Building a Custom GPT for Every Rep on Your Team

00:14 Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're hanging out with Rich Lane to talk all things sales coaching. Rich has a great background in running long cycle enterprise deals and he's specifically talented in managing complex groups of stakeholders within an opportunity. He was in marketing at L'Oreal for about five years before deciding to break into sales the hard way right back in square one as a BDR. He moved up through some A.E. at Sedna, Verkada and now he's the head of commercial at Kepler, the maritime data intelligence company. In today's episode, Rich is going to walk us through how he's using AI in coaching himself as a leader, but also coaching his reps. I'm really excited to walk through an innovative way for sales leaders to sharpen their coaching game, something we don't spend nearly enough time talking about. All right, let's get into it. Hey, Rich, thanks for taking the time to talk to us about sales coaching today. Welcome to the show.

01:03 Rich Lane: Thanks, Warren. Thanks for having me. Super excited to be here.

01:06 Warren Kucker: Great, well Rich, tell us a little bit about why you wanted to make this switch from your role at L'Oreal into sales and then tell us a bit about what you're focused on today at Kepler.

01:15 Rich Lane: Yeah, amazing. So yeah, so as you said, I spent five years at L'Oreal, started off right on the graduate scheme, straight out of university, and then moved into a variety of different marketing roles and then made the switch actually at L'Oreal over to commercial. But really randomly on an evening in London, having a friend of a beer, he was an account executive working in SaaS. I didn't even know this industry existed and her day in the life sounded like so, so cool. managing lots of deals, closing lots of business, speaking to so many different stakeholders, and particularly the C-suite. So I was at a point in my life and my career where I made a big jump and a big gamble. And I always remember the really strong piece of advice that they gave me was even though I could have gone straight into an AE role, he always said, go straight into a BDR and generate your own pipeline. It's such the most important skill in the job. And that always stuck with me. And I'm so thankful I did that.

02:17 Warren Kucker: That's awesome. What are you working on today Kepler?

02:19 Rich Lane: Amazing. So I've actually recently just stepped into a new role where I'm heading up new business for Europe and for Kepler working across the full maritime suite of products.

02:30 Warren Kucker: That's great. That's awesome. Well, let's dive in deeper. I'm super excited to launch into this topic. So let's start off. Most sales coaching happens in a 30 to 60 minute meeting once a week. What do you feel like is broken about how sales leaders coach reps today?

02:50 Rich Lane: Yeah, I think this is an interesting question. I think what you see traditionally across many organizations is that typically managers get promoted into their roles because they've been the best I see. Everyone typically has been promoted because of that, but they don't actually get shown or support on how to lead or how to coach or how to be the best manager. And I think the default style in a lot of organizations goes back to, well, here's how I did it. or make more calls or work as hard as I did. And I think this is because no one has ever actually shown them how to coach or how to lead or in other way. And they've been rewarded for that performance, not actually for growing or developing other people. And I think a lot of managers, they have their own quota to hit, right? Or they have a team quota to hit. There's a lot of pressure that comes with that. And a lot of managers are purely focused on, How do we get to this number as they should be? But it means by any means necessary. So that means a lot of the conversations with reps, they turn into pipeline calls or forecast calls. know, every conversation begins to formulate into business or how we move in deals forward. And the focus isn't actually on coaching their reps to become better salespeople. And I think it's actually Warren super important to distinguish between coaching, training, or like feedback. And I think those three get, get mixed up all the time.

04:19 Warren Kucker: Patrick, can you give me a little bit more on that, like that coaching, training, feedback? Like what do you see is actually the difference between those three?

04:27 Rich Lane: So I think about coaching as thinking and taking ownership. So when I coach my rep, it's maybe asking questions like, Warren, what was your intention going into that call? What happened? Like what options do you see happening next time? Whereas training might be, you know, I'm going to show you how to show you about X product works or how we should run discovery or how you should be using MedPic. And then feedback could be like an observation. So Warren, I noticed you skip. decision criteria and the last call. What was the reasoning or how would you do that next time? So that's kind of how I do it.

05:08 Warren Kucker: Yeah, so I think there's like a line that gets blurred a lot and it's between the coaching on deals and improving like rep skills, right? So there's like, and when you're coaching on deals, you should be doing so in a way where like reps should over time improve. But I think we lean a little bit more heavily towards the how do we close this deal on that side of the fence? When you think of like, Is there like, is there a split there? Would you use two different frame frames of mind there? Whereas like coaching ideals and coaching reps, how would you kind of work through that mentally?

