How Should My AEs Be Using AI in Live Deals?
Practical ways to use AI in live deals without sacrificing judgment or deal quality
DEAR STAGE 2: We’re encouraging our team to use AI tools (duh), but I’m getting hung up on implementation. I want them to move faster and be more prepared, but don’t want generic emails, sloppy thinking, or automation that kills common sense. How and when should AEs be leveraging AI in active opportunities? ~CAUTIOUS CRO
DEAR CAUTIOUS CRO: AI doesn’t change the quality of your sales team. It amplifies it. Thoughtful reps get sharper. Average reps get faster at producing average work.
So the question isn’t “Should they use it?” It’s really “Where does it improve thinking inside a live deal?”
In working with our portfolio, the trend I notice: AI is most powerful when it strengthens preparation and inspection, not when it replaces judgment.
NOTE: I’m not going to comment on specific LLMs or products for the purposes of this article. This advice can just as easily be applied to Gemini, Claude, OpenAI, etc…
Let’s dig in…
Before Discovery: Raise the Quality of Preparation
Strong reps don’t walk into discovery hoping the buyer tells them what’s wrong. They walk in with a strong hypothesis based on research.
AI can accelerate the formation of that hypothesis. It can help synthesize likely business priorities, surface industry pressures, and suggest angles the rep may not have considered. That’s useful, especially for newer AEs or when the team is feeling time-constrained.
But you have to set the standard that the rep refines the thinking before it ever reaches the buyer.
If they can’t articulate why they’re asking a question, it shouldn’t be asked. AI-generated discovery questions are raw material and the rep’s job is still to connect the dots.
The real win here isn’t speed. It’s depth of preparation in less time.
Between Stages: Improve Deal Inspection
This is where AI can create real leverage.
You’ve seen deals stall in the pipeline or surprisingly go silent after weeks of engagement. Deals collapse when risk goes unnoticed. Risk comes in many forms - weak access to power, unclear decision process, lack of urgency, etc...
After a call, a rep can input their notes and ask for a structured critique. What buying gaps exist? Where is the economic buyer missing? What objections are likely to appear late? Here’s a sample prompt to get you started:
System Role: You are a senior B2B sales manager with deep expertise in enterprise deal qualification and pipeline risk assessment. You think like a skeptical sales leader preparing for a forecast call. [Add any industry or company specific insight]
Instructions: Review the call notes or transcript below and provide a structured deal inspection critique. Be direct and do not soften findings. Your job is to identify risk, not validate optimism.
Evaluate the following:
Access to Power - Is the economic buyer identified, engaged, and on record supporting this deal? If not, what is the path and timeline to get there?
Decision Process - Does the rep have a clear, confirmed understanding of how this company buys? Who is involved, what are the steps, and what could derail it?
Compelling Event / Urgency - Is there a real, documented reason this deal closes in the stated timeframe? Would this deal slip if the rep stopped pushing?
Competition and Risk - What competitive threats or internal alternatives exist? What has not been asked or answered that a competitor could exploit?
Buying Gaps - What objections have not surfaced yet but are likely to appear late? What does the rep not know that they should know by now?
Recommended Actions - List 3 to 5 specific next steps the rep should take before the next pipeline review to reduce deal risk.
End with a one-line overall risk rating: Low / Medium / High and a single sentence explaining why.
Call Notes / Transcript: [INSERT HERE]
That exercise forces clarity and introspection, and the more data you provide the better the output will be.
To be clear, this doesn’t replace your pipeline review, but can make your pipeline review sharper. Reps who consistently pressure-test their own deals show up differently in forecast conversations because they are actively thinking about risk mitigation.
Late Stage: Elevate the Champion
In enterprise sales, your champion is selling internally when you’re not in the room. We’ve been arming them with material for years and AI can help here too.
AI can absolutely help draft an executive summary, outline a business case, or structure a mutual action plan –as long as you read it, edit it and treat it this as a draft. That’s an appropriate use. It saves time on format so the rep can focus on substance.
Bonus points if you roll this out at a team or org-wide level. You can build a skill or agent trained on the best business cases (or exec summaries, or action plans, etc…) that your org has used over the years. This creates consistency for the team and removes duplicate work.
I’ll say it again…no late-stage communication should be sent without thoughtful editing. Tone, sequencing, and nuance matter more at the executive level. The rep always owns the final message.
Set the Standard Before the Tool Sets It
If you simply tell your team to “use AI,” quality will vary wildly. Instead, define what good usage looks like. For the examples shared today, you can boil it down to:
AI drafts. The rep rewrites.
AI surfaces risk. The rep decides action.
AI suggests ideas. The rep owns judgment.
AI will widen the gap between thoughtful sellers and transactional ones. The reps who win will use it to prepare sharper hypotheses, identify risk earlier, and strengthen their champions, not to send faster templated emails.
As a leader, it’s on you to define what “great” looks like when your team uses AI.
Until next week!