INSIDE Inside Sales – Ep 52: Asking the Right Questions

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Have you ever stumbled when you’ve finally been able to speak to a prospect in the C-Suite? Were you intimidated by their position of power and it threw you off enough that you botched your pitch?

In this episode of INSIDE Inside Sales, Darryl speaks with the brilliant Matt Reuter, Sales Development Leader at GTT. Darryl and Matt discuss the importance of being able to craft the right questions. They go over ways to avoid getting simple yes or no answers, and how to create the proper structure for questions that will bring you nearer to closing those deals. They also talk about important tips such as the value of listening to your recordings, as well as deftly handling objections with questions that keep the conversation going. It’s all 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:  Matt Reuter, GTT

 

Darryl Praill: Welcome folks, to another episode of INSIDE Inside Sales. As you may or may not know, we recently crossed the 50 episode marker. And that was pretty significant. The show began, I don’t know if you know this, the show began with us just doing kinda like, one podcast a month. And we’re just squeezing it in, there’s somethin’ to talk about. And then over time, we’re gettin’ some feedback from people, internal, external, you guys, and you were like, “We want more.”

Darryl Praill: And I’m like, ugh more? My schedule’s already busy but I was havin’ so much fun I’m like let’s do it. And before you know it, the shows just go crazy. And the numbers have been fantastic. We watch the numbers continue to go up and up and up. I continue to get contacted by each of you, either giving me crap saying, “You sucked here Praill you missed this point, “you didn’t talk about this.” Or givin’ me compliments or saying, “You know you need to have people on your show, “on a regular basis.”

Darryl Praill: And in fact today’s guest we’re gonna get to in a little bit was the result of a recommendation. And in fact I got another one this morning and I’ve reached out to, so you know what’s really cool about this community that you and I have with one another and our colleagues, is it’s a show for us by us. That’s how I kinda view it. So, if you’re a long time listener thank you so much. If this is your first time welcome to the family. One request that we family members like to do with one another of course is ask us to support one another.

Darryl Praill: So to that effect I’m gonna do a little push here a little shout out. Please if you get a chance go on to you know, iTunes, or Spotify, or anywhere else, give us a like, give us a share. It’s grateful it raises us in the profile and gets us more listeners so that’s fantastic. With that, I wanna share a story. I was recently at an event where we were talking about the significance of asking questions. And it wasn’t just asking questions around things like discovery.

Darryl Praill: Not too long ago we had Randy Riemersma on the pod. If you didn’t catch that go check out his episode, actually it was a really good episode. In fact I just called it out as one of my top five episodes of the year that I loved. And, we were talkin’ about how to do discovery, which is a frame, a form of asking questions. But I was sharin’ with these people how framing questions the right way is so powerful and I had a couple different instances I was talking about. One I was talking about was a personal one for me.

Darryl Praill: It was when I’m looking for a job, it’s all about asking the right questions in the interview and you know the drill, right? Do you have any questions for us? Anything you wanna know? And you’re like no, no that’s good I’ve done my research and I know what’s the salary, what’s the role, what’s the career plan, what’s the promotion plan. You know the basics. And that’s great we all do the basics. And then what happens though as you all know, is you get into the job and you start to understand some nuances, some idiosyncrasies, that perhaps you recognize upon reflection you should have asked a few more questions. And you would’ve known about what to expect.

Darryl Praill: And then, it woulda been your choice whether to take that job, now you took the job, you’re there and those nuances, those idiosyncrasies are effecting your performance. They’re perhaps not as represented in the job interview and here you are you left and old job to take this job and all of a sudden that old job is lookin’ pretty good. It all comes down to the power of the questions. And too many of us don’t take time to ask good questions.

Darryl Praill: And there’s lots of reasons, we’re overwhelmed, we don’t wanna scare it away, we don’t wanna ruin the opportunity, we don’t wanna jinx the mojo, the good feelings, the vibes that are goin’ on. But we don’t ask ’em. Or, better yet we don’t prepare. Right, so we know in that job interview example. We know we’re gonna have a job interview, we know we’re gonna have a chance to ask questions yet we don’t prepare. We don’t go around maybe some of us do, some of us don’t ask questions of other past colleagues.

