So What? How To Use Generative AI To Build A Sales Playbook

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In this episode of So What? The Trust Insights weekly livestream, you’ll learn how to use generative AI to build a robust sales playbook. You’ll discover how to leverage existing data from various sources such as call transcripts, CRM data, and Slack conversations to create a comprehensive sales playbook. You’ll also explore techniques to refine and streamline your sales playbook, making it more efficient and user-friendly for your sales team. Discover the power of generative AI for creating a sales playbook and improving your sales team’s success.

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So What? How To Use Generative AI To Build A Sales Playbook

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In this episode you’ll learn:

The components of a great sales playbook
Using generative AI to audit your existing sales processes
Building an enhanced sales playbook with generative AI

Transcript:

What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode.

Katie Robbert – 00:37
Well, hey everyone! Happy Thursday. Welcome to So What the Marketing analytics and In-Ear Insights live show. I’m Katie, joined by Chris and John. How’s it going? Oh, nice. We’re getting good at that pre-show. We were just kind of chatting about bread recipes and other interesting stuff that gets passed down through families. Speaking of families, your sales team—that’s part of your family—how is she?

John Wall – 01:05
Going to weave this one?

Katie Robbert – 01:08
Not well. Is the answer not well? This week, we are talking about how to use generative AI to build a sales playbook. Now, I asked in our analytics for marketers Slack group, which is free to join at Trust Insights AI analytics for marketers, if people had created a sales playbook and, if they had, was it just checking a box, or were they actually using it? The majority of people are saying, like, one of the jokes was, “Oh, it’s, you know, it’s in the break room holding up a table”, or you know, that kind of thing. So, the general consensus, from a very small number of people, is that it is not being used.

Katie Robbert – 01:53
And I’m wondering—and this is going to be a question for both of you—if it’s because it’s just not good, it’s too cumbersome, it’s not helpful, and is there a better way to do it? You know, because sales is one of those things—it’s essential for any company. You kind of have to have sales in order for a company to run. So, I guess, John, I want to start with you. What, like, you created our original sales playbook, and until I met you, I actually had never worked at a company that had a sales playbook, which—looking back on my career—is baffling. So, like, how did you create this sales playbook? It’s huge, it’s in-depth, it’s detailed. So, what was your thought behind, “We need a sales playbook”?

John Wall – 02:40
Yeah, yeah, it’s great to talk about because there’s a number of different levels. It evolves as your company grows and changes. Right. When you’re a startup, pretty much every deal, you’re making it up as you go and trying to figure out how things work. So, there’s no need for a sales playbook. But then the next stage—which is where most of our sales playbook is—you start to have some repeatable stuff. You know, there’s some things you use over and over again.

John Wall – 03:16
And really, I need it because my memory is so terrible that, you know, three weeks from now, I’ll be like, “Oh, wait a minute, like, I already did this. I already wrote something on that.” And so, you go to the sales book, and there it is. You can copy it and paste it and redo it.

John Wall – 03:16
And it’s great because you’ve got your notes. It’s like, “Okay, we tried X, Y, and Z, and these things didn’t work.” So, next time you do it, do you know ABC? And, yeah, it stays really organic and messy at that early stage because you’re just kind of listing out all the stuff you’re doing and trying to find patterns and figure out what works and where to go. The next stage of it is once you get big enough where you’ve got more than one person selling, it becomes a huge value then because now you can just say to the person, “Hey, go read this.” Or whenever you come up with a question, search this doc. And at least they’ve got some kind of guidance, as opposed to most startups where people are just looking around, not knowing what to do, and start breaking things.

John Wall – 03:59
So, yeah, that’s kind of where it’s at now. It’s been interesting to me because, yeah, there’s so much stuff in there, but our product and our services are just moving so fast that so much of it gets left in the dust. But at least, you know, we’ve got some kind of documentation as to what we’re doing and where we’re going.

Katie Robbert – 04:18
Well, you know, it’s interesting. A couple of weeks ago on LinkedIn, I posted about how the same things always go wrong in a digital transformation. You know, AI integration, whatever you want to call it. And one of the things, one of the ways to prevent that is to document everything. And I got a comment saying, “But things move so fast that, you know, what’s the point of documenting?” And, you know, we could do a whole episode on documentation. But, to what you just said, John, there’s, you know, things are moving so fast that in order to know, like, what worked, what didn’t work, what we said, the big thing, the big reason I use a sales playbook is like, what are we currently quoting certain services as? Like, what’s hitting, what’s landing, what are people responding to?

Katie Robbert – 05:06
So that everybody has the same shared understanding of, like, how much things cost. That, to me, is huge. And so, you know, now, yes, things are moving quickly, but technology is moving in such a way that you also have the opportunity to keep the documentation in an automated way. However you want to do it, up to date as well. So, there’s really no excuse anymore to not have a living, breathing, up-to-date playbook or any kind of documentation for that matter. Which is now where I would turn over to Chris to say, “So, how the heck do we do that?”

