Bryan Charlton: How Slowing Down Can Speed Up Your Sales Wins

All right, I never thought I'd say this, but I don't take notes on my sales calls anymore. It's not because I'm getting lazy, it's because I'm using Otter to take them for me. Otter.ai has a new sales assistant called Otter Pilot for Sales that automatically takes notes for me during my calls, transcribes them in real time, summarizes them, pulls out sales-specific insights, and syncs everything to my CRM. And their AI chat function also allows me to ask any question about any meeting or even multiple meetings with the same person. The amount of time it saves me is absolutely ridiculous. And that's not even scratching the surface of what it can do for teams. I'm super excited to be partnering with them to give you an exclusive offer to get Otter Pilot for Sales today for free.

Go to otter.ai forward slash jbsales to get your free offer and start saving time and selling more effectively today. I'm really looking for two things I think that separate the reps. One is that they've got that self-starter, like that they're kind of restless and they just want to go. That attitude is really critical. And the second thing is just a curiosity. If someone has both those qualities, I can teach them process. I can work with them on their skill sets. I can teach them how to do a good demo. I can put all the other pieces together. But if you lack one of those two fundamental things, it's really, really hard to like add those two to the repertoire. Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us.

Today's guest is Brian Charlton. Brian's a sales manager at Otter, which is one of my new favorite platforms and a new sponsor of mine. But don't worry, this isn't a sales pitch for Otter other than at the end, like the rest of the podcast. Now, this conversation was all about sales and how to drive more deals into and through the pipeline. We talked about how to uncover the true why behind the client's decision and why without it, it's most likely not going to close that deal. We also talked about the variables and which ones we can control and which ones we can't throughout the sales process and how it's important not to skip steps. You've heard me say it before and I'll say it again. The reps who are solid in their fundamentals and do the basics consistently are usually the ones who win in the long run and how many times you need to slow down to speed up.

Finally, we talk about de-risking the decision and how Brian maps out a 30-60-90-day plan for implementation that he shares with the clients early in the sales process and the difference that that makes. This episode is filled with good tips and techniques that should help you close more deals, so I hope you enjoy this as much as I did. Let's make it happen. And Charlton, welcome. We'll make it happen Monday podcast by Fred. How are you doing? Hey, it's good to see you, John. I'm doing great. How are you? I'm doing well, man. As we were prepping for this, we were talking about kind of history. What was it back in, you said, 2014 when you went through, like, one-way trainings or something? Yeah, that's right.

Yeah, it's amazing that it's been that long, but I loved it, man. Really excited to be here today and come full circle. Yeah, it's exciting to have you. Like we were saying, it's always cracks me up. Hey, it makes you feel old, but also, you know, kind of reminds me of why I do what I do, right? You know, 20 years later, if you will, still kicking it and still having people come up and pass the torch, if you will. So it's good to see it. Absolutely. Hopefully, I'll have some of that in my career here, too. Yeah, I'm sure you will. My friend just got promoted, so congrats again on that. But as we get still, we're going to talk today about some of the, you know, deal advancement stuff, like trying to expedite deals and everything else because urgency is probably one of the biggest questions I get in as far as sales training standpoint.

So how do you create urgency? And we'll talk about that. But also, like, you know, making sure you're doing all the right things, you know, getting back to fundamentals and doing all the right things consistently. But before we do that, Brian, give me a give us a little background story. Give us your origin story where you're coming from family, where you grew up, all that stuff. Not not the stuff that we can all read on LinkedIn, because that's the easy stuff. But what makes Brian Brian? And then we'll get into it if you don't mind. Yeah, absolutely. So I grew up in Southern California. You know, one sister, dad was in computer science. He's got a pretty interesting career story. He actually thought he was going to study psychology and then was getting his master's degree in that and had to use some computers in like the late 60s to do some data analysis and thought this computer science stuff's even cooler than the behavioral psychology.

So he ended up going that route. And kind of midway through his career, I had like an unexpected sort of forced entrepreneurial moment. He was working as a VP of IT for a, I think a savings and loan at the time. And they went, they went tails up and the government needed somebody to like run the systems, the database systems for a couple years while they tried to transition the business. And he was like, well, I'm out of a job. Like they'll give me a guaranteed contract for like two years. I might as well try and turn this into a business. And the reason I mentioned all that is that, you know, it was kind of being around his business, which he ended up running for about 12 years before he sold it.

And being around the salespeople in his business and kind of seeing that, that gave me a sense that sales was a career that I wanted to go into. I really liked the guy that was his head of sales at the time. And I was always, you know, very sort of comfortable and outgoing. And people told me, you should get into sales, you know, because you're outgoing. And I look back on it and I think confidence in being able to be articulate and speak in front of people's, a key aspect of it. But, uh, certainly not the only reason to go into sales. No, I'd say it's funny where everybody, like, that's kind of the criteria that people, Oh, you're charismatic. You should get into sales. It's like, Oh, that, like, that's not the reason you should get into sales.

Like that, don't give me hell. I mean, being a, but you know, being a, you know, I mean, I'm an introvert quite frankly, for the most part, but you know, being an extrovert definitely helps, but you know, there's so much more to it that obviously you kind of realize once you get like, Oh yeah, no problem. I just talk to people. It's like, Oh shit. That is such a small fraction of what this job is all about. That's so true. Yeah. And you know, that probably led to the first couple of years actually being pretty rough for me because I thought, you know, that, that, that confidence in like outgoing, this was going to actually help me open doors. And my first job was, was inside sales. Um, and it was, uh, it was, it was a rough couple of years.

