Setting The Human Tone

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You're no longer chasing what everybody else is doing. It's not always just about the stuff, the things. It's about you're really happy with the experience that you're gaining. Then your perspective shifts even further.

Meet Matt Riddell

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Welcome to another episode of Sell Me This Podcast. This week we host Matt Riddle and we dive into a fascinating conversation around the humanity behind sales and some of the trends that he's seen with his leadership coaching practice. We hope you enjoy. Welcome to another episode of Sell Me This Podcast. I am super excited to have a guest with me today, uh, Mr. Matt Riddell. Um Matt, super fun to have you here.

SPEAKER_00 0:42

Awesome to be here. I've been looking forward to this for a while, especially after you and I've been talking in the last several months.

SPEAKER_01 0:48

And I feel like we've had a pre-podcast already. Like I made a joke that we probably should have put a camera right in here and recorded the preamble, which I feel like would be a moneymaker.

SPEAKER_00 0:57

I think you should. I think that would make for just like really good clip content that you could pump out there because there's such great organic conversation that happens before the podcast.

SPEAKER_01 1:08

I feel like we made what was the joke that we made beforehand that it's kind of like uh the night of the roxberry. It's the club outside the club. Right, right.

SPEAKER_00 1:15

We're using that reference that the whole concept of like make the outside of the club look like the inside, because you got to wait out there anyway, right?

SPEAKER_01 1:21

Yeah, we can just make the actual podcast incredibly awkward and while we're just kind of twiddling our thumbs waiting to start recording.

SPEAKER_00 1:26

Right.

SPEAKER_01 1:27

And then just have the preamble be where the money's.

SPEAKER_00 1:29

Yeah, talking about the weather. Oh, what's up with you? Oh, not much. What are you doing this weekend? Oh, the same shit as I did last weekend.

SPEAKER_01 1:35

The stock market. I just curse.

SPEAKER_00 1:37

Can I not we can't? Oh, okay, good. It's a real podcast.

SPEAKER_01 1:40

There's not too many children that listen to the IT uh podcast landscape.

SPEAKER_00 1:44

You know, it's odd, and I think it's something that we all need to work on changing, Keith.

SPEAKER_01 1:48

I know. I feel like we can start them young.

SPEAKER_00 1:50

We should.

SPEAKER_01 1:51

A listener for life.

SPEAKER_00 1:52

We should. This is great. I'm glad to be here.

SPEAKER_01 1:54

Yeah, I'm super excited. So for people that that don't know you, I feel like you and I have known each other for many years. Um, why don't you give a little bit of an overview of who you are, uh where you came from?

SPEAKER_00 2:03

Yeah. Yeah, thanks for that. So you and I crossed paths several years ago, both in the uh let's call it the enterprise IT vendor space. Um I was at a manufacturer or a vendor, and you were at a reseller that you had been at for quite some time and building up uh pretty significant services practices. So that's where you and I initially crossed paths. But you know, I think very much in the vein of of the discussions you've been having and and the discussions that you and I have been having lately, um there was a connection there and and and some alignment. And um at that time, serendipitous as it was and interesting how it reflects other parts of my life right now, that it's like you and I didn't get to work together, I think, as much as we would have liked to, and really crush a few things.

SPEAKER_01 2:45

We almost worked together a lot.

SPEAKER_00 2:46

Almost worked together a lot. There was a lot of opportunity that just didn't quite make sense. But now, you know, here we are several years later, that it's like, okay, well, there's other ways of working together, and that's kind of what's coming together.

Burnout And Leaving Tech

SPEAKER_00 2:59

Um, so I spend a lot of my life really, I I say that I'm a 20-plus-year sales exec. And I really equate that all the way back to owning and operating a retail operation through building up a financial practice as a certified financial planner, and then that somehow sold me into selling business analytics software with IBM to CFOs in Western Canada, which grew into more software sales and so on and so on and so on. And it was it's been a wonderful and storied career, but also like so many of us in sales that are facing customers or carrying a quota or really feel uh I would say a heavy burden of responsibility, I burned out. I burned out and I rung out, and that was kind of call it late 2022, 2023. So I took an exit from IT altogether with an intention that I probably wouldn't be back. And through that journey, I got separated from my wife very amicably. We're best friends, but realized that we're not meant to be together anymore. I went down to Los Angeles for about six months of 2024. I spent a lot of time there, kind of just exploring what I want to do, who I want to be. At the time I was suppressing a lot of my business and sales acumen. But then I started to realize, well, there's a lot here that that I haven't great experience that I could pull from. And somehow I I sort of fell into coaching people one-on-one. And it was a little bit of life coaching down on the beach in Venice and and just making connections that way that people were started to pay me to do it. And that just slowly started to grow into an executive coaching practice that predominantly I work with managers, directors, sea level executives, just on, you know, maybe causing some sort of a shift, that there's stagnation in their career or their life, they're looking for some catalyst to personal and professional development. Um, and so I work with individuals on a one-on-one private basis for that. As well, I was building a practice to, and you and I had talked a little bit about how can we how can we make the sales community a little bit better? How can we help

