From Zero To AI-Ready Leadership

Still feeling stuck at step zero with AI—lots of prompts, no real leverage? We walk through five concrete moves that flip AI from novelty to advantage for frontline sales leaders and ambitious sellers. It’s a fast, tactical tour: onboarding that compresses ramp, a coaching memory that never forgets, development plans that stick, a leader-specific GPT that encodes your standards, and a pipeline risk radar that tightens forecasts without more meetings.

We start by rebuilding onboarding so reps get high-quality “at bats” in week one. By training an assistant on your ICPs, buyer personas, and competitor positioning, you can simulate role-plays, rehearse objection handling, and focus on the three messages that matter for each persona. Next, we set up a per-rep project that stores one-to-ones, call clips, and commitments, eliminating recency bias and turning scattered notes into trend-aware coaching. From there, we spin that context into personalized development plans with clear weekly agendas and outcomes chosen by the rep, not imposed from above—because ownership drives practice.

Then we introduce a Leader GPT that captures your playbook, stage definitions, must-ask discovery questions, and go-to moves for sticky moments like pricing or procurement. With your norms searchable and consistent, the team self-serves tactical guidance and you recover hours lost to repeat questions. Finally, we assemble a pipeline risk radar that blends transcripts, CRM notes, and emails to surface the real drivers of deal slippage. Instead of relying on generic call scores or single-source tools, you’ll get nuanced risk calls, evidence checklists by stage, and next-step coaching that aligns to your methodology.

The throughline is simple: let AI handle repetition, recall, and synthesis while you lean into nuance, judgment, and presence with customers and reps. Pick one use case to deploy this week—onboarding drills or a rep project—and measure one outcome like faster stage exits or tighter forecast calls. If this playbook helps, share it with a teammate or your VP so the whole org can move beyond experiments and into durable wins. Subscribe, leave a review, and tell us which use case you’ll try first—we’ll send follow-up prompts to help you launch.