Uh, it, it probably like, it probably took the point of me realizing that, you know, you could approach sales in like a process driven way for me to really feel like I, I wanted to stick with this and make this a career because I just didn't like that feeling that, you know, it was potentially just all about like energy, energy, uh, and like good luck as opposed to realizing there's things that you can manage and control, which is cool. We'll talk about some of that stuff today. Yeah, absolutely. I think what, you know, from me, I don't know about you, but to me, it was, I didn't know much early on, right? So what was your degree? I forget. You got to do this in, uh, communications. So, okay.

I don't know what I want. I want to do career. Yeah. So I got marketing kind of similar, right? As I was, I think we graduated around the same time. I graduated in 98 and graduated in 99. Um, yeah. And it was kind of like, there was no sales degrees. Right. But then you kind of fell into sales and you know, at first I knew I wasn't the brightest kid out there, the smartest kid out, the most charismatic, but the one thing I knew I could control was my effort. Right. And so I, like my approach was, I'm just going to work harder than everybody else. Like I, I really am just going to grind harder than it, make more calls, go on more meetings. But to your point, like I've been kind of thought to myself, I'm like, Jesus, I'm like, if this is what it takes to be successful in sales, like I am not going to last.

Cause I, I have energy, but not this much fucking energy, you know, I didn't need for a consistent, but Jesus Christ. So, you know, process, I think when, when did the idea of process hit you in, in kind of like, Ooh, wait a minute. There is a, um, a structure I could follow a process I could follow. Cause I remember when it hit me and it was more, wasn't necessarily my, like anything that, that happened from a sales standpoint, it was more about when I was a VP of sales for my first startup and we have no money. And my CFO was just a total dick. And, and he kept telling me like, I got a double revenue, you know, we got a double revenues, double revenues, double revenues. I'm like, dude, like, like, yeah, when we were 500,000, it was easy enough to build revenues.

Now we're 3 million and I got a double revenues again. Like, sure. I need three more people. I need this. And he's like, Oh no, no, no. We don't have the money for that. And so it was, it was almost like a forcing function for me to like, to learn how to speak itself, to learn, to learn the science of sales and start to put some process so I could predict some outcomes and conversion ratios and everything else. So, but it, you know, I was kind of forced, I would probably say I was like, well, 24-ish, 25 when I got kicked in the teeth and almost forced to. When did you kind of realize that for yourself, that, that charisma and hard work really weren't going to get you where you want it to be and that you needed to really start to study the science of sales and the process behind it?

Yeah, it's a good question, John. I'd probably say the first couple of jobs I had, um, it was a fairly like transactional sale. And so, uh, a lot of it was just sort of like being the first one in the conversation or the one who was there at the right time. And that didn't lend itself to me having a ton of process other than like learning that grind and learning how to do a lot of outbound. And that's a really, really valuable skill. And I think that even today, uh, I coach a lot of my reps on just the need for having that like self-starter intentionality. It was probably actually funny enough. I took a little teeny detour in my career where I, I kind of backed off from being a direct seller, uh, and actually was part of a, uh, a team.

I took a customer, um, success or customer support role at a company called FICO. It's a big company. Not a lot of people know about them. Uh, but they provide, um, you know, you've got your FICO score for the consumers. They actually provide a lot of, a lot of like operational software to financial institutions. So the reason I took a step back is that somebody that was a family friend was a, like an enterprise sales rep. And he was probably like five, 10 years in his career ahead of me and was telling me, he goes, Hey, I was asking for some advice about, you know, my own career. And he goes, Hey, he goes, we just lost a person on our team, our CSM. And it was really more of an inside sales role for an enterprise team.

And he was managing, I think, uh, a couple of large North American banks at the time. And he had another guy that was managing a couple North American banks. He goes, why don't you come join us and be our CSM? And so what I got to do is actually like a lot of like the day to day kind of, uh, supporting like the run rate business and like watch how they would do larger deal cycles. And it was working with those folks and seeing lots and lots of decision makers in and seeing like long deal cycles that might be like nine months to get budget unlocked and to get like approvals and legal and all that stuff that really, I think started to unlock for me that the notion of like sales being something that could be process driven.

And having done that now, I actually do think that you can take that complex process driven piece in an enterprise sale and actually push it down to something that's much higher velocity. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process. It also includes monthly workshops that I'll be running on specific sales skills and different tech skills like chat GPT and how to leverage AI throughout the entire sales process.

Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. Totally. And I actually, I'd also think that experience in the customer success role is invaluable. And I wish more sales reps would have that experience. I actually think, you know, the whole predictable revenue model that I thought it was breaking before I knew it was breaking before AI. And I, and it was great for us as a skit, you know, from a scale standpoint, right?

You hire young, you know, you put them behind me, make calls and then they grow at you, but it was never customer centric. And so now I think the, a great way I've talked to a couple of people who do this where they actually have their SDRs. And before they go to the AE, they actually make them go customer success or commit because that way they learn how to close, but in a much more safe environment, right? So it's more about cross sales, up sales, renewals, but more importantly, my opinion, you learn empathy because you see how the client uses your stuff. You see what happens when a sales rep sells a piece of shit deal and stuffs it down to clients throughout and the problem that causes. And so, you know, if you spend a year or two over in customer success, then you move up to account executive and that's where I, you know, if we could make that transition as opposed to like an SDR throwing them right into a closing role for mid-market or enterprise, which is a high failure rate.

So I love that you kind of have that back back. Did it, did it give you outside of the process? Did it give you that perspective on, on the client side that, that, that was, that you were conscious about? It really did. Yeah. And it did a couple of things for me. It, it, it helped me focus on like, you know, the realization that it's not just about the finish line. Isn't the deal signature, the contract signature, that's like the client starting line. And I've worked with some great people who talk about that as well. And sort of use more of that vocabulary about talking about the, the deal signature is like looking forward to getting to the starting line with you. Um, so it definitely influenced that.