Christopher Penn – 05:49
How the heck do we update our sales playbook? Well, yeah, to both your points, we’ve got a lot of the good basic ingredients, right? We’ve got lots of data, we’ve got some examples from existing sales playbooks. One of the hardest things about this process is—and this is going to be hard for any organization that has typical sales professionals—there’s a lot of ego in sales. I know the right way to do this. I can sell this right. And the process we’re going to walk through today requires putting some of that to the side, at least temporarily, which is a tall order. The first thing we want to do is ask the question, “What are we missing? What, what don’t we have in our sales playbooks?”

Christopher Penn – 06:33
And this is where a tool like any of the deep research tools, Google Gemini, ChatGPT, Perplexity, can put together a best practices for what belongs in sales playbooks. The framework I would recommend you use is the Trust Insights Casino framework, which is for deep research specifically. You can get your copy for free at Trust Insights AI Casino. No forms to fill out, nothing to, no information to give. And this is exactly the format I used. It says what belongs in a sales playbook. And it gave me a nice 38-page report about what belongs in a sales playbook. Things that are true, you know, universally. For example, universally accepted things in sales playbooks. This is what every sales playbook should have: company information, ICPs, buyer personas, value proposition, product and services, sales methodology, sales plays and tactics, and objection handling all this stuff.

Christopher Penn – 07:27
This section right here is the template for your future sales playbook. You want to have all these pieces. If you don’t have all these pieces, that’s a miss. And that’s something that you can incorporate into the sales playbook. So, in our sales previous versions, we had a lot of this. We didn’t have as much on competitive, and we didn’t have as much on sales enablement as we could have, no fault of anyone’s. Which is like John was saying, “We’re just trying to get, it’s trying to get things done.” But now we’ve got this template. We also need data, and again, this is, I can’t hammer this point at home enough. You have to have good data. And for this process, I pulled three sources of data.

Christopher Penn – 08:15
We use an AI transcription service that attends all of our meetings, and it records all our calls and transcribes them. So, one of the three major data sources for updating our system is using the last year’s worth of Monday and Friday sales calls. So, we do sales calls Mondays and Fridays and just grabbing all those transcripts. Now, there are some little tips and tricks along the way for doing this. Your system probably outputs a big old pile of PDFs that looks like this. This is going to be very hard to put into AI. Most AI tools will have firm limits about how many files you can upload. And we have here 70 transcripts. On most systems that have a command line, you can run a script called PDF to text that will convert all of your sales call PDFs into individual text files.

Christopher Penn – 09:21
Still haven’t solved the problem of lots of files, but we’ve now converted them into a much smaller format. And then, from there, you can use any form of concatenation software to glue it all together into one big text file. And that’s what we’ve done here for those weekly calls. One big text file and now it has all the data. This is about 400,000 words because we’re a chatty bunch.

Katie Robbert – 09:50
Well, I was going to say. So what you’re saying is, I don’t have to open 70 files and individually copy and paste them all into one document.

John Wall – 09:57
Drag and drop.

Christopher Penn – 09:59
You can. You shouldn’t, but you can. I have. Now, I will disclose, I have a special piece of software that I wrote that prepares files for AI that tells you what each file’s name is, the line length and stuff, but it basically just glues them all together. But if you have any competency with managing, you know, file system management, that’s something you can do. Pretty straightforward second data source. And this is something we’ve talked about many times with sales. The CRM. You’ve got to get the stuff out of your CRM. And specifically, you want your: all of your deals closed and won, and lost open deals as well. And you want the notes fields, which is where all the information about the deal occurs. Most CRM software like HubSpot, Salesforce, or whatever, can export this as a CSV file.

Christopher Penn – 10:56
And as we’ve talked about many times on the show in the past, you never ever give generative AI a CSV file. I was just asking for trouble. There’s a free utility called CSV JSON—which is ineptly named—that will convert your CRM data from a CSV to a JSON file. JSON is JavaScript object notation. It’s a programming. It’s a scripting format that formats your data not for humans, but for machines. Machines really like that format, and they can read it easily. And so, it converts all the columns and the column headers and the rows into what is essentially a very long transcript. So that’s our next ingredient is to say, “Okay, here is our CRM data.” So, the third bucket that we use a ton—and it’s going to vary based on your company—is Slack. So, we use Slack.

Christopher Penn – 11:51
We have a sales channel in our Slack instance. And so I can take the, I can go as I’m an admin for our Slack instance. I can export our whole Slack instance, pull out the sales channel, and then take that, glue just the transcripts from the Slack sales channel into a big file. And now we’re ready. And so now we have three different perspectives on our sales. Things we say to each other in Slack, things we say to each other in calls, and then the CRM data. What we want to do is for each of these things, we want to go into a tool like, I would strongly suggest Google’s Gemini for this because it is. These are very large data sets, and most tools like ChatGPT and stuff cannot handle this much data.

Christopher Penn – 12:36
You’re talking hundreds of thousands of words, well past their system limits.