Finding Coaching In Los Angeles

SPEAKER_00 5:16

people become better listeners, be a little bit more active and curious in in how they're approaching customer conversations? And so from that acumen that I started to pull, it was like there's maybe some need for some sales coaching out there. And so I was looking at a lot of the reseller space that you and I have lived and worked in for a while, catered to some of that in some initial sales coaching of teams or individuals, and that got me thinking, what if I was to come back? What would that look like? And so it was there was uh a short list, but a very focused list of what was important to me that I would come back into the industry as a sales executive. And it was the right people, so people in culture, of course. Um but really that's deeper than just the you know, this punchline of people in culture are important. It's am I gonna be working with people that are still deeply invested in personal and professional growth? Because if they're not, well then I don't know that I'll be elevated by that, and I don't know if I can elevate that. So that was one. The other thing is I don't want to give up coaching. I love working with individuals, and I get a lot of fulfillment out of that. I think I've said to you, kind of those the four pillars of my coaching practice are inspiration, motivation, support, and accountability. And I love that that's a two-way street. So I wasn't willing to give that up. And I love going to LA, hence why I picked this.

SPEAKER_01 6:43

You picked the LA background. I love it.

SPEAKER_00 6:45

Um I have a great community, a great well, I even consider some of people their family. Um, and so it was important to me to still be able to go there with frequency and and make live and work there, you know, on a four to six-week or couple month basis. So when a new opportunity came with people that I had worked with successfully before, leadership that I aligned pretty well with, and that I was able to have really good, candid conversations of what I'd like to help build, that opportunity showed up and I said, okay, you know, maybe the universe is just shining a spotlight on something here that this is the right inflection point, this is the right path to come back in and take all these versions of me and everything that I've worked on over the years in my career, again, personally and professionally, and really put that to work in some way that I could be of of service to myself and of others. And so that's kind of a long-winded Matt Riddell sales guy way of answering a very short question, but that kind of

Returning To Sales With Purpose

SPEAKER_00 7:46

thing. I do though, like that.

SPEAKER_01 7:47

And I th I think that there's there's so much there to unpack there. So I feel like I have a hundred questions already. Um and I I want to make sure we get to all of it, but I I think that I'd like to start off with the idea of that kind of coaching mentality. And so a lot of the most successful salespeople that I have come across aren't the DNA that you'd think, right? So I think that if you if you watched the movie, you know, if you go back to like the Glenn Gary, Glenn Ross, and like your um wolf of like the traditional, traditional sales like movies, the the persona is like I can talk really well, um, I'm smooth, I have this kind of carrot charisma. Um, and I think that's actually not true, especially right now. Like most of the most successful salespeople that I know are the ones that listen, are the ones that are curious, but I think they kind of have behind it all this kind of coaching mentality with their customers. Yeah. And I'm so I'm really curious if you've kind of seen that connection, if that's something that you um are like a skill set that you've had to develop or build, or if like how did you build that coaching muscle?

SPEAKER_00 8:53

Yeah, okay, so a great question. Um let me think about how to approach this. So I I agree, I I think I agree on all points, Keith, because I think this isn't gonna make for a good radiance.

SPEAKER_01 9:06

We need we need vehement disagreement here.

SPEAKER_00 9:07

Well, well, I'll let me then let me echo some of it and pull harder on some of those threads because I think I think yes, there needs to be an aspect of coaching in sales with your customer. And again, I think that's a two-way street. I think that's how the relationships are built. But to get there, to get there, there needs to be a level of transparency and a confidence in transparency. I did a talk track and a little workshop on that recently, that it's like there is so much more confidence when you just show up and you're like, look, this is what I'm here for. I'm I'm genuinely here to help. Because and even if even if your coin operated helping you puts money in my pocket. So I want to do more of that. Right? Like, I yeah, we all deserve to be profitable, but we all deserve to work well together, and we all deserve to show up and and be uh

Coaching Mindset In Modern Sales

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authentic. I'm trying to avoid the buzzword of authentic right now because it is a bit buzzwordy, but that's the that's the true sense of it. Just really be what you say you are and show up and and don't bullshit people because they'll see right through it. And if it's all about, you know, getting the Lambo and the Rolex and showing up with an expensive suit and you know the the Jordan Belfort ism and boilerisms as you described, like of of the stereotypical ABC sales guy. I think people are just sick of it. And and it's it's a veneer that that is so transparent now. Nobody, unless you got a really slick product and you're already embedded in there, I don't think that's gonna open doors. It's just gonna be transactional.