I think the other thing that it influenced for me, John, which is kind of a, uh, a very tactical thing in my playbook. And then I work with my reps a lot on is focusing with the client, dreaming the deal cycle on how we're going to help them be successful. I think that, I think that every company has some motion of how they're going to support their, their, um, you know, their clients in the use or consumption of the product. And very few people talk about that and use that as like a selling advantage. And that's been something I've used in my career. And I feel like that's one really easy way to like immediately separate yourself from a lot of people and a way to like, almost like negotiate the value of your product without talking dollars and cents.

I love that is. And I think that's where we're tying into, have you read Jolt Effect the book? No. So I, I recommend it not necessarily. I I've come to the conclusion. I don't love how they address the problem, but I, I think that they've nailed what the problem is right now. So it's the third book in the group of, um, challenger sale, challenger customer, right? And Jolt Effect, the, the, what they're saying is, you know, everybody says we lose to no decision. Okay. Fair enough. But what their data suggests is that it's actually not no decision. It's indecision. And the reason is, is because things are moving so fast right now. And there's just so many options that the risk of making the decision is so high that even if you have somebody who agrees to, yes, my current state, you know, gap, right?

My current state is not where I want to be. Future state is where I got to go. You know, your solution is even better than what I'm doing right now. And shit at this point, it might even be cheaper, but people still aren't making the decision. And the reason is, is because they're scared to make the decision. People are, you know, nobody got fired for not making the decision. People get fired for making bad decisions. And so what you just mentioned there was as you articulate the support structure, host signature, what you're doing there is de-risking the, the, the situation for them, which is imperative right now because everybody's been through bad implementations. Everybody's made decisions that have screwed them over.

So the more you can de-risk this situation, this decision for them, the higher likelihood they're going to go for it. Yeah, absolutely. I think that's, I think that's really critical, really critical thing. So with like, let's talk about order here, like how you, with your team, how do you do that? Cause when I, when I bring this up about Joel defect, like I look at theirs and they're like, yeah, we'll de-risk it. And they talk about like, we're giving a money back guarantee and give it, you know, adding more services. I'm like, well, the reps don't have control over some of that shit. So, you know, I can de-risk it. I'm the CEO of my little company here. I could be like, look, this sucks. You know, I'll give you your money back, whatever.

Let's just do this. But you know, the average 22, 24, 25 year old kid is not going to have the ability to just, oh yeah, sure. We'll give you an L clause. No problem. So how do you, with your team at order talk about the, the, the implementation, the support structure and where do you bring it into the conversation? Yeah, it's a great question. I always like to start with, like the understanding the customers. Why? Um, a lot of my reps will, uh, you know, I challenge them because they'll, they'll get a yes that like Otter is the vendor of choice or that they want to move forward. And I'll always ask them, you know, do you know why? And some of them are learning to stop and ask those questions and understand the clients why, and it goes back to the beginning of what they're trying to do and what they need from the solution.

So I think there's a couple of ways you can like, you can de-risk it. One is for us, people come to us with, um, I'm just going to say like kind of the iceberg example. Like they can see like the visual part of the iceberg above the water. And we know that there's so much below the surface that we can do and solve. So part of our sales process is just understanding other areas of impact we could have building like a, a committee of people who are behind that change together. When I think when you get more people around it, um, you start to like, uh, create more momentum and it's, it's hard. It's easy for one person to ghost you and go silent. It's really hard for like a committee or team of people because now there's a group momentum to it.

So even if one person slows down, that's really hard to derail the entire thing. And, um, that's a big, yeah. Let me ask you on that though, because the complexity of adding more people. So there's a benefit of adding more people because you're multiple thread, you get hopefully multiple champions here, that type of thing. But the complexity of it is you're bringing in multiple different opinions, multiple, multiple, multiple different problems and, and potentially multiple different whys. And, and a lot of times, you know, let's go back to the second in book and in the succession of challenger sale, the challenger customer talks about like, you can be the biggest challenger you want, but if the internal politics are such that it's just not worth it, the person's like, look, I don't care.

You could challenge me all you want. I'm not going to go through this effort. So how do you get, is it a divide and conquer and then bring it all together approach for you or is it bring it all together to try to get them all on the same page approach for you? Yeah, that's a good question. Uh, I think it depends. So, uh, it depends on the state and the scenario, right? We definitely like, we are not in a state where we try to like get the entire company to, to make a decision and shift gears. The only way that we will typically like support or sell to an entire company is, is if an executive is saying, I'm just going to buy this on behalf of everybody. So we're not, we're definitely not trying to bring in complexity.

Like if we start with marketing or sales, we're not trying to like bring in customer support and engineering and operations, all those all at one time. But we do recognize that there's usually multiple people that are going to be part of this like decision-making committee and we want to interact with them. So my perception, at least in our deals is that those people are going to be involved, whether you like it or not. You know, it's usually someone from it. It's usually someone from, from finance, probably an executive sponsor and your champion might be someone mid-level or lower level or even high level, but all those people are going to be involved to one degree or another. So it's more about just being thorough and getting them all involved.

Um, what we typically find is, is that, um, usually we'll start with like a champion or one or two people. And then there's an, there's an education process that takes place and I don't want them to be involved. There's a right balance of how much they're involved. And you, you really, you totally hit the nail on the head. It's like, I want to get them in to get them educated, get them excited, connect to a couple things of value. And then I sort of want them to disappear because after that, it's like the longer they stick around, uh, you know, it's almost like people feel like a responsibility to like come up with, uh, like objections or reasons, like think about the risks. Right. So it's like, let's get to the yes.

