Asking leading sales questions is a great way to get to know your prospects, but do you know how to build the right framework around those questions?

In this episode of INSIDE Inside Sales, Darryl and Scott Kaplan, the rockstar sales coach with Quick Hit Sales Tips discuss the power that effective questions can wield and teach you how to dig deeper during discovery. They will also share valuable advice on how to craft the questions you need to be asking, show why pitching must come later in the process, and share Scott’s unique “F-A-C-T” discovery process for getting the quality information from your prospects. Subscribe now and learn how to close more deals by asking the right questions.







Host: Darryl PraillVanillaSoft

Guest: Scott Kaplan, Quick Hit Sales Tips


Welcome Scott Kaplan

Darryl Praill: Hello, everybody. Welcome back to another episode of the INSIDE Inside Sales show. Yes, it’s true. I still love saying that. And the best comment I ever saw posted online was somebody made a point of trying, it was on Twitter, of doing the whole INSIDE Inside Sales. And they made sure the capitalize the first word and then just sentence case the rest. And then they stopped. And they said those who know, know. Meaning when you read that it’s in you’re head, you’re sounding just like me.

Darryl Praill: So by all means, I want you just to hear my voice every time you read that online. Welcome back. How’s your week been? Are you hitting your numbers? Have you hit your quota? Do you still hate your sales manager? Do you love your sales manager? I just got off a panel not too long ago. And it was a really interesting conversation. I was on a panel with my counterparts from Zant and Drift, and ZoomInfo. And we were talking about the whole idea around playbooks.

Darryl Praill: And it was really around… come up on this tangent around activity versus outcomes. And it was an interesting one because as we’re talking about how do you do a playbook, or how to, is it still relevant and what makes it not relevant? And what do you need to do to make it relevant? And how do you optimize it and blah, blah, blah, blah, blah, blah, blah, as you might imagine. It was a lot of people in the peanut gallery were basically everybody who wasn’t on the panel were saying, yeah, you do when you’ve got a management who’s just hammering you to hit activity numbers. You have to spam, you have to not personalize. You don’t have time to research. You have to go.

Darryl Praill: So we got in this whole tangent of research versus, I’m sorry activity, are you measured by your activity or are you measured by your outcomes, outcomes being, you got appointments set and you had conversations had, whatever it might be. I’m a big advocate of outcomes, but of course you have to do activity to achieve outcomes. That’s the little fine line that gray area. And what I find works best, and this is where the segue, so because we also got a conversation around, well, how do you achieve outcomes? And that was the whole idea of automation versus personalization, as it relates to playbooks.

Darryl Praill: And automation, meaning just set it and forget it. And you’ve just got all these canned email templates or social media touches that go, and you don’t change a damn thing, but personalization, meaning you actually stop and you actually personalize it. And then that got to a conversation. Well, it’s well, how much can you personalize it? If you’re trying to balance activity versus outcomes.

Darryl Praill: And it truly is a balance, if you didn’t. I don’t have time to spend 10 minutes to research every single outreach, that’s a tough one. And I like to believe that a simple way to personalize it is to actually ask questions that are relevant to your ICP, your Ideal Customer Profile and your persona, or the role of the job title, wherever it might be. So for example, if I’m gonna playbook that’s segmented by my ICP, maybe it’s somebody who is insurance and an insurance agency between 10 and 50 agents. And they sell life and health insurance throwing it out there.

Darryl Praill: And then my ICP could be an actual agent, and I’m sorry, my persona, it could be a natural agent, or it could be the managing director of the office that manages the whole team. The questions are very different who I’m talking to the owner of the team or the agency is gonna be, are you tired of buying leads and your reps don’t follow up on them? Are you tired your leads are not converting. Are you tired of your reps being afraid to pick up the phone or to not use social media? When was the last time you were a reps updated LinkedIn or used Facebook?

Darryl Praill: All right. If I’m talking to the reps, it’s going to be, are you just tired of your boss hammering you and would you like to actually be a lot more productive so you get them off your case? Do you find it hard to manage your time? Do you wish you could do multiple touches, but you struggle with this? What if we could make it easier for you? So in the end, what you’re seeing I’m doing there is I’m asking a lot of questions and the questions are twofold.