Transcript

Setting The Stage: Step Zero

SPEAKER_00 0:00

Welcome back to another episode of the AI Powered Seller, episode number 36. That's three, is that three years? Okay, I guess maybe. Maybe I've been talking about AI for too long. Um, or maybe we did some double up episodes. But today's episode is a really special one for all my frontline leaders in particular. Most organizations I talk to, when it comes to AI, we're still at step zero. And the good part is you might listen to a lot of what I'm going to talk about later and say, gosh, we're behind, et cetera. Do not worry about it. I talk to hundreds and hundreds of teams every single year. And everybody is still at this kind of step zero, right? And step zero is, you know, I'm using AI to generate emails, I'm using prompts, I'm buying some tools that say they're AI. And so what I went ahead and did is of course I used AI to take the notes out of my head is I created a deck last week that had the top five AI use cases for frontline leaders, and it's blowing up uh the amount of comments, opens, replies of like, thank you, like this is what I've been waiting for because I in my team is kind of using it, but I wasn't sure how to use it. And if you're a frontline seller, make sure you stay tuned in because you're gonna be able to reverse engineer all of this for yourself. Build yourself a better onboarding plan, a better development plan. And I'm gonna jump into all of those details throughout the episode. Right now, I think we're getting a 50% open rate, 35% click rate of people uh looking at the deck and wanting access. So today's episode is jam-packed with value. It's about 12 minutes, really quick and easy. Use case number two, I think, is the most underrated for both sellers and sale leaders. So make sure to stick around for that. And then number five, I'm gonna solve forecasting forever for you, maybe, or at least make you a little bit better at forecasting and making it more in terms of how you want to do forecasting as well. So make sure to stick around for both of those. So without further ado, let's jump into use case number one. AI-powered seller. All right. So, use case number one for my frontline sales leaders. Let's talk about your onboarding accelerator. Every leader, we've we've kind of accepted this concept of like a three-month ramp where I'm a rep, I gotta learn, I gotta have a bunch of calls and fail. But the very first place most organizations should look for where AI can make an impact is your onboarding. And I want to call out some very specific ways that AI can basically run a big chunk of your onboarding. The first is ICP and buyer personas. What you can train AI to do is it knows your buyer personas, it knows the industries. And then sprinkled throughout your onboarding, maybe you've got an hour where we role-play the VP of finance and another hour where I learn regional banks. I don't know. You pick whatever it is for your business. But AI onboarding for me is the very first place everybody should start because I can get the reps that it used to take me two, three, four, five, six months with sales calls. I can get the reps in during my first two weeks of onboarding. I can start to learn, like, oh, a VP of finance cares about this, a VP of ops cares about that. So ICP persona, that's one of my very, very big ones. Uh, ideal customer profile. If you're like Jake, what is ICP? Somebody asked me that the other day. The other thing it can help you with is positioning. Maybe you've got a specific way you you position against a competitor or how you position certain features. So it can certainly help you jump in, help you to understand, oh, let's talk about these three things, not this whole big product sheet you gave me as like 52 or 53 things. The last thing is objections or questions. The same questions come up. And it this always shocks me with reps. It's like they get a question or they get an objection, and it's like they got punched in the mouth. It's like, well, what happened? Uh oh, they didn't just go along with it. Of course they didn't. Most of you have like three or four or five common objections. So why not get your reps at least some at bats of whenever I phrase things this way, I know I'm gonna get this objection. So AI onboarding, no brainer here. We've built a couple different custom GPTs for this. Uh, and it can literally, I think we can probably ramp reps, I don't know, three to four times faster. So that's number one, onboarding. If you are listening to this, put your headphones down, hit pause, and then go set up some time to fix your onboarding because it's it's a really, really easy win use case. You probably already have a lot of your product docs, your buyer personas, et cetera. Use case number two is your own personal project, custom GBT, whatever for every single rep. I'm borrowing this one from my folks over at OpenAI. We had a chance to interview the head of enterprise sales at OpenAI last year. And what he does is he literally has for each rep his own project. He puts his one-to-one notes in there, uh, recordings from their one-to-ones if they have them, maybe a call that they want to that you want to talk about. So, as you're thinking about that next conversation, what are we going to talk about? Imagine a project that has all of the information you talked about. Because I don't know if you're like me, I forget what I talked to somebody about two or three months ago. And if I instead of just having recency bias and just giving you feedback based on what happened now, why coaching is so broken is we're not compounding the learnings. We're only talking about what just happened. And so if you have a project for every single rep, you never forget. And instead of just going back and rehashing and, oh, this month we focus on this or this month we focus on that, you can truly have this like ongoing memory that never forgets your rep's commits. It never forgets what you talked about in the last agenda. It never forgets patterns that you might miss. So again, if you got a rep, they're trying to work on certain things, make sure you create a project so you never miss a beat. That leads perfectly into number three, which is AI assisted personal development plans. Very similar concept. This is something that I wish I would have had a chance to do for all of my reps, which is truly help them to build customized development plans. So, what Gen AI can do, again, I can do it in the same project, I can do it outside of it, is I can say, look, Jake is struggling with multi-threading. And so, in order to get better at multi-threading, here are the behaviors I've noticed. And again, if you're doing it in the project, it'll already notice all this. And you can say, build me an eight-week training program with weekly 30-minute agendas that Jake and I can work on together that has homework, that has pre-work, you know, whatever that might end up being. So just imagine this world where every single one of your reps doesn't have just a tip or trick from you. It's literally this like ongoing professional development plan. So, hey, Jake, this quarter, you know, you mentioned that you want to work on discovery. So we're gonna build a six week, eight week, 12-week program to do that. Pro tip here for all my frontline sales leaders, make sure you let the rep pick the skill they want to develop and you don't pick the one for them. I'm gonna tell you right now, one of the biggest reasons I see people not build skills or get to where they want to be is, you know, the the leader keeps picking for them. And so make sure whenever you're picking the skill, it's something that they are, you know, excited about. For all my sellers, if you are ready to get serious about Gen AI, you have to go sign up for