And then let's just quickly move past it. It's like that scene in, um, the money ball. You ever see that with, uh, Brad Pitt? You ever see that one? Yeah. Right. Oh yeah. And then the, and he says yes and he just hangs up on them. And, and, uh, what's his name? He's like, what did you do? He's like, when you get a yes, hang the fuck up, like just shut up and hang up. Right. So it's the same way. It's like, okay, cool. I got the, the, but I guess, how do you look at, cause there's so many variables these days in deals, as far as things that happen to the business, you know, people coming in and out of the process, how do you work with your team to like, what control, what variables do you try to control and which variables are you just aware of and, and, and adjust accordingly?

Yeah, it's a good, it's a good question. So, I mean, a lot of times people come to us and they're thinking about AI and they're trying to figure out, uh, what place this has in their business. So what can we control? Like by educating people, I think we can control the perceptions of where we fit in the use case. I think we can take a small area of value and turn it into a larger one. Um, you know, what's, what's hard to control or what we can't control necessarily is people's like risk appetite. You know, what part partially what makes us valuable is that, you know, clients are contributing data to our platform that, you know, is meant for themselves to use, but people start to get nervous and they're like, well, we're not sure if we want our, you know, confidential business data in a platform.

Now, of course we take precautions around that and we're careful around it. So someone's risk appetite is something we can't manage. So what I tell my reps is, is that you need to identify it, ask about it and understand it, but you're probably not going to change it, you know? Um, so that's one of the things we can't change or control. I think that's, I mean, again, identifying it is key is to say, okay, again, are you risk adverse? Right. And then there's some things that you can kind of see. I don't know if you use crystal nose, but that, that actually the disc profile, right. And it does kind of give you like, okay, is this person optimistic? Is this person risk adverse? Right. See, sometimes you can kind of get a sense of it and then act and then address it or adjust accordingly, but, but it's really, you're going to be able to change it.

It's almost, you have to sell to it and be proactive about addressing it. You really do. Probably the other thing we can influence is a lot of, a lot of companies will come to us and say, you're in an AI bake-off and we're like, great. Who's the competition? They're like, well, no, we really like you for what you do. We've actually used your product or we've had other people at other companies who've used it, recommended it. So in terms of your platform, like, you know, conversation, intelligence, meeting intelligence, they're like, otter's our choice. I'm like, who are we in a bake-off with? They're like, we're looking at five other AI tools. We're trying to figure out if we should have something that helps us generate proposals.

If we should have something that helps us do outsource BDR, you know, the like research, something that would help us, you know, create marketing content. I'm like, oh, you've got a pie and you're trying to decide how to slice it up. So that's where we can kind of come in and control it and try and influence it more. And that's actually pretty fun because you can start to throw elbows like against other solutions value in a way that you, you know, you would never do against the competition because you're sort of, you're, you're sort of throwing like different use cases, um, throwing shade on those use cases or elevating yours, uh, which is like being personal with a certain company. Totally.

And that, that, that you're, I like that where you just, you're kind of free to, I don't want to say talk shit, but like, like, they're like, Hey, look, does that make a lot of sense here? Like, is that really a priority? Right. Helping them understand that. I think that's the question, you know, a lot of reps miss is that, you know, Hey, who's top great, whatever, but it's also like, okay, well, what other initiatives are you working on right now? And where does this one fall on the priority list? Quite frankly, because I get so many reps who are like all in all in all, they definitely are evaluated. And I'm like, yeah, but they have probably 10 other initiatives that they're working on right now.

And this can't be number one. So why is this going to get done anytime sooner than later? And if you can't figure out what those other things are, you're not going to get this to you. Well, and in your business, right? Sales training, I imagine this is something you've got to navigate all the time because, you know, sales teams are, are well known to, to kind of chase the shiny new, um, technology and sales teams are, you know, they obviously, there's a huge, um, you know, relationship between the technology or solutions that a team uses and the, the outcomes that they can drive. Um, you're probably competing against things like technology budgets and stuff like that. How do you, how do you identify that in your deals and navigate that kind of value?

You know, it's tough because I, you know, I do ask, first of all, I, you know, I, as far as the qualification, I get all of the, the tech stack details and those types of things. And if they have, you know, I, for me, if they have a pretty legit tech stack, and then I ask what other initiatives that you're working on, I don't know, I can usually pick it apart, right? Because I could be like, well, you already have some, why would you break? But I also get a sense of how serious they are with this. You know, I think the bigger challenge on my end is definitely the, um, what the, the Advil versus the vitamin, right? It's like training is never something somebody has to do, right? I mean, literally just, okay, open up YouTube and get a couple of videos there.

Like you could literally go that route if you wanted to. So for me, it's more about, I got to get up. Like I, I look at the intangible factors. I don't have a conversation around ROI. Quite frankly, I always roll my eyes at ROI when somebody's like, well, what's the ROI? You're trained. Like, please, are you really going to have this conversation? Fine. What is your current conversion ratios for your tier one accounts, email cadences to CEOs in the tech industry? Like what's that conversion ratio? Oh, I don't know. Okay. What are your cold call conversion ratios to this? And I just go through metrics. I'm like, do you have that number? No. If you don't have a fucking baseline number, don't talk to me about ROI.