05:49 Rich Lane: Yeah, so I think I like to, with my team, I'll typically have like a forecast call once a week where we purely talk about deals, pipeline, forecast, and then we'll have a completely separate one-to-one, which is like a personal one-to-one. So that is anything they want to bring to the table, whether it's the career development, where they want to be in the next two to three years, what they might be struggling with, pressure they're feeling, et cetera, et cetera. It can be anything and they form the agenda and a lot of that does turn into, actually, I think I'm stronger in this area than that area. How do I develop? What can I do to really work on that?

06:27 Warren Kucker: Gotcha. Cool. All right. Well, let's continue to keep those lines of thought as we move through the rest of these rest of this discussion. You told me in particular you've been trading like creating a custom GBT for each one of the reps that you're working on. Can you walk me through what that actually looks like? What goes into it and what makes it useful?

06:46 Rich Lane: Yeah, so I think to before I go into that, I think it's really important to kind of understand my thinking behind it. So I'm thinking the way I'm thinking about AI, right is humans and AI have complimentary like superpowers, right? So if we can work together, we can overcome each other's weaknesses. So that might be that might look like say my friend is an example, he might have like a super bad memory. And they don't remember a lot of things, right? They have a transcriber and all their zoom calls. And also they get implemented or impacted by their environment. Whereas AI, on the other hand, remembers so much more than they do and then has instant access to the internet, essentially, right? And it doesn't get affected by the environment. So if there's a fire going on, an earthquake happening, they still think the same way and operate in the same way. But it also doesn't have that fire in the belly that, let's say, I might have or that unique context. always start when you're creating, or when I've created my custom GBTs with my own point of view. And also it's like a pocket rocket. So how I describe that is, as you mentioned, created these individual chat GBT projects, let's say. So it could be like one-to-one forecast review deal coach. And I like to think of it as essentially basically my own CRO in my pocket, where they've seen every single deal pattern imaginable. So... What I've done is I've created like instructions where I've wrote, it's about probably a thousand words on my coaching philosophy. So what I've learned over the years, some of the best VP of sales, CROs I've worked with. So it's how I think about qualification, what red flags for to look in a potential deal, know, exposing particular questions that could expose deals. And also I've instructed it to act like the best performing CRO, like a John McMahon, for example. And I've tried to create that kind of digital twin that I can take into that. Then within that, you upload all of your forecast calls in there, and that gets added to the product knowledge, right? So what that looks like is when we review X deal next week, it will remember that three weeks ago, the rep hadn't identified the economic buyer, and then they committed to achieving that. And then by building that context into it, obviously, one of the kind of things with that is it doesn't comprehend my personal behavior. So, you it doesn't understand maybe the reps unique selling style, their strengths, their weaknesses, for example. And then essentially then you have to build your challenge, those assumptions that come out of it. And that's what I found really, really reliable from using those kinds of custom GBTs. And then on top of that, I use these forecast calls and these custom chat GBTs to actually challenge my own assumptions about the forecast call. So what assumptions did I make in that forecast call that maybe might not be true? Or what would have made my coach in 10x better? Challenge my assumption that I said about x risk on that deal. Or even type of things like how was my tone during the call? What did you sense from my reps' reaction? How did they respond, et cetera?

10:03 Warren Kucker: Cool, let's get through the tactics then. This is awesome. I'm gonna peel this back so if someone else wanted to implement this, they could. So let's say I'm your rep. You've decided

10:12 Rich Lane: Hmm.

10:13 Warren Kucker: that you're gonna implement this process with me.

10:16 Rich Lane: Mm-hmm.

10:17 Warren Kucker: We've been working together for like six months, so you have some historical data, but you haven't set your GPT up specifically for me. Tell me, tactically, what do you do to get off the grounds as you're preparing for our first and next forecast call together?

10:33 Rich Lane: So based on like a six months working together, I would have formed maybe a hypothesis in terms of where your strengths may lie, where your weaknesses are. And I will instruct that custom Jack GPT based on my knowledge on you in terms of maybe how you think, how you react, what your performance history has been like, why maybe potential deals may have slipped in the past. Are you not getting to the economic bias soon enough? Are you only speaking to two stakeholders instead of nine? What does that look like? So I will put that hypothesis in, but then I would also give it context to say, you know, what would, in reference to this, what would a top account executive be doing? What would it, if they want to progress, et cetera, and then start building it out that way. But then I would also be kind of setting my parameters of what I look for in terms of managing a deal as well.