Katie Robbert – 12:43
Is there, perhaps this is part of the CRM data, but is there a reason that you didn’t export the input calls, the transcripts of input calls from the AI transcription data sets?

Christopher Penn – 12:58
I did input the those calls because I couldn’t find them in a quick and efficient manner because they’re not labeled input calls.

Katie Robbert – 13:06
Okay, so that goes back to basics of just good governance of, you know, if this is an exercise you want to go through, then things have to be named in a way that you can find it.

Christopher Penn – 13:18
Yes.

Katie Robbert – 13:19
Now, okay, that’s helpful.

Christopher Penn – 13:21
The CRM data, the notes field has a lot of that information in it already.

Katie Robbert – 13:26
And that was my other question is, I guess, it really depends on how your organization is set up, because I know we’ve been making a concerted effort to. I think now it does it automatically. It adds the transcript to the notes field after a call, which is super helpful.

Christopher Penn – 13:43
Exactly.

John Wall – 13:43
Yeah. One thing in that, though, is I should be naming those initial appointments input calls specifically. And then you’ll be able to scrape those out of Fireflies.

Christopher Penn – 13:53
Exactly. That’d be super helpful. So, this is our prompt that we used. I said, “Using the following,” and I did this three times using the following CRM notes as the sole reference. “Infer and extrapolate a complete, comprehensive, verbose sales playbook using the sales playbook, best practices, and the included templates.” I put the Google Gemini Deep Research Doc in. I put one of those three documents in. I said, “Here’s who Trust Insights is. Don’t use other named entities.” And then from our best practices document, I said, “These are the 12 things that you must construct from this particular data source.” We end up with, for example, this is the sales playbook from our CRM data, all 12 items, based solely on what’s in the CRM. I reran the prompt with a new prompt.

Christopher Penn – 14:42
Same a new chat, same prompt, same sales best practices, different data source. For Slack, I said here. Oh no, sorry. For weekly calls. So, here is a playbook based solely on our weekly calls. And then of course, the third one is our Slack instance. Here’s a playbook based solely on a Slack instance. And the reason I’m doing this is because I want to distill down the hundreds of thousands of words into just thousands of words. So, we have three different versions. This, by the way, is a really interesting thing to look at. And Katie, I know you’re going to ask, “These are in Google Drive for you to look at after the show.” But based on the data source, there’s slightly different views of the same organization. A view from a call perspective, from a chat perspective, from a CRM perspective.

Christopher Penn – 15:34
And for sales leaders, those differences might be very interesting to see. Like, are we are opportunities in one place that aren’t in others? Is there language being used in one place that isn’t being used in others? And what could we do to. To unify that? So, we now have these three sales playbooks built from our data, plus the two other ones from 2020 and 2024 that John had. Our next step in the process is to say, “Okay, we now need to do a merge.” The merge process says, “Okay, here’s all the documents.” And there is extensive system instructions for how to do a document merge. The instructions are, tell me what you’re doing. Summarize each document, summarize the pieces, summarize all the table of contents. Then start merging things together. Identify conflicting information, reconcile the conflicts.

Christopher Penn – 16:36
If two out of three reports are majority, say one fact, and the minority has a different fact, prune the minority fact. If there’s no clear majority, attempt to determine it based on the thing, merge the duplicate information, and then ultimately boil it down into a single consolidated document. This set of system instructions, plus our playbooks, and then specified. Here’s the template. You got to use this template because we want it to be apples to apples across everything so that the tool doesn’t have to work as hard to figure out how to merge all this data together. It goes through and it goes through. And, boy, does this take some time.

Christopher Penn – 17:13
This is why we’re not doing this live on the show, because just the first path of analysis took five and a half minutes, and then the actual time to glue it all together was 13 minutes. So.

Katie Robbert – 17:30
Which in real life is not that long, given the amount of information and background data that you’re working with. But on a live stream, that’s like forever. But in real life, that is really efficient.

Christopher Penn – 17:45
Yeah.

Katie Robbert – 17:45
John and I only have so many sea shanties. We can sing.

Christopher Penn – 17:51
I mean, we can. I can pause and let you sing.

Katie Robbert – 17:55
Yeah, I think we’re good. I think we just keep going. Hey, but it’s what I appreciate. And this, I mean, again, this is true of really anything you’re creating with Generative AI is the more data you give it, the better the output is going to be. So, like, you have the Trust Insights knowledge block. You have, like, the deep research we did for our competitive analysis. Like, I know all of those things in the back of my mind because we’ve done them on different live streams. And if you want to see some of the stuff we’ve done, you can go to trust insights AI, YouTube, and go to the So What Playlist and find all those old episodes. But, like, we’ve done the work to get all of this background information. So we’re not just saying, “Hey, Generative AI, here’s our URL.”

Katie Robbert – 18:45
Here’s what we want to do. Build us a sales playbook. Like, we’re giving it everything we do related to sales, everything it’s asking for. When you brought up that initial deep research of, like, here’s all the elements that should be included in a sales playbook, I didn’t sweat once because it, like, we have. I know with confidence, we have all that stuff today in 2025. So now it’s just a matter of putting it all together in a more succinct way.