SPEAKER_01 10:48

Well, and I think that transparency, like I I love that you called that out because a lot of the information too like is available, right? Like people people do, and I think there's a Gartner stat where people, you know, 70% of their decisions are already made up by the time they reach out to someone. Right. And so they're looking for someone to create an experience for them as they go from that 70 to 100%, and and unlock those doors, make it fun for them, make sure that it fits with what they need and kind of massage that last little piece rather than um you know, show up with the brochure and kind of point at the 14 points on it.

SPEAKER_00 11:22

Right. And I think I think that's exactly it. I've always go I I use a lot of analogies. It's okay.

SPEAKER_01 11:28

We're good, we're good with analogies, yeah.

SPEAKER_00 11:30

And I always think about that, like I'm I'm a gearhead, I love cars. Um, but I I've used this analogy with other people that even if you're not and you go to shop for a car, most, most demographics are gonna do a level of research. Now it's just a question of how much research, how many YouTube reviews of this model have you watched? So to your point, by the time you walk into a dealership, the likelihood that you can or will know, maybe even as much as some of the the product consultants, the salespeople, is pretty high. So what's the value that you're gonna deliver? And I think if nothing

Radical Transparency Builds Trust

SPEAKER_00 12:10

else, uh honestly, if nothing else, Keith, you be compassionate. Just be kind. Because if a transaction's gonna happen, then why not why not have it happen with somebody that you actually like to deal with? That it's like I uh you know, I feel better when I'm around this person. Yeah, right? That's so I think if you restore to the default of that as like even just compassion and showing up with a level of honesty and transparency, all you need to do is listen. That's all you need to do. I'm reminded of like I I quote this Mark Twain quote frequently that it's like if you always tell the truth, you don't have to remember anything.

SPEAKER_01 12:49

Yeah. Yeah, you don't uh that's really powerful, I think. That it's it's it definitely makes sense. Well, you can think of the scenario, it's okay. Well I said this, this, this, and you all of a sudden have to think about this elaborate um spider web of truths and half-truths and things you're trying to emit. And like I I love the idea that you talked about of being kind of candorous too, even about why you're there. And um, I know we we've shared this joke before, but it's you know, the the cold call that comes in that says I'm not here to sell you anything. So why are you calling me?

SPEAKER_00 13:22

Yeah. Yeah, you and I have joked about this, and and I've never been too punchy or gun shy. I would go all the way back to, you know, when I was in financial planning, and I think this speaks to you know sales too, of course, because the approach to to to how to get meetings. Um I think that as we gain more success as salespeople, we also think we need to be more clever. There's this um part of Stoic philosophy was you know you don't need to you don't you don't need to build some complex contraption to just reach out and pick up the thing. It's there, just use your hand. So as we gain more success, I think we try and be more complex. And the way we're approaching customers and deals, and the truth is ask for meetings, ask for business, ask for referrals. Listen, take notes, be curious, don't be judgmental. And eventually things come together. Sometimes it's a longer game that way. I'll I'll I'll give you that. I have had peers say to me, you know, Matt, to your credit, you're less successful because of the things that you won't do. And at the time I kind of winced, and now I can I suppose I take that as a compliment. Because one of the individuals who said that to me once before, you know, a good person, but they're no longer a salesperson. And they were very successful for a number of years, but you know, if you do certain things or you I don't want to say commit acts, that's not it. But I think if you approach uh if you approach sales and if you approach your customer with any sort of cloak and dagger, it doesn't have staying power. You and I have seen that both before in the industry with peers or or you know, even with myself where I've made bad

Buyers Do The Research First

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choices. And and I thought, okay, well, this is what I'm supposed to do. I'm supposed to let the customer know one thing when something else is really going on and try and shield it. And that bit me and burned me and it got me kicked out of the account. It's not something I'm proud of, but holy shit, what a lesson.

SPEAKER_01 15:29

Well yeah, you learn those lessons the hard way sometimes.

SPEAKER_00 15:31

And sometimes you need to. I think sometimes you need to learn them the hard way so that they stick. Ones that you learn that are easy, I I don't even I can't even think of what I can't I can't think of a single one.

SPEAKER_01 15:42

Well, and and I I I feel like I've told this story far too many times um over my career, but I I still vividly, vividly remember, you know, my my first like true B2B sales job. So before that, yeah um I actually did a stint in the financial services. Like um like in university, I kind of wore a couple of different hats. Nice. Um it wasn't my favorite thing in the world, but right out of that I sold photocopiers. Like that was my first B2B sales job.

SPEAKER_02 16:08

Right.

