The Death of Coffee’s for Closers: Helping Beats Hustling feat. Tom Whalen

Tom Whalen didn’t set out to be in sales - he just needed a job. Fast forward a few decades, and he’s built his entire career (and even a college course) around it. In this episode, we talk about how modern sales has evolved past cheesy scripts and high-pressure tactics. From building trust with customers to staying human in hybrid teams, Tom shares real stories and practical wisdom on what it means to lead, teach, and sell in today’s world.

Key Takeaways:

• Why reluctant sellers often make the best long-term sales leaders
• How to keep remote and hybrid teams connected through small, intentional rituals
• The real value of AI in sales (hint: it’s not doing your job for you)

Key Moments:

00:00 Introduction and Guest Welcome
00:21 Tom's Origin Story
04:09 The Evolution of Sales
08:57 Teaching and AI Interests
18:01 Team Dynamics and Remote Work
24:28 Conclusion and Contact Information

It's time to say "goodbye" to the Sunday Scaries.

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Transcript

0:00

Welcome back to taking back Monday. I am so excited that you decided to say goodbye to the Sunday scaries and hello to a brand new future of work, and I'm even more excited to introduce you to my new friend, Tom. Tom, welcome to the show. Thank you. It was, I'm super excited for this. Longtime listeners will know. I love this opening question. They're, they're used to it. They could probably do this, this whole interview at at this point instead of me. But I wanna know, what is your origin story? How did you get here and what forged you into the person that you are? Sure. Yeah. No, this is good. Um, so when I graduated school, I guess I had the dilution of, uh, the world kind of owes me a job and, uh, that was my thing. And, uh, I couldn't find work. And my then girlfriend, uh, now wife, I. Sent my resume into this company selling wire, and, uh, I needed work. And so they ended up hiring me. They hired me. Uh, the interview did not go well, but the, the guy said, okay, you know what, I'm gonna give you three months and if you work out, we'll give you, we'll, we'll keep you in, if not we'll part ways as friends. I was like, sign you up. Cool. That's what we did. I came in and uh, you know, I didn't wanna do it. I didn't wanna be a salesperson and, um, you know, I would get there maybe two, three minutes late and kind of make my coffee sorta. Lolly gag a little bit in the very beginning. And, um, it was a small wire company and one of the owners had kind of stopped me, not my boss, but somebody in the production side of the house and said, Hey, listen, do, do you wanna be here? And of course anyone has by the owner of their company gets that question, he's, of course I wanna be here. He's like, well, you don't seem like it, so like, maybe you, you should do that because, you know, um, that would help. And I was like, all right, fine. Um, and so that's what kind of, at that point I was like, you know what? Sort of sat back and I said, you know what? I don't wanna be in sales because I didn't. Um, but I'm here. Um, I'm here for eight hours a day. I might as well care or act like I care. Um, and then as I started learning, um, I said, you know what? If I could, if I could get good at this, I could make some money. Um, so then I, that sort of like changed my trajectory or my thinking on, uh, you know, selling and sales.'cause I was like, well, if I can, maybe I start studying and reading books and, and at that point, uh. This is a long time ago. It was cassette tapes. And so I got the, you know, the sales cassette tapes and, and started listening and reading and, and getting better and, and learning my craft. And, uh, and then, you know, now that's all I've ever done. Every, you know, I've, I've, you know, every house I've ever bought or kids tuition or has only been in sales, I've done, I've done nothing else. And, you know, truth be told, it's sales over the phone. So I've never even, like, um, I did have a field sales team for a while. Um. But I found it more efficient to do it over the phone. Um, not to say I haven't gone and seen customers and called on more trade shows, because of course I've done all that too. But, um, yeah, my whole, my whole life, my whole career has been, has been in sales as of, you know, when it was just a, a swish in the thinking of me saying, you know what? I'm here. Let me, let me try it, you know, and let me invest in myself, um, as I did. I think it's so funny 'cause uh, the, I don't wanna be in sales, but I guess I'll do it. Uh, pipeline is is quite full. There's a lot of people that I talk to that are like, the last thing I wanted to do was sales.'cause sales gets a bad rap and honestly sometimes deserves that rap.'cause we've always had that rep who just ruins the entire profession. For us, I was the same way. So I joined a small startup when I was, um, coming out of college