Darryl Praill: A recruiter friend of mine once gave me an example about the first thing he tells people to do is go on LinkedIn, find former employees of that perspective hire, and call them up and say, “I just wanna ask you what was it like? “What do I need to know? “Who are the individuals I should be aware of? “Who should I give a big high five to? “Can I reference your name, that we talked “together so they know I did my homework?” Whatever it might be. Brilliant advice. It’s always about asking questions. The other part I was talkin’ to somebody actually was a new hire here at VanillaSoft.

Darryl Praill: And they were in the support role. And I said, “Listen you’re gonna get some grief. “Some customers are just not nice customers. “They call you up, they’re gonna yell at you, “they’re gonna bitch at you, they’re gonna swear at ya, “they’re gonna hang up on you.” And I said, “The trick to diffusing “that whole situation is not to endure that abuse. “The trick is to in fact, ask the questions “to engage them so they feel like part of the process. “They feel like you’re actively listening.” I said, “You know your success at bein’ “a rockstar support person really comes down “not to your technical product knowledge, “it comes down to how you can connect with the other person. “It is a soft skill that you need to master right away.”

Darryl Praill: So then I had that moment, that epiphany, where you go man I’m talking to somebody the other day about job interviews, I’m talking with this person about technical support. And the overriding theme is how do you ask good questions? So then I went to my good friend Ollie. Ollie over at Creation Agency. And I said, “Ollie, I need a rockstar individual “who knows how to ask good questions.” And Ollie said, “Dude, have I got the guy for you. “You need to talk to Matt Reuter.”

Darryl Praill: Now, Matt if you don’t know him. If the name is new to you, he is the Sales Development Manager whose hitting it outta the park by the way. Ollie couldn’t stop bragging about him. He’s with GTT. If you don’t know GTT, they’re the third largest networking backbone in the world. They’re all about internet connectivity, voice insecurity, and they provide their services to Enterprise customers. So hey, you’re third largest you’re doin’ somethin’ right. So with that, I reached out to him, Matt said, “I’m on, let’s do it.” Matt, welcome to the show my friend. So nice to have you here.

Matt Reuter: Thanks Darryl, yeah it’s great to be here. I’m big fan of the show, I love just sharing all of this knowledge that I’ve gained over the years of doing sales development so I’m happy to talk.
Darryl Praill: And now as a Sales Development Manager, as someone who’s knockin’ it outta the park using Ollie’s terms. I’m guessing you’ve had a question or two in your time frame that caught you off guard. As well and it’s two-fold right, ’cause you’ve got the questions that are bein’ asked of you but then the reality is as a sales professional your whole point is to get information from the prospect. And how you frame that question not unlike the support person who needs information from them so they can fix their problem, fix their technical issue. You’re tryna fix a business issue. Were you good at the beginning when you started asking questions? Or is that gift you have, you think? One of your soft skills that you just by the gift of God you’ve got it? Or was this a skill set you had to actually work on?

Matt Reuter: So I think it’s kind of two-fold. I think I do have a natural gift of curiosity, of just trying to figure out what the person is actually saying. A lot of times it started by them giving me an objection and I began taking that objection and saying okay what’s the underlying reason of why you’re telling me you’re not interested. I’m not gonna take it at face value of what you say, I’m gonna dig into that and ask deeper questions to kinda get to the root of that.

Matt Reuter: So it’s definitely something that I’ve been working at. I had a sales trainer at my last organization. Dan Reinbold, I gotta shout out to him, Because he was just a master at this. And just teaching us how to ask open ended questions and have a goal for getting to where our questions, or a goal of where we want our questions to go to at the end so it’s somethin’ I’ve been working on but it’s also something I guess is internal to me, and it’s something that I’m good at.

