Issue #126

How to Weaponise AI in Real Deals

Enterprise deals can be like being trapped in a political drama written by a bored toddler.

There’s always a finance bloke asking if the numbers are realistic, an ops director whose team is at capacity, and a head of IT auditioning to be a Bond villain.

And that’s before procurement shows up with a 37 chapter RFP and an attitude problem.

You want to win in that chaos? You need backup and maybe another coffee or six.

You also need AI, not as a gimmick, but a tactical co-pilot. Here’s how to use it in the deal.

1. Decoding Stakeholder Psychology

Say you’ve had five calls with a client’s project team and confusion is starting to bite.

Simply paste your notes, meeting recaps, and internal comms into ChatGPT (or maybe something better because at the moment it is a bit crap).

Then ask, “Identify the buying motivations, internal fears, political friction, and unspoken goals for each stakeholder.”

It spits back:

• “Nina in Ops is worried about losing headcount if automation goes through.”
• “Raj in Finance only signs off if there’s measurable ROI in-year.”
• “James in IT wants technical validation to boost his profile.”

You now get to sell the outcome each person needs to look good, not the thing you thought you were offering.

2. Predict and Preempt Objections

Upload your 20-page proposal for a supply chain software rollout, for example, then ask your AI bot, “You are the senior leadership team of [describe prospect in 20 words]. Give me the top objections from Procurement, IT, Ops, and Finance.”
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You will get this (and a whole lot more):

• Procurement: How does this compare to existing framework pricing?
• IT: Does it integrate with our legacy systems?
• Finance: What's the ROI window? Is it opex or capex?

That’s your slide deck for the next meeting. You’ve just turned objections into talking points instead of delays.

Drill into each area separately if there are particular expected sticking points.

3. Design 3 Possible Deal Structures

The client says they’re nervous about committing to a full rollout upfront.

You ask AI, “Give me 3 commercial structures that reduce our client’s risk without costing us cash or time, avoid reducing price.”

It gives you:

• Milestone model – start with a 3-month pilot, convert to 3-year contract if KPIs hit
• Credit-back model – credits against first invoice for internal implementation time
• Shared upside model – Extend payment terms if certain business outcomes aren’t hit, until they are.

You walk into the room not with a discount… but with choices, real ones. They see control and you keep margin.

Of course you can get it to suggest way more than three options and choose / combine whatever gives you the advantage without costing too much.

4. Model “What If” Trades

You’re told, “We can’t do £200k upfront. Maybe £140k if we stagger delivery.”

Ask AI, “If the client refuses upfront payment but agrees to staggered delivery, what variables can I trade to protect margin or gain advantage?”

It will suggest:

• Extend contract to 3 years with uplift
• Add paid training and support packages
• Front-load user limits and scale over time

Instead of panicking or going quiet, you say, “No problem, let’s look at a ramped rollout with a success clause.”

Don’t guess, plan.

5. Create Executive Simplicity

Say, you’ve got a 50 page proposal with four pricing tiers, integration notes, and rollout timelines.

Tell AI, “Summarise this into a one page decision brief for a time poor CFO. Use plain English.”

Make sure you give it a good edit afterwards, as the model’s job isn’t on the line but yours might be.

It gives you a readable version of:

• Problem
• Proposed outcome
• Commercial terms
• Risk mitigations
• Timeline

You send it to the CFO with the subject line, “1-page summary: Faster fulfilment, reduced stockouts, contract flexibility built-in.”

They will read it and reply asking for detail, instead of letting git sit in their inbox for a fortnight.

Final Word: AI Isn’t Magic, Always Check

You still get to handle the human chaos: politics, trust, fear. But AI can handle the objections, trades, and editing for length (you must edit for clarity yourself).

This will save you time to focus on better relationship building and deeper customer research. Make those extra calls to get context and background.

While the competition are chasing people for feedback, you will be four moves ahead with an answer for every scenario.

Don’t just use AI like a writer. Use it like a negotiator, strategist, and analyst rolled into one.

Steal these prompts to develop your own and win more deals.

House of Sales

I help people use what they’ve got and develop what they need to sell the way big customers buy.

If you liked this then you'll love the LinkedIn post linked above, see you next week.

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