Okay. It's more, I get into the conversations and again, I'm, I'm more of like a mid market, right? So it's not, I'm not too expensive for the whole organization to have eyeballs on it, but I'm not so cheap that it's just a no brainer. So for me, it's like, I tie a lot to like emotion in a lot of ways. It's like, how are your reps feeling right now? Are they motivated? Do you feel like they're getting, it's like, cause yes, there's an upskill component to it, but also there's the subjective part of this of like, you're investing in your team. Well, that has to do with technology too. Like if your team doesn't feel like they're being invested in from a technology standpoint, these days they'll bounce and go find somebody else.

Now I do think that's a little bit of a danger here that reps expect the technology. They expect the training from their companies. And I am begging them not to, because if you expect your company to invest in you, you're probably not going to last too long, which is why I want to kind of turn this to, to the fundamentals here and where you see this going, because you see a lot with honor, right? You hear a lot, you see a lot, what good reps do, what bad reps do. I'm trying to figure out where this goes and where the future sales reps are going to come from. And the reason I say that is because all the grunt work that, that I did and you did early days of sales, all the shit work, the taking the notes, the updating CRM, the, you know, making the calls, like all that stuff is now obviously going to get replaced by, if not already replaced by AI.

But all that shit work is what made you and I, the sales reps that we are and gave us the ability to have a business conversation without reading the script. If all that stuff is going to be taken care of now, where do the future sales reps come from? And what are the fundamentals even going to be forward? Yeah, that's a really good question, John. And I think you're right. It's funny how much I think things have come full circle. It made me think of the way that clothing styles have come full circle. And I remember growing up, you know, that, uh, uh, you know, the mustaches were kind of like an 80s thing. And in our generation, we sort of looked at that and kind of did the eye roll. And of course, then that's all come full circle.

Now, a lot of those styles are back in and, you know, mustache is super cool for a lot of people. Totally. Um, I think it's kind of the same way with sales. Like I think is, I think is some really cool technologies came out in the last couple of decades there. They're almost this felt to me, and this is just anecdotal, but it felt to me like salespeople became a little bit of like demo machines and that like good sellings was equated with the ability to do a demo more than it was to understand a client to problem solve to, you know, equate value to challenge to uncover process. And to me, it seems like it's almost now come full circle on that a little bit where the maybe just information's better.

Maybe customers are finding other ways to get, you know, demos. Maybe it's just that there's too much competition. I don't know, but it feels like when I, I bump into a lot of reps and here's what I find is a lot of them who have worked in the, like the last come up in the last decade are of that kind of demo, demo driven mentality. I really looking for two things. I think that they separate the reps. One is, um, that they've got that self-starter, like that they're kind of restless and they, they just want to go. I'm the people who kind of lean back, lean back versus lean in, um, are the ones that I worry about. Cause I, you just can't teach that. It's like they say in football, like you recruit speed and you can, you can teach certain skills and smarts, but you can't, you can't teach speed.

I think that that attitude, um, is really critical. And the second thing is just a curiosity. If someone has both those qualities, I can teach them process. I can work with them on their skill sets. I can teach them how to do a good demo. I can put all the other pieces together, but if you lack one of those two fundamental things, it's really, really hard to like add those to the repertoire. Do you think you could, I asked, I used to ask this question a lot. I'm still on the journey of, of trying to figure it out. Do you think you can teach curiosity or do you think it's, it's, it's more like meeting your surround curiosity? I don't know. I'm not sure. I, I, I think for some people it's born.

I think, um, I think for other people I'm thinking of gosh, this line from this movie just pops in my head. I think it's, uh, what is it? Like the Italian job where he's asking about the, the guy about like dogs and he's like, you don't, you don't like dogs. And he's like, I had a bad experience. And the guy's like, tell, tell me about it. And he's like, I had a bad experience. Like end of conversation. I think for some people it's like that. It's like the curiosity comes because they had a bad experience. Like they got burned for not being more curious. And like that, I think that kind of wound, uh, that, that trauma can like cause you to like choose to grow from it. Right. So you're either born with it, or I think you have an experience that causes you to internalize that.

Yeah. And I also think it comes from just being interested. You know what I mean? Like if you're, if you're interested in a topic, no matter what it is, you're going to be curious about it. So I think it's, it's encoded upon leadership in a lot of ways to get their rep to be interested enough in the clients and enough in the problem to be curious enough to, to, to really get, get to what you had said earlier, which is the why, like, why are you doing this? Right. And I, and I think that's where, you know, how do you look at, you know, from a, from a rep standpoint, I would say, if you don't believe in what you sell, right, then good luck selling. It's a brutal profession. And if you don't believe it, go find something else to do.

Cause you're just one of those two sales reps. So how do you like reverse engineer here? Yes. We want to be curious. Yes. We want to get to the why, but I think you have to have a belief system of your product, your service can make a difference. And, and so that you can get to that why and be curious enough. So what do you do with your team to try to get them to not like believe in, in, in the profession of sales as a profession, but also in order so that they look at it and say, no, well, this shit is off the charts. Like I, I really am curious to see if we can solve that problem because I know we have. So is there something you do on onboarding or anything like that, or just continuously to get people both the belief system up?

Yeah, that's a really good question. I mean, one of the things just to, you know, prop our product here, like it's really easy because we're, we're, you know, recording the conversations to like highlight what looks good, uh, and what we're seeing. So, I mean, when I onboarded my team, I went out and hired like four new reps, but actually five new reps all within a short stretch of time when I got promoted and I had one existing, um, rep who was doing really well. And, and so it was like, how do I get these five people like up to speed and ramped up really quickly? And one thing I did is I just went through and looked at what me and that other rep had done and cherry picked a lot of our conversations from different stages of deals and different types of customers and put them in a, we call it a channel, but it's basically like a repository they can go back and look at.