Christopher Penn – 19:14
Yep. If anything, one of the things that I discovered in this process is how much we’ve forgotten about. Right. So, when I asked to do a master consolidated list of our services, I’m like, “Oh, yeah, we do that.” Like, I forgot we did that. That’s not a thing that we talk about on a day-to-day basis, but we still do that thing. So after AI Studio spits out the results. Yeah, you glue it all together, and this is the Trust Insights master sales playbook, all 153 pages of it.

Katie Robbert – 19:54
To which my initial reaction was, “Oh my Lanta.” And if you know.

Christopher Penn – 20:04
But what’s in it? Company information, organizational structure, key sales context, ideal customer profiles. And this is interesting, it didn’t find one, it found six of them. Six different ideal or five different ideal customer profiles, and then seven buyer personas. Synthetic individuals drama those ideal customer profiles. Because remember, ICP is not a buyer Persona.

Katie Robbert – 20:29
I was just going to say, I so appreciate. And this was a conversation I had with Andy Crestadina a couple weeks ago on the Doodle webinar, because he was approaching it as ICP was the same as buyer Persona. And we had a really good conversation about how they are very different. And that’s a lot of the gap that we feel with our ICP is people think they have it, but they really all they have is the buyer Persona, not the potential customer.

Christopher Penn – 20:59
Exactly. So, we’ve got the data-driven enterprise, the growth-focused mid-market company and so on and so forth. Our value proposition, our product and services. And this is where you’re getting into all this stuff like, “Oh, I forgot we did that.” through our strategic consulting services and all these different things. Our AI and data science projects, our analytics and reporting services, education and enablement, influencer and content services, and so on and so forth. So, all that is documented in there. And by the way, if any of these are appealing, you can just ask John, or go to Trust Insights, a contact. Then our sales process methodology. So, it goes, it went through and based on our conversations, our Slack chats, all the stuff, it figures out what our way of doing sales is.

Christopher Penn – 21:44
So, if you’re not clear or maybe as some companies have, there’s a bunch of people doing things kind of their own way, you can merge that together with a good deep merge prompt and come up with a consolidated “This is the way we do it.”

Katie Robbert – 22:00
This also to me is an amazing onboarding document because one of the challenges that I’ve seen for us as a small company is we just haven’t had the time to create good, well-thought-out onboarding documents. And so, I’ve always been hesitant to be like, “Okay, we can bring someone new on,” because I don’t have anything to give them. But now I’m like, “Oh, damn, this is exactly where they start,” because everything they need to know is in this document.

Christopher Penn – 22:30
We get the sales plays, the prospecting plays. These are all the different ways that John and the whole company have in some way tried to do outreach to, to build some pipeline outbound. Discovering, solutioning plays, demonstration plays, closing plays, scripts, emails, targeted questions, templates. It put together all these different pieces. In fact, I’ll just scroll down just so we can get take a quick peek at what some of this looks like. This is section 6.5. So, in here you have targeted questions, need budget authority questions, additional questions. Voicemail script hit here. “Hey, this is John Wall from Trust Insights, following up on your, we specialize,” and so on and so forth. So it has built all of these components for us from what we’ve had to say over time.

Katie Robbert – 23:22
And that’s the thing that I love the most is that this is just us in a very organized way.

Christopher Penn – 23:29
Exactly. Objection handling: how we have overcome objections for different types of sales calls and things. Cost and budget, AI complexity, ROI. How do we answer objections on calls, competitive intelligence, who we compete against, and what we do about them. How we, the tools that we use for our mark of our sales process. So, what’s involved in our sales process? What are our KPIs and metrics? All the enablement materials that we have to help make sales happen. Content, company services, case studies, proposals, speaker kits, all that’s been cataloged and put together and then coaching frameworks. How do we grow our sales team capabilities based on the known best practices and based on. On everything we’ve said. How do we build stuff like this playbook? How do we build these tools?

Christopher Penn – 24:22
So this is the final output of the generative AI aggregation of us essentially and our sales for the last, however many years.

Katie Robbert – 24:34
John.

John Wall – 24:36
It’s all there. This is the kind of thing I will spend the next couple days just pouring through, trying to see where stuff’s at and what kind of enlightenment we’ve got. Because it’s amazing to close the loop between the process document and the stuff that’s actually in the CRM system and in the Fireflies calls that we’re doing, that stuff is really kind of buried, and we’re just having to kind of feel as we go. But to have that actually put into chunks and codified and give us some opportunity to really dig down on who those personas are, and who the buyers are, that kind of stuff is really useful.

