Questions are the simplest tool that you have available to you. Can you frame your questions so that they are heard, received, and respected by your prospects? Do you know how to formulate a good question so that you can have that deep 2-way dialogue your prospects crave? Are you asking sales questions that add value?

In this episode of INSIDE Inside Sales, Darryl speaks with Deb Calvert, the President of People First Productivity Solutions and Founder of the Sales Experts Channel. Darryl and Deb talk about how to craft those questions that can create instant value, bonding experiences, and even build trust in your prospects. They also discuss ways to stay in the moment, listening to the emotional tone of the conversation, as well as steps to avoid asking questions that make you sound like a census taker. Learn ways to enrich the dialogue with your prospects, right here on this episode of INSIDE Inside Sales!

Not in the mood to listen? No problem, you can read the transcriptions below.

Host:  Darryl PraillVanillaSoft

Guest:  Deb Calvert, People First Productivity Solutions


Good Question!

Darryl Praill: How ya doing folks? It’s another wonderful day. You know, I was actually, true story. I was listening to some of our podcast recordings, and you may think that sounds a little vain. What it is that when I’m so in the moment of the recording of our guests I just love the conversation, I’m enthralled with the conversation and I’m thinking about what are the questions I’m going to ask?

Darryl Praill: As you know we try to wrap this up within a half an hour to respect your schedule and there are times when I sit back, and I say I didn’t really have a chance to fully embrace the lessons that were learned. So, I’ll go back, and I’ll play the sessions. And what’s really cool about that is when I do that, I actually get so much more out of the exact same episode that I was part of in the actual live recording and I actually have chance to hear it a second time.

Darryl Praill: And I make that distinction because hearing it a second time, And, I’m hearing it as you do, as a listener. Not as someone who’s, you know, part of the two-way conversation. So, you here it differently. And then the second part here is, what’s amazing is I really embrace the lessons because I hear them, you know? I think part of it is the repetition, right? Because I’ve already heard it once before and now, I’m hearing it with a capital “H”. And I’m going yeah, that’s brilliant, that’s gold!

Darryl Praill: And what’s so cool about that is, it’s the wisdom that we share on this show. I had a unique opportunity recently because as we record this, it’s the start of the new year, and I had done some of my best of shows. And I had a chance to go back and listen to some of the shows, as I mentioned to you. Either shows where I didn’t have time to listen because I was trying to re-evaluate a year’s worth of shows to do a best of.

Darryl Praill: So, ­­I would skim, we transcribe every single one of these shows so, there’s multiple places you could listen to the show. Obviously is the home page of the show. But if you were to go to under resources podcast, at that location we actually have every single show transcribed. And so, I would skim the transcriptions looking for the highlights and we have call outs for Tweets and everything else that are really really cool that you can share.

Darryl Praill: And every single show, I had the exact same experience over and over again which was A. I have learned so much and then B. I wanted to ask more questions. I wanted to follow up, I wanted to drill down even further, it’s like a half-hour is not enough time. And I had this conversation with a couple different people recently about the power of questions. I was talking to my son. Now my son he’s 25 years old, you’ve heard me talk about him before. He’s a broadcast journalist and he anchors a morning show out west. And we were talking, he was asking me questions about you know, when I get to know the guest or when I deal with my boss.

Darryl Praill: You know, can I ask questions that don’t look stupid and I’m like man listen. Questions properly framed are brilliant, every boss wants to hear questions, every subject matter expert you interview wants to ask questions. And if you frame them well as opposed to obnoxiously or like a moron or too sarcastic then they will react to that. They will viscerally react to that and they will willingly share that information. So, that was on the boss side.

Darryl Praill: The other part I was sharing to Luke was some of my employees recently, they’re probably the same age bracket, 25, 27, 28 years old, and I was saying you know, when you’re in a meeting, you don’t know. Do not feel intimidated by the individuals who are in that room. You have a question, ask the question. You’re going to sit here and think, well this is a dumb question, or they are going to react negatively to this question. And I’m like no dude, in fact it’s the complete opposite. You have the courage, you have the curiosity, you have the desire to learn. What we forget is what’s obvious to us is not necessarily obvious to you. We sometimes think that you should just know the answer because we know the answer.

