AI-Powered Seller

‘Hidden’ Decision Makers? How AI Maps Internal Politics Before They Kill Your Deal

• Jake Dunlap • Season 1 • Episode 18

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Your champion just went silent. That $100K deal you've been forecasting is officially dead, killed by someone in a completely different department you never knew existed.

In this episode of AI-Powered Seller, Jake Dunlap reveals how to use AI for sales stakeholder mapping to identify the TRUE power dynamics in any organization before your deal gets derailed by internal politics.

Most B2B sellers focus on organizational hierarchy when they should be mapping the "powerarchy", the real influence networks that determine whether enterprise deals live or die. Jake demonstrates his exact AI sales prompt that identifies ghost stakeholders, maps informal approval processes, and gives you tactical strategies to navigate complex organizational politics in B2B sales.

This sales AI episode covers:

  • Why traditional B2B stakeholder mapping fails in today's complex buying environment
  • The difference between your sales champion and THE decision maker (and why it matters for deal closing)
  • How to identify the "shadow CIO" and other hidden decision makers using AI
  • Jake's complete AI framework for political deal analysis and sales strategy
  • Specific discovery questions to ask different stakeholders based on their motivations
  • Warning signs your enterprise deal is about to be torpedoed by internal dynamics

Using a live demonstration with ChatGPT for sales, Jake walks through analyzing a fictional deal scenario, watch how AI identifies informal power structures, predicts potential deal blockers, and provides actionable next steps to win the political game in enterprise sales.

Every enterprise sales rep and mid-market seller needs to be running this AI sales process on every deal.

📍 Chapters

00:00 Your Sales Champion Went Silent - Here's Why

02:30 Why Traditional B2B Stakeholder Mapping Fails

05:15 Hierarchy vs Powerarchy: Understanding Real Sales Influence

08:45 Live AI Political Analysis for Sales Deals

15:20 Tactical Next Steps and Enterprise Deal Warning Signs

18:30 How to Future-Proof Against Political Sales Landmines

New episodes drop every other Wednesday @ 8 AM CT / 9 AM ET

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►Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Speaker 1:

Your champion just went silent. That $100K deal that you forecasted probably a couple of times in the last month is officially dead, and it wasn't killed by the group you were talking to. It was put to pasture by someone in a completely different group that you never even knew. So today I'm gonna talk to you about how AI can help you to map the true power dynamics in any organization before your deal gets derailed. How many of you out there have got an email or a call it's like, hey, sorry, this thing happened. You're like, wait, wait, I can talk to that person, et cetera. Well, the problem is too many sellers right now and just in general, have always been too focused on the hierarchy. The reality is, every deal my friends has a powerarchy and both of them are important to know. And especially if you've been following along with the pod, you know we've done episodes about, you know, mapping the hierarchy, etc. But in today's episode, number 13, I am going to talk about how to utilize ai to never lose a deal to internal bureaucracy or politics ever again. I really I can't like.

Speaker 1:

As we were putting this episode together, I feel like this is like the missing piece. You know, I see there's so many tools out there today. They're like well, did Johnny follow Medic or MedPick? And it's like oh, my gosh, look at, johnny followed MedPick, but guess what? Medpick and these other gong, these other tools, guess what they don't listen for. They can't comprehend the concept of power dynamics, right? And you know today's day and age, there are so many people involved in deals. My gosh, you know I've seen 11 in like a small company, at least 11 people involved. So in today's day and age, you know, we have to try to map this and to think two or three steps ahead. And so, throughout today's episode and make sure you kind of tune in through the end, if you are listening right now, we're going to have a great visual on YouTube. You all know this, though you know I do a pretty good job of walking through what we're going to cover. So, if you're just listening amazing, thank you for tuning in.

Speaker 1:

If you are watching right now, make sure to subscribe to the channel, as I'm going to jump into how to make sure you never lose a deal to internal politics again, and I'm talking internal to prospects company. Ooh, actually that's not a bad idea. We can actually do an internal, internal politics one where how to make sure you can get approvals from all the different groups for the you know, the stuff that you want to pull as a seller. Uh, maybe that'll be a future episode, um, but, like I said, I think today's episode is just going to be another one of those copy and pasters where we've got the team has built out one of the most insane prompts that I have seen in terms of like breadth and depth, and, and we're also going to be converting this into a custom GPT as well too. So, if you're somebody who already subscribes to our custom GPTs, those are continuing to get better. So we're coming up with a name. I think it's going to be like you know, political analyzer internally, prospect, internal politics analyzer, something like that. Uh, but it should be a lot of fun. So make sure to stay tuned and I'm going to walk you through the exact prompt that is going to make sure you never lose that big deal again to internal stakeholders. So let's jump into this.

