Latest / I Used To Be Crap At Sales / Social Selling Superstar Shares His Story To Success | EP01 | Tom Boston

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Social Selling Superstar Shares His Story To Success | EP01 | Tom Boston · I Used To Be Crap At Sales

• Tom Boston 00:00 So I really enjoyed that because it was so relaxed. When I got a job as an energy consultant, that was my first b2b, cold calling sales role. And it was like a bucket of water to the face compared to working at the Apple stock. Mark Ackers 00:19 When you work that kind of crap. We're talking definitely Tom Boston 00:22 crap. People hang it up on me. People saying that I'm the worst call they've ever received. It's constant rejection. You're struggling every day. Mark Ackers 00:33 Was there a moment when you thought, Wow, I'm crap at this. Tom Boston 00:39 What I always talk about is going to cry in the toilet. Mark Ackers 00:46 When you start going, Okay, what's this thing called again? I used to be Kraft salad bar costs, right? Okay. Hello, and welcome to another episode of I used to be crap and it sells. I'm Mark Akers, co founder and head of sales at my sales coach, and I'm your host. Today I'm joined by, I'm gonna need my tablet for this. I'm joined by a comedy sales content creator. Yes, that's a thing. A social selling trainer and keynote speaker, a Personal Brand Champion, the host of the no nonsense sales podcast, a wiser, elite champion, an ambassador for STRS of London. Sales lofts very own brand awareness manager, LinkedIn top social selling voice over the time of recording 44,000 followers, the man who is on a mission to make sounds fun. If you've not guessed it by now is Tom Boston. Tom, welcome quite a lot there. How you feel to be in the big orange chair. Tom Boston 01:44 I mean, the chair is comfy. What a mouthful. That was I mean, when you read it all out like that, that that put a big smile on my face. But so good to be here. And I can confirm, just convene real life as it looks when I saw the picture. Mark Ackers 02:00 So Tom, in this section, she's going to look at your journey to date, we're not going to go into extreme detail. I know you would have gone through that loss, but going through your CD, and some things surprised me like Wix seven and a half years. That must have been like, I suppose it's interesting for someone to be at Wix have a half years to where you are now that that that feels like if you'd go back to yourself at Wix and say, in what must be 15 years time, you're gonna be where you are today. You wouldn't believe that, I'm guessing. Yeah, Tom Boston 02:31 I mean, just to make it clear, you know, it was it wasn't a managerial role. It was cashier, right? It was on the tills in a DIY store, with people saying, you're gonna work here for the rest of your life. I think, you know, Mark Ackers 02:46 did you believe him after like four years, five years. Tom Boston 02:49 I mean, at some points I thought, you know, in my defence, I started working there when I was at like sixth form, right? To get some extra cash now work there while I was at uni. Before you know it, that's five years, right? And then you kind of keep working there after university for a little while. Suddenly, you've been there for seven years and you start to panic a little bit. And like you say they they called me a lifer. They often said, You're wasted here. I don't know if you ever heard that before in your, in your read everything that highly. People said to me, You're wasted here. You're wasted here. And I felt deep down. I think I think I am I agree with you. But I sort of couldn't get out of that. Of that role. It was clear, it was comfortable. It was easy. And I was just a bit lost. I often use that word. format. My wife was just, I've just lost that was that is the truth. Have you Mark Ackers 03:45 ever gone back since like, painting deck round one weekend and seen some of the lifers and they see what you're up to now, Tom Boston 03:52 my parents went in a couple of weeks ago, and they gave me some of the names of people I used to work with. You know, 15 years ago, they still they're called lover. That's what I that's what I think Mark Ackers 04:05 we need people at work. So Tom Boston 04:07 I'm always going to DIY styles now, you know, much more than I ever did when I worked there. Mark Ackers 04:11 So from there, you've had a couple of interesting moves, that we could talk all day about you being on the street team for a radio station, a breakfast show radio presenter, but let's move on to what could be your first sales role. You worked at the Apple Store. As an apple connoisseur myself, give us one hack for the iPhone that you think everyone should know. They probably don't. Tom Boston 04:36 Oh, my I've been put on the spot here. I mean, there. There are a few things that you can do with your iPhone that you might not necessarily know about. I know that for me is a hack. But if you use the non standard iPhone charger, the Belkin charger to be specific If your phone will charge faster, did you know that didn't? Something I discovered when I was at the Apple Store? I'd always just use a standard charger? Because why? Why would you not? But actually, if you if you kind of open up your world and you look at other options, you can find that your device charges much faster. So there's a there's a hack for you, there we Mark Ackers 05:22 go. Have a