Darryl Praill: The fact of the matter is, you cannot learn, you cannot do your job, you cannot solve today’s problems that you need to be solved unless you ask those questions. Questions are the simplest tool that you as a sales professional have available to you and sometimes, we get in our own heads. So, what have we said here? We’ve said you’ve got to have the courage to ask the questions, you have to intentionally ask the questions and you have to frame the questions in such a way so as that they’re heard and they’re received and they’re respected and they respond. The power of questions is the one tool that you’ve got that you’ve been doing since you were toddler, that you can apply with no additional training to make yourself a rockstar salesperson. Take yourself from level A to level B. And many people overlook that they’ve got this skill, they’ve got this secret weapon that they’re perhaps just not leveraging enough.

Welcome Deb Calvert

Darryl Praill: So, who do we go to, who do I ask questions of when it comes to asking questions and you’re going to love this one. We’re bringing on Deb Calvert. Now Deb, if you listened to our webinars at our watch our webinars VanillaSoft, is a past guest. She, the response to her in that webinar was overwhelming. So, I know her content, I know her personally and I’ve had a chance to previously interview her before on the webinar. So, I’m like bam, top of mind, let’s get her back and she’s here today. So, Deb, welcome to the show!

Deb Calvert: Darryl thank you! It is always a pleasure to be here with you!

Darryl Praill: Oh you’re so sweet.

Deb Calvert: I love that you appreciate questions! Yes, questions are all that.

Darryl Praill: I do!

Deb Calvert: Yeah!

Darryl Praill: The only person who mocks me when I ask questions, well it’s two people. My wife mocks me, she just rolls her eyes at me and my kids mock me because they just, you know, my questions are usually dad questions. So, you know, like, what is Instagram? I don’t get it and then they roll their eyes, as an example so. Other than that, everybody else loves questions. Now you though, you are the rockstar when it comes to this. Now full disclosure folks, I actually talked to Deb about this in advance because I wanted to get her thoughts on it. And she and I, well mostly she, I just took notes, she came up with five things that we want to share with you today. So, Deb if it’s okay with you, why don’t we just get right into it. Does that work for you?

Deb Calvert: Absolutely yes!

Darryl Praill: Okay so one of the things you talked to me about, you, Deb used this expression. I asked you, I wrote it down because it was brilliant. She says quality questions are like magic, just magic, the way they can engage. Talk to me about that, that’s the human dynamic. I elude to that a little bit, but I think so many people don’t understand the sheer power of the magic of the question.

Deb Calvert: Yeah you know, at a time when our buyers are expecting us to do so much for them. They want an experience that has to be relevant, that has to be meaningful, it has to be personalized. They want value creation that is unique to them, in a moment, in an instant. And we don’t have unlimited budgets, we don’t have the ability to read their minds. So, there’s only one thing that I know of that can create value instantly and create a bonding experience and even build trust and that is if you ask good questions. Now, that’s a qualifier. It has to be a good question. The old standbys like, hey what’s new or how’s the weather there, there’s no magic in those. Those are hackneyed, they’re trite, they’re they’re junk. But by contrast, a thought-provoking question can unleash all kinds of power in a relationship.

[bctt tweet=”So, there’s only one thing that I know of that can create value instantly and create a bonding experience and even build trust and that is if you ask good questions. ~@PeopleFirstPS #SalesEngagement #SalesTips #SalesStrategy” username=”VanillaSoft”]

Darryl Praill: So, just for context, can you give me an example. Totally putting you on the spot here, I apologize for this. Well I a little apologize, a little bit I’m watching you squirm. Can you give me an example of a good question versus a not good question that you’ve seen in your experience?

Deb Calvert: You bet! And I’m going to cheat a little bit because I’ve taught a class at U.C. Berkley. And I’ve worked with many many companies and so, you know. Although I do have 25 years’ worth of research on questions, I’m just going to give you the ones that I know work with SDRs and BDRs who have contributed back to me that the questions that they thought were magic. So, okay here’s a good example. Let’s say you have content, your company puts content out, webinars or whatever it might be, and then they give you a lead list and you call on the companies that listen to your webinar. What you might be saying right now that’s a not so good question is you call somebody, and you say, hey so I saw you listen to our webinar, do you have any questions for me?