Darryl Praill: Part of it is me qualifying part of it is you doing a little discovery, right? That’s the first part of it. Part of it is those questions are what you’re using to actually personalize it. So if I know I’m reaching all these insurance companies in the state of Florida, I can actually put questions in there that are specific to this moment of time. Isn’t it crazy what’s going on down there in Miami Beach right now? That’s a comment and then away I go. All of this comes back to the reason you do what you do, which is you do it to have conversations. And when you hook them, you gotta hook them from a relational point of view.

Darryl Praill: And then you gotta hook them from our point of view, you gotta hook them and yet you get them live. So you hook them to reel to get them to nibble. And then you reel them in and you get them live and you gotta carry on that whole conversation. And you gotta do it with questions. And it brings me back to when I had kids and then my kids are older now, they’re in their 20s. But when they were young, man, did they ask so many questions?

Darryl Praill: And I know a lot of you right now have young kids. And you know. The thing about kids is they’re the best fricking sales reps ever. ‘Cause you know why? Because when they’re young, when they’re a toddler, what’s the one thing they ask you over and over and over again? “Why?” “Don’t do that.” “Why?” “Don’t touch that, it’s hot.” “Why?” “Get dressed up we’re gonna go out.” “Why.” “It’s cold outside today, you need to put your boots on.” “Why?” I mean, the list goes on. It’s nonstop fricking why.

Darryl Praill: And you get exhausted. But you know what they’re doing? They’re learning from you. They’re asking those questions to learn from you. You to channel your inner toddler. That’s what you need to do if you wanna be successful. If you wanna engage, you wanna have playbooks, you got to channel your inner toddler. That’s my point of view. So I thought to myself, how can I do, how can I bring this conversation to you with an expert? And then I thought, Oh my gosh, Scott Kaplan.

Darryl Praill: Scott Kaplan is the guy. Scott Kaplan has trained over 15,000 sales reps. He’s trained over 5,000 sales managers. He is all about helping sales teams, double and triple their bookings. He does it with sales tips. He does it with professional proven techniques. And most of all, he does it a lot with questions. Scott, welcome to the show, my friend.

Scott Kaplan: Well, I thank you, Darryl. It’s good to be on the INSIDE Inside Sales.

Darryl Praill: I like it. Those who know.

Scott Kaplan: With that voice of yours, it haunts me at night and I love it.

Darryl Praill: You’re far too generous. Now for those who are multitasking, you’re at a computer you’re listening to this, He is on LinkedIn and it’s, it’s the classic Kaplan. And that’s Kaplan with a K.

Scott Kaplan: Yes, sir.

Darryl Praill: So that’s the first part. You should follow him now, just do it.

Learning How to Ask the Right Sales Questions

Darryl Praill: Scott, talk to me about the power of asking questions. You’ve trained all these sales reps, you’ve trained the sales and managers. What is it you’re seeing with the power of questions? Are we doing a good job of it? Are we not doing a good job of it? Are we flubbing it? Like what is it you’re seeing?

Scott Kaplan: Sure. So a huge passion of mine is talking about questions. And I love how you talk about this idea of how we start to ask all these questions when we’re kids. Why, why, why or what does that mean? Or how are you doing that? And all those different types of curiosity style questions. And I think as sellers, we have forgotten that curiosity, and we were so quick to pitch and, Oh, we’ve heard something that we can go out there and solve, I must tell you all about it.

Scott Kaplan: We forget to take that step back and really make sure we understand what we’re trying to solve and help the customer understand what they need to solve. We’re experts in what we do. We talk to more of our personas than that persona talks to the like personas. So if we’re going out there and talking to a CFO, we talked to CFOs all day, every day, CFOs don’t. And so we have to ask a lot of questions to really get into what we can do and how we can help solve them.

Scott Kaplan: And so here’s a couple of things I think people do fairly well, right? Sellers do a pretty good job of understanding the different dynamics of the fundamentals of the business. There’s a lot of good questions where people get data in history. And I know you and I have talked about some of the things I threw on LinkedIn, but I have this kind of questioning process, this discovery process to get the facts, right? The facts that you wanna go out there now.