great devices are available, of course, then we're an energy consultant, would you consider that to be your first proper sales role or not really. Tom Boston 05:31 at the Apple Store, there was no pressure to sell, okay? That's one of the reasons why I liked the job. Because if I was making people smile, or laugh on the sales floor, I was doing a good job, there was no kind of commission. So I really enjoyed that because it was so relaxed. When I got a job as an energy consultant. That was my first b2b, cold calling sales role. And it was like a bucket of water to the face compared to working at the Apple store. I could Mark Ackers 06:08 imagine again, we could talk about you know why you made that move, etc. And go into this but let's talk about where you kind of come into the world where I think most of your followers are from like, the saas world as the as you're heading to London become an SDR HootSuite. Now I've heard you talk about that role quite a few times and how someone really looked after you and helped you. So we're come back to that. Then you've been an SDR in places but landed at sales loft. Turn up two years as an SDR but then become a brand awareness manager. I suppose most your followers will know about your work. But what about how would you explain that to someone outside of the realms of SAS? When they say what do you do for a living? Tom Boston 06:52 Yeah, I mean, even inside the realms of SAS, I often find myself saying to people what a brand awareness manager is, in a nutshell, from being on the sales team at sales loft, I'm now on the marketing team. And a huge part of my role is content creation, to build awareness of our sales engagement platform, which helps sellers and sales leaders to build their pipeline and close more deals. Like the content that I create is all catered to towards that. And I also lead an internal team of brand, champions. And I'm very lucky that I get to train a lot of our employees as well. And so yeah, in short, I work on the on the marketing team. Mark Ackers 07:47 So with the theme, this podcast, I used to be crap at sales. Appreciate you're not really in a sales role today, but we've got loads of sales experience. Let's stick with the theme. What part of the role as a brand awareness manager? Do you feel your crap at today? Tom Boston 08:02 Yeah, I mean, as a fairly new marker, you know, and someone who doesn't have a marketing background. When you're looking at things like brand awareness, it's, it's exciting to create content, what's hard and what's tough is the admin side of that, right? The planning, and, you know, shock, horror, even in marketing, just like when sales, you have to do a lot of things that you think this is gonna take me a long time or this is a lot of admin work. And I'm just as unorganised in marketing as I was, as I was in sales. So I'd probably say that as Mark Ackers 08:46 an SDR were you crap at updating the CRM? Tom Boston 08:50 I used to be yes. Before before before sales loft. I struggle with that keeping on top of update in the CRM, you know, I'd often be the guy who would 10 minutes before the meeting, be putting together an update for my manager about deals. You know, I was I was that seller. Mark Ackers 09:13 So talk to me about sales that right? How do you feel about sales is what I really want to understand here. Most people don't want to be in sales. I mean, you grew up want to be a clown, right? Apparently, it says on LinkedIn that you didn't want to be in town, you fell into it. How did that happen? Or why did you take that first sales role? Tom Boston 09:34 Honestly, money 100% We were gonna get married. And as we've been talking about before we recorded this weddings, expensive. I was working at the Apple Store and having a very fun experience. But me and my wife kind of looked at each other and realise actually, if we want to get married and do it the way we want we were going to need some more money. money, and the role that seemed the most obvious one that you can kind of, as you said fall into, and most of the time get, get a job as was a was a salesperson, you know, cold calling businesses based in basically a call centre in Newcastle. And it was more money. And that was why I took took the role. So Mark Ackers 10:27 it was a conscious choice. I'm not in sales today, but consciously I want to get into sales because of the money. What are the interviews like? Tom Boston 10:37 So the the interviews for that very first role, were very, very loose. Let's say that's probably the best way to describe it, right? This company that I was working for, they would hire 20 people a week. And it was very much a revolving door of salespeople. If you couldn't hack it within the first five days, you'd often find that you'd be out out of the door. So the actual interview was, yeah, can you? Can you hold a conversation? Do you seem like you've got something about you? Could you have the tenacity to, to call 100 people a day, and if you could, you've pretty much got got the gig. Mark Ackers 11:22 And you almost had success to stick around. Because like in jobs like that with high volume sales, they get rid of people quickly, but then you transitioned to an SDR HootSuite, so let's get into that. I think first of all, lots of transferrable skills, particularly being comfortable being on the phone. But how did you find that first role as an SDR? Tom Boston 11:42 