and. Everyone wore all the hats. And so I was sales and marketing and account management and everything, and I never wanted to be in sales. And to this day, even though I am the primary seller for my businesses, I still cringe a little bit when I say like I work in sales like, but I really think that the people who are reticent to, to claim that sales persona are some of the best sellers, right? We don't give off that like snake oil salesman kind of feel. Right. And so, um, I had a great conversation with someone a couple of months ago and we talked about the fact that sales is really just trying your best to help the people around you, whether that's your customer, your team, your employees. You know, I'd love to get your take on how your perspective around sales changed over the years. Yeah. No. Um, I think if you're in sales, like I, I think there's a misconception and it's, and I'll say this, it's gotten so, so much better in the last. Whatever, 10, 15 years. I've been doing this for a long time. Um, so it's not, doesn't, yes, there are still some bad apples out there, but I think for a long time, sales was always viewed as something you've done, you do to somebody when, uh, you know, I sold 'em, you know, I got them to sign the deal, whatever. And yeah, that's like a part of it, I guess, but that's not the way I really approach it. Nor do I, you know, teach my, my reps. I also teach a, a college course on, uh, on selling. Um, and the way I I teach it is, um, and I do believe this is you're, you're helping somebody. And if somebody doesn't want to be help or if what you have doesn't meet their needs, that's okay. You find somebody else that wants that, that you can help. Um, but if you look at it as helping folks, um, you know, helping solve their problems, help making their life better, making them look better, whatever that is, um. That's the way you need to approach it and believe that, because if you don't, I mean the first person, you have to sell it yourself, right? I mean, so if you don't believe it, they're not gonna believe it. And, um, you ultimately, at the end of the day, you need to, to help, help the people that you know need help. And sometimes they don't even know they need help. Like, this is the problem. I don't know what to do. Okay, well how about this? I, I dunno. Alright, let's dig in a little bit. Start asking some question and figuring things out and sort Yeah. that, that, that shift has really changed, right? Like it's, I I used to say sales in order for sales to win, the customer has to lose, right? And that was kind of the culture around it. A lot of people, like if I, unless the customer's losing, I'm not winning. Even if we're both winning. And I, I'm really seeing a shift in how we think about those customer relationships as people are saying we can both win. Right. It doesn't have to be I win, you lose in this, in this world. Um, some of that comes from, you know, like the movies that we would watch growing up, like always be closing. Right. Yeah, yeah, and, and cookies are, or uh, I watched Boss Baby 'cause I have small kids, so it's like cookies are for closers, right? Um, coffee is for closers and uh, and so I think that that culture is still around, right? We still see it in some of those legacy companies, but I think a lot of the brands that I interact with and even in the B2B space are starting to move towards a new direction of, more than saying they're customer centric, but actually being customer centric. No, a agreed. You know, it's, it's funny that you take copies, foreclosures because, uh, the class I teach, I do have the, um, I do have them watch as homework, uh, Glen Gary, Glen Ross, and I say, it's not a good movie. It's not, but it kind of shows a desperation. Uh. Sales culture that, um, you don't wanna be. So I'm showing you the stuff that you, you, you need to be, but this is where you don't wanna be. And, uh, you know, so hope my, again, it's a college course, so you have folks that are wannabe sales folks in it too, and then some people are just getting credits. So, uh, but, uh, my, my kind of my thinking is, is that if I could show you, you can recognize maybe a, a place that maybe you don't wanna work or maybe a a bit of a toxic culture, um, that's a, a way to help maybe identify that, you know, and. That's one of the reasons I, I, I give it to 'em as homework, but Agreed. The, the world, the sales world has changed in the last Yeah. I'm gonna say 15 years or least. I mean, I think it's always evolving, but, um, if you're not, if you're not out there to help someone, they, you just put up a website and, you know, buy what is you need and be done. Right. That's, you don't need a salesperson then, right? Um, yeah. That the salesperson is there to answer questions, provide solutions, um. I think diagnose the problem that you may not even know you have. Um, because that happens a. definitely more consultative and less like door to