So I, I had them use that as part of their enablement. Um, so they got to see a lot of different things. And then we do, we do a lot of storytelling as a team. So, you know, when my team is doing, um, you know, forecast calls, you know, I try to get past the numbers. Someone in my career said something to me, like, if you use, if you're using your, your CRM and you, you know, forecasting tools, right? Like there's some stuff you don't have to talk about. And a lot of companies just end up getting together and like, they like repeat information you could already see in a report or in the next steps. And then you're like, why are we putting it there and documenting all this stuff? It's like, you're not going to consume it.

Let's have more valuable conversations. So a lot of our forecast calls, um, we'll talk about things like, um, why would this deal not happen? Like what, what is the motivation? What are we solving? When, when reps will say things like, how can we influence the timeline in this? It'll be like, well, why are they doing this project in the first place? Why are they purchasing Otter? What are they hoping we can solve? So there's a lot of those conversations in the business. I think, I think maybe managing to that might help people just have that continual like exposure to it. It reinforces the talk track in their own minds. Yeah. I think it's a constant battle too, right? Because there's so many different emotions to manage in sales as far as just the ups and the downs and all that stuff.

So the belief system can get cracked pretty easy if you're having a bad model at that on a bad quarter. Um, so it's, I think that's probably one of the bigger challenges I see managers have is just to keep that energy, keep that belief system up so that they can keep going at it. Right. Cause this is not a, not for the fainthearted, if you will, uh, when it comes to this profession. It's really not. And that, that ramp up period, it's like tough too, you know, like even we've all changed jobs, you know, there's that like that there's that period, like where like maybe you're two months in and a little bit of like the enthusiasm is sort of worn off, but maybe your pipeline's not, you know, popping with, you know, close one deals.

And it's like, how do you survive month three, four kind of while you're waiting for stuff to really click it's tough after your ramps, right? It's like, okay, you're ripped now go. And I love the, you know, the three months ramp or the two months. It's like three months. So this better be a very small sale of the, you know, ACV for me to start ramping in three months. Cause if this is mid market or enterprise, I need, you know, a lot longer than, you know, three months, 30 days to ramp here about. I know. Right. That's for sure. So let's talk about, uh, I mean, you'd mentioned a few things when we got together here about, um, you know, advancing deals and some of the blocking and tackling to make sure that you're putting yourself in a position with urgency being, I think one of the biggest issues, most sales reps are dealing with right now as far as how to create urgency, drive urgency, uncover urgency.

What are some of the things that you're seeing that are, that are expediting deals and versus chilling? It's like, if you look at a deal is there, are there certain things that you're like, like, if we don't have this, we might as well stop. But if we get this or do this, you know, the likelihood is a lot higher. Yeah. I mean, I think there's like multiple things that I'm, I'm looking for in a deal. I think one thing that comes to mind, John, is that everybody's looking for like the hack or the, the, the step they can skip. And there's just, there's, there's no shortcuts, right. You've got to do the fundamentals. I think, I think, um, we talked about slowing down to speed up. Like, I think that actually doing running your process the right way and being mindful of it actually gets you there faster.

Um, so, I mean, a couple of things to me are like really good signs for, for a deal. One would be, um, that the client is willing to introduce us to other people to educate, you know, within their business. So if they're willing to introduce us to an executive sponsor or another department head or someone else that, that to me is a really positive sign. Um, usually if we can have like, you know, two to three people, uh, that are like active participants in a deal, it's a much more higher percentage to close than if we have one. Um, one of my reps actually right now, while we're recording, this is actually on the, on a call with a prospect and, um, it's, it's going to turn out to be a great partnership, but this, the, this rep, you know, they kind of, they got happy years and they kind of skipped some steps.

So one thing that they did was they shared pricing way too early and like gave a lot of stuff away. Um, we, we use this phrase and my head of sales, Dustin came up with this, but instead of give, get, we talk about our, we tell our reps to, um, challenge and give. And the challenge is challenge the rep to give you something back that is part of your, part of your process that could be access, that could be information that could be confirmation of certain things, um, in order to, to give something back. And so that's one of the things like for us, pricing shouldn't be talked about until we get to a certain place. I'm a huge fan of just share what list pricing is so that we all know that we're sort of in the right ballpark.

But from there, if, if somebody is asking for a proposal, I just say like, Hey, even if I gave you a great proposal right now, I'm guessing you wouldn't be able to just turn around and sign it. You probably have some things you need to do in your evaluation. The client will usually nod and say, yes. So fantastic. I'm more concerned about establishing value with you. Let's talk about what else you would need to do to see that value and who else would need to see that value. And at the right time, I'm not worried about pricing. We'll work with you. We'll get you something that, that makes sense. And that to me is a great step. Um, in, in this particular instance, John, the rep like gave away pricing, uh, didn't get access to, to, um, uh, the decision-making committee and they had a great champion, but they didn't get access to those people.

And so when it ended up happening is the initial proposal, of course, got put in front of the CFO who of course cuts it down by half. And now we're in a whole back and forth and it's all going to work out in the end, but we actually had to go back and repeat a bunch of steps, which was getting access to those people, talking about them, establishing value. The deal could have been done weeks earlier. So it's amazing how like when you, especially when you do close loss deal reviews, right. And you look back and like how many deals I've lost where I've looked back and I'd be like, God damn it. You know, I forgot that one stupid thing, or I got happy years, like you said, and I just ignored what I, I, I relied way too much on my champion and all the things that they were telling me, right.