11:30 Warren Kucker: Awesome, and so let's say we're gonna talk about like the Tesco deal on Thursday and you're getting ready

11:34 Rich Lane: Mm-hmm.

11:34 Warren Kucker: to prep for the call. What would be like the, what like information are you asking it for and what information are you getting out so that you can effectively manage that call differently than we have in the past?

11:44 Rich Lane: So, you know, typically, you know, with my team, I'm managing like six, seven reps. It's a lot of work. Like traditionally I was watching loads of recordings, call recordings. I'm scanning CRM. I'm like diving into MedPic. I'm like, it takes a lot of time, right? Which then takes time away from coaching, joining my team's calls. And now by doing this, I'm able to ask the system, right? Did Warren, did he ask about the business problem at Tesco? Did he talk about features or did he talk about the business impact? Did he identify the economic buyer? What's the compelling event? What risk did the prospect mention that Warren might not have picked up on? Those types of questions, I'm kind of then adding more context and actually when we sit down, we're able to think more strategically and I think, in my opinion, have a better conversation.

12:37 Warren Kucker: Cool, and so this is like a good replacement for, as the typical prep work has been like watching the calls or reading Salesforce or honestly, at least half the time doing none of that and just coming in the meeting cold and like hoping to muddle your way through it is what a lot of sales

12:52 Rich Lane: Mm-hmm.

12:52 Warren Kucker: leaders are doing because they have lots of reps and lots to do. All right, great, so you walk into that information, you have a good insight in the deals. That insight in the deals also has like your... context around like an ideal sales leader behind it. So you're acting like a CRO. It also has like your past like descriptions as to like the attributes of the rep you're walking into. And so you create this whole picture that's somewhat customized and so it helps you coach better on this deal. Great. We have the call. What happens after the call tactically? What's the process that you do to keep this updated?

13:27 Rich Lane: Yeah. I think then obviously uploading a transcript of the call into the custom JET BT, then I will then be asking that custom JET BT based on what I've put in to actually review my performance as a coach, as a sales leader. So it's not just about, I think with this, something like this, the rep. It's also about myself. How do I improve as a leader? How do I improve as a coach? How do I become that inspiring leader that I want to be? So for example, I will access to assess my performance and also challenge my assumptions. Like I said earlier, what would have made my coach in 10x better? How did I coach? Where could I have pushed harder or where could I have been maybe more supportive? Based on this conversation, what should I focus on in Annex 1-1? Like actually identify my strengths and weaknesses through there as well. But then also if... For example, yourself, Warren, if you're struggling with getting access to the economic buyer, that's the skill gap. It's not actually necessarily a deal gap. So it's like then better framing our next conversation with like tangible accountability and actions going forward.

14:39 Warren Kucker: That's awesome. Okay, cool. So we've gotten through the tactical, right? So, and do you upload like every call transcript from like the meetings that you're up for having or a sample of those? All of them. like you

14:50 Rich Lane: that all of the transcript, yeah.

14:52 Warren Kucker: have a GPT that has for Warren Kucker, all the transcripts loaded into that GPT. So you know all the meeting context that I'm having, right? All right, cool. Sounds good. So give me, what's the like biggest improvement that you see? Let's keep it high level. what, like? across the business. What's the benefit that Kepler has when you execute this workflow?

15:15 Rich Lane: So it's a good question. And I think this is where the industry is kind of at the moment. It's like there's loads of use of AI, but it's like, how is it actually coming back in tangible revenue, essentially, right? So I think for me, the use of it, I think it improves forecasting. I think you're able to predict revenue more reliably. I think then you can allocate resources. You can identify skill gaps within the team. of where more time is needed. Is it on discovery? Is it on demo? Like, are we getting to a trial and then what's happening? We can adjust strategies and more proactively. I think as well, pipeline management is definitely improving because it's enabling the team to focus more on top of the funnel. Because we're taking time, we're giving them time back essentially, right? So more time on pipeline management, but also more time in front of the customer. So they're able to spend more time, and hopefully we'll see an increase in performance as we roll this out. But then also improved business efficiency, right? I'm constantly hearing that reps have a lot to do, right? Their days are full on, and updating the CRM. But they're able now, they've got more time, so CRM's updated. They can prioritize follow-ups, meeting prep, reporting, et cetera. So it reduces admin fee, essentially. And in terms of like coaching, I think it makes it more scalable. Would be my own take on it.