Darryl Praill: I hate that.

Deb Calvert: That’s a weak question.

Darryl Praill: That’s a bad question

Deb Calvert: Yeah!

Deb Calvert: It is. What you really want to know is the value they found in the webinar. What you’re really trying to do is ignite some additional interest and get them to take some next steps with you. So why not craft a question that gets to that, that gets right to the heart of the matter? So, someone who downloaded your content, maybe you say right off the bat, when you watched the webinar, what information did you find most useful? And then wait, give them time to think. Because that’s a question that creates value. They’re recollecting your webinar, they’re going to give you something that is now a nugget, that tells you what is a value to them and then you’ll be able to expand the conversation and advance the sale.

Darryl Praill: So, I love that example. I’ve actually had that conversation with our own reps multiple times. And I’m like, they’re like you know, following up webinar with calls and what not, that’s such a pain in the arse and most people don’t react. And now I’m like, this is not hard. So, I’ve been, I’m speaking as a CMO right now so, you give me your reaction.

Deb Calvert: Yeah

The 3 Main Questions in Sales

Darryl Praill: This is, this is what I think it is. I think the questions are, very much in line with what you’re saying. My first question would be, so I see you, you registered for the event, or you attended the event. Yeah, I did, great. You mind if I ask a couple questions? No problem. 1.Just for, this is me softening it up, correct me if I’m wrong, I would say, just from a pure production point of view, did it meet your needs? Did it engage you; did it educate you; did you feel it was a good investment of your time yes or no? Because then, I’m honestly trying to see their, oh they want my opinion here, I want them to get involved. Yes or no and why? Great, next. Okay I’m curious, what prompted you to register for this event? That question I think is the golden question. Because they gotta say oh but we have a problem here or I stumbled with that.

Darryl Praill: So now I’ve identified a pain. And then I would do the, you know, I might do the next one which is, Great, what was one or two takeaways that you took away from that that you’re gonna apply right now? Or, that’s one option, the other option is I can go into, oh those are the problems you had? Okay, if I could help you with those problems, would that be something you might want to discuss further? That to me, it’s not, in the end it’s not about the webinar. It’s about why did you sign up and do you want some help with that? That’s how I tell my reps to approach it, am I right or am I wrong?

Deb Calvert: No, you’re absolutely on the right track and this is what others have found is really working for them. Whether it’s a webinar or it’s some other piece of content or even just a simple website visit if you’re tracking your website visitors, right. What brought you to our site in the first place?

Darryl Praill: Right.

Deb Calvert: Because that’s what we are trying to do, find out the need and then get some place to go from there with the conversation.

Darryl Praill: All right so, quality questions you say are brilliant. Is there any kind of formula or any kind of context that I can follow, so I know I’m asking a quality question versus a dumb question?

Deb Calvert: Well quality questions, they do have a few criteria. One is that they’re well-constructed. If they’re close ended like the one that you mentioned a moment ago which has a yes-no answer, they’re close ended on purpose, you’re just looking for that initial reaction. Did it meet your need, yes or no? Follow up question, why? That’s open ended, it’s going to be higher value because it gives somebody an opportunity to think, it gives them a way to be engaged. Because what buyers really really want, they want a two-way dialogue. They, they’ve told us this in research. They don’t want to just be given a set of survey questions, like so many qualifying questions for example might be. But it’s got to be open ended if you’re going to truly engage them. Another thing that might make it a quality question is that if it goes beyond the obvious.

Deb Calvert: So, there are three types of questions that are really obvious in sales. Every buyer knows them, they expect them. Those are the data questions, the questions around what are your needs or goals and the questions around your pain points. But there are actually eight purposes for asking questions, and those are only three. So, let’s call those the three that are obvious to your buyer. That gives you five others that are less obvious that are going to be more interesting to the buyer. And Darryl, you also nailed one of those other five. You asked a question which was, what did you think about our content? And that’s a question that surprises a buyer because they don’t expect it. That’s what we call an issue question in our discover acronym.