door, and I think it's truly, my hypothesis is that when we started moving into like cloud infrastructure and more consumable products, people didn't need to be as loyal. I. To companies 'cause it's, I can switch from Zoom to Microsoft teams overnight with a click of a button. And so to keep those deals and keep those people coming back for our brand and our product, you have to be more consultative and you have to be more considerate of the process because it's, it's easy for me to switch. Oh yeah. Yeah. And, and, and like, I guess way back in the day, you know, you needed your sales person to educate you on the new products and, and that kind of stuff. That's not the case anymore, like. I'll go to chat JPT and be like, tell me about this product. Right, right. No, exactly. Exactly. And so you have to, now it's not, Hey, let me show this new thing. Let me show you how this new thing, uh, can make your business better. You know, and you know how, or maybe this is what you need, but maybe you need to customize this or that, or, or whatever. It's, um, to help make it fit to, you know, or customize it to your, your solution or what it's that you, your business does. So, you know, in addition to being in sales your whole career, what else are you working on right now? What's your, what's your thing that gets you up on a Monday morning? Yeah. So, um, I am, uh, I am teaching, which I, I do love. Uh, I've been teaching a sales course to, uh, my own employees for, oh gosh, maybe 20 years. Um, and then just this past year, um, I started teaching at the college here, uh, VCU. Um, and, uh, and that, that's exciting. I do like that it's. You know, it's, it ebbs and flows, you know, it's, it's, uh, I, what's interesting about it is teaching people that work for you is different than teaching, uh, college students.'cause, uh, people that work for you, you know, are respectful and listen, and they're getting paid and all that college kids are paying to listen to you. So, uh, you know, I find, uh, you know, engagements and that kind of stuff can sometimes be challenging, but work through it. And I have to say from a, at least a development perspective for myself, it's. It's, it's, it's a, it's a, it can be tough, you know, it's, it's teaching me to, uh, be able to engage better and, and find ways to pull stuff out of folks, which I've never really had to do. So that's, that's pretty cool. Um, I did, um, also, uh, start to, uh, because I do, I like ai. I'm not an expert at ai, but I want to really get better at it because I think that is the future. And so, uh, Richmond, um, called RVA ready now. Um. So I've started to kinda dig into that a little bit. Went to my first event here, uh, I guess it was two weeks ago. And, uh, it's pretty cool. It's, uh, just a little community of folks that, uh, wanna put Richmond on the map as the, you know, ai, uh, you know, capital of the world, which is a, it's an, it's an ambitious goal. Um, but, uh, it was, uh, it was, I, I think that's a cool thing. I went and went by myself and, uh, you know, while I, I, I use, uh, you know, chat g PT and that kind stuff, I. I, I'm not an expert at all. Um, but I was there with like, like programmers and, and all these people, and they're like so welcoming. So nice. But that's another thing that I'm really interested in. I think that could be really cool, you know, just to get good or just even if I'm not programming, which I will never probably do, um, but if I could understand it really well and that kind of stuff, and, you know, it's not so, it's not like a scary thing, you know, I don't have to worry about the, you know, the bots coming down from the sky and, and you know, taking over, you know. I, I. I'm a big believer in, in, um, the future of ai, but not artificial intelligence. I like to talk, think of it as augmented intelligence, right? It's meant to make me. Better and faster and smarter and augment me as a, as a human.'cause I think there's maybe this misconception, or this is my opinion. So, you know, wrapping, putting that wrapper around it, um, I think some people have this idea that we're just gonna buy ai. And turn it on, and our businesses are gonna run perfectly and, and we're gonna be double the efficiency and we can cut our head count, but triple our profits. And I just don't think that that is the reality. So I think in understanding the, the limitations of ai, right? As, as an early adopter, I love ai, so don't get me wrong, but I, I am talking to a lot of companies right now who are slapping AI on it and calling it a day. And I think that that is shortsighted because we're going to, to do things in our business that are going to hurt our customers. I mean, how many bad chat bot experiences have you had?'cause I've had about a million and it, it tarnishes my opinion of the brand when I go in and their new brand ambassador is, you know, instead of, uh, Samuel Jackson, it's now a chat bot that can't answer