Yeah, again, it felt like I kind of took a wrong turn into a magical forest. And I didn't know but didn't know where the unicorns were. I felt I felt really, really out of my depth. You know, again, with that HootSuite role, they were impressed that I made 100 calls a day. They they really liked the fact that here's a guy who will hit the phones. And we'll have conversations. I certainly didn't know anything about b2b saas sales than the CRM was didn't know what an SDR was, didn't know what an AE was. So so basically didn't even really know what the role I was I was applying for. I just knew it was a sales, a sales role. So as soon as I was in that world, where everyone seemed really switched on, and everyone was used to speaking to CEOs and CROs I was I've just felt like some some northern bloke who's been ringing up people selling them gas and electricity. And now suddenly, I'm prospecting C level execs in London, using a system I don't understand, surrounded by people who seem to know what they're doing. So yeah, to say it was to say it was hard is an understatement. Mark Ackers 12:59 And do you move to London specifically for that role? Tom Boston 13:03 That's right. Yeah, Mark Ackers 13:04 I suppose it's a big move, isn't it? Like a whole new city talking about cost conscious, most expensive city to live in, Tom Boston 13:13 it was a huge, it was a huge move. We, we did it just before the wedding as well. So we moved down to London before we got married in Newcastle, a few months after. And, and it was it was one of those decisions that we just thought, let's do it. Right. We as a couple. We never took a gap year or a gap year as the as the kids say, we'd kind of just you know, as you talked about, got jobs worked in dry style, you know, don't kind of bits and pieces. And we we wanted an adventure. And for us London was was certainly that adventure and we loved it. But like I say it did take some getting used to. Mark Ackers 13:54 I certainly spent a lot of time in London as a kid weekends, whatnot. Totally understand that. And then you've had a few other jobs as an SDR right, obviously move back up to Northeast and the SDR job and then new SDR at sales loft. So I'm guessing when you got the sales job, you must have been pretty good, because you are one of the first two hires in the London office. But tell me more about that. Like because it feels like you were struggling from what you've said to get in as a job well known company in London, so what your crap it sells or you're good at sales. Tom Boston 14:33 Well, when I first started I was definitely crap. You know? It's, it's easy to be to be crap at a cold calling job because it's it's constant rejection. You're struggling every day. When you then move into the SAS world, it's easy to be crap at that because you you don't know the lingo. You're not kind of clued up, but But the underlying thread between these roles is talking to humans and connecting with them trying to solve a problem. And I've always been good at that part of it. So yeah, being crappy at cold calling and being crap. At work in in saas, I've definitely got experience with that. But But like you said, there, by the time I got to SalesLoft, I'd kind of managed to navigate my, my way through and being good enough to kind of get to get the roll, you know? Well, Mark Ackers 15:40 then let's focus our time before you got to SalesLoft. Okay, when you work out how crap we're talking? Tom Boston 15:48 Yeah, I mean, I would, I would get frustrated with myself if things were going wrong. So I wouldn't have, you know, spells of months and months of being terrible. I would always try and say if I had a very bad call, I'd be like, right, let's, I'm not. I'm not doing that again. Let's, let's change it. Let's, let's tweak it. But certainly in the early days, no, we're talking people hanging up on me. People saying that I'm the worst call I've ever received. You know, being told to go away is the polite, the polite way to say it? So yeah, really, really bad. Really crap? Mark Ackers 16:28 And can you remember the moment you realised because you're quite a positive person? And everyone's got an ego to some degree, right? Maybe people in sales have got slightly higher ego. So I'm guessing when you went for the sales roles, and you started there, you wouldn't have been thinking, I'm crap, I can't do this, you would have believed you that was there a moment when you thought, Wow, I'm crap at this Tom Boston 16:54 specific moment that I kind of thought, Wow, is that I really am crap. And I can't think of a specific moment where I've kind of had that self self reflection. And the one I always talk about is going to cry in the toilets. And this is not something a lot of salespeople will admit. But I like to talk about it, because it, it just happens more than you would, you would admit, I was in my first role in sales, the gate was going so bad on the phones that I just took myself away, went into the toilet, how to weep. And then when and then went back and then kept going and did some more cold calls. Now, this is this is something that sellers are facing, all the time being so set with themselves that they're failing, that actually, it becomes overwhelming. I might not be selling a sales role to anyone looking to get into it. But that was my literal experience. I I can't do this anymore. People are being so mean on the phone. I