Scott Kaplan: And I haven’t even named it that it’s an acronym, F-A-C-T and that first letter F of fundamentals of the business, I think sellers do pretty good. What do you do? How do you do it? How often does it take? How long does it take? All those questions that give you data, history, the environment in which you need to understand. I think sellers do a pretty good job, and whether you’re selling technology or you’re selling services or something else along the lines, sellers do a pretty decent job with them, but they tend to stop there and they don’t go deeper into what they really need to go out there and understand that will get a client to move forward. But the fundamentals to help frame the need, help frame the problem, help frame the situation, I think for the most part, sellers do a pretty good job.

Darryl Praill: So, okay. So you’re asking a really valid question. Let me flip it back to you because you know, those will listen to the INSIDE Inside Sales show are a combination, mostly of sales development reps, and account exec so SDRs, BDRs and AEs. And there’s this age old conversation about how many questions do I ask as an SDR or BDR in the qualification stage versus how many questions do I ask as an account executive in the discovery stage? So you mentioned facts. Do you see a facts, sorry, do you see FACT, do you see that as more of an SDR BDR thing? And then and that’s not a sales framework, or do you see that something that both roles would use?

Scott Kaplan: Definitely both roles, but I love how I know we’ve talked about this too. How the breakdown of the difference between qualification and discovery, and I like to define qualification as, what do I need to know to determine if this is an opportunity that I wanna pursue or not. And what are the high level information? And I kind of break that down across three major categories.

Scott Kaplan: And so the first one is about the account. What do we need to know about the account? And you mentioned ICP, are there in a industry or vertical that we wanna go to, or a certain size that we wanna be able to go out there and attack, or certain geographic location, number of employees that they have, those types of information, a lot of that, you might be able to find out online or through different research tools and have that capabilities, but you wanna make sure you understand that the right type of company to go after. Then, the second thing is the contact. And when you qualify, you wanna make sure you understand who that contact is. Yes, their name, their title, their role.

Scott Kaplan: And a lot of people laugh at me for those things. Of course, Scott, we’re gonna know those things. Well, let me just remind you. We used to go to this thing called trade shows and some great looking guy with white hair and a black blazer to walk up to you. But I don’t know his name is Darryl. I don’t know where he works. I don’t know what his role is.

Scott Kaplan: And so I like to make sure that we always understand what we need to go out there and do. And if you can research it great, but you also need to understand more about that contact besides just their name, title, and the role, what’s their involvement in the decision making process, or the investment process, or the research process, and understand who else is involved within their team cross functional teams. So you wanna understand the degrees of the contacts.

Scott Kaplan: And then the third piece for qualification is the need. Now, this is where you’re gonna start getting into more, that FACT-based items, but you need to understand why did they pick up the phone when you call them? Why did they reach out to your website and request information? What is it they’re looking to solve? Is there a compelling event? Is there something on their plate that they need to solve in the next 30, 60, 90 days? You need to understand the difference of what, why they are intrigued to talk to you and learn more.

Scott Kaplan: And that’s what we need to do from a qualification. So SDRs out there, BDRs out there, anyone doing cold calling and prospecting, those are things you definitely wanna go out there and think about. But then as you really get involved into your discovery calls that first real initial touch point, and if you’re selling technology, you might do kind of a teaser demo I like to call it where you show a little bit of this sizzle, but you gotta use that sizzle to really get in depth and discovery questions.

Scott Kaplan: And that’s why I created FACT, is a really help go deeper into that discovery process. And so I know we talked about like the fundamentals, but the A being the ability to move forward, the C being their commitment to be able to go out there and move forward, right? Their commitment to change, their commitment to do something different. And then the T is just their timing and prioritization. How important is it to them or other cross-functional peers that have to approve it or do something with it to install it, implement it, adopted, et cetera. I’ll give a kind of a little story, you mentioned earlier in your opening monologue about how you’re on a panel today, talking about customer outcomes.

Scott Kaplan: And I love that idea. Or you talking about actually internal outcomes. And I wanna talk about how do we talk about customer outcomes and that whole idea of commitment to change, it’s about understanding the impact that what we can do has on their business. So imagine asking questions. So Darryl with your current sales team at VanillaSoft, what’s impacting you from being able to not just reach the clients that you want, but be able to engage them in a way to get them to listen to you versus your competitors. That’s an impact style question that will get you to talk deeper. Talk about the outcomes you’re trying to go out there and do, what’s hindering your team? What’s limiting your team?

