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I sat in a conference room in Chicago with a team of us that was pursuing a large energy infrastructure opportunity.
In the meeting were our business development leads, company leadership, global representation, technical leads, consultants, and subject matter experts. It was a packed house.
The purpose of the meeting was to focus on competitive positioning and stakeholder engagement. Where we are positioned with the customer, what we need to do to improve our position to win, and how our competitors are positioned.
Was this newsletter forwarded to you?
I have been part of this opportunity since day 1. As the pursuit grew, it took on legs and size, and the interest grew internally.
The average buying committee includes: 8.2 stakeholders for complex solutions, 86% of organizations involve at least 3 decision-makers, For large and complex deals, that number jumps to 15+ stakeholders
Sitting in this conference room, we were at the point where we needed to know the relationship breakdown.
When you are pursuing a large opportunity and need significant face time with your team, there is a lot of prep work that goes into it. You want to maximize the time that you have with those who are present, not create things from scratch.
From capture plans to account management plans to stakeholder mapping plans to updating your CRM, there are so many different layers of preparation. Which area gets the most amount of attention?
And where can AI help you? In this case…how can it help you with understanding the customer stakeholders?
I’m going to break down how you can use AI to help you with your stakeholder mapping. Every opportunity is unique; however, it can be utilized to help you save time, so you can focus on building relationships, not building the spreadsheets.
You know the customers, AI can help (to a certain extent), on who the decision-makers at the customer level will be. Let’s match it up so you can maximize your time.
Let’s dance.
By the way, check out my recent podcast with Kyu Jung, CEO of Procon Consulting, on their podcast, The Build Up! Link is below to watch!
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I’ve written on stakeholder engagement in the past; check it out here:
Going back to Chicago, we spent…well, I’ll be honest. I lost track of time on how long we spent on each relationship and where we stood we each person on the customer side.
We addressed everything from: Do they know us, do they like us, how well do they know us, how well does the competition know them, how long have they been buying from us, are they a champion of us, where are we specified in, who makes the decision, who’s missing, are we in the right spot with them, etc.
We didn’t talk about the product gaps; we talked about the relationship gaps and the relationship strengths.
How to strengthen what relationships we already have, aka double down on those, and how we can pivot on any changes we need to make on those who might not be in favor of wanting our solution.
It was absolutely exhausting. Steve (the BD manager) and I felt like we took punch after punch on giving a breakdown of the stakeholders.
What was not talked about is all the work that went into preparing for the meeting.
Oh yeah…that whole thing.
Charts, slides, websites, backups, resumes, historical documents, partners, subcontractors, the list goes on.
Let’s Break it Down
Each opportunity has its own set of decision-makers. Each opportunity is different than the last.
It is important to understand where you line up in opportunities. If you don’t know who you are selling to, they have absolutely no idea who you are either. Why would they award it to you?
Why Traditional Stakeholder Mapping Fails
Many companies still map stakeholders like it's 2015:
Manual research that takes hours per prospect
Org charts that show reporting structure, not influence
LinkedIn stalking that misses key relationships
CRM notes that become outdated the moment they're entered
Here’s how AI can help you start to break this down. I did this in Perplexity for all fun and games:
Target a specific opportunity (I gave Perplexity the specific link)

Open your favorite AI tool (I’m doing mine in Perplexity’s Comet browser)
Ask a detailed prompt (such as follows)
I need you to act as a federal government contracting expert with more than 25 years of experience winning contracts. You are the go to person for both small and large businesses to grow their business.
We are pursuing a new opportunity and new to better understand who the decision makers are on the customer side and how we can potentially stack up with them on a variety of factors. The factors are below:
Step 1: Organizational Structure
Map your client’s internal structure. Use the letter or
number correlating with the specific step that you
believe best represents where you stand with your past
client. This Map is a living document and update as
needed with your client.
Include everyone who is part of the decision making
process or affected by it. Include as many people as
possible. Leave boxes open if you know there are gaps
within your Map.