Katie Robbert – 25:10
One thing that sticks out to me. So, we’re looking at what this section 11, the sales enablement. My first thought is, “Oh, great. What I should do is go through this and add links to the appropriate final usable document.” So like, make sure, like, so if it says, you know, proposal and SOW templates, MSA, MDA, like, let me go ahead and link to the final one so that we’re all using the same ones. Let me go ahead and link to the speaker kits. Let me go ahead and link to the white papers and guides so that someone going through this has everything in one place. Like, this is such a useful thing to again, build that consistency, make sure we’re all doing it the same way so that the data that we’re collecting is also being collected in a consistent way.

Christopher Penn – 26:01
Exactly. Now, the other thing that needs to happen, we were talking about this earlier. This needs to be QA’d, this needs to be checked to make sure that it did not pick up. Because we talk a lot of crap in our sales, our weekly calls. There’s things you can find, there’s little things can find their way in here that maybe don’t belong in here. And so it does need, you know, someone does need to go through this.

Christopher Penn – 26:27
I’m sure there are somewhere. But this is 50,000 words, 153 pages. This is a book. Like, this is a business book.

Katie Robbert – 26:33
Yeah. No, and you know, I was reading through this before the live stream, and I flagged, there was like a. There was a framework that was mentioned that sounds similar to one that we have, but isn’t ours. And so, there’s those little nuanced things. So, you need to make sure that someone who understands the companies, like someone like John is going to go through these things and be like, “Oh, that’s not actually accurate.” Or, you know, “It picked up on this. It’s not really true.” Do not skip the human intervention QA part. Have your subject matter experts go through these documents. 153 pages. There’s bound to be an error somewhere. I would be, I’m guessing there’s not going to be a lot because even just looking at it, I’m like, “This is all our stuff. It all makes sense, it’s all coherent.”

Katie Robbert – 27:21
But there’s going to be those little detail things that, you know, God forbid we start to onboard, you know, like a sales associate, and they’re like, “Great, I want to sell XYZ framework.” And they start talking about it. We’re like, “That’s not a thing. We don’t have that.” Like, you don’t want to find yourself in that position.

Christopher Penn – 27:38
Exactly. So, to recap, so far, we’ve started with what we had, which is all. Which was good. We built out best practices using the casino framework to understand what we should have. We went and got all of our data. We assembled multiple versions because of space limitations of the. The different data sets. We glued them all together and merged them down using a language model. And we end up with this. Now, here’s the problem. It’s 50,000 words. It’s 153 pages. It’s a full-size business book. This is a lot for someone to digest. I mean, how long is it? How long would it take you to figure out? You’ll pick up a sales book off of the shelf and just read through it. It’s. It’s a decent amount of reading. So what happens downstream from this is as important as this.

Christopher Penn – 28:27
This document absolutely should be as robust as you can make it. And there will be people say, “No, sales playbook should be,” you know, thin and light because you want people to actually read it. Like, no, you want the book of how you do it. But we can use generative AI tools to make it more manageable. The obvious one here is to stuff it in NotebookLM. Right, which is Google’s free tool. And you could say, “I’m gonna, you know, generate a mind map or I’m gonna make a study guide, or frequently asked questions or briefing document or frequently asked questions or whatever.” And if you want to get clever, you can do things like prompt it, maybe in different thin slices to create sales training. So this I’m gonna play just a short one minute segment of a prompt.

Christopher Penn – 29:15
I gave it specifically to generate training around. Objection.

Speaker 4 – 29:19
Handling agency.

Speaker 5 – 29:20
Gotcha. So it’s not always just no money. It could be a value perception issue or a comparison issue. How does the playbook guide us to respond effectively then?

Speaker 4 – 29:28
Okay, the first recommended approach is crucial. Acknowledge and explore value and ROI. This is the most frequent reason we see foreclosed lost deals.

Christopher Penn – 29:38
Right.

Speaker 5 – 29:38
The price objection feels almost universal.

Speaker 4 – 29:41
Sometimes it does. You hear the classics, right? “This is more expensive than we budgeted for.” Or just flat out, “Your price is too high,” or “We just don’t have the budget for this right now.”

Speaker 5 – 29:50
Yeah. So why is this such a common roadblock? What does the playbook and the data suggest is behind it?

Speaker 4 – 29:57
Well, section 7.2.1 and 8.3 point to a few potential reasons. Sometimes, yes, they might genuinely have limited funds available right now, but often prospects might be underestimating what it truly costs to solve the complex problem they’ve described. Or maybe they’re comparing our very specialized services to something much more generic, like off-the-shelf software or a different type of agency.

Speaker 5 – 30:19
Gotcha. So it’s not always just no money. It could be a value perception issue or a comparison issue. How does the Playbook guide us to respond effectively then?

Speaker 4 – 30:26
Okay, the first recommended approach is crucial. Acknowledge and explore value and ROI. This is the most frequent reason we see for closed, lost deals, right, the price object.

