Have you ever hit a rough patch in sales, where nothing seemed to be going right? Were you able to reach your leads and prospects, but just couldn’t manage to close the deal? It happens, even to the best of salespeople. What’s important to remember is that failure is OK.
In this episode of INSIDE Inside Sales, Darryl speaks with Dale Dupree, the rockstar Leader of The Sales Rebellion. Dale and Darryl talk about how important it is to have a mindset and attitude that will help you embrace those failures and make you a better salesperson. They go over the simple ways to use self-awareness, mentoring, and a positive mentality to help yourself overcome the areas you may need to improve so that you can have a more successful sales cycle. All this and so much more on this episode of INSIDE Inside Sales!
Not in the mood to listen? No problem, you can read the transcriptions below.
Host: Darryl Praill, VanillaSoft
Guest: Dale Dupree, The Sales Rebellion
Darryl Praill: It’s another day to get Inside Inside Sales. How are you doing, folks? I’ve missed you. It’s like been a week. That’s what it’s been, right? A whole week since we last talked. What have you been doing this week? I have to ask you that. Anything notable, excitable? Anything that you go, it was a good freaking week, or it was a tough week or it was a shitty week or it was whatever? You know, it’s amazing, as we live our lives, how the day-to-day activity of what we do has such an impact on our own mindset, our own mental wellbeing, our own health.
Darryl Praill: And it’s like an athlete, right? You, as a sales professional, are unable to work at your peak, your peak capabilities, unless your head is in the game, unless you, and for many people, think about this. I need my sports metaphors. You know, ’cause pro athletes are always the epitome, right? They’re at the best of the game. They’re always practicing. They’re always studying. They’re always competing against the best in the game. And so they really are a great metaphor for what we do. And you can see a lot of sports athletes who are often not at the best of the game. Maybe there’s something going on in their life.
Darryl Praill: Maybe it’s a family issue. Maybe it’s a contract issue. Maybe they’re not enjoying what’s going on in social media. Whatever it might be. But they refuse to admit it, right? And you see the game on the field, and you know they’re not at their best. But they will talk to the press, they will talk to their trusted advisors, who then go to the press, and say, “no, no, it’s all good, man. “I got this, I’m under control.” They’re often in denial. And often it takes a hard crash before you finally see that. My own local team, I was watching. I live in Ottawa, and I was watching the Ottawa Senators. And we have our highest-paid player.
Darryl Praill: And he’s just not performing the way he should be performing. And we’ve all seen it for a long time. And then finally this week they announced that he has gone into a player assistance program. He was in denial. So the question is, what can we learn from that? And that, it got me thinking. We’ve talked before on the show about mindset and how it’s so important. But there’s lots of ways to view mindset. And it’s one of those things, you know, you have to study all the time.
Darryl Praill: For example, I had Richard Harris on a webinar just the other day. He and Ryan O’Hara of LeadIQ, and Richard Harris of Richard Harris Consulting. And if you follow Richard online, and you should if you don’t, he’s really big, a really strong advocate of mental health and mental wellbeing. And he talks about it frequently, and he champions the cause, ’cause he recognizes from his own personal experiences how important that is. And it’s easy for us sometimes when we see those posts in our feeds to kinda go, whoop, keep on going, keep on going, don’t wanna deal with it. I’m fine, I’m hunky-dory. But the fact of the matter is, we do have to reflect sometimes.
Darryl Praill: You have to ask yourself, if you’re not hitting your numbers, is that what’s causing it? I’ll give you an example. Today, well, just last week, I’ve got a speech I have to give next week. It’s at SaaS North. And I’m speaking on the power of social selling. This is a topic I know inside and out. I can do it all day long. And my presentation was due like last, a week ago, literally a week ago. And they’ve been all over me, like “where is it, “where is it, where is it?” And I’ve got this mental mind block. And I’m doing everything else to keep me busy to not have to sit down and build this freaking presentation.
Darryl Praill: And now my back is against the wall. It’s tough. Mindset, attitude, we have to have the right combination. So, I say to myself, as I often do, because I love talking to myself, because no one fights when they’re talking to themself, do they? I mean, do you fight? Anyway, total sidebar. And I said, who’s the guy? Who’s the guy who understands all this stuff around attitude and mindset? You see it in his disposition, in his demeanor, in his posts. You see it in the way he shares his stories, the way he talks about the influencers on his life, like his father. You see it loud and clear. And if you’re thinking what I’m thinking, then guess, let me tell you who it is. It’s Dale Dupree. Dale Dupree of The Sales Rebellion. He is the leader of the Sales Rebellion, where they choose legendary with their sales training. So with no further ado, Dale, my friend, welcome to the show, sir.