Step 2: Decision Making Influence
Decision Maker
Influencer
Advisor
User
Step 3: Your Current Status with Potential Client
A. Mentor/Very Strong D: Weak
B. Strong E. Non-Existent
C. Moderate F. Enemy
Step 4: Last Contact with Client
Include Month & Year of last contact (if known)
Step 5: Interest in Doing Business Again
Y: Yes - Immediate interest
T: Tentative - Wants more information
N: No - Not interested at this time
U: Unknown/Has no ability to make business decisions
O: Other (specify)
I will need you to put who the potential decision makers are for this specific opportunity. We need to know all the players that are involved and be able to move the map at our discretion. We need to be able to have all these items listed as well. We will add over time resources and please include all potential players and position them based on hierarchy and decision making capability.
Before going any further, let me know if you have the ability to pull this off in your "Labs" and I can give you a sample project opportunity to try it out on.
Add the specific opportunity (in this case - tps://sam.gov/workspace/contract/opp/d7c20eaea66e43d48f2f73bc0ec336b6/view)
Complete the step in Deep Research mode
*The Decision-Maker, Advisor, influencer, etc., all came from my viewpoint. If you want to develop your own, feel free to change as you see fit.
Comet will do a preliminary search of the opportunity and come back with results that are around this opportunity
Ask the AI to build you an interactive dashboard (KEY) to include all personnel that I can add additional resources. add/delete personnel, add a section for notes.
The Final Step
Here is what your interactive dashboard will look like (in Perplexity)
Get with your team and fill in the gaps. Who is missing, who has a position that does have significant authority? Who is your champion?
*FYI this is not perfect. This is a tool to help you plug gaps within your overall capture and sales process to figure out where you can find the decision-makers. It can also be used as a foundation for opportunities to see where you stand
Let me know how it goes! What did you change in your prompting that guided you to a stronger output?
Pack Some Additional Punch
Here are a few tips to really hit it out of the park when reaching out
You don’t have to use Perplexity for this. Gemini has a built-in mind-mapping toolkit, MapThis, Clay, Apollo, ZoomInfo, LoneScale, or DemandFarm
Share the dashboard and integrate it into your process with your CRM, and make it part of an opportunity gate review
The more that you have additional documents, resources, and context, the more helpful AI can be in finding the right people. Don’t rely on it to solve everything for you in finding the right people. If you know that someone is part of a review panel, make sure it is noted.
This doesn’t just have to be for opportunities; this can be for policy and lobbying efforts, too! It can be a multi-dimensional tool, whenever you need to think about those you are selling to
What the Internet Taught Me This Week
From new tools, recent trends, and market updates, here is what has been on my mind.
OpenAI announces AI-powered hiring platform to take on LinkedIn. Check it out here
Dominion proposes higher utility rates, new rate class for data centers. Check it out here
Microsoft joins World Nuclear Association as it doubles down on small modular reactors and fusion energy. Check it out here
Every deal you've lost to "budget constraints," "timing issues," or "internal priorities" wasn't killed by those reasons.
It was killed by stakeholders you never knew were in the room.
The game has changed. Your competitors who are still manually researching org charts and guessing at influence networks are about to get steamrolled by teams using AI to see the full battlefield.
You now have the tools to map every player, predict every objection, and engage every influencer before they become a problem. The question isn't whether AI stakeholder mapping works—it's whether you'll use it before your competition does.
Stop playing sales roulette with invisible decision-makers.
Build your map. Score your stakeholders. Execute your sequence.
Because in a world where deals are won and lost by people you'll never meet, the only way to control the outcome is to know who's really pulling the strings.
Give it a try…let me know how it goes!
See you next week.
Whenever You're Ready, Here are 4 Ways I Can Help You:
Unlocking Hidden Potential - Reconnecting with Past Clients for Explosive Growth - Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.
Build your Sales CRM - Download our free Sales eBook on How Your Sales Team Can Maximize Your CRM Tool. Whether it’s Hubspot, Salesforce, or another CRM tool, make sure you leverage it to your advantage.
Awesome Sales Resources - Transform your sales engagement and capabilities across Social Selling, CRM, Lead Generation, Enablement, and more.
Cribworks Advisor Program - Want more than just resources? Reach out to me and see if our Advisor Program can help you grow your business.