can't handle this. I just want to go back to the Apple Store. What am I doing with my life? You know, these were the questions I was asking myself. Mark Ackers 18:20 Take us back to that day. So Had this been coming like this? This, this call it an outburst of emotion? Had you felt that coming? Or did it take you by surprise, like what took about the build up to where you got to the point where you're like, a need to go and have a cry? Because I'm I'm struggling it? Tom Boston 18:41 I think probably like you, like you said, I try and be positive. And I've tried to do that my whole life. I would always go into those days, especially in the early days with a positive mindset. But like anyone, you know, if you get one hour, two hour, three hours into a working day, and you're not getting the results that that you need, or things are not going your way, or maybe you've just been told to go away too many times that morning. It can kind of sneak up on you. So it wasn't like like a huge, a huge buildup. It wasn't like kind of weeks and weeks of kind of bubbling up it probably thinking back to that day was something as simple as the worst morning. an outbound seller could could have nothing's landing. nobody's answering the people that do a terrible you're having a self doubt moment of what am I doing here? I don't belong here. You know, all of those things probably led me to that moment. So Mark Ackers 19:50 was there Do you remember the moment like a need to have a break that was it was it a call that was like, straw that broke the camel's back? You remember? Tom Boston 19:58 I can't remember this specific call. But I've I've certainly had calls before, where and again, tell us sellers will relate to this who've been through it, you get told by your prospects specifically that you're crap. And you can't do the job, or you should get a real job. Stop wasting your time. Stop calling me Stop annoying me. Who are you? How did you get my number like the these are things that I said to salespeople, you know no matter who you sell talk of, or what you're selling, these are the things that we that we face. So it was probably something along those lines, it was probably something like, get a real job. Mark Ackers 20:47 So we've had a bad call, it's been a bad day. Mark Ackers 20:50 We get up, we go to the bathroom. Yeah. Did you know that you were going to the bathroom to cry? Or was you just going for? Tom Boston 20:57 I think I probably did. I think I probably thought, I'm gonna go and have a weep. Now. Mark Ackers 21:02 You have that moment to yourself? How do you go back to your desk and pick up the phone again? Tom Boston 21:10 Well, if you're in a row, like I was, call times are measured. So there's no time to, you know, just focus on emails, or maybe take them on in and have a coffee, like bathroom breaks, and measured coffee breaks don't exist. And actually, if you're, if you're not making a certain amount of calls, or got a certain amount of call time, you're probably not going to be there next week. So the mindset was back to it. You know, it's that kind of stiff upper lip that we that we talk about, and a lot of salespeople have to have, which is like that, that tenacity that kind of, I'm just going to keep, keep going. And then knowing that it's not all bad. You know? What if you have a better phone call? Half an hour later? What if the afternoon, turns around, and actually you do make a sale, though, that's that's what drove me forward. Mark Ackers 22:21 So you say that's what drove you on. But you also said you took a sales role for the money. And I'm wondering if you weren't connected to the money that you needed to do the things you wanted to do? If you want to just quit there? And then. Tom Boston 22:39 Yeah, I mean, that's a good point. Because sometimes needing the money is a good thing. Because it keeps you it keeps you in seat, right? If you if you're not saving for a wedding, or maybe you you don't need the cash, then you're right, maybe take the headset off and go, You know what, there's, there's better things I can do with my life. But I think for me, and I think you're probably quite similar to me in this this way. I don't really like being bad at things, especially if that's my focus, you know. So even if I'm not 100% in, or even if it's not something I'm really passionate about. I don't like I don't like failing. I think a lot of salespeople are like that. So that was another driver for me, right? How can actually I turn this around? How can I be one of the best on on the team. And the job is that I work with my nickname towards the end of that role. They used to call me some boy. That's what they used to say. I assume boy on the phone that Laddies some boy. And it's because I'd had enough of being hung up on I had enough of of being crap. And I wanted to do well in that role. So I found ways to have better conversations. I found ways to thrive in that role, you know, Mark Ackers 24:14 so I want to get into that. But I'm not going to let your way with where we're at just yet. I want to I want to go back to that. How low were you in sales like is 10 Is this the best ever? Zero is rock bottom. When you were feeling like I can't do it. People are rude to me. I'm miles behind target. We went to the bathroom to have a weep. How Where were you? What kind of notes tender? Tom Boston 24:40 Yeah, low, really low. Two to three. I