Scott Kaplan: If I’ve shown you some value out of what I can do, I might change that question around and say, how would you be able to use that in an environment that would help make your team more successful? You’ll be able to gain more, attain more, benefit more so you can use two sides of the equation. You can make a column on that negative pain side of things, using words like impact, hinder, or limit effect, or it can do it on the positive side. What can you gain, achieve, benefit, grow, all those different ways to look at what is that customer gonna commit to, to get the outcomes that they want.

Darryl Praill: All right. My mind is racing, which is why I’m pausing. I’m writing down a thousand notes because you’re saying a whole bunch of like hot button tickets for me. It’s almost like, where do I start? We’ve talked a little bit about the role of SDRs, BDRs and AEs, but there’s also many industries where that doesn’t exist. That’s just full cycle sales reps, right? So I get it for the full cycle sales rep, they’re gonna qualify and discover, and it’s just gonna kind of flow from one to the next.

Darryl Praill: But for the organizations where they do have that split between teams, I would love to ask you this question, which is a little bit more of a management conversation, but I think my audience would really benefit from understanding where their managers are coming from. So when you’re training managers, the age old dilemma, at least I always found this, how well do they understand that there’s a qualification stage and that there’s a discovery stage, and it’s not just a drop down you pick on a sales opportunity in

Darryl Praill: There’s an actual different approach and conversation that takes place and an expectation around what the outcome is to achieve at that moment in time before you progress to the next stage in the sales cycle. Because what I see is most sales leaders confuse the two and they don’t… they’ll talk about qualification and discovery, but you ask them, well, how do the questions differ? How do you engage? And how does that differ? They don’t have an ability generally to clearly articulate that they don’t understand it. How the hell can you expect your SDR, AEs to understand it? And if that’s the case, then I’ve got confusion.

Darryl Praill: Am I over qualifying as an SDR, or am I under qualifying as an SDR? And am my meeting my AEs expectations of that work I’m supposed to do for them, or am I not meeting their expectations? So I know it’s a broad question, but I would love your take on that.

Scott Kaplan: Sure. I’m 100% in agreement with you. I see it all the time and not just the frontline sales manager level, but I would say all the way up the chain or out there and try to do, and it doesn’t just stop there, I’ll even take it to two degrees further. Whoever touches the customer even post-sale right. So if you have an implementation team or adoption team, a support team, a customer service team, an account management team, whatever the case may be, everyone’s involved at one retain and two, try to grow that customer with add-ons and expansion.

Scott Kaplan: And all of those types of questions on what you want to go out there and do are critically important. And we often forget, I was just talking to professional services leader for one of my clients, and I was talking with him about, and I asked him, “How good are your team at being sellers?” And he smiled at me and kind of nodded, we’re not. And when we’re trying to go there and they have great relationships and great rapport, and they understand not just the needs of that business, but I have other professional sales teams to understand the global aspects and the amount of information that they can provide is endless.

Scott Kaplan: And they don’t know to ask questions. They don’t know how to take even the information that they have to get it back to the sales team or the account management team to grow the account and to retain the account. And it’s a huge miss that I see across every aspect. There are few that I think get it when I first started talking to them and I started talking about sales playbooks, or sales process, or how do they really not just focus on net new, but land and expand type of capabilities. They miss that very often, like you said.

Scott Kaplan: And so I’ve done a lot of work with people to understand the difference between the types of questions. So you know what you wanna go out there and ask. And I think you mentioned earlier, we can ask questions and questions and questions and go on and on and on, but you have to be real sharp and precise and strategic with what you wanna go out there and ask. There’s a time and a place you wanna go out there and really drive those types of questions.

Scott Kaplan: And it doesn’t have to be overly complicated, but if you don’t prepare the questions in advance that you wanna go out there and ask, shame on you, you should. Now some people have it in a sales playbook or qualification checklist. And I know that when I go out there and ask, and then what they’re good at is doing other things that you said earlier, targeted to that persona and make it relevant to that person or that industry or that geographic location, or, or, or, but the idea of being able to know how to leverage that is critical and so often missed.