Dale Dupree: What’s up, David? Thanks for having me on, man.
Dale Dupree: Darryl, oh my god.
Darryl Praill: Oh, it’s okay.
Darryl Praill: It’s okay.
Dale Dupree: Is that your producer’s name, David?
Darryl Praill: No, it’s not. David is our CEO’s name, so you just assumed I was the CEO. Let’s go with that. Producer’s Daniel.
Dale Dupree: You know what, I picture you, when I think of you before I go to bed every night, I picture you kind of on a throne, like up at the top of the tower. So yeah, that’s probably what it is, so.
Darryl Praill: Well, I thought maybe it was just, you know, if I go back far enough in I guess religious history, David was the ultimate king. So I’m assuming you were just thinking of me in my royal position. Is that where you went? That must be where you went.
Dale Dupree: You nailed it, dude.
Darryl Praill: Yeah, that’s exactly what you were thinking.
Dale Dupree: Hello, King David.
Darryl Praill: All right.
Dale Dupree: Darryl, when you talk to thousands of people a week, it starts to become something that you have to be super intentional about when it comes to names. So I’m a visual person, Darryl. So like when I see your face, I recognize you. I have a very vast imagination. And I also am one of those people that has a photographic memory. So I can remember the way you look better than I can remember your name, in most cases. And so when I started, when I transitioned from being somebody that’s selling into a community and a marketplace to being somebody that is talking to people all around the world, and again, it’s thousands of people a week in some cases, it’s really hard when you see David or Darryl or Daniel back to back to back to remember which one is which sometimes, so. So it’s one of those practices, like you said, of mindset.
Dale Dupree: My mindset constantly has to be intentional. How do I be intentional with all the communication that I have with individual people? Because to me, again, sales isn’t about the commission check. I know I say this a lot, and I say it in my content. Sales is more about the connection that we make with the human on the other end and the vast amount of opportunity that comes with that that we typically gloss over because we’re so focused on our result.'My mindset constantly has to be intentional...to me, sales isn't about the commission check. Sales is more about the connection that we make with the human on the other end.' ~ @SalesRebellion #SalesTips Click To Tweet
Darryl Praill: So understanding that, I mean, ’cause you could intellectually understand that, but you know, we’re still emotional creatures. And life can affect us, right? So how do we make ourselves perhaps situationally aware, especially when we’re prospecting, that we may not be in our best mental wellbeing, it could be affecting our performance?
Dale Dupree: Yeah, and I think that kinda jumps to the awareness of self in those moments, as well, too. Like understanding what you’re good at, but most importantly, embracing the suck, is what I like to talk about, is if we can sit back and embrace the things that we suck at instead of trying to beat them or trying to ignore them, but just embracing them, naturally we get better at them. And even if we never get better, then we’re so aware at their existence that they cannot defeat us or conquer us.
Dale Dupree: And in those moments when you need situational awareness, and in those moments when you’re prospecting and you’re getting into this robotic groove, if you know yourself and you’re aware of who you are and you’re aware of not just your strengths, again, but your weaknesses and you’re embracing them, that people will, on the other end of the conversation, will not only respect that, but they’ll be more drawn to the conversation that you’re having with them in the first place. And then again, if you can apply that to their situation, as well, which again, it’s like the most annoying algebra equation you’ve ever done, right?
Dale Dupree: But when you practice this for years and years and years and you have a mentality of the long game from the start and say, look, I’m not just in this to try and make it work for six months. I wanna do this for the next 13 years. When that’s your attitude and how you come to the plate at that first at-bat, it doesn’t matter how many times you strike out over the first dozen games or even the first couple seasons, because you’ll be a veteran at some point. And other people will be coming to you and saying, “how did you get this good in the first place?”
Darryl Praill: I wanna talk to you about that, because you said a couple really powerful things. You’ve talked about embrace the suck. You’ve talked about mentality. You’ve talked about attitude. And all of that led to you talking about, effectively, that failure is okay. You know, embrace the suck, you’re gonna fail. And you’re playing, you said play the long game, which is, for those who aren’t picking up what he’s putting down, it means in the end, in the long game, you’re gonna be a rockstar, dynamite sales professional.
