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Putting AI to Work

Rehearse your hardest conversation with an AI before you have it

By Dan Belhassen

Most salespeople first practice handling a pricing objection on a real prospect, often one they've never spoken to before, and that deal bears the cost of whatever they get wrong.

Role-play is a standard part of most sales training. People dread it, and it's hard to arrange: you need a colleague willing to play the buyer, and enough trust that nobody feels foolish. So it gets skipped, or it happens once at the sales kickoff.

An AI assistant can play the buyer instead. Give it a few lines about the deal and the person you're about to face, and it will push back or go quiet the way they might.

Nobody is watching, so you can start over as often as you like. Before the real call, try your answer to "you're too expensive" a few times and compare how each one lands.

Describe someone specific: Dana, an operations director who likes your product but has a competitor's quote at two-thirds of your price, and has to explain the difference to a CFO who wasn't in any of the meetings.

When you've tried it, type "pause" and ask for feedback. An AI playing a role can step out of it and tell you how your answer came across.

Rehearsing a hard conversation with an AI. A salesperson practices answering a pricing objection. The salesperson says "Honestly, ours is the best product on the market, and you get what you pay for." Dana, played by the AI: "'Best on the market' isn't something I can take to our CFO. What does the extra money actually buy us?" The salesperson: "If you can sign this quarter, I can probably get you ten percent off." Dana: "I don't need a deadline. I need a reason." Then pause. The feedback: what worked, acknowledging the pressure before moving on; where you lost me, a claim with nothing behind it and a discount with no reason; what I needed to hear, a question first, then what the extra cost covers.

Almost anyone with a conversation they'd rather rehearse first can do the same:

  • A manager turning down a raise
  • A customer service rep explaining why a refund isn't possible
  • An HR lead walking someone through a layoff
  • Someone in finance chasing an overdue invoice from a good client
  • A project manager telling a client the date is going to slip
  • An executive getting ready for the board question they can't answer yet
  • A new hire asking a senior colleague for help without looking lost

If you build training for people in any of these roles, your learners can practice them on their own between sessions.

Dan Belhassen
Founder & CEO, Neovation

Try this

Think of a conversation you've been putting off. Paste this into any AI assistant with the blanks filled in.

Go through it twice, with a different opening the second time. If your assistant has a voice mode, use it, so you hear yourself say the words.

If you sell, start with the last objection that cost you a deal.

From Neovation

Role-play with your own material. JoySuite's /roleplay command plays the other side of the conversation, such as a buyer who says you're too expensive, and stays in character.

It draws on your organization's documents, like a pricing sheet or a call transcript, and coaches the learner on that material. You can also set it to answer only from approved sources.

JoySuite works alongside the LMS you already use. It's launching winter 2026, and the waitlist is open. Join the JoySuite waitlist

One question. What's the conversation you'd most like to rehearse? Hit reply and tell me.