All the buying signs, like, Oh no, this is definitely going to happen and that type of stuff. And it's like, you know, and you just, if you're not paying attention. So do you have like a checklist you go through with your team as far as like what you have? Like how do you, cause I don't, I mean, I use a scorecard, right. You'll get scorecard that gives them the gets and we kind of do that whole thing. But what do you get, what do you use to make sure that the fundamentals and the, and that the stuff is being done consistently that, you know, needs to be done. Yeah. There's a, there's a bunch of different ways to like look at it. And I think one of my values is not burdening my reps with, with more things than they need.

And so I'm always looking for what are those kind of, kind of fundamental things that like encompass everything, right. You know, you talked about vitamins earlier. It's like, yeah, like taking vitamins great, but like if you, if you eat, um, if you eat good, healthy food and a variety of healthy food, now you're getting your nutrients and you're combining it with eating and getting your, your calories. And, and you know, there's, there's, I'm a big fan of like, where can we like double or triple benefit from, from certain things. So John, a couple of things we constantly talk about is understanding the clients. Why understanding, Hey, why do they want to solve this? Which tends to actually lead to some problem or emotion or goal that multiple people in the company care about.

So it makes a really, really easy and natural way to get access to the decision maker. Cause if I tell you, well, let me, let me list my things out first, understanding the why we talk about the two yeses. So yes, from your champion and a yes from the decision maker. And then we need to understand basically like their, their buying process because we're AI. Um, there's actually a lot of work. Once we get the yes from the business that is around like, um, security risk, compliance, and legal. And so I make sure that the reps sort of understand that process. And that's important for forecasting and potentially knowing what's going to stop or slow a deal down. But those are kind of the, those are sort of like the key fundamentals that we focus on.

And then from that come a lot of the different things that, that you and I are talking about here. How do you, how do you make sure a rep isn't, uh, what I call story time in their forecast reviews, right? They tell it, Oh yeah, yeah. I get the decision process. And they kind of give you this vague, well, it goes from this person to this person, but you don't know who they talk to about that. You don't know who's really involved. So what's your, um, what's your forecast reviews? How do you, how do you call bullshit basically? Or how do you know they're full of shit when it comes to their stories? Yeah. I mean, so I, I really have the benefit of, of seeing Otter itself and Otter's like serves it up.

I know you've been using Otter, um, yourself now for note-taking and like probably my favorite thing about it is just, just the, like the AI generated like summaries that it can give you. So I get an email like from, from all the deals that I'm on and where I'm on the calendar, even if I don't attend and I'm constantly triple booked, Otter sends me this like quick synopsis with the categories that we care about. And so I'll scan it and I can really tell, I can really just tell from looking at, I mean, it does Otter have enough there to answer questions about authority or their decision-making process. And honestly, at a glance, I can get a sense for where a rep may or may not be skipping steps or like actually doing their job in a deal.

And then, you know, we, we go back and we work through it. And, um, that's a big part of it though. That's a big part of it. And that's why I think a lot of these AI tools, right, where, you know, they're extracting the information. I'm not relying on the rep to tell me information. And then I think that's, you know, and I'm not shit, not reps here. Like, like reps some time, like, and I'm a storyteller too. You know what I mean? Like I'm a storyteller in sales and I'm storyteller in forecasting. And so, wow, you know, and let me explain all these things, but it's amazing how few of those story components actually matter. Um, when you get right down to it, it's like, no, like you have this. And then when you really get down to it, you're like, I don't think you really do like, so let's figure it out.

We can get it right. Cause that decision process thing to your point is really important, but the details are important. So, so what's, and let's finish up on this. Like, so there's some things that you look for specifically. What are, what are some of the bigger mistakes that you're seeing sales reps make right now outside of not knowing the why or the decision process or, or those types of things? Are you seeing common mistakes now that are different than historical? What sales reps have made mistakes on? Yeah, really good question. Um, and I certainly have a different view now because I'm in so many deals versus before it was just like hearing things in, in my forecast call. Um, you know, I think I probably, it probably still just comes down to some fundamentals, John.

It's like, you know, are we negotiating price at the right time, you know, and with the right person? Um, I also think that sometimes we lose deals because, um, reps just get a little greedy and like, they try to squeeze something too hard. They just sort of don't read the room. And this comes back to like things you and I talked about early on. And maybe it's that like customer success side of things, just have some empathy and understand how the client's going to, um, use the product. And like, you know, if, if you're negotiating too hard, like maybe they're trying to just get a couple grand more out of a deal and really they should be focused on getting it done. I mean, a lot of changes at any given time in our world, priorities could change competing projects.

I think maybe another reason why they may not get a deal. And this goes back to the customer success thing is I think like not giving the client confidence about how they're going to be successful. Uh, you asked me a question earlier. I don't know if I ever answered it. Um, but you said, where do I talk about that in our process? And it's probably like late stage. Like I think around the time that we start giving like, uh, negotiated or customized proposals is when we also start giving the client some overview of our success. And I keep it really simple. I put like a 30, 60, 90 day plan together that I show the clients what we're going to do and what they can kind of expect in terms of culture and change.

And that's probably a big area where I see maybe deals getting lost is maybe it goes to like a, a CFO or like an executive, like a president who they're really not like, they're never going to take a meeting with you. They're not going to like see a demo. They're kind of relying on their people to, to confirm yes or no, but, but they're going to potentially challenge and saying, what's the risk that this doesn't work out. And if the team doesn't have a good answer, if you haven't equipped them, maybe they don't have a good answer. So that's where the C the talking about CS, I think can be super valuable because they'll go, guess what? Here's how we're going to be successful over the 30, 60, 90 day period.