SPEAKER_01 16:08

Um and you know, I I wear the the Xerox training with uh with the badge of honor, and I I still remember You're a Xerox training. I was the I was the Xeroid, I think is what Zero I was part of the era where they still flew out everyone out to Toronto for two weeks. Oh boot camp. You did the boot camp, you did the the live dial cold calls um in front of a group of thirty of your peers. Um they'd put a they'd put a phone in the middle of the room. It's like it's like a farm and they would make you do a cold call on speakerphone in front of everyone.

SPEAKER_00 16:41

Yeah, that's like this boiler room detail. Now and how successful was that?

SPEAKER_01 16:47

I mean you stayed with them, but I I think that it was some of the greatest experiences that I had. Yeah. Because the the thing that it taught was not necessarily the fundamental sales skills, like in fact, some of the things that I learned I probably would, you know, I was always a little bit of the contrary and maybe Sure.

SPEAKER_00 17:03

No, come on.

SPEAKER_01 17:04

Believe it or not. Um but I think that the thing that it taught you was resiliency. And um, you know, I will forever be grateful for the experiences.

Compassion Over Charisma

SPEAKER_01 17:15

Um, you know, my my my patch was Northwest Calgary.

SPEAKER_00 17:18

Okay.

SPEAKER_01 17:19

Which is a really challenging patch if you think about um the like the businesses there are doctors' offices, professional buildings. And and there is nothing worse than walking into a doctor's office. And at this point, you know, um I think they've relaxed a little bit since then. Um, you know, but it was full suit and tie.

SPEAKER_00 17:37

Suit and tie. Oh, yeah.

SPEAKER_01 17:38

And you know, it was 20-year-old Keith, so it was like the most like ill-fitting suit you could think of. Walk into the walk into the doctor's office and um try to get the time of the doctor as in a cold call while all these people were waiting, like, I have a cold, and it's like, well, I'd like to sell you a photocopier. And um, so I think that level of resiliency and and having to be quick on your feet was really important. But kind of but back to the story, you know, there was this um our my first proposal that I did was um at a at a church. Um I still remember the copier model, everything like that. And I um I told uh a mentor and like who's now a close friend of mine, I got this, I got this. I'd seen him do it, and I was like, don't worry, like slam done. He's like, Are you sure? Like this is like we've you've been here for like two weeks. Um and I remember going into the meeting, I had the proposal. We sit down, and I just repeat the same line over and over again for like three minutes in a row. I was like, Have you heard about our photocopier? Have you heard about our photocopier? And I was like, Well, like, um, you know, blank can take over, he actually knows more about it. And he looked me in the straight in the eyes and he goes, I think you got this. I think you got this. And he he let me like drown completely. Um, and it was the greatest experience because he was willing to let me lose.

SPEAKER_02 18:57

Yeah.

SPEAKER_01 18:58

And he and I I will never forget that moment.

SPEAKER_00 19:02

You know, I think I love that story. And tell me, tell me how you feel about it compared to like that the boiler room of you know, the cold call arena at boot camp. Which which of those experiences was more valuable to you?

SPEAKER_01 19:20

The second by far. Okay. And and the reason is because I think that it appreciated the learning experience versus the playbook.

SPEAKER_00 19:29

Right, right. And I think it's interesting. Like and I don't think one is better than the other necessarily. I don't think I think all sides are right, all sides are wrong. It's all about perception. But the that cold call arena boot camp, I've done that a few times. A few times, right? And and it's always like, I don't want to do that. And it's like it's because of that, you know, you you feel so seen, you feel like you're under a microscope, um, you don't want to be judged. Yeah. And the the situation you described where it's like, okay, well, this was a lesson learned. In front of a customer, I found those ones exponentially more valuable to my growth. Now, I don't discount the resistance that comes

Learning Through Failure And Resilience

SPEAKER_00 20:10

from having to do the cold calls and be seen doing it and heard doing it. I think that's good growth. And I think there's an apt space for it. But I I love even more like that, those stories of here's what went wrong. And if you have a recovery, great. And if you don't, well, what did you learn today? Yeah.

unknown 20:31

Yeah.

SPEAKER_01 20:32

Well, and the funny thing, I think we ended up winning the deal too, which is a you know, I think that uh I'm sure that the gentleman probably took a little bit of he was probably quite nice to the young kid trying to figure it out.

SPEAKER_00 20:42

And that's even that's even the better, right? Is that if you actually if you can pull it off and win it outside of that, I think sometimes those lessons and those stumbling situations really help to bring shields down with the customer that they're like, you know what. I like Keith.

SPEAKER_01 21:00

Well, I guess it goes back to your point. It was authentic.