basic questions. Right. So. When you're exploring the new world of sales and, and the things that you're working on with your students especially, how are you seeing that change over time? Yeah, that's a great question. That's a great question. And it's still relatively new. Um, you know, I think, uh, I, I do wonder when I kind of grade some of the work like. Am I, uh, am I just creating a, the, uh, you know what the chat bot's doing? And what's even funnier though, it's, we have a, at VCU, it's a, it's an awesome system. You could do, it's called like speed grade, and it just, it lines them all up and then you, you can pre-populate your answers before you, you do it. And so it does pick the answers. Like if they write the exact same answer, it works If they. If they put a, because I just had a quiz here recently. If they put a capital letter or add a period or space it out a little bit differently, it doesn't, and it kind of kicks it out. So I have to do a little bit of that. But it's funny, as I'm sitting here, I'm like, well. I have a, do I have a robot that's taken the, uh, that's taken the quiz and is there a robot grading it? Like, do I need to be here? Do they need to be here? Um, so, uh, you know, so I mean, we are using it there in real life applications, which I'm glad to have the exposure to. And we have our, at McKesson, the company I work for, we do have, um, our own, um, chat app. So I do use that a lot. It's a, it's kind of, um. It's chat g PT with like rails on it so that, and it's not going out into the cloud and with confidential information and that kind of stuff, which is good. Which is good. Um, but then I also do use chat gcpt too. Um, but, uh, no, I think it's a, I think it's the future. I wanna understand it better. I want to be, I wanna be good at it. Um, you know, it was that one event I had gone to and it was like. It was like a talk and a happy hour kind of thing. And, and it was cool talking about all the different prompt engineering and how this, how these guys are using it in, in way different ways than one person I talked to. They, uh, uh, he wasn't in sales, but he was doing something for the sales people. Um, they did like a, I think it was like a $10 million, uh, bid to some big company and uh, you know, it normally something that would've taken days to do. He said it did in about three hours. Uh, and it was like 40 pages of. Material and all this stuff, you know, uh, um, that was just think I had all the prompts pretty much done and added a couple others and, and it was underneath through all. So everybody, the way explained it was there was like four people that had to like, contribute to this big, this big, uh, bid. And if the lawyers were going through it and he, his was the only one that they were like, Nope, perfect. You're good. And everyone else has had to do rewriting and all this. And I'm like, wow, that's, that's pretty cool. That's pretty cool. Well that, and that's what I mean by, you know, augmented intelligence, right? Because is that bid any less good than it would've been if a person had written all 40 pages of those versus a person producing the content and figuring it out, and then letting the, the system polish it for them? Right, right. Agreed. And that's the, that's the, that's the ideal way to, that's why I pretty much use it. I like to use it for, uh, like brainstorming and things like that. That's where I think it's fantastic or like, I kind of know what I wanna say, but, so I like throw a couple words in, like, can you make this sort of sound like something and it works, you know, or it gets me close enough to maybe add that, oh, this is cool. Let me, you know, cover some other stuff to maybe make it better and polish it up a little bit. My, my favorite chat, GPT prompt is, um, I'll, I'll put something that I wrote in there. So I'll, I'll upload like a Word document and then I'll say, roast this for me. And then it goes through and it basically makes fun of whatever I wrote and flags anything that like somebody would roll their eyes at. And then I say, okay, now coach me on how to fix it. And then it goes through and like says, okay, you know, this is a super cliche. Everyone's heard this before. This is nothing new, nothing Yeah. Um, so when I'm doing, like, especially my thought leadership where I'm trying to coalesce an idea, um, I'll ask it to roast my stuff all the time. And it's, it's kind of funny, um, some of the stuff that comes up with, but it, it, it illuminates the blind spots for me. So even though I took the time to write it. You know, sometimes you're too close to your own stuff and you don't see it for what it is. So that's my, that's my secret prompt that I use for almost one. That's a. Yeah, it's, you'll get some good stuff. You'll also be like, ouch, she GBD. You don't have to be quite so hard on me. Yeah, no, I'm definitely gonna use that one. I'm definitely, I just helped, uh, one of our reps applying