Dearest Reader,

Most people use AI to save time. I use it to save myself from walking into sales calls sounding unprepared and under-caffeinated.​
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The smartest sellers don’t outsource their thinking to AI. They sharpen it with AI. When I prep for an exploratory call, I don’t want to wing it and hope my charm carries me.
I want to walk in with hypotheses, sharp questions, and a sense of where my buyer might be in their journey.

Here’s my actual workflow:

1. Profile first.
   ​ AI is only as smart as what you feed it. If you give it vague nonsense (“My client is a small business owner”), you’ll get vague nonsense back. I go deep: industry, revenue range, team size, current offers, even how they describe themselves online. The more specific you are, the sharper the insights you’ll get. Think of it as briefing your top analyst before they do the work. Garbage in = garbage out.
2. Ask the obvious.
   ​ Once I have the profile, I’ll literally ask: “What problems might they be dealing with?” This is where AI earns its keep as a pattern recognizer. It will surface pain points, industry challenges, and market shifts that I might overlook because I’m too close to the work. I don’t take these as gospel — they’re prompts to jog my thinking, not a script to read off.
3. Hypothesize.
   ​ From that list of problems, I pick the ones that feel most relevant and turn them into hypotheses I can test in conversation. For example: “I suspect they’re struggling with inconsistent lead flow” or “They might be losing deals because their buyers don’t understand the ROI.” Now instead of peppering a prospect with 20 random questions, I walk in with three sharp ones that test my hunches. This makes the conversation feel intelligent and focused — not like an interrogation.
4. Check the buyer’s journey.
   ​ Context matters. Dropping a past email thread or LinkedIn exchange into AI and asking, “Where is this buyer in their journey: awareness, consideration, or decision?” is a game changer. It helps me see whether I need to educate, validate, or invite. Most sellers skip this step and end up either over-explaining or pitching too soon. This one move alone cuts down on awkward misfires in conversation.
5. Gauge urgency.
   ​ Finally, I want to know how close they are to acting. I’ll ask AI for three questions that surface urgency and the cost of inaction. Example: “What happens if you don’t fix this in the next quarter?” or “How is this problem showing up in lost revenue or wasted time?” These aren’t just throwaway questions. They frame the stakes for the buyer and give me a clearer read on whether I’m talking to a curious tire-kicker or someone ready to invest.

By the time I get on the call, I’ve already cut through hours of “should I ask this?” mental gymnastics. I know exactly how to test, listen, and respond in real time.

And this is where the brilliance of Cari Kauffman comes in:
She uses AI like a sparring partner. She’ll feed it transcripts from discovery calls and ask it to analyze tone, voice, and patterns she might have missed while in the thick of it. She’ll ask it these two prompts which I love

“Which parts of this are too vague to convert?” or “What’s missing emotionally here?”

That’s the power play — staying present with the client while letting AI be the fly on the wall catching nuance you didn’t have the bandwidth to track. I would even recommend taking it one step further -- and uploading the transcripts from your sales calls and asking how you could better sell to the gap, or what you consistently do well vs what you consistently overlook. It'll blow your mind!

For me, AI is less “magic eight ball” and more “extra brain in the room.” It’s like having the colleague who always asks, “But what about this angle?” — the one who sees blind spots you missed because you were too busy running the conversation. Not the star of the show, not the decision-maker — just the extra brain you wish you had on speed dial.​
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​AI isn’t here to replace sales prep. It’s here to make your prep smarter, faster, and more thorough — so you can actually show up to the call present, not scrambling.

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​ In every edition of this newsletter, I’ll keep pulling apart how to use tools (AI or otherwise) to reduce prep overwhelm, sharpen your thinking, and walk into calls with the confidence of someone who already knows the ending to the movie

Now I want to know: How are you using AI in your sales prep (or avoiding it altogether)?

Until next time, Happy Selling!

Talica

PS I wrote a whitepaper about AI in sales which you can check out here if you are so inclined.