SPEAKER_00 21:02

Yeah. Genuinely authentic. It's like, I I I I I don't, you know what, I don't know. No. I don't I'm I'm new, right? I'm the new guy. And I don't I don't know where to go from here. You freeze up or that happened early in my career a few times. It's happened even you know later in my career a few times, but I've learned how to I think roll with it a bit better. You know, when you got a a a good S E and you're making a four-legged sales call, sometimes it was great. You I know you know you had met Kyle McKay when he and I were working together, and and um he was great at at making me look look bad for and I don't mean that in a deliberate sense or with any malice, but we would have so much fun with customers because I could say something and even whiteboard something, he'd be like, Yeah, you know what, you're uh let's give everybody, everybody give Matt you know a quick round because he did a good job. He's about 60% of the way, right? I'll I'll just clean up all of this, and he would go and clean up my whiteboard and go over it. And it was but it it it created this cadence that he and I were just fun to be around. And then customers wanted to be around that.

SPEAKER_01 22:07

And I think there's something to that. Yeah. Um because I I think that you kind of almost create this club they want to be part of, right?

SPEAKER_00 22:14

Yes, and this is the exact verbiage I've been using since being back in the industry. I'm like, like we have, you know, we have an opportunity to be disruptive and kind of be the cool kids, and all we have to do is just be ourselves and try and deliver good things for the customer and be honest about it. Yeah. And it sounds sounds almost salesy, even that that tone or verbiage, but it's true. It's like we just want to do the right thing. Because if we do, we win. And if we win, we're profitable. So I I I do it all under no guise. Um, you know, going back to letting people know what your intention is when you show up, especially in sales, is invaluable. How I built a significant book of business in financial planning, the first meeting was let me explain to you how I get paid. And now all of a sudden, when people understand how much I make when I'm working with them in in that capacity, I was very explicit about like, look, this is exactly how my pay structure works. You're gonna move this over, this is how much money I'm gonna make. Here's my incentive to continue to work for you. This is this is why I'm doing it. And all of a sudden, shields would come down and be like, okay, now I understand what's in it for you. How are you gonna help me? And I'm not saying show up and let everybody know what's in it for you, but a little bit find ways to fabric that into the conversation, weave it in there because it it lets people know a little bit more about you. I think you become more familiar, people begin to trust you more. And you just have better conversations, and it leads to more and more business and more and more opportunities and more and more growth.

Make The Customer Club Worth Joining

SPEAKER_01 24:05

Yeah. And and so I I think that that leads into a little bit about the Envira story as well, which is you know, you've been focused on building your leadership development practice. Yeah. You've been, you know, you need a little bit of time away. And so obviously it would have taken something special to kind of bring you back into the game.

SPEAKER_02 24:23

Uh yeah.

SPEAKER_01 24:24

Um so is it just the licensing that kind of brought you into Envira, or what what's the what's the story that um kind of put you back on the field, so to speak?

SPEAKER_00 24:33

Okay, so I love I love the question because it's a really good, it's a really good discussion point. Um I wasn't that actively looking. You knew that. He you and I had talked, and I said, I'll kick in tires on a couple opportunities, and I had talked to a couple of vendors that you know I knew the sales leaders at that there could have been some opportunity, and I it just didn't feel right. It wasn't just the licensing. I knew the licensing practice because I knew Stefia Kimmetz, she's one of my best friends, and she is the licensed practice lead. She's building out the engine and and hiring people to do that. But her and I had worked together before, and I there was some magic in that, and so the opportunity of not just working with her and continuing down this licensing path because I knew there's so much opportunity to have those discussions and help customers understand it better, then enter the right leadership, which was with Sean Ambrose. He was an old friend, I had worked together with him before. He and I shared a lot of the same vision around things. So that that helped to pump it up a little bit more. And then I met the rest of the leadership team. I started to meet with other people in in Vero and just kind of do a temperature check. And I don't know if you were I don't know if you remember stratiform years ago. Think stratiform, not like 4.0. That's kind of where we're at. It's that kind of a culture. Everybody's not not only is everybody invested in each other, but we're invested

Be Clear About Incentives

SPEAKER_00 26:08

in the customers. There's a lot of regular internal cadence, a lot of think tanking that goes on, and results that come from that. So being part of a small organization that has this strong collaborative culture that I knew some of the players that I've worked well with already, and I aligned very well with, and that I had an opportunity to come in and contribute to. That's part of it. Like I wanted to say, okay, well, with some of our customer-facing technical people that are actually implementing some of these larger scale projects in Azure. Let me work with some of them, maybe on some of their soft skills. Or is there an opportunity that as we grow our sales org, you know, let me let me help and take on some coaching responsibilities of maybe some new salespeople? Um, so there was a ton of opportunity in all sides point to to yes at Enviro that it's it's it would align with where I want to continue to grow. And it would allow me to step back into a world with a little bit of a new perspective on it. And again, that confidence in transparency of who I who I really am and how comfortable I am being that person right now.