Christopher Penn – 30:38
So what it’s done is it has created in this case a 30-minute training, an audio training from our playbook just on, Objection Handling. So if I’m a sales leader at an organization that’s, you know, more than just the four of us, I might say, “You know what, I’m going to take our sales playbook and section by section, piece by piece, I’m going to generate 15–20 minute internal podcasts to help our sales team skill up.” But it’s based on the way we do it. So it’s our stuff. It’s not some generic, you know, “Hey, motivational sales trainer.” This is straight out of our stuff. And so this, you know, having this interface allows you, obviously a sales professional, just query it, say, “Well, how do I handle this? Here’s this situation.”

Christopher Penn – 31:21
It can pull citations from the Playbook from the master document, but you can also proactively create training from it that would let a new person, Katie, to your point about onboarding, skill up and say, “Okay, I’m going to listen to this on my commute.” You know, here’s the 20-episode Trust Insights Sales Mastery course.

Katie Robbert – 31:40
So that actually brings up a couple of the things that I was thinking about. One, we can talk about offline. But the other question is, could we take this sales playbook and turn it into a custom model like a GPT, like the Trust Insights sales GPT. So, for example, if I have a pros, if I have a lead that’s closed, lost, and they’re like, “You know what, we just couldn’t make the budget work.” Could I take all the information I have about that lead, give it to the GPT, and say, “How do I respond to this?” That doesn’t feel pushy, that, you know, keeps the door open for more opportunity. But I feel like I have to say something and sort of try one more time to get them to bite you?

Christopher Penn – 32:32
Absolutely can do that. You should do that. And the place I’d like to do that, the place I suggest doing that would be in Gemini. So, going to your Explore Gems, create a new gem, and call this Sales Coach. And in the knowledge section here, add from Google Drive and there is my 2025 master sales document. So now this huge sales playbook becomes part of this and say, “Help my salesperson do better sales.” This is a terrible prompt. Sure, but you could absolutely do that and then say, “Okay, start a chat and say, I am pitching Acme widgets. They say they don’t have budget. What should I do?” And based on the stuff that we’ve put into our sales playbook, it say, “Hey, here’s the classic thing.” And there it is, straight out of the playbook.

Christopher Penn – 33:30
Validate the concerns, explore, shift to value, and ROI. Reinforce our unique value. And this is with a crap prompt. Right. So this good playbook crap prompt, this is how you would do this.

Katie Robbert – 33:44
And so where Notebook LM is more like a wiki to give you the information that’s in there. This sales coach, you could say, “Help me draft a response based on their objection.”

Christopher Penn – 34:04
They want our services for $500. We start the services they asked for at $50,000. Help me draft an email using these best practices to resolve this impasse. And obviously if you wanted to you, in your supplementary documentation, you might have things like your brand style guide, tone of voice, certain things like that you might want to incorporate. But this is just very simple example of like, “Yeah, help me figure this out. I don’t know what to do here, but this 50,000 word document is going to help any sales professional figure out, “Okay, well, what do I do? Hi, Acme widgets, thanks so much for your interest. We appreciate you sharing your budget of 500.” Now, normally, we’re all saying in our heads, “Go take a long walk off a short pier.”

Christopher Penn – 35:00
The specific services you acquired about, and so on and so forth, generally start at $50,000, reflecting the comprehensive nature and substantial value delivered, so on and so forth. Sometimes, a very specific, tightly scoped question can be addressed in a more limited engagement. We do offer one hour expert consultation. Our academy courses, our free newsletter resources. Right. So, these are ways that you could respond.

Katie Robbert – 35:20
I like that it’s offering up solutions, so you’re not just like, “All right, peace out.” Which is, it takes the emotion out of it, which I think. And you know, John, correct me if I’m wrong, sales can be really emotional.

John Wall – 35:34
Yes, there’s plenty of GFY responses.

Christopher Penn – 35:38
That would always be closing.

Katie Robbert – 35:41
Yes, but I, but like in reality, but that’s like, it’s, you know, to Chris, where you started. You know, there’s a lot of ego involved. But there has to be, like, there needs to be a confidence, there needs to be an assurance that, like, we know what we’re talking about. But that also comes with being able to handle rejection and you know, heartbreak and frustration and anger. A lot of really strong emotions. And I know for me, I’m a very emotional person. I usually wait 24 hours before I respond to something so that I’ve taken a lot of the emotion out of it. I can do it more clear-headed. But having a sales coach, for example, to be like, “This is what I like.”

Katie Robbert – 36:23
It’s a very early use case that we talked about with generative AI of, like, “Have generative AI take your emotional response and clean it up and so that it sounds more professional” because I know Chris is an example you give in your talks of, like, “Hey, Bob, I gave you the effing receipts and blah blah.” And it gives you like the more “Bob, due to the nature of the delays of the invoicing, blah blah.” I like that you can take a very specific use case, which is sales objections, which is something nobody wants, and have it use your words, your work to create a very professional sounding response that includes solutions.

Christopher Penn – 37:00
Exactly. And there’s so many templates and examples from our own stuff from the CRM, from our Slack messages and things, because we say in our Slack channel, “Hey, how, hey Katie, can you read this response?” And you know, that’s easy in here now. And so when it’s referencing the master sales playbook, all 50,000 words of it, there’s a lot of that in there. So, it has examples to draw from, it doesn’t have to wing it.