Speaker 1:

Okay, let's talk about why traditional stakeholder mapping fails, and I'll tell you there's a couple of reasons. Over time and I'm sure all of you can attest to this over the last I mean, I've been in B2B sales for like 20 years. So, sir, I'm just going to say over the last 20 years, because that's my experience it used to be, I kid you not, I'm going back. I was a sales rep at a company in the job space. This is probably 2006, 2007. I could get a CEO or VP of HR on the phone and I could close I kid you not Like on the second call. I could close on the call like a 15 to 30K deal sometimes.

Speaker 1:

And you know, it was really this idea that people used to make a lot more decisions on their own up high People didn't use to consult 55 people, and so why the traditional stakeholder mapping is failing is that there are so many people now that have influence, so many executives, so many people are scared to make decisions today. So what they do is they get in a room with a bunch of people and they look around. They say, well, what do you think? What do you think? And they're like hoping to God that there's consensus here. And then you can have this one person who's like two levels below the economic buyer or champion or the decision maker, and they're like, look, I just don't think this is going to work. We tried to implement this tool before blah, blah, blah, it didn't work. I think this is going to be the same. And then that person is the loudest voice and your deal gets shot down.

Speaker 1:

Okay, and what I think AI is uniquely amazing at is is it can kind of map out the like hey, this is actually how things work at a company based on a product that you might sell. You need to make sure that you talk to these people as well, too, and I think, look, sometimes in sales we are taught, you know, less meetings, you know, is better. What can we do digitally? And look, as you know me, I'm all about providing digital experiences for people, but I also need to make sure I'm providing digital experiences differently to different types of stakeholders. And so, politically, you know, to pacify this person, I need to talk to them about this, and to pacify this person, I need to talk to them about this. Right, and when you combine in your call transcripts, you combine in email copy, you combine all those things together plus a seller's, you know, experience, we've got some really cool signals that we can try to map to. That will actually help you to reveal kind of true organizational power dynamics.

Speaker 1:

And so here, in about 10 minutes, I'm going to walk you through you know the prompt and I'm going to walk you through exactly how to make sure that these things you know don't you don't lose a deal again because of this. And what I want you to think about is look, your champion isn't your champion and the decision maker that you've been pitching to is not your decision maker. My friends, every deal in today's day and age has multiple people and multiple champions that might be peers. They have multiple people within the inner circle that can say yes or no, and so just looking at an org chart is a 100% recipe for losing more deals. You need to make sure, if you're talking to the end user team, you have at least one or two people you talk to regularly.

Speaker 1:

If you are talking to the ROI or the business team if you wonder what I'm talking about, this is our framework called intent. Hopefully you are talking to the ROI or the business team. If you wonder what I'm talking about, this is our framework called Intent. Hopefully you follow along on Innovative Seller If you don't check it out on YouTube. But Intent talks about this concept of teams. So you've got your end user team and you've got your buying or ROI team, and so you need to make sure, in today's day and age, you have multiple relationships. You cannot be single-threaded. I mean, that's a recipe for disaster.

Speaker 1:

So what can we do to try to mitigate some of this? Okay, and I'm going to talk. I'm going to go through kind of three or four key areas here. Yeah, the first is I'm going to talk about the concept of a champion, and I have said some relatively controversial things about the whole idea of a champion over the years. I love champions. I want to be very clear. I've had many, many deals where I had a champion who literally did the work for me and it was awesome, it made my life way easier. But look, as salespeople, we can't rely on having only champions to close deals. We have to be our biggest champion.

Speaker 1:

And the big issue that I see with a lot of you know, upper, smb, mid-market enterprise sellers is they look at the process through the lens that the champion tells them is the process. Guys, most champion, most of the people you're dealing with are probably, you know, like mid-level on the end user team. That's kind of usually where that champion bucket come from. They're not used to buying things, they're not used to collaborating. They're like they might buy one thing a year, one thing every few years, and so they're telling you what they think the process is, but they don't really know right, and they really only interact or know their own kind of peer group. They don't interact with this other department or this other sub department within their department that much and they don't really know Jill, jill in finance or whoever right. And so because we don't understand the actual decision-making process, because again we're taking one person's opinion, you know we lose deals, right, that stakeholder map of this goes to this and then this goes to this. It just falls apart.