SPEAKER_01 27:26

Do you think the last couple years has really shifted that perspective and that confidence?

SPEAKER_00 27:32

Uh yeah, 180 degrees. I think, you know, I I tell people, you know, I've been I tell people sometimes about this book I've been working on, and I keep picking away at it. And it's not really a memoir, it's just this kind of collection of my experience when I had first separated from my wife. We were living in Victoria at the time. I drove down to LA and I was just going there for a five-week stay. Before what happened was I came back and we

Why Envira Felt Right

SPEAKER_00 28:00

decided to separate and I moved back there. But that initial five weeks, when I when I drove down, I drove myself down, I took three days down the 101. And the Oregon coasts, all the way Northern California, got turned around at Big Sur on the PCH because it was still closed, and went back down the 101, hooked back up with it. I tell people that part of that story is because I think every mile of the 101, particularly that trip, I kind of glossed myself on there deliberately. I'd go hours without listening to anything. I had a like a fat stack of podcasts lined up and a, you know, a couple of great playlists. But I tell people I kind of went down there with a broken heart and left it open for five weeks. So to your question around, you know, the change of perspective in the last couple years, I think I needed that as the catalyst coming out of that initial burnout. That I needed to I needed to be vulnerable for a little while and just let myself kind of observe and take things in. And what that experience did for me, and why I say it's like I had, you know, this heartbroken open and left it open. By the time I got to LA, I was talking with everybody I came into contact with. And that's part of how I made so many connections. Good friends. Um, I got embedded in you know parts of the car community there. I got a great community of people in Venice that I keep in good contact with. And it taught me that this approach of just showing up and asking, asking good questions, and not not trying to show up and intimidate or be cool or make people think that I'm more than I am. I think that comes from sales too. And even as I had more and more success previously, I think I kept thinking that I was elevating and what I was doing was one way I was setting the bar higher each time, and I was getting frustrated and stressed to try and reach it. And the other way is I wasn't really celebrating those wins and reflecting at all on what went right, what was really great, what I was grateful for about those big wins. I just kind of used it as fuel to be like, well, now I need to get the next big one. And if I'm not, I'm not enough. So one of the things I've worked with a lot of people on, friends and coaching clients, and even just peers in the sales community, is like, celebrate those wins. Make sure you're taking care of that. Like, really reflect, find a way to record it in some in by some means that you've got these accomplishments, you've done a lot of great things. So when you're beating yourself up at the end of the quarter because it slipped, or at the end of the fiscal, and that ego at 170 decibels is shouting, you're only as good as your last quarter. Like, listen to your intuition, pick up a effing pen and start to write out all the great things that you're grateful for in your career or in that week, or some of the customers you've worked with,

Perspective Shift After Burnout

SPEAKER_00 31:20

and what you've been able to do with them. And it will almost immediately shift your lens to be like, this is just a shitty quarter. It's all it is.

SPEAKER_01 31:31

So so you have the unique perspective of not only delivering as a like individual salesperson, but also coaching a bunch of salespeople. And at the beginning of our show, you mentioned um some of the challenge that exists um in the kind of minds of sales folks, right? It's a it's a hard job. Um and it does carry some baggage with it. Oh, yeah. That I I think you have to be live to understand. Um can you expand a little bit around kind of what that baggage of a salesperson and you know, as you're coaching some of the different salespeople you work with and and different leaders, how are you helping them separate those um the kind of performance-oriented culture from themselves as a person, which I think is is maybe the separation.

SPEAKER_00 32:23

Yeah, and I I think you're right. And I think that's uh sometimes that's oil and water, and sometimes it's just mud. It's just it's just it just it just and it gets muddier and muddier, right? Um and I think that's it leads to so much burnout. Because you're chasing something that it's um like it's an external validation. And so when I when I'm approaching these conversations with with the with a coaching client, especially in sales, not even if they're in sales. I had a I had a coaching client who was a COO at a major bank. I have an active one who's a COO elsewhere at a startup. I have one who's the manager of an LNG desk here in town. I have another one in Los Angeles who's in film and television. Every single one of them I tell the same thing to. You you cannot control what happens to you. You can only control how you react. If you distill it down to that simple kind of stoic value, then you can be confident in everything that's outside of your will. Because it's out of your control. There's nothing you can do about it anyway. And then you can approach everything that's within your will with caution and question it a little bit, not from an ego perspective, but more from a curiosity perspective, and say, is this really where I should be betting my time? Is this really what I want to be doing? And I go back to Stoicism because I read a lot of stoic philosophy, I think as you know, and like I I I remember, I think it was a Marcus Aurelius line in meditations of like, is this what like is this what you're living for? Like, is this why you don't want to die? You're you're afraid of death because you want to keep doing this? Like that was kind of the attitude behind it. I'm like, like that there's such great perspectives in that. So when it comes to salespeople, and some like you need to kind of be ready, I think, to start have different having different conversations because you don't feel good in that environment anymore. Maybe that never happens. But with regard to salespeople, um, I think you need to get to a point where it's like I kind of just want to keep making my number and 30%. Just have a quiet life and you know, maybe a couple of toys, but a nice vacation, and and I want to I want to do some hobbies, and I want to, you know, whatever it is. And and you're

