them imagining the contract between the future state and the current not so great state that they might be in. The more that they can envision that experience, the richer that example can be that they give us, the more and more they do the selling work themselves which I love when that happens. I’m throwing a lot out there, this just feels like a fire hose.

Marylou: No, I’m lovin it. I’m just like a sponge over here.

Deb: Let me talk about the question that’s an easy one in theory and a hard one in practice, because we have a natural resistance to asking it, and that’s the eye. It’s an issue question. This is the only one out of the eight that is about us as sellers. We can ask it in two ways. We can ask it reactively, so they have told us some objection or they have some barriers doing business with us or we screwed up in the past. Whatever it is, it’s already an issue on the table. What many people do is duck and dodge and maybe apologize but we seldom ask a question at this moment to allow people to vent and get it all out there so we can move past it.

Reactive is your question sounds something like, “Oh Marylou, I’m really sorry that happened. Tell me what the implications were because that happened.” You’re going to give it all to me. You’re going to exhaust and expend all of that negativity. It’s no longer going to be a barrier between us. I just listen to you. I created value because we’ve took this bad thing and I allowed you to give part of it back me, so there’s an opportunity there to build some trust.

The question in that moment of crisis, uncomfortable but very powerful. The other way you can use this easier is proactively, but it requires a little humility to do this. Again, the natural resistance occurs but a proactive issue question tries to prevent this from being an issue. It’s about, “Tell me what I can do. I hope we continue working together. I want to make sure that I’m doing business the way you like to do business with sales people. What would you like to see me do?” Or, “Hey, we’ve been doing business together a long time. I want to perform a service check. What would you like to see me doing differently?” All questions that prevent issues, even small niggling ones that are in the back of someone’s mind, just get them out.

And then finally, another very powerful, buyers like this question a lot. They like them all by the way, the least they like is data because it’s boring to them. The last one to talk about is the S, that’s the solution question. A solution question plants seed. It keeps people reacting to alternatives, not that you proposed to them, but that you ask in the form of a question so that you can get a read on potential objections so that you can make them think outside of what they’re already doing.

It usually starts something like, “What are your thoughts about?” Or if you want to make it very narrow and get a close ended answer, “Have you ever considered?” When I put the idea out there, they’re going to have a reaction, I know what that reaction is. They will often say, “Hmm, that’s a good question. I’ve never thought about it that way.” And then you know that you’ve got something germinating. You’ve got the beginnings of an idea and you don’t have to come in cool later on to surprise them or dramatically change something that they have never thought about before. That’s rapid feed, those are the eight.

Marylou: Amazing. My first question that came to mind as I’m listening to this is a lot of folks nowadays are leveraging technology to have conversations within an email engine. Not necessarily having the phone dialogue questioning, but want to learn more about embedding questions within email so that they’ll lean into the computer a little bit, the buyer, then say, “Wow. No one’s ever really asked me that.” Does this work with non-voice communication, as well? Have you experimented with it?

Deb: Email, voice mail, as I mentioned I do a lot of field research. I shadow sellers, I interview buyers. I have first-hand examples. That little tool that I mentioned, there are questions that are used in the first minute of the phone call, but at least six out of the eight, I have to go back and at least six out of the eight have also had email variations that were effective.

Marylou: Interesting. Hear that, people? We try to start working on 68 touches where they’re creating value in our email engine to just help us warm up the chill of accounts and people who are either dormant or we haven’t spoken with for a while or they came inbound to us. We haven’t started the conversation yet. We’re always looking for ways to be able to like you said, get people stimulated, get them excited, get them thinking about what kind of conversation they’re eventually going to have with us when we do reach them on the phone.

Having a tool like this isn’t valuable for those of us who are hyper personalizing our emails, for those of us who are still working through cold emails where we have a list that hasn’t been touched for a while. You kind of want to warm up the chill and see who’s going to bubble up on the top. But adding the value within the email is a way that we’re going to shrink that lag in the pipeline and also have the first conversation be more meaningful. This is great stuff Deb, I love it.

Deb: It’s valuable. It really works and it gets you to a place where you’re more comfortable asking questions. You have to try some things and not be afraid that questions will get negative reactions. They really don’t, not nearly as often as we think they will. You aren’t like the prosecuting and turning with your witness up in the courtroom. Scenarios that are negative about questions are really exaggerated. The positive perceptions, the reactions of buyer far vastly outweigh anything negative that you might be concerned about.

Marylou: Plus, this is grounded in research. For those skeptics out there in the audience, this is based on statistically relevant research of buyers and what they want to see in terms of conversation from us. It’s not like you’re inventing this out of a vacuum, Deb. You have data to support each of these elements and why they’re important to utilize within the sales conversation as we march people down the pipeline. This is great.

Deb: [00:21:38] sales results [00:21:41] as it comes directly from our buyers and we still seldom get an opportunity to have that kind of data.

Marylou: Sponsored by universities, you said as well. You’re going to have a good breadth of audience. Usually, when you think of audiences, you think of maybe all SAAS people, or all tech companies or health care. It sounds like this is a broad spectrum of verticals that you also were able to get information from. That’s great.

Deb: It was [00:22:14] University [00:22:15] panel study and a 530 B2B buyers represent every sector, different age group, demographic sort of every type, complex sales, more transactional sales, all B2B. People who were buying for a lot of years, people who are newer to buying, people who make full buying decision versus those who are working groups. You name it. It’s in there, you can slice and dice a lot of ways.

Marylou: Is that available in for people in our audience, leaders who want to get in the data a little bit more?

Deb: There’s a movement called stop selling and start leading and there is more and more of that becoming available as we continue our analysis. Stay tuned for that on the webpage for stopsellingandstartleading and in webinars and podcasts like this. We’re releasing a little at a time. We’re continuing to do seller side research which I invite your audience to be part of it if they’d like to be. It’s all coming together in various articles, the sales journal, journal of professional sales management is featuring articles soon. There’s a lot of coming out, lots of places where people could go for that.

Marylou: And I’ll be sure to post some of these links on the show notes page so that people can just click on the link to get more information about where Deb is, what she’s doing, what she’s up to. What’s the best way for us to get ahold of you for a one on one or to get more information about the work that you are doing?

Deb: Just email me. I welcome and enjoy talking to people deb.calvert.peoplefirstps.com. PS stands for productivity solutions.

Marylou: Okay, and the book again? The title for everybody to go immediately download from amazon.

Deb: The book is called Discover Questions Get You Connected.

Marylou: Discover Questions Get You Connected. And also, Deb has a BrightTALK channel, the Sales Expert’s Channel. A lot of people are starting to share their expertise there as well. For those of you who want to continue to learn and master in the comfort of your own home and listen when you want, that channel is available, and I’ll put that link in as well.

Deb, thank you so much for your time. This is a wonderful framework that you have and it’s truly something that the folks are listening to this podcast must really adopt because we are only doing those three, maybe four that I counted, out of the eight. If we can sprinkle in the others and start getting in the rhythm with our cadences and sequences and voicemails and emails, boy, life is going to be a lot more fun when we finally get into that conversation with our prospects. Thanks again, Deb, really appreciate your time.

Deb: Thank you Marylou, my pleasure.