mean, my wife always makes fun of me for this and we've already talked about my favourite film being Shawshank but when I was marched into that call centre, dressed in a shirt and tie And real trousers, you know, something that's not me at all with my new, shiny shoes. And there was, I think 20 or 25 of those that day, were starting on the sales floor. And we were marched up that staircase, the dramatic person in me, especially after having so much fun in the Apple Store, was like, this is this is my prison sentence, I'm being I'm being put into this huge building with all these people and have to come here every day and do something I don't want to do. And, you know, even on day one, ours was, you know, about a four or a five. So when that kind of rejection came, and when that realisation came that, oh, wait a second, this is the toughest job in the world was really little, you know, couldn't have been lower at points. Mark Ackers 25:53 And when you were that low, who'd you talk to? Tom Boston 25:57 Well, I'm very, very lucky, you know, my wife is an absolute rock. And I wouldn't be where I am today. Without her. I know that. People see the content. People say, Oh, Tom, you're You're very funny. And I'm really appreciative of the of those kinds of compliments. But I know deep down that without my wife, I would probably still be working in a dry store. And she is the person that I speak to when I've been in law, she is the person who inspires me to do better. And yes, she was the one for me who would kind of go look, you can you can do this. You can. You can thrive you can succeed. Mark Ackers 26:42 And did you tell her about that day? But you cried at work? Oh, yeah. Tom Boston 26:47 I probably called. Mark Ackers 26:50 So talk me through this, then Tom, you How did you go from being so low? crying in the bathroom? To people saying some boy him Tom, how did you go from one to the other? Tom Boston 27:05 Yeah, I mean, it was certainly a journey. A big part of it, I think was just seeing what other people were doing, who would been successful in the role around me. So there was there was one, one of my colleagues in particular, she was really great on the phone. She sounded like she was having the time of her life, maybe calling an old friend or even a neighbour or her mother, you know, why she laughing on an on a call or at work? And then you realise, oh, wait a second, she's building rapport with prospects. And she's making sure that that call, just because it's a cold call doesn't matter, is the best call that they'll have all day better than any call or have with a friend. And I was like, I'm going to steal that I'm going to do some of that. And having that mindset, and starting to really enjoy it. Being someone who's having fun at work, and not being so tied to the outcome of the call. That really helped me because I went back to that Apple mindset, right? My job is to make the person that I'm dealing with, feel happy. And we don't talk about that with cold calling. No, it's not we're not bothered if they're happy, or we just want them to convert. We want them to book a meeting. But when I started really enjoying it, trying to bring some fun, and make people smile. Everything just kind of felt like it clicked into place. Mark Ackers 28:45 So you've mastered cold calling. Is that too strong a Tom Boston 28:50 word? I mean, has anyone mastered cold calling? I don't know. I don't know if I could ever call myself a master. I'd certainly started enjoying it more. Let's say Allah, Mark Ackers 28:59 let's go without that. Yeah, you start to enjoy cold calling. You then get the job HootSuite. Now, this is a similar role in the sense of part of that is going to be picking up the phone having conversations with strangers, so to speak. But there's loads more to being an SDR and I'm guessing loads of things that you've just never done or experienced before. So therefore, keeping in theme with the podcast, I'm guessing you're going to be in crap. Lots of new elements, this SDR role. Tom Boston 29:29 Yeah, I mean, certainly, it's a step up, right from working in a call centre. Suddenly you're an SDR and you're almost like a little manager of your own territory. Also of your own time, right? You've almost got this freedom to do the roll in your way. You know whether you're going to be emailing cold call and building your brand, whatever that might be. But no, I was I was certainly crap at a lot of Ella. Once I remember someone has now the room for a disco. And me not being too sure if they were going for a dance, you know, genuinely never heard that phrase before for discovery calls. And then and yeah, it was. It was tough. It was a whole new world for me. Mark Ackers 30:18 So when you're an SDR not only have you got to be cold caller that enjoys it but good air, you've got to be a creative email writer, personal brand, video content and a researcher all of these things, what parts did you struggle with the most? Tom Boston 30:39 Definitely, the research the admin side of things. And I used to joke that, you know, you jump on a discovery call that you've booked, and five minutes before you were on the website, trying to get some key words to maybe look like you've done some research. That was me, I was the person who would really struggle with, okay, so I'm going to spend now half an hour 45 minutes researching, or really getting to grips with the