Day 9 of 20 · AI for Sales
Objection Handling — AI Role Play
⏱ 7 min
📊 Beginner
Today is different from every other lesson in this course. Instead of learning a technique and watching a demo, you're going to practice. You're going to use AI as a sparring partner — a tough, skeptical buyer who pushes back on price, timing, competitors, and every other objection you'll face in real deals.
Here's why this matters: the average sales rep hears 5-8 objections per deal. Most reps have practiced handling exactly zero of them before they hear them live. They fumble, they get defensive, they offer discounts they didn't need to give. And the deal slips away.
Athletes practice before the game. Musicians rehearse before the concert. But salespeople? They practice on live prospects. That's insane. Today, AI becomes your practice partner — available 24/7, endlessly patient, and brutally honest with feedback.
Why role-play changes everything
There's a massive gap between knowing how to handle an objection and doing it in the moment. You can read every sales book ever written about handling the "your price is too high" objection. But when a VP of Finance looks you in the eye and says "We can get the same thing from your competitor for half the price," your brain freezes.
The fix is repetition. Research from the Sales Executive Council shows that reps who role-play objection handling at least once per week close at 23% higher rates than those who don't. The problem was always finding someone to practice with — your manager is busy, your peers feel awkward, and your friends don't know enough to push back realistically.
AI solves this perfectly. It can play any buyer persona, push back with realistic objections, adjust difficulty, and give you immediate feedback on your responses. Let's set it up.
Knowledge Check
Why is practicing objection handling more effective than just studying techniques?
A
Because role-play is faster than studying
B
Because AI generates better objections than real buyers
C
Because reading sales books is a waste of time
D
Because there's a gap between knowing a technique and executing it under pressure — practice builds the muscle memory to respond confidently in real conversations
Knowing the "feel, felt, found" technique is useless if you can't deploy it when a CFO is grilling you about ROI. Practice builds neural pathways — the more you rehearse a response, the more naturally it comes when you need it. Athletes don't study playbooks during the game. They drill until execution is automatic.
Setting up your AI sparring partner
The magic is in the prompt. Here's the template that turns AI into a realistic, tough buyer:
"You are a skeptical [Title] at a [industry] company with [size] employees. I'm selling [product/service] at [price point]. Your job is to push back hard on price, timing, and competitor alternatives. Be realistic and tough — don't let me off easy. After each of my responses, rate me 1-10 on confidence, specificity, and persuasiveness, then give me one thing I did well and one thing to improve. Stay in character between ratings."
This prompt does three things right: it gives the AI a specific persona, it sets the difficulty level, and it builds in a coaching feedback loop. Let's see it in action.
You are a skeptical VP of Finance at a 2,000-person manufacturing company. I'm selling a $180K/year cloud ERP platform. Your job is to push back hard on price, timing, and competitor alternatives. Be realistic and tough — don't let me off easy. After each of my responses, rate me 1-10 on confidence, specificity, and persuasiveness. Give one thing I did well and one thing to improve. Stay in character between ratings.
Let's start. I just finished my demo and asked what you think.
*Leans back in chair*
Look, the demo was fine. The product does what you say it does. But I've got some real concerns before we go any further.
First — $180K a year. That's significant. We looked at NetSuite last quarter and their quote came in at $120K for similar functionality. So right off the bat, I need to understand why I'm paying a 50% premium.
Second — timing. We're mid-fiscal year. Our IT team is already stretched thin on two other migrations. Adding an ERP switch right now feels like asking for trouble.
Convince me this is worth the money and the disruption. Because right now, I'm leaning toward waiting until next fiscal year and going with the cheaper option.
Great questions. On price — you're right that $120K sounds appealing, but I'd ask what's included in that quote. NetSuite typically doesn't include implementation, training, or the manufacturing-specific modules in their base price. When our customers have compared apples to apples, the total cost of ownership is actually within 5-10% of each other. But here's the real difference: our platform was built for manufacturing from day one. NetSuite is a general ERP that bolts on manufacturing. That means longer implementation, more customization costs, and workarounds your team will be dealing with for years.
On timing — I actually agree that mid-year is tough. But here's what I've seen: the companies that wait until 'the right time' are still running their legacy system two years later. What if we started with a scoped pilot in one department this quarter, prove the ROI, and then roll out company-wide at the start of next fiscal year? That way your IT team isn't overwhelmed, and you walk into budget season with hard data instead of a vendor's promises.
*Pauses, tapping pen on desk*
Hmm. The total-cost-of-ownership argument is interesting — I'd want to see those numbers side by side, not just take your word for it. Can you put together an actual TCO comparison?
And the pilot idea... I don't hate it. But I need to know: what department would you recommend we start with, and what does "proving ROI" actually look like? Because if we do a pilot and the results are vague, I've just wasted a quarter.
---
**Ratings:**
- Confidence: 8/10 — You didn't get defensive on price, which is strong
- Specificity: 7/10 — The "5-10% TCO difference" is good but could be sharper with an actual dollar figure
- Persuasiveness: 8/10 — The pilot idea was smart reframing
**What you did well:** You reframed both objections instead of just answering them. The "built for manufacturing from day one" line is a strong differentiator.
**What to improve:** When I mentioned NetSuite by name, you could have asked ME a question back: "What specifically about their proposal appealed to you?" That would give you intel to sharpen your pitch and shows you're not afraid of the comparison.
Want to keep going? I have more pushback.