Detaching Identity From Quota

SPEAKER_00 35:05

no longer chasing what everybody else is doing. It's not always just about the stuff, the things, it's about you're really happy with the experience that you're gaining, then your perspective shifts even further. And now it's like whatever the rest of the team is doing, that's fine. And if we're taking part in some sort of a team activity or it's like a team challenge this quarter, that who can get the most you know, meetings for this type of service that we all really want to provide, okay, cool. There's great competitive nature in that in sales. But if I'm doing it because I want to buy the car so that my sales manager is impressed or that my peers are impressed, or worse yet, what most of us don't realize, I'll show them. I'll go and crush it and I'll show them, and I'm gonna buy the fattest Rolex that I can, right? Why are we so concerned with impressing people we don't even like? And that is rampant in sales. This constant of like it's it's almost like a feeling of one-upmanship. Like we get very defensive, especially as A-type personalities, whether you're an A plus or an A minus. I've always said I was like an A minus because I don't think I don't I don't I don't care as much about the accolades, but for a long time I really cared about being right, especially with a customer, especially with one that was giving me a lot of pushback, or one that was bottlenecking something, like in procurement. And the last two years has really given me a level of perspective and reflection that I can say, this person in procurement that's giving me a really hard time because he wants an extra $2,000 out of this $200,000 PO. Do I really need to do I really need to have be so principled that I'm not like, is this the hill I want to die on? No. He just wants to be seen and heard. He wants to, he wants to feel like he's doing a good job, or she does, or they do. And I think I think when you're able to just pause and reflect for a moment, when really maybe toxic or hard stuff shows up, right? Whether that's ideal slipping or hard meeting with your manager, um you can put yourself on their side of the table really quick and and say, oh, okay. This is a hard conversation for Teeth, too. He doesn't want to have to reproband me as his subordinate. So I'm not gonna hate on him. I'm just gonna be honest with him and be like, look, man, I'm sorry. Here's what's going on with me, here's where I could use some support. It opens up better conversations.

SPEAKER_01 37:50

And I think if I I love what you said, and I I you know I've always believed like if you go in with the belief that everyone's just showing up trying to do their best. And whether it's you know your boss or your customer or um you know the the person in accounting that kind of bugs you, um

Curiosity Beats One‑Upmanship

SPEAKER_01 38:10

no one goes to work every day and it's like, you know who I am really gonna piss off today? Actually, there probably are some with a there are probably some.

SPEAKER_00 38:19

There might be some.

SPEAKER_01 38:20

I think we know a couple, but but I think that if if you genuinely have the belief that everyone is trying to just they're just trying to do their best. And some people have different motivations, some people have different aspirations. But if you have the belief that people are trying to do their best, and you give them that benefit of the doubt, things become a hundred times easier.

SPEAKER_00 38:39

Oh, so much easier. So much easier. I think it's uh like there's a Walt Whitman quote, like be curious, not judgmental.

SPEAKER_02 38:47

Yeah.

SPEAKER_00 38:47

I think that's also Ted Lasso. Also Ted Lasso. Ted Lasso's laptop. Also Ted Lasso, yeah. Ted Lasso, yeah. We'll give it to Sidakis, right? He's more, he's it's that's more than zeitgeist, right? But you're right, like that's I think that's exactly how you described that. Is you know it almost assume everybody's just trying to show up to do their best. Um you know, everybody's really we're all in our own head to some extent. You know, we're all trying to be self-aware, maybe, but you know, you're always a little bit weary of how you're being seen. So I think like just show up, genuinely try and do your best, and then you've got nothing to worry about.

SPEAKER_01 39:34

I love it. I I think that there's there's a hundred directions that we could take this, and I think that there's you know a couple things that I want to give you an award for. Um this is the longest I think one of these episodes have gone this year. Well without without mentioning an AI. And so I think that we're speaking of AI, and so I I feel like I've I probably could have gone the whole episode, but I I think that um I I love the humanness of the conversation we're having. I love that um, you know, and it's not about the technology. And regardless of if it's, you know, we we took a slight detour in some Microsoft licensing, but sure um, you know, I think that the work that we do is is very human.

SPEAKER_02 40:13

Yeah.