company that I was kind of selling to, I think it was one of those things that like, there's so many industries, right and you try to be an expert, in all of them, especially as an SDR I really struggled with that, because I would try and invest in research and but my heart wasn't in it and never get bored is the the honest answer. You know, get bored of that kind of era go now really into A into an admin phase of the day. I struggle with that. And Mark Ackers 31:46 in general, I remember you saying to me, you struggled at HootSuite when lots of elements who helped you when you're in that role? Tom Boston 31:57 Yeah, well, I, I was very lucky, I was sat next to an AE, who I was very honest with. I mean, you know me, I'm almost too honest, for my own ghost. Sometimes. I remember sort of saying to him, I don't know what I'm doing here. I've kind of I've managed to get this role. They've given they've given me this role. I just I just Googled sales jobs. Now I'm in London, in an SDR role. So he was very pivotal in honestly, showing me how to use a CRM, like helping me with the acronyms. Right. So I would have a conversation with my manager. Hey, there's gonna be a CSM on the call. Is that okay, no problem. What's the CSM? You know, I he would be my kind of confident to talk to about that. So yeah, I think it's always good to find someone that you can. You can trust and you can speak to openly. I Mark Ackers 32:57 think it sounds like you were quite vulnerable with him. Like I'm able to open up and say, I'm struggling. How did you do compared to targets in that role? Tom Boston 33:08 Yeah, I didn't. I didn't do too bad. You know, I've, I've often talked about how, how tough it is to start and a new role. But but actually hitting targets is not something I've ever struggled with, even even in the early days. And I think that's probably the the competitive side of me. I always like to be in top of the leaderboard. As an SDR I, I enjoyed seeing myself at the top. It was rewarding to God. Now I'm succeeding in this role, you know? Mark Ackers 33:42 And I mean, only one person at the top Hmm. Have you ever had a periods where you've just struggled to get to the top? Someone's constantly beating you? Tom Boston 33:52 Oh, yeah. Yeah, there's been, there's been moments throughout my sales career where I've slipped, slipped to the middle, even gone to the bottom, and my highest record of being hitting targets. And top of the leaderboard, funnily enough, was when I moved in to my marketing role, the last kind of four to five months of my sales career. When I was in the process of moving away from sales, I did better than I've ever done before. I think I was very, very relaxed. And that's a huge, huge part of being successful in sales, not worrying about the result can often lead you to get in the result, you know. Mark Ackers 34:43 So that's what I was gonna say. Interestingly, when you know, you're not there much longer you can transition into a new role. What about someone that hasn't got that luxury? How would you advise it is that they'll listen to you thinking, Well, that's all well and good. I have just started out as an SDR. I've just started as an AE, I'm here for the next couple of years. And I'm attached to success and outcome out of people break away from that. Tom Boston 35:11 Yeah, I mean, hitting targets. So important in sales. If you're new to sales. It's, it's all you want to do. It's all you think about. It's your it's what you have for breakfast, right? How am I gonna hit target today? My advice would be speak to a top performer, on your team, ideally, if not, beyond, buy them a coffee, bind them, egg, mayonnaise, sandwich, whatever, whatever it may be. And ask them, What are the three things that you can attribute your success to? Tell me three reasons why you're at the top of the leaderboard right now. What are you doing today, that other people on this team are not doing? And how can I bring that into the My, into my working day? I think the phrase, I hear this a lot on LinkedIn, pick your brains. I hate that phrase, right? The amount of people messaging me. Hey, Tom, can I pick your brains? Oh, no, no, you know, you're not a zombie. But what I often say to people is, look, give someone some value add to getting that information, right? If you allow me to pick your brains, give me 10 minutes, let me ask you three questions. I'm gonna buy your drink today, you can do something small, I'm gonna get you a chocolate bar, right? Let's just use kindness to be genuinely inquisitive as to how people are being successful, but also wary that we don't just want to steal everyone's ideas and not do the work ourselves. It has to be a two way thing. Mark Ackers 36:44 So I love that. And like you say, I think realising that if you're going to ask something of someone, it doesn't need to be being like, say a chocolate bar. Right. So there's your key raisin and biscuit. Tom Boston 36:54 I'll have that. Yeah, Mark Ackers 36:55 try the honeycomb one. I've not got one in Module downstairs. Tom Boston 36:59 Okay, let's have a little bit so maybe as a thank you for this. We can share one. This whole podcast just been me trying to get a free chocolate bar. Mark Ackers 37:08 What about your manager? Like you've obviously got a manager at HootSuite that's hired you believing you can be successful in the role. They've set goals that they're asking you to