↻ Replay conversation
The four objections you must master
Every sales rep faces the same core objections in different packaging. Master these four and you can handle almost anything a prospect throws at you:
"Your price is too high." The most common objection — and the most mishandled. Most reps immediately offer a discount, which trains buyers to always push on price. The right move: reframe to value, compare total cost of ownership, or ask what they're comparing against.
"We're happy with our current vendor." This isn't really an objection — it's a shield. Nobody is perfectly happy with their current vendor. The right move: ask what they would change if they could, or share a story about a customer who said the same thing before switching.
"It's not the right time." Translation: "I don't see enough urgency to act now." The right move: quantify the cost of inaction. What are they losing every month they wait?
"I need to think about it." Translation: "I have an objection I haven't told you about." The right move: surface the real concern. "Absolutely — what specifically would you want to think through? I might be able to help with some of those questions right now."
Knowledge Check
When a prospect says "I need to think about it," what's the best response?
A
Say "No problem, take your time" and schedule a follow-up next month
B
Ask what specifically they want to think through — this surfaces the real, hidden objection so you can address it directly
C
Offer a discount to create urgency
D
Send them more case studies and product documentation
"I need to think about it" almost never means they need time to think. It means they have a concern they haven't voiced — maybe budget, maybe a competing priority, maybe they're not the real decision-maker. If you let them walk away without surfacing it, you'll never hear from them again. A gentle "What specifically would you want to think through?" opens the door.
Role-play scenarios to practice
Here are five role-play scenarios you should run through this week. Each one targets a different common sales situation. Copy any of these into ChatGPT and start practicing:
Scenario 1 — The Price Hawk: "You're a CFO who believes all software is overpriced. Push back aggressively on every dollar. Demand a 40% discount or you walk."
Scenario 2 — The Status Quo Defender: "You've used the same vendor for 8 years. You don't love them, but switching feels risky. Make the rep prove that switching is worth the pain."
Scenario 3 — The Tire Kicker: "You're evaluating 5 vendors and have no urgency. You're happy to take calls but never commit to next steps. Be polite but evasive about timeline and decision process."
Scenario 4 — The Technical Blocker: "You're a CTO who cares only about security, integrations, and scalability. You don't care about the business case — you want technical depth."
Scenario 5 — The Ghost Resurrected: "You went dark for 3 months after a great demo. The rep just got you back on a call. You have a new objection you never mentioned before."
Run each scenario 2-3 times. Watch how your responses improve with repetition.
Advanced role-play techniques
Once you're comfortable with basic objection handling, level up with these techniques:
Stack objections: Tell AI to throw 2-3 objections at once. In real life, buyers don't politely wait for you to handle one objection before raising the next. Practice managing multiple pushbacks in a single response.
Increase difficulty gradually: Start with "be moderately skeptical" and work up to "be the toughest buyer I've ever faced." Building difficulty over time is how athletes train — you don't start with the heaviest weights.
Practice different frameworks: Ask AI to evaluate your responses against specific techniques — the "feel, felt, found" method, the "isolate and address" technique, or the "acknowledge, bridge, close" approach. Get feedback on which frameworks suit your natural style.
Record your patterns: After 5-10 role-play sessions, ask AI: "Based on our practice sessions, what are my biggest strengths and recurring weaknesses in objection handling?" The patterns it identifies will surprise you.
The role-play practice loop — set up the persona, handle the objection, get feedback, iterate. Repeat until your responses are automatic.
Knowledge Check
What's the benefit of stacking multiple objections in a single role-play exchange?
A
Multiple objections are easier to handle than single ones
B
AI performs better when given multiple objections
C
Real buyers often raise multiple concerns at once — practicing this builds your ability to manage complex pushback without getting flustered
D
It makes the practice session shorter
In a real sales call, a VP might say "It's too expensive, we're locked into a contract with your competitor, and honestly I'm not sure we even need this right now" — all in one breath. If you've only practiced handling one objection at a time, this moment will overwhelm you. Stack practice builds the composure you need.
Making it a weekly habit
The reps who get the most from AI role-play treat it like gym time — a scheduled, recurring practice. Here's a simple weekly routine:
Monday: Role-play the objections you expect to hear in this week's calls. If you have a meeting with a CFO on Wednesday, practice price objections on Monday.
Wednesday: Mid-week check-in. Replay any real objections you heard this week that you handled poorly. Ask AI to show you a better response.
Friday: Practice one "nightmare scenario" — the toughest buyer persona you can imagine. If you can handle that, real calls feel easy.
Total weekly investment: 30 minutes. That's less than the time you waste on one deal that slips because you fumbled an objection. The ROI on practice is infinite.
Knowledge Check
How should you decide which objection scenarios to practice each week?
A
Always practice the same five scenarios for consistency
B
Practice the specific objections you expect to face in upcoming calls — tailor your preparation to your real pipeline
C
Only practice objections you've never heard before
D
Randomly select scenarios to keep things interesting
The most effective practice mirrors real life. If you have a call with a price-sensitive CFO on Thursday, practice price objections on Tuesday. If you lost a deal last week because a prospect chose a competitor, role-play the "we're going with someone else" conversation. Targeted practice produces targeted results.
💰
Day 9 Complete
"The best salespeople don't have better answers — they've practiced more. AI gives you a sparring partner who's always available and never holds back."
Tomorrow — Day 10
Proposals That Close Deals
Tomorrow you'll turn discovery notes into polished, personalised proposals that win deals — in 15 minutes instead of 3 hours.