[bctt tweet=”Every buyer knows them, they expect them. Those are the data questions, the questions around what are your needs or goals and the questions around your pain points. ~@PeopleFirstPS #SocialSelling #SalesGoals ” username=”VanillaSoft”]

Diagnostic versus Dialogic Questions

Darryl Praill: Right and that’s to me, you know, I ask that so I’m not nearly smart enough to put it in the framework you put it in. But I ask that because I genuinely want them to engage with me, I want them to know that I’m seeking their opinion. I’m not trying to pitch them something, although I do want to have conversation. I do genuinely want their feedback and that helps me build rapport and trust. So, that’s a big part of that. Now you, you mentioned something just a second ago, I wanna jump in on, you said buyers want a two-way dialogue. And then I know when I talked earlier, you talked about the difference between dialogic and diagnostic, niche assessment. So, help, let’s drill down a little bit on what you mean by that.

Deb Calvert: Okay so, diagnostic, that’s what needs assessment or needs discovery, has historically been and I think it’s frankly gotten even worse because we’re all so pressed for time and we’re just racing to cram in as many questions as we can. So, we’re just looking to ask few questions, enough questions, to see if we can diagnose the problem and then give a solution. And I see it as going to a doctor, when you walk in and you’ve got three or four things you wanna talk about but they come into the room, they’ve already got their prescription pad in hand and as soon as they ask you two or three questions, they’re writing out some painkiller prescription that you don’t even want, you know?

Darryl Praill: Yep, yep

Deb Calvert: So that’s diagnostic and buyers feel corralled, they feel minimized and it feels impersonal to them and that’s all there is to it. Not only that but you can leave so much on the table if you just pounce on the first hint of a need. There’s a lot more that you might miss out on. So, dialogic by contrast, that’s a needs discovery process where you are facilitating a two-way dialogue. You’re asking bigger questions, maybe even fewer questions but you’re yielding the floor to the buyer because they’re thinking they’re sharing that process of thinking and sharing just like you mentioned.

Deb Calvert: That’s bonding, that creates trust and for people who that sounds a little strange to, let me just say it this way. If you think about the person in your personal life, whoever it is, the person that you trust more than anyone else, think about the conversations you have with that person and you’ll soon realize that yeah, they do, they ask you more questions. They ask you some of the harder questions and they yield the floor so that you’re the one who’s sometimes doing more of the talking. And that creates trust, it’s human nature.

Darryl Praill: You talked about the whole, you said, kinda basically you ask questions and then basically you were saying, shut up. And, and that’s one of the things I see happen over and over again where it’s a mistake people are making. You’re asking questions because you wanna give your response as opposed to asking your questions to listen. And the biggest thing I’ve seen is, ask your questions and explore, drill down, you know, make notes of when you want to circle back. But, but this initial point here is not necessarily so you can say oh, oh you’ve got that problem? Well our product fixes it. No, no, no, no, that’s not where were at yet. So, we’re going to come to that in a second because I know you have an opinion about qualifying versus needs discovering. The second thing is, you eluded to something here, and I wanna drill this, pull this out of people a little bit.

Darryl Praill: Remember, the whole purpose of this call, asking these questions, every call, is to make sure there is a reason to have another call. You don’t need to get everything out of the way in this call. This is not a one and done, typically. This is part of a process. So, you know, pace yourself. That’s the other thing you know, use the timing as a strategic. Yes, I get it, you’re hungry, yes you wanna close the deal. But do you wanna lose the deal?

Darryl Praill: It’s kinda like fishing and I’m not even a fisherman and I know this right? You bring the fish in when they bite slowly, you don’t just, you know, go for all like a bat outta hell cause nine times out of ten, you’ll lose the hook, you’ll lose the connection. So, you wanna do this very intentionally. All right, we’re going to take a quick break because I did leave a teaser there, the difference between qualifying and discovering and when we come back, I’m gonna have Deb answer that. Stay tuned, we’ll be right back.