Darryl Praill: But there’s a process to get from here to there if you’re not there already. And you literally have to give yourself permission to suck, exactly as he says. Embrace the suck. It took me, personally, years and years and years to get, and the only reason I got there, I think, was simply because of age. I don’t think I had the skill sets when I was younger to embrace the suck, ’cause I was so competitive and I was so focused on that next step in my career.
Darryl Praill: And I was so focused on that next pay raise or that next commission check that I took every loss personally. And it’s a wonderful thing when you give yourself permission to suck. You give yourself permission to be a work in progress. And too many people are not giving themselves permission. And I wanna be clear, ’cause I know what’s going on right now. A lot of you are saying, “that’s bullshit. “I don’t wanna give myself permission, “because then I’ll settle for mediocrity.” And I push back on you, and I say that’s just a bad plan.
Darryl Praill: Never settle on mediocrity. Just understand that Wayne Gretzky, for example, in hockey, wasn’t always Wayne Gretzky. He had to build those skills. That’s the same truth in every discipline in life. A doctor, a heart surgeon started off as an entry-level med student who knew bupkiss about how to use a needle or how to use a scalpel. There’s a process. And you need to give yourself that permission. What about, what do you see, Dale? Do you see, ’cause you do, I mean, my gosh, you’re all over the fricking place, training city after city after city. We’ve got this incredible, the Rebellion Tour going on. Do you see this a lot? And do your students, your clients, do they come up to you and acknowledge that they’re suffering from this? Or is it just something we don’t talk about?
Dale Dupree: You know, what’s interesting is that I think really my message causes people to want to come and talk to me about exactly what you’re stating and to be open with me. And the first things out of their mouth is, “I don’t wanna sound like I’m complaining.” That’s what typically I hear from reps. “But these are the things that I’m going through.” And usually I’m pretty intentional in the way that I just listen. But also, I have one question whenever I hear them start talking, which I think is telling to not just our industry overall but also people, how people are.
Dale Dupree: ‘Cause I typically ask them, well, am I the first person that you’ve told this to? How are you getting help right now? And usually it’s like, my wife or my husband, and yeah, you. I can’t talk to my boss about these things, because my boss, specifically, has done so much for me. They’re trying to help me. And I feel like I’m letting them down if I go to them and talk about these things. So at the same time, it’s almost like even though they’re getting so much out of the relationship, they feel, they’re also, it’s kind of a one-sided relationship. Or there’s an agenda on the other side. And I don’t think they know how to express that, though, in some cases, or express themselves when talking to someone when they feel that way about them.
Dale Dupree: But the other side of it is that there are a lot of leaders out there that just need to get slapped. And honestly, what they need to do, beyond getting slapped, is they need to seek out counsel. They need to be able to humble themselves. They need to be able to understand that it’s not like, they haven’t become perfect in their walk on this earth through their 30 years in sales. If anything, it’s caused them to become less sharpened over time because they’re not growing. They read a couple articles here and there.'There are a lot of leaders out there that just need to get slapped 😲 ...beyond getting slapped, is they need to seek out counsel. They need to be able to humble themselves.' ~ @SalesRebellion #SalesTips Click To Tweet
Dale Dupree: Listen, we both know you disagree with everything you read. And you’re sitting there rolling your eyes the whole time, going, “ah, that’s not how we do things around here “in the first place.” You need accountability. You need somebody helping you from a growth perspective and helping you to be able to become a better coach. Too many managers manage. They don’t build. They don’t relate. And they don’t coach. And because of that, we have a failing sales system over it. And they’re so focused on metrics that it causes their people to feel like a number. And when their people feel like a number, they feel like they’re failing. And they feel like, constantly, that they can’t get better at what they’re doing.