Darryl Praill: So, give me an example of when you realized perhaps you weren’t the best question asker. Early in your career, you’re nodding your head already I see that. Is it kinda like when your manager is saying, did you get this information, this information, this information, you know talk to these people, do know you who the people are? And you were like no. Or, was it you just were getting one word answers and not able to get the information you want? Like talk to me, what was your experience when you realized perhaps this is a skill you needed to improve.

Matt Reuter: Yeah so for me the scariest thing was I was selling IT networking services to CIOs, VPs of IT, people who have degrees in this. People who research this for fun and they understand this in a whole different realm than I did. And so, one it was scary trying to figure out what if I ask a question that I don’t know the answer to? Where do I go from there? And for me it’s all been about, that’s actually as an SDR the perfect reason for us to get on a call and for us to talk. Is if they ask you a question that you don’t know. ‘Cause that’s a reason that they should talk to an AE or somebody who can give them that information. So, it’s been something that I’ve had to work at for sure.

Darryl Praill: You know the one thing, it’s funny to hear you say that because that’s the one comment I hear from people over and over again. And if this is what you’re feeling folks, you’re not alone. Which is people are often afraid to ask questions because of the fact that they’re talking to somebody who is either higher up on the totem pole in the organizational org chart you’re talkin’ to a C or a V level, and you’re not, and you’re like oof what if I look dumb? Or what if he laughs at me and just hangs up on me ’cause I’m a moron? What if he outs me for not understanding my product that he knows my space and my category better than I know my space or my category? So, how did you overcome that? ‘Cause the sheer skill of askin’ a question starts actually to your point, having confidence in yourself and confidence in your offering. So how did you overcome that, that insecurity for lack of a better word.

Matt Reuter: So it’s just learning about the products in more in depth. It’s learning on your own, it’s learning how to communicate with them about that. I think the main thing is just repetition, just learning from failures, failing, overcoming that. Going back listening to recordings, listening to how it worked or how the conversation went. It’s something that obviously it takes a lot of work to do. It’s not something that comes easily to anybody and so you have to constantly be changing your craft and getting better at it.

Darryl Praill: Okay so folks I love what Matt just said. And we’ve talked about this before in the past. Let me ask the question. You’ve talked about learning your product. How many of you are actively learning your product? I don’t know if you picked up what Matt did. He said something really matter of fact. He said, “Learning my product on my own. “After hours.” In other words, he committed to his craft. So that’s the first thing. And I know a lot of you are you know, it’s a life-style working nine to five. So if you choose that, and that’s cool, then you may not have the success that you want to if you do something like Matt’s suggesting. Which is learning the product intentionally, seeking out experts, asking questions.

Darryl Praill: And here’s the irony right, asking questions not of prospects but asking questions of your in house subject matter experts. It’s all about knowledge. Second one he said was repetition, oh my gosh I love this. You need to give yourself permission to ask dumb questions. You need to say it’s okay I’m going to get shot down. I’m going to look like a fool, I’m gonna stumble and fumble and bumble. But I shall get better because of it. So whether it’s 10 conversations, 100 conversations, 1000 conversations, at the end of the day I’m gonna be kick ass better, eventually. And I’m working towards that goal.

Darryl Praill: The last thing I love what he said was he said, “Listen to your recordings.” We’ve talked about this before too, right? Is if you’re not recording, well you should look at a solution that can do that. A lot of sales engagement solutions can do that, VanillaSoft it’s part of our offerings. Or you can go do conversational analytics, whether it be Gong or Chorus, Refract, you know those kinda solutions. And they give you a lot of insights. They tell ya, crutch words you use all the time, are you listening more than you’re talking, are you so busy focused on what you wanna ask that you’re actually not hearing what they’re saying.

Darryl Praill: Because your questions should be driven largely based on the conversation in other words is it back and forth, it’s not about you. So that’s a big part. I love that, I love that Matt. All right, now you’ve got kind of four approaches to this. We talked in advance about your philosophy and I wanna hit those up. So let’s start with the first thing, when it comes to asking a good question the first part is structure. Is that not correct? Talk to me about structure.