for, uh, another job, and she had asked me, said, Hey, can you help me out? I said, okay, well, you need to come with first, the most har the, the hardest questions you possibly could think of. Said, ah, so we put it into, into the, into our chat app. I said, okay. And then she's, oh my God, these are so hard. I answers, well, let's ask the answer. And then we had to take, put it in answer, oh my God, is the best thing ever. You know, just stuff like for prep. Exactly. I actually, um, saw someone who used it to practice. So you can use like the voice mode on Chachi pt and you can say like, I want you to pretend like you're interviewing me for this role. Here's the specs of the role. Here's my resume, interview me and give me feedback on my responses. Right. So I really do think the future of, of how we. Unburn out ourselves is let that chat pt, let those AI agents do the stuff that we just don't wanna do anymore. And so we can elevate ourselves to the stuff we actually care about, free up our time and, and frankly, for lack of a cliche, that I would get roasted for work smarter, not harder. No. Agreed. A hundred percent. A hundred percent. awesome. So, Tom, as you're thinking about all of the incredible people you've had a chance to meet, who in your mind is leading the charge? Who's taking back Monday? That's a, that's a great, great question. You know, and, um, I, so many people I could think, but you know, there's. Uh, if, if I could say a group of folks, I think, uh, I think my team has taken back Monday and they, they, maybe they'll tell us they otherwise, but I think so. Um, you know, um, uh, this, we just, so in, in our, in our company, uh, we just ended our, our fiscal year, um, in March. And so April one was our, was our new year. And, um, you know, we, we had a tough year this year. Uh. You know, we're fortunate. We had a, you know, last 15 years of, you know, exceeding plan, all that, which is, which is something I'm very proud of this year. I'm waiting for the final, you know, because we're a publicly traded company, I'm waiting for the final numbers, all that stuff to come in. So I know I'm very close. Um, but the, uh, the team, uh, this, you know, this year surprise me with how much they were just stepping up and getting after it, you know, and, um, there was, it was a super proud moment for, for me and, and, and I have a team of managers. As well of how hard these guys were, were, even if I had reps that were 120% to plan, killing themselves, to bring stuff in, reps that were, you know, maybe, uh, still below their, their plan, um, you know, doing everything they possibly could. And it was like, wow, this is really cool. And it was, it was inspiring to me. And one of the things that kind of, you know, makes me, uh, like, I guess reinvigorated me and be like, wow, I, I, I love my job. I'm not gonna say I don't, but maybe like, man. I really do. You know, I don't have a job. I appreciate these guys. Um, you know, mon, uh, for Monday, specifically what we do as a team, so we're a hybrid team. We're, we're in the office, uh, one day a week. Um, and then we will come in, um, if we have meetings or something, which maybe it's one a quarter or something like that, if, if that, um, so what we do, I'm, again, I'd like to say it's, you know, super fancy, but it's really not. Um, we do like, uh, we do what I call a roll call and, um. I have a, it's my, uh, my calendar. I love that. You know, and, uh, we do a roll call. So, you know, I ask a question and they, uh, answer factor crap. It's a, you know, true or false question. And if nothing else, I know it's front of the computer. Everybody's kind of, at least they're usually kind of silly questions. Everybody's sort of laughing, putting things in the chat. I go through, Hey, this is what we're working on this week. This is what's coming up. Oh, by the way, if you haven't done your, you know, what compliance trainings do those, and that kind of stuff. And it gives me a chance to connect to them because as a, as a person who's worked in an office pretty much my whole career, um. I miss the guys, I miss having them around, you know, and I miss, uh, um, I miss kind of just the, the banter and that sort of thing, but this is kind of a one way, uh, to get a little piece of that back. And, you know, I think, uh, so I, I guess my, if I'm gonna say my team, uh, you know, my, uh, uh, my custom extended care inside sales team, and I know that's probably, I don't know if that's not cool, but that's, that's the way I feel. I, we play factor crap with my kids. Um, so I have a nine-year-old and a five-year-old, and they think it is the funniest thing in the world. Like, um, if you're not familiar with the questions. Are like, how many toilets are in the White House? Or something like that. And it's, and it's the things that, like, you would never think, but my five-year-old and my 9-year-old thinks that's, it's hilarious and they love it and it's