Darryl Praill: All right Deb so we are back. We teased our audience when left about the difference between qualifying and needs discovery. So, when I hear that at first blush, I think they’re the same, are they not?

Deb Calvert: They are not and if you’ve got a list of questions that you’ve been handed, here ask all of your prospects, your leads these questions. Chances are that at least half of those are qualifying questions. Here’s the difference, qualifying questions are self-serving. They tell you whether or not this person needs to talk to person A or person B inside your organization. They tell you whether or not you’ve got the decision maker.

Deb Calvert: They tell you what the budget might be, these are questions that help you figure out whether you can or will want to do business in the future with this individual. That’s completely different from the needs of the buyer. Needs discovery is about discovering what their needs are. Qualifying questions are making sure you’re needs get met. And it’s really important to understand the difference otherwise you’ll have an imbalance and you’ll disenfranchise the buyer.

Darryl Praill: That is, here’s the thing, I’m pausing because, let me share. When I, when you the sales rep are calling me and you ask the questions, I know there’s a set number of questions that you need to ask to qualify me. Actually, I’m not stupid, I know that, I’ve been down, I’m the guy with the money and everybody else who has money and you’re targeting, you get the same calls I get. So, it’s not like this is just unique to Darryl, every buyer is in the same boat. We’re not stupid, we get it. And most of us are willing to indulge you a little bit to do that. But when you only ask those transactional questions so you can see if I’m a fit for your pipeline, your opportunity or not, then it feels like a transaction and already I feel like I’m just a deal to you and I’m looking for a partnership, not a transaction.

Deb Calvert: If you wanna try, I can buy a product like yours from another vendor, I’m pretty confident nine times out of ten I can. So often, assuming your product is good, and it solves my problem, the way you’ll win this deal is by actually having a relationship with me. So, the questions to your point Deb, about actually asking qualifying questions, not just discovery questions, both. And understand the difference is huge so that’s what will set apart the relationship. That’s for me at least.

Deb Calvert: It is and there are just different ways that you can handle that. You just have a little finesse instead of drilling down this list of ten questions rapid fire, boom, boom, boom. How about we incorporate some natural follow ups, we stay in the moment, we listen to the emotional tone that comes with the response and we make it more conversational, more dialogic, instead of feeling like it’s some kind of a census taking.

What are those Sales Questions that Add Value?

Darryl Praill: That’s brilliant, that is so so huge. All right now, one of the things we haven’t talked about yet is how, if we do our questions right, they’re well crafted, they’re thought provoking, that that will actually get email and voicemail replies. So, talk to me about that because right now, for the most part we’ve been talking about having a live conversation, one on one. But email and voicemail reply, we haven’t talked about the email or voicemail. So, drill down a bit on that for me.

Deb Calvert: Well questions captivate people, they capture people’s attention and they make people think, no matter when they come across the question. Questions have a way of rattling around in your mind until you come up with the answer. And whoever you associate with that question, the book you read where the question was posed, the commercial that made you think or the person who sent you the email.

[bctt tweet=”Well questions captivate people, they capture people’s attention and they make people think, no matter when they come across the question. ~@PeopleFirstPS #SalesTechnique #SalesProspecting” username=”VanillaSoft”]

Deb Calvert: Whoever is associated with that question is more likely to get your ongoing interest, right? They might want some more of that so, it’s not that somebodies going to read your fabulous question in an email and feel compelled immediately to reply to it but the chances that they will reply at some point are substantially higher if you ask a really good question. So why not, why not put a great question in the subject line or in the first paragraph of your email. What do you have to lose? And doing some maybe testing to see if that doesn’t work out.

Darryl Praill: So now is, is, on that side, do you frame the question differently in email versus what you would during a live conversation or in voicemail? Or is it the exact same formula?