hear? What role if any, did they play in helping you? Tom Boston 37:23 Well, they they got the mask. They didn't get the real Tom who was struggling who didn't know the buttons and the the words, they got someone who was altogether confident. Doing okay, not struggling. Thank you for hiring me, you made a great decision. I look back on that now. And I think honesty is the best policy and it sounds so cheesy. With your manager, if you are struggling, that's the person that you need to speak to. They hired you for a reason. I think I was so worried that I was just gonna get turned around. We made a huge mistake. Off you off you go. Last year I kept that kept that from them. So that was a huge learning for me actually. being open and honest with the person that you report into is the way forward. Mark Ackers 38:21 How did you learn the lesson? Tom Boston 38:24 I think it's just that I grew in the in the roles as I as I got older, you know, I often joked that I was an older SDR especially when I was at SalesLoft. Right? A lot of STRS who will join companies, you know, 1920 21 years old. I was you know, 30 Plus, in my most recent SDR role. And, you know, in my late 20s When I was at, at HootSuite, it took me a long time to realise and mature in those roles. That actually it's okay. To be honest and, and be open with with everyone. You know why? Why struggling in silence. I think that's that's the message that I'd like all salespeople to take away. Mark Ackers 39:23 So I like that. Can I challenge it? Obviously, we can't speak for every sales manager now. And I'm guessing you've had a few different managers, different relationships, different styles, etc. But do you feel the average let's say 1920 year old SDR and be honest with their manager, they can say let me just give you an idea of some of the things they might want to say. I've got cold calling reluctance, anxiety. I've got impostor syndrome. I've got a need for approval. I struggle to talk about money. When I get hit of objection. And I want the phone to hang up. Can I really say that to the manager? Tom Boston 40:08 A lot of them probably not, especially if it's a new role. Because they'll be worried about what may be said back to them. But hopefully, you've picked a role. And a manager, because let's not forget, whenever you're going for a sales role, make sure you find out who your manager is going to be. That's a huge, that's a huge part of it. Right? You want to know who you're going to be reporting in? So hopefully, they've got to a stage where they can be open, and, and honest. And if and if they don't, what's the alternative? You know, finding the toilets, speaking to the people around you, and, and being open and honest with them, but never letting your manager know that you're struggling? How are you going to progress in the role? Unless you do I did, which was, take everything on yourself and have to progress and, you know, struggle with I'm gonna have to do this, I'm gonna do that. Well, actually, no. There's someone that there's someone there for you, who you report into who can have that conversation. And I would say try it, you know, if you're 20 years old, you've never spoke to your manager, about call reluctance, have that conversation, see, see what happens, they're not going to fire, they're not going to, you know, tell you to leave the role, you might just be surprised at the response you get. Mark Ackers 41:42 And obviously, we're using the example of young STRS. AES can have problems like I've just spoken about. First time, sales managers can have those difficulties, you know, first time sales manager, great example. They've just been promoted, probably internally, they were a great rep, but now they've got to do all sorts of new things, right? One, run one to ones start to forecast, start to look at dashboards and data and make decisions. When you're struggling in a role. And you feel like you can't talk to the manager. But all the reasons I buy into right, this, this is your boss, this is someone that can give or take away opportunities. How important is it to not do what you did and take it on yourself? And have someone to speak to about that stuff? Tom Boston 42:25 Well, it's so important because, you know, what's the phrase a problem shared is a problem half does that is that I think that's the one we've got with that one. So important to have someone that you can, that you can connect with. And if that's not your manager, you know, I would encourage people to find someone that they can have that conversation with, because if you internalise everything, you're never going to progress. But what also it's just not good for your mental well being like, that's so important in sales. You know, nowadays, it's so important to have a clear mind. And how can you do that? If you're fogged with doubts, worries, etc? Mark Ackers 43:10 Have you ever had a coach Tom? Tom Boston 43:14 I don't think I've ever had one specific coach or mentor that I had kind of sessions with. But it feels like throughout my career, I've I've had different people that I've been able to confide in, ask questions of look up to, and it's never been kind of one person throughout. And I'll some people will have that kind of my coaches XYZ. But no, certainly I've I've used kind of colleagues and people who are in higher positions to, to make sure that I get get that feedback. Yeah, in every stage of of