Matt Reuter: Yeah absolutely, I mean you’ve gotta understand first off what the goal is of asking the question. And you’ve gotta formulate a question that’s gonna get you to that goal. That starts with asking open ended questions. You don’t want a yes or no answer because that shuts the conversation down and that doesn’t open up the prospect. So when I’m teaching my teams or SDR’s it’s who, what, when, where, why, how, tell me more, please explain. Those are the ways that you start the conversation off that’s gonna give you an answer that’s detailed and not just an answer that ends in a yes or no.

Darryl Praill: So, how would you structure a ques– Give me an example.

Matt Reuter: So if you’re gonna say I’m not interested, instead of what I call running the objection rabbit hole right which is where– I’m not interested, why are you not interested? Tell me this, tell me that, and you just end up way away from the goal which is setting an appointment. So if you said you’re not interested, I would dig in on that and I would say, “You know out of curiosity why do you say “that you’re not interested?”

Matt Reuter: And it’s the way that I ask that question, I can’t just say “Why are you not interested?” It’s, “Out of curiosity why are you not interested?” Because that’s gonna allow you to give me the underlying objection which is gonna be, I’m not the right person. And then that’s gonna allow me to ask a good question on why do you think that you’re not the right person? I’m not gonna ask who is the right person, because that’s gonna lead down a trail that leads me to you saying I can’t give out that information and then I’m done. Does that make sense?

Darryl Praill: Wow, that’s actually subtle. So let me see if I can dissect that structure a little bit. One of the things you did was it was very disarming. It wasn’t why not? Which is adversarial, you said why do you, out of curiosity can you tell me why you’re not interested? Second part was it wasn’t a yes, no. It was open ended. Which is always interesting because when it’s open ended they’re gonna ramble a little bit and give you lots of answers. And one of those things you can pull apart one of those threads you can pick apart to go further. But I really like the part, you’ve actually really impressed me in the part where you said, “Why do you think you’re not the right person?”

Darryl Praill: Because I get so many people on a regular basis saying to me, they ping me not even the conversation, it usually starts with social selling or an email and they’re like, “Hey are you interested in our solution?” And I’ll actually take time out of my schedule to say, “We’ve already got that solution. Thank you so much” And they’ll respond back to saying, “Well who’d be the right person to talk to?” And I shake my head in my case and I’m going if you look at my LinkedIn profile, if you look where I am in the organization chart, you’re actually asking who truly has authority clearly it’s not you Darryl.

Darryl Praill: And there’s only one person higher in my company than me. So that shouldn’t be hard to figure out. And I find it offensive and I’m like really? And that’s when I shut it down, but here’s the big thing. I then turn around and I call my colleagues and I say, “If you get contacted by some guy “named Matt Reuter I’ve already shut him down, “just ignore it.” And they do the same to me, too. But if you said to me, “Why do you think you’re not the right person?” My reaction is completely different. That’s huge. So, are there other kinds or styles of questions, you’ve got the disarming approach, you’ve got the open ended approach, are there other structure aspects that you use from time to time?

Matt Reuter: Yeah, so I mean I think that kinda leads into one of my other points that I’m just gonna get off topic a little bit and talk about. But so the whole thing comes around, you know you have to have a goal, for asking these questions. You can’t just ask questions to ask questions. You have to have questions that are pinpointed to get to the goal that you want.

Matt Reuter: So what I like to do with my SDR’s is have them pick five, six things that our business could help the prospects business out with, right? And so we know in the telecom industry that customer service is something that people struggle with. If you’ve ever had to call your cell phone provider you know that it’s a nightmare trying to get ahold of them to do anything. And to make any changes to your bill or anything like that. So that’s one of the avenues that we go down and so the goal is to formulate questions that get you to that goal.

Matt Reuter: And so what they’ll do, is they’ll say, okay my goal in mind is customer service. If I can get the prospect to talk about an issue that they have with customer service that’s a reason for us to book a meeting so that’s where we need to get to. So they will go and formulate questions to get to that goal. And so as you put those goals down on paper and you figure out your different avenues that you have to get to the meeting, once they shut down one of those avenues let’s say customer service is not a problem. You move to the next goal and you have your questions in line. So it’s all about getting a pathway and having an avenue I guess to say, to get to that overall goal. Does that make sense?