Darryl Praill: So there’s a number of bad habits I see my team do, I see others in the industry do, that undermine their ability to ask those questions and get the information to move it forward as you’re talking about with FACT. And in no particular order one of the things that I see is we wanna rush right into our pitch as opposed to ask and ask and ask, all right, so we just wanna talk, first part. Number two is, before even that you mentioned it, we don’t plan our call.

Darryl Praill: For this individual we’re about to talk to in their industry with their role, their title based on, as you said, their vertical, their location, their size, all these factors and attributes you were describing earlier, what are the right questions and outcomes and issues that we should be poking at before we even have the call? The next thing I see is a lack of patience. I really don’t, I’m gonna ask you why, because I’ve been taught to ask you why, but I really don’t wanna get to the why, because I’m measured on activity and appointment set.

Darryl Praill: And as soon as you’ve fit, like for example, “Oh, you have a need, there’s something you want to achieve? Let me book you for my AE so I can get rid of you. ‘Cause I got a number to hit.” Meanwhile, this person’s opening up with you. That’s a problem. So lack of patience. And the last thing I see it over and over again is as you alluded to already, and this is a big one is making it relevant. So I get reps calling me all the time talking about, cause they go into the pitch. This is what we do.

Darryl Praill: And the problem with going into the pitch right away, as opposed to talking to me is I have no idea how it’s relevant to me. But if you would’ve talked about and ask me some questions to say, if I have some certain pain points that have me admit to you, I have this pain I’m trying to achieve this outcome. I’m being blocked by these roadblocks and I need a solution. Then I’ve got relevance when you say, well, okay, based on that, you know, if I had a solution that could help you overcome that by doing this, would you want to learn more about it?

Darryl Praill: And by the way, your competition is already using it. And I can tell you more, I can tell you exactly how they’re using it. Okay, I got relevance, both in a pain and relevance and a competitive situation. You’ve got my attention. So I see it over and over again. Lack of planning in the call, lack of having patience, they would just wanna talk, they don’t wanna listen. They wanna go right to the pitch and they wanna qualify you right away. And they don’t want to make it relevant to you because that’s too much work. At that point in time, all of your questions that you’ve been programmed to do that guys like you have come in and said, you gotta ask these questions, just go out the door.

Scott Kaplan: Out the door. Out the door completely. And it’s funny, you talked about the patience aspect. I’ve always called it kind of having happy ears. That is sales. Oh, you mentioned something. Yeah, I can go out there and do it. And so oftentimes when I talk with different sellers and it’s funny because I’ll bring it up as the idea of it’s actually, you mentioned the word roadblock, but I’ll call it an objection was for common terms here.

Scott Kaplan: Let’s say, Oh, does your product do X, Y, and Z? And if it does, Oh my gosh, we’re so happy! Yes, Darryl! Let me tell you all the ways that I can’t wait to tell you. But what we need to do to leverage that patience, to not have those happy ears, Darryl, we do, but I don’t wanna make an assumption that I know how to work for your environment. Can you tell me a little bit more? What is it you’re not able to achieve today that you really want to, so I can make sure I answer your question specifically. People don’t take that step back.

Scott Kaplan: And if you look at the casualness of that question, look at what I did “that you’re not able to achieve today” will speak to your pain. Well, how important is that to you? That speaks to the prioritization. Is it important than others? You can get so much more in depth and imagine a customer gives you an objection. Like you mentioned those questions earlier, like the whys or how we do that.

Scott Kaplan: And because I don’t think we necessarily need your type of solution, that’s interesting cause I’ve talked with a lot of people in your industry a lot, I know your types of roles. I’m just kinda curious, how do you guys want out there and solving that today, mean with regards to, and then you can enter a couple of specifics if you wanna throw some value points with regards to getting your team up to speed, being sure that you can have great onboarding and then great ramp to your sellers. Darryl, how are you achieving that today to make sure you’re not missing something? You can still leverage these questions to overcome objections.

Scott Kaplan: And so what we wanna do is really get in depth and it’s so common that we do all of those types of items that you mentioned where we don’t prepare, or we don’t necessarily know what exactly we wanna go there and ask or how to make it relevant to the customer. And there’s just some great opportunities. And I totally agree, kids are fantastic sellers. I got some that are in college and then go from there.