meetjourney.ai. Go check it out right now. The link is in the show notes. It immediately knows everything about you, about your company. You sign up, and within literally two or three minutes, it's already trained on what you do, what you sell. But the most important part is it truly has become your sales co-pilot on every deal. Imagine every single deal you're working in Salesforce. It knows all the research you did, all the notes from your discovery call, the proposal, everything in one centralized place as opposed to 52 other systems and tools. So if you're a seller, you're ready to get serious, make sure to go sign up for meetjourney.ai. So number four is the leader GPT. So insert what your name is. We'll call it Jake GPT for this uh example here. But what leader GPT, Jake GPT can do is all of your best practices in one simple place. And I'm not just talking about your playbook, which you 100% could have in here. Let's say for you as a leader, you want to make sure that your reps um are always asking these three questions. Put that in your custom instructions. And so not only will your gong or your whatever score it, that's great, but it can know all the norms about you. It can say, hey, I always want my reps at stage three to have this. And so all the little things about you of how you evaluate a deal, how you think about handling parts of the customer interaction or legal or procurement, put all of that into the Jake GPT. And that way, what I I talked about, I just did a training with one of our clients, the Atlanta Hawks, shout out to the folks at the Hawks last week on this exact topic. I said, How many questions do you answer 50 times a year? Most of the leaders said, I don't even know, maybe like 50 questions. So you're answering the exact same questions 50 times a year, 50 different questions. It's a lot of time you spend answering the exact same question that has like very, very little value add back to the rep. And it's not an incremental value, it's just how to handle very specific situations. Maybe when someone has price pushback, you have a very specific way you want them to do that. So guess what? Put that in your list. And if you're struggling to do it, here's another pro tip for this one: go to open up ChatGPT or Gemini, I really don't care which one, and say, hey, I want to create this Jake GPT. I want you to ask me a series of 10 questions. I'm a frontline sales leader. This is what I do. I want you to ask me these questions in order to capture my norms for how to handle very specific situations. And within about 25 minutes, it will do it for you. So then a rep comes up, they already start to know, like, okay, well, let me ask Jake GPT first. And then if I want to go deeper, I'll slack him. Right. So get all of the stuff out of your head that really makes it not that value add in your actual interaction because it's really tactical advice. Last but certainly not least, use case number. And if you haven't already checked out the deck, there's a whole deck that I put together that has these top five. And if you just do one of them, I promise you're gonna be a better leader. Your people are gonna like you more because you actually remember stuff. Somebody asked me to, you know, in your project, yeah, put their kids' names, put their birth dates, put all that stuff so you never, you know, forget about any of those deals. The last one that I want you to put in there is your pipeline risk radar and forecast coaching. So again, another thing that Gen AI is very, very good at is looking at patterns and deals. So again, you could do this within your project if you have it for a rep. But what I like to do is put in deal notes from the CRM, upload a transcript, upload uh some emails or whatever it might be, activity summaries. And again, you don't even need to upload some of this. You can copy and paste it. You can just tell it, hey, this is what's happening. But I want you to imagine a world where I say, hey, Jake has been struggling with late stage deals. Here's three or four deals. You could upload, you know, just grab the transcript, upload the last three or four transcripts. Which one of these deals is most at risk? And based on, you know, you could use the Jake GPT. Which one of these do I need to go talk to her about or him about right now? You can do this right now, my friends. Right. So you can create this kind of yourself-enabled pipeline risk radar. And that's the issue that I see with a lot of these tools that exist today. A lot of the tools are very specific to medic or medpic or that that kind of overarching, but it doesn't capture all the nuances of it, right? It's it's just looking at the call data. It's not looking at the notes, it's not looking at the email data, it's not looking at the way that you evaluate it. None of these tools are doing that, right? So if you're just using one of these tools, call scoring, you're missing out on at least, I don't know, 70% of the deal. So use, you know, one of my favorite use cases, and is why I kind of saved this for last, is this ability for you in about five minutes to give Chat GPT, Jim and I, Copilot, whichever one you use, Journey. If you use Journey, you can use rep GPT for this as well. And you can literally just put in some of those nuanced details, and it's gonna help you forecast so much more accurately. And so those are my five. Okay. If you're a frontline leader out there, or you can, if you're a rep, by the way, you can use all of these to get better at sales yourself. Uh, most organizations are still at step zero. They're doing a lot of busy work, they're answering the same questions over and over again. And for me, if I wanted my reps to ramp faster, get better faster, one thing, and I think as frontline leaders, we hate to admit this, be more consistent in the the feedback that we give people. A lot of leaders don't even realize that. We don't even realize that, you know, if you ask me a question on a Tuesday at 9 a.m., I might give you a slightly different answer answer at Thursday at 5 p.m. So if you want to get more standardized in how you give feedback, if you want to detect pipeline risk, Gen AI is your best friend for this. So if you're a frontline leader, start with one of these and just really think through the impact that just one of these could have on your new hires, on your current team, and also on your ability to level up the work that you do and the interactions that you have. I was in a session with a team, frontline leaders, and a leader said, Jake, well, if I do these things, what do I my reps need me for? And I said, look, the beautiful part is where does the human come in? It's in the nuances. It's not the basics, it's not the blocking and tackling. It's okay, with Jake, I need to phrase it this way, or I need to do it a little bit more that way. And so what this should be freeing up time for you as a leader to do is spend more time with your reps in front of customers, spend more time in coaching moments and less time in the day today. So that's what I've got for you in today's episode. Those are five very tactical ways that you as a frontline leader or as a rep, you can just reverse engineer these, can make your life easier today with Gen AI. And so hopefully today's episode was useful. And make sure, as I always say, share this in a Slack channel, share it with your VP, share it with somebody who you think can benefit from hearing like, why aren't we adopting AI faster? And if you're looking for ways to create leverage as a leader, if you're thinking about ways, I'm always stuck in the minutia. I can't get off the hamster wheel, just implement what we talked about today. That's what I got for everybody. Thank you as always for tuning in, and I'll see you on the next one.