Speaker 1:

So now, my friends, let's enter the world of AI. I have a little coffee, okay, so let's talk about what AI can do. First, email communication. It's interesting I see a lot of focus around the call. I want you all to understand that most of these companies are not able actually to judge true sentiment. What these companies are actually doing on the call is looking at words and they're bunching words together and they're saying these companies are actually doing on the call is looking at words and they're bunching words together and they're saying these words are typically positive, these words are typically negative. It's very much AI and machine learning, not generative AI. On the email side.

Speaker 1:

What these tools can do is quickly help you to see the unsaid things. This was a shorter reply, jake. You had six replies here. They were all short. At no point did they loop anybody in All of those types of nuances. The other thing that I really like about AI is and whenever we go through the prompt here in a second is it also will say, hey, who hasn't been involved that you should probably think about talking to, and I really love that application. You know, the ability to say, here's who you know, here's kind of who I've been talking to, like what am I missing, etc. I think that's a big one as a part of it, and I think, too, what the other thing you can do is pick up, maybe on some subtleties between you know, maybe internal groups disagreeing. You know maybe a subtlety that was mentioned by this department. That's really important. And so, as you know, in terms of mapping the political dynamics, when I put together the proposal, I want to make sure that I, you know, have those nuances in my proposal. So then this person who could, you know, shoot the deal down, is happy. So all those things go really into it. And so how do we actually implement this? Okay, this prompt that I'm about to.

Speaker 1:

If you're watching on YouTube, we're getting ready to fire it up. If you're listening along, thank you again, as usual. If you're enjoying what you hear so far, make sure it does a lot. If you guys, you know, take a couple of seconds to subscribe on your you know favorite either podcast or your favorite you know medium that you're listening, or you know, obviously, if you're watching this on YouTube or LinkedIn, you know, please, please, you know, always helps give it a like, share it with your network as well. We always appreciate those things. Subscribe to the channel. You know the things to do, so we're going to get into the implementation.

Speaker 1:

So what generative AI is able to do better than any technology we've ever possessed is really synthesizing and taking in a whole bunch of unstructured data and making very smart correlations between things, or at least, maybe not correlations or causations, but inferences toward things might be a better way to think about it. It can also, over time, it already will start to learn your map, right? So those of you if you're using ChatGPT, I'm going to show you the example in ChatGPT today. Chatgpt memory is a really great thing. Also, this is more of a pro tip, I'll tell you Look, chatgpt memory messes up a lot and you need to prune it at least once a month. So the quick way that you can do that, the little pro tip, is just ask chat GPT what it knows about you. Just hey, chat GPT, what have you been storing about me? And let's do a quick cleanse session that I can get rid of anything that's noise. So you need to run that little memory I'll call it a memory cleanse about every month at least as a part of that. So, again, like, over time, it's going to start to understand the typical people that need to be involved, etc. And it can really create this kind of deal risk assessment, right, based on political factors, knowing the nuances of hey, cios typically care about this thing. You better watch out, johnny, because you're going to be in trouble as a part of this. So, my friends, are you ready?

Speaker 1:

Okay, it is time in the show where we are going to get into the AI details of how is AI going to actually help you with this, and I think this. You know we do a lot of these episodes and I think everyone has value. This one, I think, is one that I you know, I'm I really hope every enterprise seller and mid-market sellers like heck, yeah, I'm going to use this thing like crazy, uh, as a part of this, so let's jump into it here, all right. So here we are my friends, so we have this is um, all right. So here we are my friends, so we have.

Speaker 1:

This is ChatGPT03. For those of you who know, I'm a pretty big ChatGPT03. And especially with deep research. I did not turn on deep research for this one, but I'm going to walk you through the prompt right now. I took out and if you all remember from the episode last week or the week before maybe I take out sometimes some of the things that would you know, expose calls that I've had. But in the actual link that we will provide, you will get the full prompt that prompts you to upload a call transcript, upload a few emails, etc.

Speaker 1:

For those of you, the next question I'm sure a lot of you, but Jake, can I? Is this okay? Is this allowed? Look, a really easy thing you can do is say, hey, replace the company name, replace the person's name. Scenarios are scenarios. We're really just looking for the scenario here. It's not really company specific, you know. Also, if you didn't know this, if you have a ChatGPT Teams account or an enterprise account, no information is shared back with the model and I think even the paid Premier account it's the same. I'll have to have the team do some check on the show notes with that. So here's what we've got.