my career, I've done that. Mark Ackers 43:55 And like you said, it feels like when I played back sort of what you said today, like you say, when you had the lady that was good at making calls, you could lean on her the AE, you've had that manager, people at sales loft. If you hadn't had that access to people that had already walked in your shoes, had success in the role that you're in people that you could be vulnerable with and open up to and really hear what you needed to hear and learn what you need to learn. And he wouldn't have had that. Where do you think you'd be in your career today? Tom Boston 44:30 I don't know if I would. I don't know if I would have been be in the role. I mean, I think I might have stepped away from sales because it is sort of an it is so hard. And without having people to share that with without having someone to speak to about what you're going through, to learn and to grow from. I'd have probably gone right back into retail and I tried it. It didn't work. I wasn't very good. Not for me, Mark Ackers 45:05 though, like that. I've always in a way, though, what you've shared today and your personality, probably Tom Boston 45:09 I would have never, never forgiven myself really for but not succeeding. I don't like failing. Mark Ackers 45:17 While you have succeeded, you've had an incredible career. I mean, it was such a mouthful to introduce you. It was, wasn't it? Yeah. And you've got so much more to come to give, I'm sure. to sort of wrap this up. Mark Ackers 45:32 If you had your time again, let's let's go back to your at Wix. You're called was a lifer? Ally for that's what they used to say I'd be if you're a Wix and you'd be in Coralife. And you had your time here, but with the knowledge that you've gotten now, would you go into sales? Tom Boston 45:52 Yeah, if I could go back what I do, I do it all again. I would, you know, I would I have learned so much about myself. I met so many great people grown so much. I mean, you were at the event. A few weeks ago, I spoke on stage, the keynote, Thea. And I remember saying to my wife when I got home, guess I'm a keynote speaker. Now, you know, this has all come from sales, that role manifesting into another role. I wouldn't change a thing. Mark Ackers 46:33 What do you think you have learn about yourself? Tom Boston 46:38 I've learned that I I like everything to be perfect. But I've also learned that nothing usually is everything that I try and do has to be, I want to do the perfect cold call the perfect discovery call. I want to do the perfect LinkedIn video, whatever it may be. But I've also learned that, you know, sometimes just trying different things, trying to get better. That's the best way that's, that's how you learn and grow. And so yeah, that kind of perfectionist in me, has helped me a lot. But I've also had to tell that side of me, look, it's fine. To get things wrong sometimes. Mark Ackers 47:27 And for lots of people listening to this podcast, they might resonate with some of the things you share today being crapping their roles, but not wanting to be struggling. What would you say to someone in sales that perhaps has just realised they are crap? Tom Boston 47:45 What just now? Yeah, Mark Ackers 47:46 they've just realised this is That's me. I'm crap at this. Tom Boston 47:50 Yeah, well, I would, I would own that. I wouldn't shy away from it. Because the only way to get better is to know deep in your soul, that your craft, if you think that you're great. You're probably going to fall down faster than someone who thinks that they're not very good. Having that mindset of Look, I know that I'm crap. And I know I need to get better. Use that as motivation to spur you on. Self awareness is a huge part of of sales and growth. Being aware that things need to change. Use that. Don't get comfortable, don't hit yourself and convince yourself that you've got all the answers, no matter how confident you might think you are. Understand that. Okay, well, actually, if I am crap, why? Where do I want to be in 18 months? How am I gonna get there? Set some goals. You know, my work for Coach? A, why not? Mark Ackers 48:54 Last question, you said you've met some amazing people. Give us the name of one person who you'd love to see. Come on this podcast and talk about how they used to be crap in sales. Tom Boston 49:07 Yeah, it'd be great to hear from some of the big, the big names, the confident voices that we see on on LinkedIn, the sales coaches, Larry long Jr. was the first guest of my podcast, one of the biggest voices literally, that you'll ever meet. But it'd be interesting to find out about his journey. So maybe someone like that maybe someone who seems like they've got it all figured out. Right. Mark Ackers 49:38 I'll put you on the spot. Yes. I'm going to send the next 20 seconds to Larry. This can be from you tell him why did you come on this podcast? Tom Boston 49:46 Larry, you should come on this podcast because these guys understand just like you how important it is to invest in yourself and The weather it's a thankful Thursday. That's one of Larry's our Super Saturday, whatever it may be whichever day you record. It'll be worth your time. And you'll enjoy speaking to this guy because Greg Mark Ackers 50:16 Tom, thanks so much for joining me on the ISP crap and sales podcast. Been a pleasure. Great Tom Boston 50:20 to Great to be here. Thanks for having me.