Dale Dupree: So sometimes even, Darryl, I think what’s important to say here, especially for people listening, that you might not really suck at sales like you think you do. It might just be that what it is that you’re doing inside of it, the awareness of what it is that the people are telling you to do on a daily basis is lacking. They don’t know your strengths. And instead they’re just feeding to your weakness in the first place, and they’re not allowing any kind of growth as it is, right? And then there’s always the crazy stuff that I hear that I just wanna mention, right?'You might not really suck at sales like you think you do. It might just be that what people are telling you to do on a daily basis is lacking.' ~ @SalesRebellion #SalesTips Click To Tweet
Dale Dupree: Like I’ll say, “well, what CRM do you use?” “What’s a CRM?” Oh man, I mean, and this is the thing, Darryl, too. Look, I’m a millennial, okay? I’m in my, I’m just turned 34, right? I’m right in the cusp of it. I’m a senior millennial, as they like to say. But, so I think they call us a zillennial, actually, something like that, where we are, my dad worked his ass off and was a great example as a baby boomer of how to do it with your own two hands, but also had that empathy and that compassion and that sense of community that related to me, as a millennial. And because of that, I had this, I have a different upbringing than sitting on my phone all day, typing away as a keyboard warrior. I have the concept of hard work in the way that I look at life, too. And so when someone says to me, in the millennial generation, that, oh, a CRM, or I’m not allowed to use LinkedIn at work, things like that, it’s nuts. It’s absolutely nuts. It’s people digging their own sales grave instead of their own sales garden.
Darryl Praill: I had someone the other day say to me, “have you talked to this guy?” This guy’s an elder statesman in the sales profession. “He’s a legend,” you know? And I, like, oh my gosh, every exit in the world, which he might’ve had. And I look him up on LinkedIn, and he literally had zero posts. And I said, “I have no interest.” And they’re like, “what do you mean? “Look at, he’s managed teams of 150 or more. “He’s got millions of dollars.” I said, “I have no interest.” He’s not done a single LinkedIn post. He’s irrelevant. I’m sorry, that’s the way the modern world sells. I’m sure he was successful in his era. I have no interest.
Darryl Praill: They look at me like I have three heads. I’m like, it’s the way of the world, kids. Get over it. One of the things I loved that you said was about accountability. I’m a big fan of accountability and accountability partners. Yes, it may not be your boss. If it is, fantastic. But it may be a trusted colleague, a trusted peer. It could be the outside advisor, like they go to you, Dale, saying, “I need your opinion on that.” An accountability partner is someone that’s going to check on your wellbeing. And it’s reciprocal relationship that you check in on them, as well. Often, setting that up is amazing. So now let’s get to the cure. If those are the symptoms, let’s get to the cure. The first part is, it all comes down to you being aware of you, because you’re the one at the center of this story. And you’ve gotta be aware of what’s going on so you know how to respond. Dale, talk to me about that.
Dale Dupree: Yeah, so I think the big piece of this puzzle for me started with a practice that I put in place as a cadence for myself. But the first time that I did it, it was because my father and I were sitting and having a little bit of a mentoring session. And I had told him that I was feeling, I was just feeling something different. Something was evolving in my life. I was starting to see that maybe I wasn’t treating people the way that I thought I was. And it started kind of in my sales role, right, where we were mentoring and talking about clients and prospects.
Dale Dupree: And then through the process of that, as my father was helping me to understand that the number one thing is that if you can sit back and say to yourself, maybe I’m not doing this right, that it’s the eye-opening portion of self-awareness. It’s the first step. And so once I had hit that, what my father had helped me to understand in that process was, well, maybe it’s not just your clients. Maybe it’s not just your prospects.
Dale Dupree: Maybe there’s people in your life that you need to talk to. And actually I wrote down 20 names. And I individually called each person and did one of the hardest things I’ve ever done in my life but one of the most fulfilling. And that, I got on the phone with each person, and I highlighted something that was bothering me. It was on my heart. It’s that thing that everyone listening right now can relate to, where before you go to bed, you’re just, you’re wondering, why is this this way? Or I regret doing this. Or, and really it comes down to communication. The thought itself, it comes down to understanding what it is at a deeper level that’s bothering you through communication. And so I called each of these people. And 19 out of the 20 of them told me that they forgave me, as I slowly apologized to them. There was only one that told me to pound sand, and I haven’t talked to him since.
Dale Dupree: But I’ll tell you straight up, Darryl, that I pray for him as much as I possibly can and that he’s always on my heart, because again, for me, my self-awareness is that I can very easily be a terrible person. It’s not that it’s inherent in me. It’s that I was cultured, through a dark side that I struggled with, through depression, I was cultured toward kind of being different. And because of that, I was in the punk rock scene, I was in the metal scene, and fighting was a big thing that happened. And so if I can sit back and be extremely self-aware of things like that, imagine what it does in my business block. Instead of separating the two, sitting back and saying, no, no, no, I don’t suck at this in business because it’s business.
