Like most skills, your ability to negotiate improves with practice. However, getting opportunities to practice isn’t easy.

There’s a lot on the line during a negotiation with the buyer. You need to focus on your objectives, your prospect’s goals, potential landmines, and more.

In addition, this isn’t an optimal time to try a new technique -- if it doesn’t work and things go south, you could lose the deal.

Enter negotiation role play exercises. Working through a hypothetical scenario with a team member or coach gives you a low-stakes opportunity to identify your strengths, weaknesses, and stumbling blocks.

These activities are also a fantastic way to practice responding to difficult events, such as unreasonable discount requests or unexpected demands.

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1. Practice dealing with extreme situations

Many sports coaches “overtrain” their athletes. "If you can run six miles in high altitudes," they reason, "you’ll be in great shape to run a race that’s three miles at sea level."

The same concept can apply in sales. Once you’ve successfully negotiated in an extreme situation, you’ll be mentally and emotionally prepared for a straightforward one.


  • The salesperson
  • The prospect

(This role play is designed for two participants -- one salesperson and one prospect. If you want a challenge, have the salesperson negotiate with two-plus prospects.)


  1. Write down the most extreme negotiating situations you’ve ever experienced (tight deadline, massive deal, legal complications, and so forth) on pieces of paper. Shuffle the papers and randomly pick one.
  2. Choose who will play the salesperson and who will play the prospect(s).
  3. Run through the scenario. After an agreement is reached -- or you reach a standstill -- debrief. Which responses worked well? Which were unsuccessful? How will you apply these takeaways to future negotiations?
  4. You may choose to redo the negotiation with the same circumstances or pick another scenario from the options. Complete the entire exercise as many times as you’d like.

2. Get comfortable breaking up with a prospect

Breaking up is hard to do -- and even harder when you must tell a customer (and their commission) goodbye.

It’s important to practice these scenarios because they can be nerve-wracking for new reps, and they can get tense. Role playing prospect breakups is a crucial part of sales training -- and one that, if handled correctly, can win you more business in the future.


  • The salesperson
  • The prospect


  1. Write down a variety of situations in which you would need to break up with a prospect. Perhaps your product/service isn’t the right fit for their business, they don’t have the budget, or they’re just not ready for your offering (but might be in a year or two).
  2. On separate slips of paper, write down possible prospect responses, including anger, dismay, and thankfulness.
  3. Choose who will play the salesperson and who will play the prospect(s), and cycle through these slips of paper, so your reps can get used to a variety of breakup scenarios and prospect responses.
  4. At the end of each exercise (when a resolution has been reached), write down what worked and what didn’t. Then, have the reps discuss what they would do differently next time.

3. Challenge prospects on why they’re stuck

Every salesperson will experience stalled deals. The prospect might repeatedly reschedule the demo, ghost for weeks at a time, or drag their feet in returning a signed contract.

Whatever the situation, it costs reps time and money. It’s important they be able to identify these situations and discover the root cause to successfully discern whether to cut ties or move the deal forward.


  • The salesperson
  • The stalled prospect


  1. The person playing the prospect should choose which stalled behavior they’ve been exhibiting. Are they calling to push back the demo again? Are they resurfacing after six weeks of unresponsiveness? Are they asking for more minor tweaks to the contract in the eleventh hour?
  2. On several pieces of paper, write down and distribute the real reason a prospect is stalling (i.e., their budget was slashed, their boss wants a different vendor, or they just don’t know how to say “no”). Stalled prospects have many different emotions when a salesperson pushes them to be honest. Anger, frustration, and relief should all be emotional responses each prospect is encouraged to exhibit.
  3. Have each salesperson ask their prospect questions to understand why they’re being evasive. Questions like, “Usually, when someone pushes back the demo several times, it’s just not a business priority for them at the moment. Is that the case here?” can help your prospects confront whether they do or do not want to move forward.
  4. Once the salesperson understands why the prospect is stalling, and have successfully either moved the deal forward or cut ties with the prospect, have reps discuss what went well, what made the prospects feel uncomfortable, and what they could do better next time.

4. Overcome common objections

Every sales team encounters a few of the same objections regularly. It's important to easily overcome those objections to move deals along. This exercise is great for new hires unfamiliar with these objections, and it's helpful for veteran salespeople to keep their responses sharp.


  • The Salesperson
  • The prospect


  1. One person is "it" as the rep.
  2. The rest of the group acts as the prospects and takes turn hurling common objections at the rep. The rep has a set amount of time -- it could be 30 seconds or it could be two minutes -- to respond to that common objection in a way that satisfies the group and moves the deal forward.
  3. Once one objection has been overcome, immediately throw out another until the rep's five- or 10-minute time in the hot seat is complete.