Scott Kaplan: But I got five kids in a blended family from age 15 to 22. And I loved watching them as they were younger get really, really good. I know which some of my kids will be great sellers just by how they engage with different types of questions. How do you do that? What does it mean? And when they start to engage, they get people to talk. And the questions always go more in depth and the conversation always goes more in depth. I don’t care if it’s a business conversation, a personal conversation, but anytime you go out there and you ask those types of questions, you get more information that you can continually use and leverage to help that person be more successful.

Scott Kaplan: And I believe in 100% ethical sales and making sure that the value I provide, if I’m not a good fit for you Darryl, great, let’s remain friends. Maybe I can help you with other contacts or other people go on your merry way. But if I can help, I wanna make sure I know that the layers of which I can go out there and help. And here’s here’s another trick that I’ll give all the sellers out there.

Scott Kaplan: Imagine you finish that conversation and you’re gonna send a followup to that customer. You’re gonna say, “Thanks for talking about this. I understand that we’re helping you with regards to…” How would you finish that sentence? Do you know what you want to go out there and in that help you ask the questions, but it also help you make sure I don’t finish my conversation until I know those things. In every discovery call that I have, I have a note section where I look at impact is how I label it for my own kind of cheat sheet in my notes.

Scott Kaplan: And I also look at prioritization, timing and prioritization. It’s my fact process. I obviously have questions on the fundamentals of what we’ll go out there and do. But then I start going into, I know I’m gonna ask about their decision making process and what’s involved next. They say, “Hey, Scott, send me some pricing.” I can definitely go out there and do that for your Darryl, then what’s next? Help me understand, what do you guys do with it from there? I don’t get the happy ears of “Oh, Darryl wants pricing, sure.” Okay, great Darryl, so I can go up there and get your pricing then what comes next? What are you gonna do with it?

Scott Kaplan: So I understand you’ve got to have what’s important to you, how you leverage others so I can make sure it gets to the right information. Just go deeper in those conversations.

Darryl Praill: Mark Hunter has an expression of you ask why three times, most of us stop after the first why. So I love the example you were giving. In my case, I imagined if someone were to call me, they would say, “What’s your biggest problem?” My biggest problem is my reps aren’t making enough outbound dials and outreaches. Great! You’re gonna love our product. Our product does this and this and this and this. And it’s all about making more outreach. You will have your time, patience here kids, to have that conversation. That was only the first, we haven’t even asked, what’s your problem? We haven’t got to the first why. They’re not making enough outreaches. Why?

Darryl Praill: Okay, impatience, well, because they don’t know how to prioritize themselves. Well, why don’t they know how to prioritize themselves? Well, because they’re, I guess we don’t have a repeatable process that we rolled that out. But why is that? Well, we really suck at sales enablement. We’re winging it, we’ve had turnover. Oh, so maybe the issue isn’t they’re not making enough dials, maybe the issue is you don’t have the infrastructure to actually have a repeatable process. You see how it changes all of a sudden, that’s why you do the three whys.

Darryl Praill: Let’s just one example, too many of you rush to that. What I like about today’s conversation, folks, Scott and I didn’t talk, and Scott’s the expert here, but you know what? We need to actually tell you what questions to ask. What we talked to you was you gotta be asking questions. You need a framework around the questions you’re gonna ask, because if you do that, it’s as he said, the whole point here is to move this deal forward to the next step. So to do that, you need to understand what’s kicking you in the ass. You need to understand what your process is. You need to understand what your role and responsibility is.

Darryl Praill: Maybe you’re the SDR or the BDR versus your counterparts role and responsibility, because you’re actually a team. All right? You need to understand the big picture, just like your prospect needs relevance and context, so do you. And now all of a sudden, when they come back to you and say, “We want you to follow the sales framework, we wants you to do these things?” You will understand why, and then you will adopt it. But for the love of God, don’t make these obvious mistakes that you were all making over and over again. So without judgment, truly without judgment. Ladies and gentlemen, this is my good friend, Scott Kaplan. He’s on LinkedIn. You can check him out at He’s prolific in his content. Scott, thank you for joining us today.

Scott Kaplan: Thanks, Darryl. Thanks everyone. Make it a great day. Good selling.

Darryl Praill: And with that we’re done, another episode in the books of the INSIDE Inside Sales show. Take care folks. We’ll see you next week.