Katie Robbert – 37:25
That’s amazing.

Christopher Penn – 37:27
Now, the other thing you can do with this is you can use this, you can guide this for creating new sales enablement materials. So, for example, I went to Gemini and I said, “I don’t know what we sell anymore because we have so much stuff. I said, “Make me a menu.” And it said, “Hey, here’s the Trust Insights menu of services, data-driven insights, and AI-powered solutions served fresh your pallet. Sparking, sparking appetizers, you know, online courses, speaking stuff, building the perfect mise en plus data governance, AI strategy. You can see universal analytics that needs to go away because that’s obviously no longer relevant. GA4 email list hygiene, our signature insights and strategies, ICPs, competitive analysis, digital customer journeys, the AI chef’s table of all the advanced AI techniques, and then of course, master classes and continued empowerment.”

Christopher Penn – 38:16
When we say, “Like, what do we do as a company?” Well, remember what we do.

Katie Robbert – 38:21
You know, the question, you know, that we got early on, as we were struggling to articulate, was, you know, people would say, “I don’t know how to buy from you,” or our partners would say, “I don’t know how to sell you.” And I feel like this after, gosh, we’ve been in business, what, seven years? Seven years, seven and a half. Call it seven and some change. Now, we’re very clear about what it is that we have to offer. And I would look at this and say, “We can probably scale this back a little bit to make it more focused.” But, like, this is very clear to me now.

Katie Robbert – 38:54
You know, if you still don’t know how to partner with us, then I don’t know what else to say, because I feel like now, with seven and a half years of data, we’re very clear about what we have.

Christopher Penn – 39:05
Exactly. And this is then something that you can, you know, with. With tools like Gemini, you could say, “Turn this into the outline for a slide deck.” If you’re doing, like, a capabilities deck. Turn this into, you know, an infographic. Turn this into whatever you want to, I hear.

Katie Robbert – 39:25
I can hear all the way across the world, Kelsey cursing me out for making her do our capabilities deck. Before, this was a thing that we had built.

John Wall – 39:35
Right.

Katie Robbert – 39:36
She’s probably, like, “I went through all of those versions, and now it’s right here.”

Christopher Penn – 39:41
Exactly. Also, with something like this, you know, when you think about, like, “It’s just remembering what are all the things we can do?” Because we forget sometimes, you know, we have voice of the customer analysis on here. We do that. That’s something we’re actually extremely good at. We don’t often say, “Like, hey, buy. Buy this thing from us.”

Katie Robbert – 40:02
Yeah. And I think it’s. Yeah, Kelsey is cursing me. Sorry, Kelsey. Listen, I didn’t know this was a thing either. I would have. Yeah, we’ll talk. But I mean this, to me, it’s like, “Okay, do we need a capabilities deck?” Like, here we go. Yes, we do need a cape stack. Sorry, Kelsey. We do need one, but this becomes the foundation for it. And then to your point, Chris, you can say, “Okay, great, this is everything. Help.” Like, now, generative AI, outline what a capabilities deck would be, what in elements would be included. Because this. Man, we really got to get a website updated.

Christopher Penn – 40:38
I was just going to say, and this is also now our services page.

Katie Robbert – 40:43
Dang it. Yeah, it’s. Well, again, it’s, you know, we’ve been so close to it for so long that I feel, you know, we can take a step back and be like, “Wow, we really overcomplicated our website by trying to really articulate what it is that we do when really, they just want this.” Like, this is pretty descriptive. We don’t need the deep pages that go on and on about what it is. Like, this tells us what it is.

Christopher Penn – 41:11
I would even see, you know, if we go to the point of doing things like sponsoring conferences or events, this printed out as an actual restaurant-style menu, as like one of the things on the table that people can just walk away with, like, “Oh, here’s the menu.” Everybody understands the menu. Like, you’ve all eaten at a restaurant. Like, “Oh, okay, I can see what you, I can see what I want to order here.”

Katie Robbert – 41:33
Yeah, Kelsey’s still mad.

John Wall – 41:37
Kelsey’s still running.

Katie Robbert – 41:38
She’s so mad.

John Wall – 41:40
It closes the gap because so much of what we do talks about what and how. You know, it’s very specialized and unique technology and new approaches. But really, this covers the why this is, you know, customers look at this and it’s just the one paragraph of, like, “What’s in it for them?” And it. Yeah, and that’s just bang on for the website too.

Christopher Penn – 41:59
And so, if we go back to our 2025 sales playbook and we look in section 11 on sales enablement materials, there may be things. One of the questions you can ask is, what sales enablement materials aren’t here that should be? And we can say, “Okay, we know we have all the data. Let’s make them have the machines make them for us.” So that’s the process of building from all the data you have, plus using deep research tools, plus using merging prompts, plus basic use of large language models that have big memories into something that is actionable and useful. This is your master sales playbook for the organization. And then from there, you spin off all the products. Call scripts, email scripts, nurture sequences in your marketing automation software. If you’re doing a nurture campaign, social media content.