16:49 Warren Kucker: Cool. That's excellent. It's obviously like a big impact on the strategic side. So like when it comes to coaching and like from a sales leader standpoint, like the goal of the coaching calls is actually the opposite of a scenario where you think you're trying to find ways to like find gaps, holes, those types of things. You really want

17:11 Rich Lane: Mm-hmm.

17:11 Warren Kucker: in a perfect world that the rep is never surprised by a question, right? They should almost

17:16 Rich Lane: Mm-hmm.

17:16 Warren Kucker: be able to, when you get to a rhythm, be coaching themselves, right? Like if you're doing your job as a sales leader, if the rep feels in this relationship that like actually they don't know what they're going to be asked, then like it means the rep's not, the sales leader is not doing their jobs, right? So from your perspective, this is a different approach. One, you're acting with much more information and two, it's a more personalized view of coaching. How should the rep prepare differently maybe than they have in the past? from this type of like forecast coaching call.

17:48 Rich Lane: Yeah, think it really depends upon the reps mindset. So, some see coaching as something that happens to them, the best reps see it as their own development, right? Opportunity. I think the data that you're getting out of the, let's say the Custom Jack GBT allows us to coach reps and guide their next actions, I suppose. So I think what they want to be preparing is... Well, what happened last time? So what did they commit to? This is huge, right? So they should be asking AI, like, well, here's a transcript for my call with Rich. What did I commit to? Did I deliver on that this week? Like you said before, there's no more showing up and being like 10 minutes to get the CRM up and, this is what we did, blah, blah, blah, blah, blah. So I think it holds you more accountable. I think it allows you to prep your data updates. So there's no more, well, you know... It's actually, here's what happened last week on my top five deals. Here's the questions that Rich might ask. And it allows them to prepare that in a more effective way. And then they're already drafted their next moves, right? Well, it's giving them time back. So there's no excuse for outdated CRM or vague next steps. So can you do, can they come in with, well, here's what I think we should do this week. Do you think this is the right move? And then it allows the conversation to be more strategic and be adding more value instead of... Rep showing up, 10 minutes takes to get the admin up or you're trying to upskill them on what happened last week. This is a deal we're talking about. What's the context, et cetera.

19:24 Warren Kucker: or cool, let's say, let me get real tactical again. So like a rep can prepare appropriately. Let's pretend that you're now a sales rep, have a manager that follows the process just like you. What are you doing

19:34 Rich Lane: Mm-hmm.

19:34 Warren Kucker: tactically to be ready as best you can for the manager that's using a custom GPT with all your transcripts and like custom instructions and like some training gaps descriptors in there? What could the rep tactically do?

19:50 Rich Lane: Yeah, so I'd be like basically doing a role play before I go into the meeting with my manager and understanding, this is typically what he's going to ask me. This is the type of questions he's asked me. This is how he's tamed and tends to challenge me. He's particularly challenged me about an economic buyer. What can I do then to address that? So it's kind of like briefing it on how I think essentially so they can best prepare. And it's the same when you're going in and having a conversation with a customer. you can do the same thing.

20:21 Warren Kucker: Would you like, how would you remember like what technology should they be using to do that?

20:26 Rich Lane: But they can be, know, whether they use, there's loads of, a lot of sales tech out there, right? I mean, Gong does this. You could be using a transcriber, Gemini, Zoom, whatever that looks like, as long as you're getting a potential transcript, you can use that and leverage it into, for example, it's ChatGBT, Gemini, Claude, whatever your kind of system of choices.

20:49 Warren Kucker: Yeah, and even let's say, AppSense software, right? Like the rep should almost be creating a mirror custom GPT, right? But there's like a different subset, right, that you could be using. So now I want to, not only do I want to have an effective coaching call, right? So like this process of like asking questions and prepping for the call can actually help me close my deals. I also want to like manage up to my boss, right? So you could even be asking your sales leader, great, can I have the transcripts from your other coaching calls? that you have. You're loading them into student my way as well. And so like now I don't have just how he's coaching me. I may want to be like the top rep of the company and there may be 10 reps I look up to. I want to know how he's coaching or she's coaching them, right? So like what questions can I get ahead of? Because right

21:30 Rich Lane: Mm-hmm. Mm-hmm.

21:33 Warren Kucker: now what shouldn't be happening is I shouldn't be the status quo when you're coaching me, right? Like I should be advancing so that you never have to ask me a question twice in a perfect world,

21:40 Rich Lane: Mm-hmm.