5. Identify and overcome personal negotiation weaknesses

It’s crucial to be aware of and prepared for your personal negotiation shortcomings. For example, maybe you tend to get nervous and offer discounts prematurely -- or conversely, your unwillingness to compromise leads many potential buyers to walk away.


  • The salesperson
  • The prospect


  1. Write down one personal area for improvement related to negotiating.
  2. Choose who will play the salesperson and who will play the prospect. (You can play multiple times so each team member has a turn as the salesperson.)
  3. Go through a standard negotiation. The person playing the salesperson focuses on overcoming, avoiding, or dealing with their specific weakness.
  4. After you come to an agreement or decide your needs are incompatible, debrief. The person playing the salesperson reviews their performance for their specific area of improvement. The person playing the prospect then gives their feedback.
  5. Switch roles. The salesperson becomes the prospect, and the prospect becomes the salesperson. Complete the exercise again with the new salesperson focusing on their personal weakness.

6. Practice negotiating with difficult prospects

Normal negotiations are challenging enough. Negotiations with irrational or demanding buyers may be one of the most challenging situations you’ll face as a salesperson. The more practice you have, the better your chances of crafting a mutually beneficial deal.

This exercise will give you experience staying calm and dealing with difficult personalities.


  • The salesperson
  • The “difficult” prospect


  1. The person playing the difficult customer chooses two to four behaviors to use during the role play. Ideas include frequently interrupting, making threats, delivering “all or nothing” ultimatums, abruptly changing your mind, bringing up irrelevant details, using critical language, becoming excessively loud, shutting down topics you don’t like, refusing to commit, and/or letting your attention wander.
  2. Run a standard negotiation for 10 minutes.
  3. Spend five minutes writing down which responses and techniques worked and which did not.
  4. Switch roles and go through the exercise again.
  5. Compare your notes. What worked? What didn't? Identify the most productive ways to respond to a hostile prospect.

7. Learn the value of mutually beneficial negotiations

The three basic negotiation practices are win-lose bargaining (one person gains at the cost of the other), win-win bargaining (both people benefit), and mixed-motive bargaining (both people benefit by “expanding the pie.”) This exercise from MIT, known as the Two Dollar Game, illustrates all three -- and shows mixed-motive bargaining usually leads to the most desirable outcomes.

The Two Dollar Game requires a moderator and at least six players, so ask your sales manager or another member of your team to lead it. (And don’t read the guidelines below, or you won’t be able to play.)


  • Three (or more) groups of two


  1. Tell everyone they’ll be negotiating three times with three different partners.
  2. Put everyone in random pairs. Each pair is told they have $2. They must divide the $2 between themselves.
  3. Players typically first think, "This is easy -- we can each have a dollar." However, every person receives a piece of paper with secret instructions. These instructions discourage a simple 50-50 compromise. (You can find a printable version of each participant's instructions on this page.)secret_instructions_1.png
  4. Give the pairs 10 minutes to negotiate.
  5. Organize them into new pairs and have them run through the exercise again. Give each partner a piece of paper with new secret instructions. (You can find a printable version of each participant's instructions on this page.)secret_instructions_2.png
  6. The participants will be expecting to switch partners again. To demonstrate the importance of mutually beneficial agreements and preserving healthy business relationships, ask them to run through the exercise for the third time with their current partner.
  7. There are no secret instructions for this round: Participants can use any strategies and styles they’d like. Some negotiators will reward their partner’s kindness in the last round with kindness in this round, while others will use this round to take revenge on a hostile or difficult partner.
  8. Ask each person to share their secret instructions with the partner they had in the second and third rounds. Ask them to review their individual performance (either in a group or on paper), along with the approaches they found effective versus ineffective.

8. Practice using different negotiation tactics

From the considered response to always making the first offer, there are hundreds of negotiation strategies out there. Identify the top negotiation tactics your company uses, and run through each until reps are comfortable.


  • The salesperson
  • The prospect(s)


  1. Write the negotiation tactics your company uses on several slips of paper, and hand them to reps playing “salesperson.”
  2. Pair each salesperson with a “prospect.” Write your company’s price on one slip of paper and the prospect’s corresponding budget on another. Try to use real numbers your reps have encountered, to give this exercise a realistic feel. Then, give the salesperson and prospect their price/budget.
  3. Have each salesperson use their designated tactic to negotiate the price. Encourage some prospects to ask for discounts, and have your reps role play how they would respond in real time.
  4. Once negotiations are complete, review what worked and what didn’t. Did the salesperson cave to the prospect’s request for a discount too quickly? Did the prospect feel the salesperson was too pushy? Discuss concrete improvements each rep can make next time, and run through these exercises as many times as you wish.

Practice makes perfect -- or at the least, makes you a stronger negotiator. Use these exercises to prepare yourself for every technique and scenario imaginable.

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Originally published Aug 2, 2019 5:33:00 PM, updated October 29 2019


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