So. So I actually asked that I've started to ask that to, to de-risk it, right? I used to say, you know, reverse timeline. So, okay, you want to go live by this? That's two weeks to do this to whatever. Then it turned into, okay, great. Well, what happens if we don't go live on that date? You know, what's the impact of the business? And that kind of dictates forecast. Um, but then I've added the, Hey, what is a wrong decision? What does the bad decision look like for you? Like say you go, whether it's us or somebody else, like say you make this decision and it doesn't do what you want it to do. What does that mean? And that, so that's a scary question to ask because it's like, you know, this, and it, but what I found is it almost turns into a therapy session because clients are like, Oh Jesus.

And if, if, if this pops up again, you know what I mean? Like my asset, like the last time we did, it was horrible. And now I'm uncovering all those things that I need to sell against at this point. Right. Cause they're committed to making the decision. Now they just need to make the decision. And if you can't de-risk it, they're going to stay with what they got. And so I'm, I'm trying to uncover all the horrible things in their head that they're thinking of what happens if this goes wrong. And then my whole job is to say, okay, well, let me make sure that that doesn't happen. That's so powerful, John, because, you know, we're always assuming the things that we think are going to be like the top factors in their decision.

And, you know, that probably price is one of it, maybe a certain feature, this or that. And, and you just, you just brought up a great point that there's probably something that we're not thinking is super critical in the decision that is going to be a huge factor. I really like that. Yeah. And to play around with it, cause it's a, it's weird, right? Cause again, again, you have to give the reason why you're asking. It's be like, look, you know what, as well as I do that, we've all had bad implementations. We've all had shit go sideways. So I'm trying to figure out T for you, like, what's the risk in you making this decision? If it goes wrong, my goal is to make sure that none of this goes wrong for you.

And it, and now you're putting yourself in that position as that, oh, okay, this person gets it. Like my ass is all lying here, which is why we see so many more people involved in the decision-making process. Cause even if you have the decision-maker, if I'm the decision-maker and, and I'm, and I make this decision and six months later, this shit doesn't work. I'm my ass is on the line, right? That's why, Hey Brian, could you come in? I need your eyes on this. Hey Sarah, could you come in? I need your eyes on this. Hey, you know, because I need plausible diabolical, right? So I have a good tool to listen to me, right? So my whole thing is like, all right, let's assume this gets fucked up. Let's assume you make the wrong decision.

What does it look like? And it's a, it's a weird conversation because we're taught to sell the dream, right? Like, oh, let me put you out. Perfect. Your life is going to look like after we, nobody believes. So a little bit of a different, that's why I think sales is shifted pretty drastically here in the past couple of years, just based on the AI, the information, the access to information, and that just the sure amount of potential solutions that are out there to solve any group of problems. Yeah. That's really interesting. That's really interesting. You know, that actually kind of dovetails and I'll kind of wrap my thoughts on this is one of the things about Otter is that it becomes more valuable the more people in the company are using it, the more trust there is, right?

Because there's an element of it being a personal productivity tool, but Otter is also being used by our clients as like a knowledge base, right? We're capturing verbal conversations. And if it's being talked about, it's probably relevant and important and current. So we're at this knowledge base. And the more people that actually in a company can do that, contribute, and then consume that knowledge, the more valuable and the bigger impact you can have. So I think that's really interesting. The question you asked, because I think maybe one of the things that in our world might take place is like, what if people don't use this or what if it doesn't take off? And that's actually some of our best projects.

Clients have been willing to kind of go big and make this available to more and more people. And it's sort of like there's this threshold of like, if you kind of intentionally hold it back and put it in just one department, you're almost writing the future that it's not going to be a huge success. You're capping it. So I like that question. I think that really, that really relates to what I see go well and makes me think about how I can work with my reps to try and create more of those winning scenarios. Well, I mean, to your point, like I've been, I was introduced to Otter, I don't know, six, nine months ago or something like that, when all this stuff started really popping. And, you know, I'm, I'm pretty old school when it comes to sales.

In a lot of ways, I, I, I handwrite my notes, you know, I, I write summary emails and all that shit. Um, but Otter has, uh, uh, out of all the technologies in my tech stack. Uh, I, I'd give it outside of like the core, you know, fundamental stuff like HubSpot, whatever, but, uh, it's definitely on my top three right now, as far as productivity, as far as insights, as far as collaboration. So, um, you know, highly recommend, love the partnership that we're working on right now and, uh, tell people where they can find out more information about you, about Otter and everything that you guys do. Yeah, absolutely. Our website's really easy to find. It's otter.ai. Um, and we've, uh, we've got a direct to consumer version of the product.

Like literally there's millions of people using it. Um, and then the neat thing is that the same, the same tech that powers, uh, our enterprise version is there. So go use it, um, go, go, you know, listen to, uh, a lecture or use, uh, the mobile app somewhere, do, do a recording on a, on a web conference, get a sense for how good it is. And then, um, you know, raise your hand, uh, and come talk to our team. You can fill out a contact sales, uh, form on the website. John, I think there's probably some links maybe through your resources here. They can get a, I think a free trial of Otter, um, through your, your resource or just hit me up over LinkedIn. Uh, I, um, I'm always happy to talk to people.

So. Sure. And for those of you listening to this, it's Brian, B-R-Y-A-N and it's Charlton, C-H-A-R-L-T-O-N. Brian, thank you again, man, for coming on. This has been a fun conversation. I'm looking forward to seeing what we can do together. Yeah. Thanks, John. Enjoyed it. Take care. Oh yeah. And as, uh, hopefully y'all enjoyed the conversation as much as I did. Like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day is done or how bad you think it went, you make somebody smile and you know, you've had a good day and the world needs a lot more of that right now. So thank you all very much. I will see you on the other side.

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