Dale Dupree: I suck at this in business because I suck in general at this. I suck at this in my daily walk. So self-awareness isn’t just, oh man, I can’t stand picking up the phone, right? If you’re listening right now and you’re thinking, “well, I’m not really good at prospecting,” it’s not prospecting itself that you suck at. It’s something much deeper. And for me, it was an attitude adjustment that I needed. It was anger that I needed to overcome. It was also a sadness that I needed to face and that I needed to make sure that I was aware of in the first place.
Dale Dupree: One you start to gain that awareness of yourself, as well, too, you start to gain awareness of others in the process. You start, you’ll be on the road driving, for example, Darryl. You’ll be driving your car, and someone will cut you off. And you’ll flick them off, and you’ll, in your head, you’ll go, that’s that thing that I suck at. And you’ll start to slowly work on, through these little instances of revelations for yourself, you’ll start to work on who you are.
Dale Dupree: You’ll say, instead of saying, you know, I don’t want my human interactions to be me flicking people off on the road, you’ll start, you’ll pull into a gas station, and while you’re pumping gas, you’ll say to the person at the car across from you, “I hope you’re having a good day,” or “hey, how are you?” And you’ll practice your sales walk that way, too, because being intentional in communication and conversation and awareness of any situation that you’re in, not just yourself and not just others, but the situation itself is powerful. And if we practice that outside of a sales cycle, it makes the sales cycle much more human. And it makes it much more successful.
Darryl Praill: So many things of what you said, you said practice the behaviors that you want to exhibit, right? I wanna exhibit forgiveness. I wanna exhibit friendship. I wanna exhibit respect. I wanna exhibit awareness that that person maybe cut me off, but maybe it’s because they’re having a bad day. They were oblivious, right, giving them the benefit of the doubt. You want to not always be the one who is, woe is me, the world’s against me. Maybe they’re not against you. It looks that way, but have context that maybe it’s just, no, you’re just having bad luck. That’s all it is. That’s all, nothing personal.
Darryl Praill: And don’t hold a grudge. And then, in fact, feel for them, embrace them. Help them have a better day. And when you approach your cold calling with that mentality, that mindset, that’s huge. For me, a wonderful story for me was I was always being corrected of certain communication challenges, that I was always had to be right and I was argumentative when I was younger. And ironically, I didn’t agree with them. And I argued with them. And finally I got to the point where I said to my boss at the time, I said, “I don’t see it, I don’t see it. “Next time I do that, stop me. “I don’t care what we’re in the middle of. “Stop the conversation and say “Darryl, now, this.” He goes, “okay.” That was how we had a middle ground. And you know, fast forward a week, and he said, “Darryl, stop, now.” And all of a sudden I had situational awareness, ’cause I’m in the situation. And I went, “Oh. Oh shit, they’re right.” Shit, they’re right. Okay, okay, I get it.
Darryl Praill: But now I had context. And now I could fix it. So the big thing here, mindset and attitude is not just something that you have to be intentional about and give yourself a runway to do it. It’s about being aware of who you are and who you wanna be, as well as being aware of others. It’s about being confident enough to actually take the hits to say you might be weak and being self-assured enough to say, but I wanna be better, and I’m gonna do this, where this is my approach. So I may not do well at cold calling right now. But I wanna be better. And I’m gonna learn from the others. I’m gonna park my humility. And I’m just gonna go and do it. And I’m gonna make mistakes, gotta give myself permission. I’m gonna embrace the suck, as he says. Dale Dupree, you are a rockstar. Dale, if they wanna learn more about you and your Sales Rebellion, where do they go?
Dale Dupree: So the best place to head is to LinkedIn. LinkedIn.com/Iam/copierwarrior is how you find me. You can head to SalesRebellion.com as well, too. And I’m on all the social channels. If you just wanna come and get a glimpse inside of my rebellion and what it is I’m doing on a daily basis, on a weekly basis, and what I’ve done for the last 13 and a half years in B2B sales, as a millennial coming up at the forefront of our generation, experiencing these things, please find me. Connect with me. Snap me, tweet me, Insta me, whatever.
Darryl Praill: Dale, my audience knows this, but you may not. My first sales job ever? Selling photocopiers. You and I, brother, we are copier warriors together. Copiers unite. And also since there’s a bit of an age gap here, folks, so copiers have been around for a long time, that’s all I’m gonna say. With that, we’re done. That’s another episode in the books, me and Dale, hanging out, talking to you about mindsets. This is INSIDE Inside Sales. We’ll talk to you soon, folks, take care, bye-bye.