Speaker 1:

Okay, I want you to analyze so here's the prompt. I want you to analyze all available data to map the internal politics and decision-making dynamics. Okay, act as an expert organizational psychologist specializing in B2B buying committees, with deep knowledge of corporate power structures. Right here, guys, this is where so for those of you listening along, there's a little blank spot. This is where the prompt that you will see. If you go to the show notes on the podcast or if you go to the link in the YouTube comments, you'll see kind of the additional details which are, like you know, upload the transcript, emails, additional context.

Speaker 1:

All I said here is I said I have a deal, that I'm worried the IT team will block us. We met with a VP of digital strategy and they are in, but not sure who else should be looped in. I work at a company. I use this company, yoda, and selling to a mid market IT brand. This is a fake. I also said this is a fake scenario, so don't commit it to memory.

Speaker 1:

As a part of this, I said, okay, now let's get weird. All right, stakeholder power map. Identify all known stakeholders, right? So it's going to say, okay for a company like this. Who do they sell to? Who's probably involved? Assess their likely influence level, detect informal power dynamics not visible in org charts.

Speaker 1:

Map reporting relationships. Identify missing stakeholders, flag potential blockers or ghost stakeholders. Guys, I mean this is better than I mean. Look as someone who's managed hundreds, if not thousands, of sales reps. I mean, god, it would take me to give a breakdown like this to a rep like an hour, maybe even more, and we'd have to go back and forth, back and forth.

Speaker 1:

The next thing I said is let's let's analyze their decision process. So not just who is the stakeholder power map, what's the decision process right? What's the actual versated decision-making right? We talked about that, you know, hey, the champion keeps saying this. But what are they maybe missing? Identify approval gates. Map the flow of information, highlight organizational constraints impacting it and note previous purchasing patterns if available. So again, this goes back to what did I say? The reason that a lot of people might lose deals is they believe the one process. Okay, they believe a process they're told from somebody who's just not used to buying things. Right Next up.

Speaker 1:

We ask it to do a stakeholder motivation assessment. We say analyze individual priorities, identify potential conflicts this is where your call recordings can really be helpful. This is a really good one. Detect career considerations affecting the decision Right, you know, if you're selling a project it's a few million bucks, or even if it's less than that, a smaller company someone's gonna have to put their neck on the line for you, uh-oh. Well, what if I'm like, kind of bought in but not all the way bought in? That's a real thing. Coalition analysis right, what are the natural alliances among stakeholders? Political risk assessment, flagged deals, signs of political complexity Again, your call scripts will help with that.

Speaker 1:

Communication network analysis. Map how the information flows, identify gaps, et cetera. Okay, and then we tell it really clearly how we want the data to lay out. Okay, and now, now guys watch what happens, okay. So again, I'm work at this company, I've been working with digital. I'm worried it. Just to summarize again, it is going to be a blocker. I need to make sure, as I'm working, this deal these guys don't have. This doesn't happen. So the first thing we ask it for it's thought for a whopping 15 seconds. If I had turned on deep research, it might've been even a little bigger.

Speaker 1:

Executive summary what are the five fast truths? The IT architecture board equals the ultimate gatekeeper, even when budget sits. In digital strategy, nothing ships without an architecture security sign-off. Your VP champion controls vision, not the keys Shadow CIO. Dynamic Mid-market tech brands often have a long-tenured director manager who quietly dictates stack standards and kills non-fit Ooh okay. Security performance, site performance ROI resonates, but cyber risk avoidance is a non-negotiable right. Yoda solves for site performance.

Speaker 1:

This calls out hey, don't just focus on that. Focus on something else too Procurement. I love it. It even said we'll flex late. It says procurement will flex late. Finance is under cost containment orders. They push anything infrastructure adjacent through the RFP light. If you're not multi-threaded. When they enter, price will become a dominant narrative. Digital revenue KPI equals leverage point. Ecom lead gen owners need faster pages yesterday to carry revenue targets. That can outrank IT in the ELT if mobilized into coalition.

Speaker 1:

So here it starts to map the stakeholder influence map. Check this out, guys. It goes through all these different job titles in IT. It says what's their formal role, what's their actual influence? This actual influence one is filthy. It's like, okay, the CFO controller low to medium influence, but there's budget oversight Medium to high. Right there, they have the CIO. Oh man, I love what it called out here. There, they have the CIO oh man, I love what it called out here. It says, hi, a kingmaker is. This is the senior director of enterprise architecture, the shadow CIO and InfoSec the CISO.