21:41 Warren Kucker: right? We don't live in that world, but you may have to do that. I want to get way ahead. Like how is everybody else being coached? And there's a deal impact. Maybe I'm like finding gaps in my deals I haven't thought of maybe. But there's also like an effective coaching impact. So I'd almost want to create a mirror GPT. This is my manager. This is how they're managing forecasts. I never

21:58 Rich Lane: Mm-hmm.

21:59 Warren Kucker: want to be asked a question more than three times in a row. Give me a question that my manager might ask based on three times in a row. I'd almost want that shadow GPT basically to prep me in the exact way that my sales leader is going to bring it. Well, it takes me like the interesting question. What if the sales leader is doing great coaching and the rep is always getting better and gaps are being closed and the rep is using a mirror GPT and they're getting ahead of all the questions. What if there's an end game where they don't have to have the coaching calling?

22:31 Rich Lane: Yeah, I mean, it's an interesting topic, right? It's like lot of, there's a lot of talk around, can AI replace jobs? Can it replace sales leaders? But I actually think there's a way where, whatever, there is a way where it makes selling skills, I think, and coaching more essential. So I think it's all about context, right? And I think you need to start with your own point of view first, because I think over relying on AI is not selling in my opinion. think... You have a lot of data accessible, you have mechanics, you have a lot of context, right? But it doesn't, it still cannot, in my opinion, creatively like problem solve. It cannot negotiate for you. It cannot build political capital and navigate an organization, understand the politics, understand the people, understand personalities within an organization and navigating that in an enterprise sale. So I think... I think it will enhance it. I don't think it will be a negative towards it, in my opinion.

23:36 Warren Kucker: Awesome, great. Before we head out, just quick, if someone was gonna start this process tomorrow, what's one thing they shouldn't do? What's a mistake they could run into really quickly that could help derail starting to implement a process like this?

23:51 Rich Lane: I think it's easy, right? I think it's very easy to go on a tangent with AI. And I think a lot of people will make mistakes by not starting with the end goal in mind. So like, what are they looking to achieve? I would always say, you know, what, looking at the next quarter, what metric are you looking to improve and focus on that one? Is it win rate? Is it your average deal size? Is it average deal cycle? Like, what is that? And then start small. Are you doing it on your, let's say, your ICP definition or your account selection, territory prep? Pick one thing and then my other piece of advice would just be start just diving in and playing around with it and getting yourself into the depths of AI.

24:41 Warren Kucker: Awesome. Cool. All right. Well, hot take then real quick. What's something about, let's say, and sales that you think sales graders might not be ready to hear?

24:52 Rich Lane: Tricky question. I might be a bit controversial here. think AI could expose maybe the managers who were never actually coaching in the first place. I think historically, as we've talked about and briefly touched upon, think coaching has been plagued by... It's quite manual, it's quite generic sometimes. Managers, like you said, don't really have the time. You enter a meeting and it's all quite rushed. have 30 minutes and before you know it's over and then another week goes by. And I think as we've mentioned, a lot of sales leaders might be scared AI might replace them. And I think it's wrong because I think AI will expose maybe the bad ones and make the good ones even better. And focusing on more quality interactions rather than like quantity.

25:40 Warren Kucker: Yeah, that's a common theme that we're coming across and actually in these conversations is that AI can actually help improve the human to human relationship. When you're managing five, seven, nine, 11 different folks, that management can become quite impersonal and quite un-customized because there's too much information. The AI helping you synthesize information, sales coaching is just a great way to do it. If you're changing how you coach rep to rep by about 30 % because you're leveraging what you set up, that's a phenomenal outcome. for the relationship between the sales leader and their reps. Great, and before we head off, Rich, do you have any other, do have any events on the docket that you're gonna be going to? And in particular, where on social media can someone find you?

26:23 Rich Lane: Yeah, amazing. yeah, find me on LinkedIn. So Richard Lane, I'm sure Warren can share my profile. Yeah, and I'm always up for chat conversation. I'm pretty nerdy when it comes to this type of thing. And yeah, obviously working within the maritime industry. So we'll be going to a host of events coming up. We've got, you know, IE week coming up shortly in the new year, then off to the big ones like Breitbalk and Posidonia next year. So yeah.

26:51 Warren Kucker: Awesome, great Rich. Well, I appreciate you spending the time with us, walking us through how you're using coaching, honestly in a different way than I've heard before. And I hope our listeners get a chance to implement. Appreciate you the time.

27:03 Rich Lane: Thanks mate, thanks for having me.