Darryl Praill: It does make sense. So that kinda goes back a little bit to what we were talking about earlier, which is the whole point of knowing, of how to plan. Of prepping. So in your case, you used the example I have a goal. When I talk to this person I wanna have a conversation around customer service. Therefore my questions I’m gonna ask are gonna be around that. So I’m gonna assume that when you’re selling a certain product or service, some of the goals are gonna be the same everything single time. What are your thoughts, do you tend to create a collection of questions that support certain goals? So I can reuse them over and over again? Is that an approach that you recommend? Or are you more of the style, let the conversation go where it goes, just have a goal, but let it be organic and natural. It doesn’t need to be the same question every single time.

Matt Reuter: It’s kind of a mix. I think there are a couple questions that are really good to have in your back pocket. And to know by heart and to know. But you also have to have that human element of being able to navigate a conversation and knowing what avenue you’re gonna take next. I think a really good exercise for this to get started with is to write down your goals, and the ways that you’re gonna set, the reasons that people will take meetings for and then write down five to 10 questions about each of those goals and you’re gonna start practicing using those and inputting them and you’ll start to find the ones that you go back to over and over and the ones that worked the best for you. That get the best outcomes.

Darryl Praill: And if you don’t know that, let’s say you’re early in your career as a Sales Development Rep or you’re at a new company, what’s the best way to figure those out in a hurry? Is it to talk to your boss, is it to talk to colleagues, is it to figure out who in the company is the kick ass, top notch, over and over again award winning SDR and then just steal their questions? What’s your experience? And it’s interesting because you as a Sales Development Manager I’m sure you’re actually very cognizant of the questions that are being asked. You probably want some consistency.

Matt Reuter: Yeah so, to put it into perspective on how important this is to me, the first thing I did when I got here was contact the Director of our training department and say, “What are the three to five things “that you say is our differentiator?” This is what makes us unique and the reasons that people like to meet with us. You can ask your AE’s that, they have a lot of conversations with prospects on a day to day basis. You can talk to marketing folks, I mean Darryl I think if I was at your company you’d be a perfect person to ask, hey what are the five things, that that we’re trying to sell and pitch, what value are we bringing the organization and then start there.

Darryl Praill: So, and here’s the irony of what Matt just said. He got to his company, he went to his learning folks, he’s saying you know if someone starting a job at VanillaSoft come to me. What’s he doin’? He’s asking questions, do you see the irony here? He’s asking questions to figure out what questions to ask the prospects. Which is all about that continuous learning thing. So that’s huge and I will tell you this. If you’re scared to go to somebody more senior in your company, don’t. One, I want you to come to me.

Darryl Praill: Two, I want you to understand the message that we’re already putting out there ’cause that means I now have a consistent customer experience from the time they see my marketing, then they talk to you, which is the next step. Or sometimes it’s vice versa. If you find the lead on your own, and then while talking to you they decide to hit my website, I want that exact same experience. I want a consistent experience. So ask the questions to figure out which questions to ask. Love that one. All right so, what are your thoughts on scripts? I’m totally goin’ off ’cause I know we’re talkin’ about questions but the idea of having the questions, maybe not in a script per se, maybe it’s a calling guide. Ask this question if they answer A, go this branch if they answer B, go this branch, or C that branch. Which leads to another question, which leads to another question. Are you pro that, or are you against that?

Matt Reuter: I’m more under the mindset of you need to have a guide. You need to know how the conversation’s gonna flow. So I coach to, you have to have an intro, you have to have a story. And I use that specific word right there, a story, because I don’t want you to have a value prop. I want you to have a story. Give an experience to the customer on the other end of what they’re gonna get out of it. And so, once it comes to that it’s just learning there are really seven objections that I’ve found that people say.