Speaker 1:

So again, if you're a seller, I cannot tell you how many sellers are like, yeah, yeah, it is involved. It's like, no, no, no, no, no. Who is involved in IT? What are the roles? Who needs to be involved as a part of this? So again, I want you all to just think about that as a construct of what it's going to help you to do. It's like you know what man we have never talked to? Security or enterprise ops man, these people are going to have some influence. It's like, hey, you haven't talked to these people? Okay, right, your contact is credible, but politically they're mid-tier, they're mid. I should be able to. It's mid as a part of that Decision process. Reality Okay, boom, informal, there's going to be an informal architectural review, a security view and a procurement funnel.

Speaker 1:

How are you prepared for that? Okay, so think about those types of things, what that might actually look like. Stakeholder motivation map, risk tolerance low alignment, neutral will follow board advice. Ciso job preservation via zero incidents. So one of the columns here is called personal drivers and it says what is a personal driver for CISO Job preservation? Minimize attack risk. Right, the risk tolerance is very low. Right, architecture influence, create technical purity I love that. Call out, et cetera. So here's your political strategy recommendation. Your optimal influence path is this the VP of digital strategy loop in the director of digital experience, the revenue owner, jointly brief architecture lead before the security review and position the CIO as executive sponsor, not evaluator. And position a CIO as executive sponsor, not evaluator. Package a revenue uplift plus zero risk architecture narrative if you want to win this deal.

Speaker 1:

Risk mitigation pilot in a controlled segment. It offers that idea, other people to multi-thread. And then, last but certainly not least, it gives you tactical next steps. It says here's some questions that you might want to ask Okay, the architecture lead. Which reference architectures or cloud governance standards? Must any performance tool align with Love that Revenue impact. Co-host a revenue impact workshop for digital experience and VP. You know, make them feel better about the ROI you can generate. Vp. Make them feel better about the ROI you can generate. Send the CISO a one-pager mapping Yoda to OWASP and ISO 27001 controls. I do not know what that means. What additional penetration evidence would you need for an approval pilot? Then, number four verify threshold for the. Is there a competitive bid? Try to loop in procurement early, quietly it even says so dope. And last but not least, a gear exec level check-in with cio after technical alignment.

Speaker 1:

Guys, I literally gave this thing a prompt. I told it absolutely nothing about you know the nuances of this deal. I didn't upload the trial transcripts, I didn't upload all the emails, but I think you can really clearly see this is a freaking game changer Like. This to me is just one of those prompts where it's like you need to be doing this in every deal. Right, it talks about warning signs. You know if your architecture lead postpones the call, hidden objection, security team requests a generic questionnaire. Only Procurement suddenly escalates to RFP. Digital experience disengages. Right, and this is crazy.

Speaker 1:

The key insight, it says the key insight this deal is won or lost in architecture and security. Treat them as co-buyers, not compliance steps, and arm your champion with revenue evidence strong enough to outweigh IT's risk bias. Strong enough to outweigh IT's risk bias. My friends, like it really does not get any better than that. Like that, like again, like me as a senior tenured sales leader, like this is the type of stuff where I would you know again, I'd have to spend hours studying to even think through all these scenarios. And now here we are and literally I have a bulletproof political landscape map. Guys, you got to be running this for every single deal, and our team, we're going to turn this into a custom GPT for sure, political deal analyzer that you can just upload and it will do it for you. But in the meantime, borrow the prompt, as always.

Speaker 1:

So that is this week's episode, episode number 13 of the AI-powered seller. I really feel that this is one of those episodes that you're gonna win some deals on this year. If you copy and paste what we just put together, if you go into every deal understanding how to use AI to map politics, you're gonna win deals. You're going to win a lot of deals, and so make sure. Hopefully this is helpful for all of you out there. I know there's some good insights in there, so, as usual, make sure to follow along. You can follow along on YouTube. I'm on LinkedIn very, very active as well, too. If you're following there, make sure to subscribe to the channel or follow on YouTube or LinkedIn, or like the video. If you're on TikTok or IG Reels, and definitely if you're liking the podcast. Please, we love reviews. If you don't mind leaving a review, that would be amazing as well, and so that's what I got everyone. Episode 13, ai-powered seller. Make sure, my friends, you are avoiding those political landmines and you're going to close a lot more deals.

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Jake Dunlap

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