Sales managers chase training like it is a traveling circus. A new seminar. A four-hour webinar. A three-month program with worksheets nobody fills out. Someone always promises a breakthrough. Someone always has a new acronym. Then Monday morning hits, and everybody goes right back to pounding out emails, dodging gatekeepers, guessing their way through objections, and retaining 3% of that expensive “How to…” content.
Meanwhile, that twenty-dollar AI sits on your desk the whole time, waiting patiently. Not as a guru. Not as a trainer who shows up with a clicker and a 350-card deck full of clip art. As something simpler. A system you can teach to teach you.
Continuously.
Without the theatrics. Without the bagels. And without the consultant who disappears as soon as the invoice clears.
I’m a fan of technology and the art of selling. If you read my earlier Imaging Channel pieces, you already know how reps use AI to clean up emails, build side-by-sides, or fix proposals. That was the warm-up act. Today, we get into the part nobody talks about because it ruins the training business. This is not about using your LLM. This is about shaping it. Training it. Building a digital version of the sales coach everyone claims they want but never actually follows.
Here is the uncomfortable truth. Most reps do not need more training. They need someone to tell them the truth about their own work. Training is what a dealer buys when they want to look proactive. Feedback is what a salesperson needs when they want to get better. Feedback is rare. Managers are buried. Colleagues are distracted. Nobody is reviewing your voicemail and telling you why it sounds like you’re apologizing for calling. Nobody is reading your email and pointing out the part where you drift into brochure-speak. You get nods. Not guidance.
That is where the LLM earns its keep.
When you open a chat window, stop treating it like a vending machine that spits out mediocre drafts. Treat it like a rookie riding shotgun. A junior teammate. Someone who shadows you. Someone who learns your telltale phrasing. Someone who watches how you handle pushback. You teach it like you would teach any new rep. You correct it. You give it examples. You show it how to talk like you instead of like the company’s marketing department.
Start with your own voice. Pull a few real emails you are proud of and drop them in. Then say: “This is how I write. Match this.” You are not showing off. You are giving the machine the baseline it needs. It will adjust.
Next, hand it your objections. All ten of them. Price. Lease terms. Loyalty. “We don’t print much.” The standard stuff. Give the model the exact exchange you had last week. Your words. Their words. The ending. Then ask: “What did I miss? Rewrite my response so it sounds like me and makes more sense.”
You’re giving it the same details you’d hand a sales coach, but the feedback comes without the pitch for their new workbook, keynote series, or “elite program.”
Now things are getting useful. Use your LLM as a clarity mirror. Before a call, paste your planned questions and ask: “Which of these wastes time?” It will show you where you wandered into filler. It has seen thousands of sales scripts. It knows the bloat and when you are trying too hard. It will strip out the weak spots without sugarcoating.
Then train it with real field information like your territory, vertical industries, past installs, even reference accounts and statements. If the office has a toner graveyard in the break room, feed that into the model too. It’ll start recognizing dysfunction faster than your service desk. If you sell to clinics, feed it scheduling pain. If you sell to insurance, feed it compliance headaches. The model will start building associations. This is how a real one-on-one trainer learns about their students, but you’re compressing years of knowledge into minutes.
Once you have that foundation, let the machine grade your work. Take an email you already sent and ask: “If you were the buyer, what would make you ignore this?” Then tell it to fix the problem it just identified. Critique first. Rewrite second. That is how you learn and how you develop instincts.
And when you want to test your talk track, put the LLM on offense. Paste your cold call script and say: “Act like a skeptical office manager.” The machine will stonewall and dodge. It will challenge your assumptions. It will behave like the people who tell you to call back next quarter. Keep running it until your responses stop sounding like a sales book and you start sounding like you know what you are doing.
One thing worth mentioning. The LLM adapts to your habits. When you get sloppy, it gets sloppy. When you tighten up, it tightens up. It mirrors your discipline with brutal accuracy. Some reps think the machine gets dull over time. It doesn’t. It gets honest.
Here is the real secret. You are not training the LLM to sound like you. You are training it to reflect the version of you that shows up on your best days. The version of you who writes cleanly, asks sharp questions and cuts the nonsense. The version that listens.
This is not a replacement for selling. You still walk into the office where the manager has been burned by three leases and keeps the old service invoices in a filing cabinet labeled “Never Again.” Ai will not handle that conversation for you or hand out candy bars. But it will make you sharper when you walk in.
Our industry has never been flush with training excellence. Dealers love old playbooks. OEM rollouts. Breakfast meetings. Four-hour seminars with recycled content. The world changes weekly. Some of our manuals were written during the Bush administration. Meanwhile, Ai sits there, waiting to become the coach you never had.
Look, you don’t need to be a prompt engineer, whatever that means. Just talk to the thing.
You do not need a certificate; you need to sell five “widgets” this month. You just need a sounding board available on a Sunday afternoon, or three minutes before the big meeting, in the front seat of your car. Feed the LLM your world, your mistakes, your wins, your patterns. Let it push back and argue. Let it show you where you slip.
I have said before that AI is the most significant tool a salesperson can use today. This is the next step. AI as YOUR trainer. Not a guru. Not a coach. A mirror.
When you help the LLM learn you, it will show where your message drifts, where your confidence dips, where you talk too much, and where you get it right. Every single day.
If you want a training program that learns you back, Ai is the only option.
Sell on. –
Bonus Pro Tip
There are plenty of LLMs out there today – and they are not created equal. You’re in sales and selling, we use words. We do not design the next rocket to Mars – so we rarely, if ever, need help with trig or geometry. So why would you want a nuclear physicist as a personal sales trainer? You don’t.
In the world of LLMs, choose one that is geared toward using words over creating images or making orbital dynamic calculations. I like ChatGPT.
My overarching recommendations:
- Pick one LLM and stick with it.
- Pay for it yourself.
- Avoid corporate LLMs if you want a system that learns you, not your employer.
Buy it, it’s yours. Most of the ‘corporate’ LLMs are just that – corporate. Top down, central command and control oriented. Designed for your employer, not you.
The more it is used, the better it gets for you, individually. LLMs learn your patterns and match feedback to those patterns.
Your LLM will remember from Day One; if you can help it, don’t switch LLMs and start over.
Greg Walters
is an entrepreneur and founder of the notorious destination site TheDeathOfTheCopier, where he comments on all things imaging, the rise of managed services and the advance of business technology. A prolific writer and frequent speaker, Greg shares his passionate, unique – and often provocative – view of technology and people, addressing the impact of digital on 21st century business. His 2014 book, Death Of The Copier, offers a controversial summary of the early days of Managed Print Services and the not-so-distant future of the hard copy industry. Reach out to Greg at greg@grwalters.com.