SPEAKER_01 40:14

And and even with the some of the technology shifts that are happening, it's the humanness that keeps it really exciting. So I I love the conversations you're having. Um, I I love what you're doing in building. Um is there any kind of final thoughts or or kind of pieces of wisdom, especially when you think about um, you know, maybe Matt from um through three years ago, right? So if you think about um right before shit went down. Yeah. Um, and you could kind of have that conversation with yourself, um, what what words of insight or wisdom or grand revelations would you would you share with yourself?

SPEAKER_00 40:55

Um that's a yeah, I I think I would go back to I would tell myself three years ago or thirty years ago to be more mindful at that pause and reflect motion. It's something that I mean you know, we didn't talk about some major practices or changes that that have really caused this

Assume Good Intent And Listen

SPEAKER_00 41:20

shift in me or or helped me to shift my perspectives, but one of that is like every day when I get up, like I I you know, the alarm goes off at 6 30, and then I get up and I I I do yoga for five to twenty-five minutes, and then I meditate for twenty minutes. And that's not for everybody. I'm not I don't even my coaching clients, I don't say you have to go and do these practices, but my point there is like find stillness and find quiet reflection. People say, I get that at the gym. No, you fucking don't. You don't. Find some stillness, find some quiet reflection, even if it's a walk. Or you know, I'm a driver, so sometimes sometimes just rowing gears on a on a on a back road on a really nice sunny sunday is great. But those moments where you can kind of get lost in reflection. And if you can do it daily and set an intention to do that, it will it it will change your life. The other aspect is I would have told myself way back then too, in that reflection to start recording it. I think a lot of people have difficulty, I think a lot of men have difficulty with the act or idea of the act of journal and I do it every day. I d I miss it if I don't. And it helps me so much to process what's going on. Even at the end of the day, where it's like, God, I just don't I don't feel like it. It's like the gym. I don't feel like doing this because I had a shitty day, I had a frustrating day, or this is kind of eating at me and it's giving me anxiety. As soon as I pick up and start to just write about that, just and it does it could it's complete gibberish. And once I turn the page, it may never see the light of day again, it processes it. So that's what I would put out there is you know, find those moments of stillness and reflection, find a way to record it. Always remember you can't control what happens to you, but you can absolutely control how you react to that.

SPEAKER_01 43:23

That's amazing advice. Um, Matt, I feel like we could talk for like another six hours.

SPEAKER_00 43:29

Um we should do another one of these on AI because I'd have a whole talk track on ethical AI that we could approach. I think it would be wonderful.

SPEAKER_01 43:36

We could compete with the Jays game from last night. I feel like this will date the carbon date this episode. I think so. Um unless there's maybe the longer game tonight. We'll see what happens. We'll see.

SPEAKER_00 43:45

Um we'll see. It's uh it's Otani's off day. So I think he's pitching tonight. Is he on the mountain night?

SPEAKER_01 43:51

He's pitching tonight.

SPEAKER_00 43:52

Um you all are screwed.

SPEAKER_01 43:55

We've definitely carbon data this episode. Um, if people want to um connect with you, if they want to talk to you about either the the services you're offering Rivero, your coaching, yeah, um, take you out for a beer, um what's the best way for them to get in touch?

SPEAKER_00 44:10

Uh there's a number of ways. I'm always on LinkedIn. Um I know a large part of our audience is on LinkedIn. Um so I'm just Matt Riddle, M-A-T-T-R-I-D-D-E-L, is how it's spelt. Um and then on Instagram, I'm on Insta.

Stillness, Journaling, And Control

SPEAKER_00 44:25

I do some content on Insta every once in a while, um, which is Mattyriddle.com. So it's or at Maddie Riddle, sorry. Um so M-A-T-T-Y-R-I-D-D-E-L on Insta. Otherwise, hit me at Enviro, uh, Invirodigital.com. Uh is the website. Like like my coordinates, hit me on hit me on LinkedIn, hit me on Instagram. I'm on there. I will respond. I will respond. But there's also access, uh, there will be links to my website for my coaching practice, what that structure looks like, the options I offer for around that, as well as um I do a blog, I haven't really touched it in a while, um, but there's all means to there's there's no shortage of ways to contact me.

SPEAKER_01 45:05

If someone wants to get in touch, they would be hard not to find you, is what you're saying.

SPEAKER_00 45:08

It would be hard, uh yes, absolutely.

SPEAKER_01 45:10

Amazing. Thank you so much. This has been an absolute pleasure and uh and a blast of a conversation.

SPEAKER_00 45:15

Oh, it's been an honor. I I I'm so glad you asked me to do it, and thank you so much for having me, Keith.

SPEAKER_01 45:18

Awesome. Until next time. Awesome. Awesome, cheers. Cheers.

Humanity Over Hype

SPEAKER_01 45:22

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