Christopher Penn – 43:03
Hey, we, you know, every eighth post should be a promotional post. How do we do that? Sales playbook. Give me a promotional post for this service. Right? Content, calendar, landing pages, services pages, videos, audios, podcasts, training. There’s so much you can take from that master document, if you’ve done a good job of.

Katie Robbert – 43:26
Building it to begin with, could you, similar to what we’ve done again in past episodes of the live stream, could you use the sales playbook to create a scoring rubric against past or, you know, basically, could you use this to analyze past campaigns that didn’t work and have it point out, like, “Here’s where you could have made improvements.” Like, if we’ve sent out, like, email pitches and something like that, you could have it scored against the updated sales playbook to be like, “Yeah, here’s the five things you missed.”

Christopher Penn – 44:04
You could do it that way. You could also take all the prep documents themselves, put them into NotebookLM, because you’re gonna have a lot more very granular detail. Like, “Oh, back in 2023, we tried this, and it went.” It went sideways. And so, having the source documents in a separate notebook LM instance, might be a good way to do that so that you can say, “Okay, here’s what the sales playbook says of the consolidated known, good stuff.” But here’s the raw data in a separate notebook to say, “Like, have we tried before?” And the answer might be, “Oh, yeah, you tried this in 2021 and it went sideways.”

Katie Robbert – 44:35
Well, there’s that. There’s what have you tried? But then there’s the actually telling you why, based on your sales playbook. So, I’m thinking more of, like, the scoring rubric to be like, “If I draft a cold pitch email for, like, our courses, for example, and it’s well documented.” I’m a terrible marketer because I’m way too blunt and direct. You know, I could, you know, put together an email, and could I then give it to the sales plan playbook scoring group? It can be like, “Is this going to work? Are they going to object? What am I going to miss? Like, does this actually talk about any of the services we actually offer, or am I just making things up?” Like, could you do. Could you use it that way?

Christopher Penn – 45:11
You absolutely could. I would take it a step further and say, “Of the seven buyer Personas we have, which buyer Persona is a best fit for?” And then say, “How will this resonate with this buyer Persona? What would this buyer Persona prefer to see instead? Rewrite this for me for buyer Persona five.”

Katie Robbert – 45:30
John, write that down.

John Wall – 45:32
I’m ready. We’re tagging the Personas. We’re getting them straight.

Katie Robbert – 45:37
I mean, this is. I. I’m excited. This is really cool. And, like, ready. I’m ready to start doing the thing.

John Wall – 45:46
Ready to go.

Christopher Penn – 45:46
Katie’s got new toys.

Katie Robbert – 45:48
I do. Like, this is the kind of toy that I’m like, “Oh, this was a good surprise.”

Christopher Penn – 45:56
Exactly. So, I would encourage people to do this, walk through this process. We walk through the steps, each of the pieces. If you’ve got questions, you’re trying it out for yourself. Things you know, pop on by the Slack group, go to Trust Insights AI analytics for Marketers. So the all the supporting materials and things you have somewhere in your organization. I will tell you, the hardest part of this is probably going to be getting all the data together in one place. And if you don’t have the data for some reason, one of the, but you do have a decently sized sales organization, one of the easiest things to do is start doing interviews with customers like, “Why did you buy?” Ideally, if you can get in touch with a few friendly non-buyers like, “Why didn’t you buy?”

Christopher Penn – 46:42
And then interview every member of your sales and marketing team individually and say, “What do you think we sell?” And then consolidate all those transcripts and it’s a way to mitigate if your CRM is just a hot mess, for example, and you don’t have Slack, and you don’t have call transcripts and things.

Katie Robbert – 47:03
Well, and I can definitely see if you, you know, there’s a lot more data that you could include in your sales playbook should it exist, like, feedback surveys and testimonials, and you know, all that good stuff, you know. But again, it’s just a matter of finding it, getting it. And I think that, you know, to your point, Chris, that’s the hardest part. But once you do, like this is such a powerful tool.

Christopher Penn – 47:27
Exactly. All right, any final parting words, John?

John Wall – 47:33
You know, I love looking at the whole map of the city in the skyline, but yeah, this afternoon, I have to go down and get involved in that specific street fight. So, hopefully, we’ll get a chance to dig into this stuff more. But yeah, I’m same as Katie, very excited with the opportunities that are around this.

Christopher Penn – 47:49
All right, well, folks, that’s gonna do it for this week’s show. Thanks for tuning in, and we will talk to you on the next one. Thanks for watching today. Be sure to subscribe to our show wherever you’re watching it. For more resources and to learn more, check out the Trust Insights podcast at Trust Insights AI, TI podcast, and a weekly email newsletter at TrustInsights AI newsletter. Got questions about what you saw in today’s episode? Join our free analytics for Marketers Slack Group at TrustInsights AI analytics for marketers. See you next time.

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