Deb Calvert: I use very similar questions. But I’ve been doing this a long time, so I know how to be really concise and to the point with my questions. If you’re going to put a question into an email, of course you want it to be hard hitting, you want it to be short and you want it to be relevant. So, I can’t give you a question that’s going to work for every single buyer in every situation. I’d be wealthy and retired by then if I could but if you were doing some research and [bctt tweet=”had the intention to personalise what you put out there, you’ll soon get good at putting questions out that do capture the attention of any buyer ~ @PeopleFirstPS #SalesEngagement #SalesDevelopment #SalesTips” username=”VanillaSoft”].

Darryl Praill: Okay, so now, I began the whole podcast talking about how I was doing a best of recently and that compilation. And that talked about, that lead me to believe, I actually pulled out five of, podcasts that jumped out to me. And that was for those who listened to us regularly, that was the most recent podcast, so that’s kinda cool. So, it’s top of mine. So, if you heard that one, either one of the things I talked about, number one, the first best that I talked about was the assessment I did with Andy Paul. And we talked about, you know, learners equal earners. If you invest in yourself, you will physically earn more money because you can develop your own skills.

Darryl Praill: Now, building on that, you’ve heard Deb talk today about, for example how she talked about the eight different kinds of questions as one reference and about how email is perhaps a little bit different. But there’s a lot of overlap from voicemail from phone and about how I have diagnostic versus dialogic and all this wonderful stuff. And you’re going on myself, I love it, but I need more samples. Well guess what, here’s your chance to learn so you can earn. Deb, I’m looking at Amazon right now, but I know this is on your own website too, Discover Questions Get You Connected for professional sellers. It’s guys, it’s four and a half out of five stars on Amazon. These things been elder kicking butt for a dogs age. But again, it’s also on your website too, So, talk to me about the book, because I love this, you talk about discover, D-I-S-C-O-V-E-R, each of those have, it’s an acronym. So, if I’m listening to this, is this book something I should make an investment in.

Deb Calvert: Absolutely because there are tons of questions in that book. The book was written based on 20 plus years of research with buyers. I interviewed buyers after sales calls that I had observed and also with then salespeople, some before training and then again after training to see how their questions improved. So, it’s a tutorial on all the things that help you to craft a good question, how questions build trust but then it’s loaded up with lots of sample questions. It does not have a list of questions; you’re not buying a list of questions that you can copy paste and expect that to do the magic.

Deb Calvert: It teaches you how to be a good question asker in a situation, so that you’ll be more effective. And it’s worked and I love that almost every week, even still, seven years after the book was released, I still get about, once a week, an email from someone saying this changed everything for me. And I think that’s why it makes lists like the top 20 most highly rated sales books of all time. So, it’s, it is, I think it is worth the investment over on Amazon.

Darryl Praill: And it’s all, I’ll draw a parallel here, a parable I guess here right. The classic metaphor if you will that said, teach a person to fish, they’ll eat for a day. So, if she would have given you questions, you would have used them, you know, once. But teach them how to fish, like this book teaches you how to ask questions. Then you’ll fish for forever and eat well. So, with that, I rarely give you folks a call to action. Today I’m giving you a call to action, invest in yourself, do this. You’ll thank me, you’ll thank Deb, go to Amazon, go to her website. It’s called Discover Questions Get You Connected that’s with Deb Calvert. Deb, if they wanna reach you, talk more to you directly, to connect, to learn from you, what’s the best way to do that?

Deb Calvert: Well please do, get together with me on LinkedIn that way we’ll be in touch all the time. But email me, if you have questions that really work for you, I’m a collector, I would love to hear about your experiences. And if you’re struggling well, email me too. I don’t mind giving you a little free coaching or a sample question or two. That’s a wide-open invitation, I’m not afraid even though I know you have a giant audience and do lots of promotion Darryl. That to me is what this is all about, so I welcome any questions.

Darryl Praill: And that’s why Deb is here folks right? It’s about giving back to the tribe. I preach it, you just saw her living it out there, physically saying yeah, I could be overwhelmed but I would love to help you folks out. That’s what we’re about, that’s what makes Inside, Inside Sales so fantastic. I hoped you enjoyed today’s session, thank you so much Deb. In the meantime, folks, we are done! At least for another week, you take care! We’ll talk to you soon! Bye, bye!