Matt Reuter: And knowing your responses to those objections and questions that you can ask to automatically pivot to a different topic. That’s probably the best way but I tell my people all the time if I wanted a team full of robots I could hire them for a lot cheaper than I can hire these guys so I want them to have genuine conversations with people because at the end of the day people buy from people and they don’t buy from robots. There’s a reason that as a company we’re investing in people to tell the story as opposed to technology to tell the story.

Darryl Praill: So you said a couple of things here I’m taking notes. One of the things you said, building on top of your point where you had said ask questions of your in house experts on your differentiators. You then said, know your objections and how to pivot using different questions. So there’s how I differentiate, and there’s what push back I’m gonna get and questions are a great way to lead to one and pivot away from another. It’s all about the questions. So quick question, for you. Do you know, this is not an open ended question. Do you know what my least favorite question I get asked is?

Matt Reuter: From an SDR that’s trying to prospect you?

Darryl Praill: Correct.

Matt Reuter: When do you have time for a quick conversation?

Darryl Praill: Actually damn, you’re right. Okay there’s two. There’s that one I can’t stand that one. If you send me an email out of the blue and that’s what you’re gonna lead with, delete. But when you get me on the call, you actually have me live on the phone my least favorite question is this. Don’t laugh at me. How are you today? I hate that question.

Matt Reuter: I should’ve gone with that one.

Darryl Praill: It’s like, you don’t care and I don’t care. Let’s just move on you’re wastin’ my time. Please respect my time. So let’s recap what I’ve heard you say here. And it’s been gold. All right, so you’ve said, the power of asking good questions is multiple. I can use them to get to outcomes but you need to have that goal in mind. What is the outcome you want? The power of a good question is also a good way to pivot away from an objection. All right, got a bad situation? Pivot.

Darryl Praill: And so, document those common objections so you know them, just like you would document questions that support attaining certain outcomes or certain goals that you want. So invest some time, talk to your in house experts about that. The other thing you said was the structure is huge. Being open ended, delivery in such a way that is not necessarily aggressive or off putting but one that elicits a response.

Darryl Praill: Why do you think that, sir? Or ma’am. Or whatever, or actually never use ma’am. Why do you think that? They don’t like ma’am I’ve learned that the hard way. So that’s very strategic the stuff you’re saying. What I really like about this was you said, there’s some foundational stuff. Learn your product, just have that comfort so you’re not scared. Repeat it, you’re gonna screw it up in the beginning, repeat, repeat, repeat, repeat. And then, listen to your recordings, huge. And finally you said, adapt. The ability to be self-aware and say okay I screwed that up, I’m gonna try, it’s gonna AB task, that didn’t work, A bombed, let’s try B, let’s try C, let’s do a this of a week and mix it up A B and C.

Darryl Praill: And see statistically which one gets a better response. All of that was huge. And it was all about the power of the question. Matt, you’ve been a rockstar today. I appreciate your time. I am so thrilled. This conversation admittedly, one of the areas I hadn’t even thought of but what I like about it was it’s just relational in the end, it’s intentional and it’s relational. But you’re using it as a strategic advantage that doesn’t make the person feel that they’re being sold to. ‘Cause you’re tellin’ a story and you’re havin’ a conversation. Dynamite. Best way to get ahold of you sir, I’m gonna guess it’s LinkedIn but you tell me.

Matt Reuter: Yeah, LinkedIn is definitely the best way to get ahold of me. Unless you’re trying to sell me.

Darryl Praill: Unless you’re trying to sell me then don’t call me. There we go.

Matt Reuter: Then don’t call me

Darryl Praill: So if you wanna know anything about how to ask a question contact Matt Reuter he’s you’re guy, he’s at GTT. Check him out on LinkedIn, follow him now don’t hesitate. In the mean time, share this episode with all your colleagues because dammit, they’re probably doing it wrong. And you my friend will be the rockstar bringin’ them these wonderful nuggets about the power of asking good questions. My name is Darryl Praill, I’m with VanillaSoft and this my friends is another episode in the can of INSIDE Inside Sales. Take care folks.