a game that's accessible. But I also love that you specifically take time out of your, um, workday to just have human moments. Right. I felt like when I worked in an office, because I'm fully remote now. I knew the names of my coworkers dogs, and I knew what they were doing on the weekend because we would have like coffee time or you know, water cooler time and you just did it naturally. But now that I'm fully remote, like I get on a Zoom call and we talk about work and we get work done, and then we get off and that's the end of it. And I think you have to be twice as intentional in this post covid hybrid remote world to build relationships beyond the tactics of your job. Oh no. You have to be so deliberate about it. Um, and yeah. Can you do the work? Yes, you can at home and, and that's fine. Um, I'll be honest. Uh, it's funny, one of my, uh, uh, reps, um. Who was, was on my team now on another team. Um, I had come in on Thursday for Sunday. They said, oh, Tom's here. Let me go see if I can send to one of new teammates. Oh, see if he's in his office, they're like, Tom's have an office. And he's like, oh, it's right there. Um, he's like, oh, I never see him in his office. So my goal is literally when I'm, when I'm, uh, if I have a call with you, obviously my office, right? Tampa, one-on-one conversation with a rep, I'll, or, or manager, I'll use my office. But my goal is to, I blocked my calendar so that I can't have any meetings. Um. I spend more, most time on the floor helping coaching. But a lot of it, you know, yeah, there's helping and coaching and that sort of thing, but a lot of it too is like, you know, hey, what's, how's, you know, how did you know, uh, your new baby and, you know, and oh my God, I know your dog had to get some surgery. What happened with that? And, you know, that kind of stuff. And, oh, your son just graduated, right? Like, just being with the people and talking to them and, you know, seeing what, what's going on in their lives because. I don't know. I kind of wanna know that stuff, but, uh, I also think, uh, you know, I miss that. I genuinely miss that. And so that's, uh, you know, also too, I, I, I, we do, again, I don't wanna be like, Hey, we're just having a social hour the whole time we do coaching and that kind of thing. And, and what's cool about it is that while we're there, we, you know, hey, can help with this. Do. What's funny is I never get more, I get so many more questions when I'm standing like, Hey, what about this? What about that? What do you about this? How would you just bouncing ideas. I'm like, you can call me whenever I'm there, you know, you can call me. I'll, I'll help you out. Um, but I think it's, uh, and I, when I ask people I like just call, they're like, well, I don't wanna bother there. I'm like, you're bothering me now, Right. so why not just doing It's more socially acceptable to bother you in person, I think. Yeah, that's exactly right. Yeah. It's funny, but not, they're not necessarily bothering me. Um, you know, but, uh, yeah, it's, uh, yeah, you have to be deliberate about it, but it's, I think it's such an important part of work. I think it is yeah, yeah, I agree. So, especially in sales, and especially if you're gonna do any kind of coaching, 'cause I'm sure they're much more receptive to coaching if they know you as a person versus just the person who comes in and coaches them all the time instead of the person who talks to them like a human. Right. Agreed. A hundred percent. So Tom, if someone is really connecting with you, if they wanna learn more, where can they find you online? Uh, LinkedIn, definitely. I have a, you know, respectable LinkedIn presence. You'll probably find me there. Um, and then I do have a, I have a book, uh, you can find me on Amazon. So it's the. Book of professional selling. Do you see that there? And it's a picture book, so it's not, it's easy to read, you know, um, there's some pictures in there of, you know, the team and different things about, uh, selling and there is a, yeah. So it's, it's easy to read and I, you know, I use it in my class too. And so, uh, um, actually tonight we're doing a, a persuasive presentation. Put some the material from it, so Awesome. Well definitely connect with Tom on LinkedIn, check out his book. I love the idea of a picture book because you know, it's different. It's easy to understand, it's easy to comprehend, and uh, yeah, we'll definitely be checking that out. Thank you so much for taking back Monday with me. I appreciate it. Thanks for joining us on taking back Monday where we say goodbye to the Sunday scaries and hello to meaningful and fulfilling work. If you enjoyed today's episode, let's connect on LinkedIn. I'd love to hear your thoughts, and if you found value here, share the podcast with your network. Don't forget to like, subscribe, and leave a review. It helps us inspire more leaders to join the movement. Until next time, let's take back Monday.