Why Live Roleplays Suck: Vivid Memories of a Sales Roleplay Judge

I was a roleplay judge – and I can assure you I learned more than the seller did that day. I, along with 19 others, judged a roleplay competition at a major university. It was my first time judging. Eighty students were competing for a prize and bragging rights – and maybe a job. But only one would win. The competition was combined with a recruiting event and prospective employers were watching closely.

It was very well organized and buttoned down.

  • The sellers were given a setup sheet on their company, their product, the prospect, the prospect’s problem, and the objectives for the sales meeting they were about to hold.
  • The buyers were given detailed instructions and a setup sheet detailing their company and situation.
  • The judges were given an instruction sheet, scorecards, and specific guidance on our role. We all knew exactly what we were supposed to do.

Round One: Everyone Gets One Roleplay Opportunity to Advance

Let the meetings begin! The seller walks in and introduces himself. He’s smart. He’s professional in every way. He asks good questions, but I know what a hunter looks like. This guy is not a hunter. We continue. Things started to break down in the roleplay.

The buyer didn’t push back. He was instructed to do so, but he didn’t. He just let the seller talk…and talk…and talk. I was given a detailed scoresheet to use to score each seller, including a section for Overcoming Resistance/Objection Management. But there were no objections to score the seller on. None. After the session we reviewed with the seller his strengths and weaknesses. After the seller left the room I did the same with the buyer. “Chief, you’ve got to give the seller some objections to address or it’s nothing more than a ‘show up and throw up’ fest.” He concurred.

Enter seller number two, an attractive and charming young lady. The 29-32 year-old buyer, who is a sales manager in the real selling world, engages. Deep inside my head my eyes are rolling. Are you freaking kidding me? No. He flirts a little – just a little. She responds because she knows it works. But I’ve been around the block – and I have a judging job to do and I’m taking it seriously. She begins selling. She does fairly well, but clearly needs time to develop skills.

The buyer (I’m chuckling as I write this memory) couldn’t be more agreeable and gives her “softball” objections. She handles them (with ease) – much to his satisfaction and approval from the perspective of his role. The roleplay concludes. The buyer said, “She was like an amazing seller! I mean, like, I would like hire her if she came to me like looking for a job.” Without moving my head my eyes rolled to the side-corner of their sockets to give him that “are you kidding?” expression. I said a few things – and we moved on.

Round Two: Narrowing the Field of Aspiring Sales Reps

Other students conducted their roleplays and we scored them accordingly. Then we got to the finals. Twenty of the eighty students would go through this process again. This group included several top-notch sellers. They were good. Even great. Polished, confident, very comfortable, knowledgeable about the situations. It was impressive to witness.

But we had two aspiring sales professionals come into our office at different times who caught my attention – a young woman and a young man. Both were spot on. Impressive. By this time I guided my “buying partner” to a place where he was able to push back, ask tough questions, stop being so agreeable and easy, and create more of a real world selling scenario for the seller. Both students nailed it.

They both demonstrated exceptional sales skills, they exhibited strong selling judgment, and they appeared to possess the key behaviors of a stellar seller. We gave them extremely positive feedback, commensurate scores, some tips for the next (final) round, and our best wishes for success in the competition and their futures. We were certain one of these two, if not both, would be among the five finalists who would be chosen to compete for the number one spot – which would net them recognition, bragging rights, a cash prize, and maybe even a job offer. Not bad!

But much to our chagrin, neither of our selling stars made it to the finals. We were shocked. We knew these people were rock solid and should have advanced. We were especially shocked when we saw the skills of those who did make it to the top five.

The Final Round: NOT the Group We Expected

I had always known live roleplay had its challenges. We all know that. But we usually don’t think much beyond the actual conversation. We should.

So, we’re watching five reps compete – all of whom are good – but not nearly as good as our two exceptional reps. One of our star reps looked at us with disappointment. That felt bad. What happened?! Did we score them too conservatively? Were the five finalists scored with less scrutiny? The judges looked at each seller subjectively. My seven may have been someone else’s 10!

This experience was revelatory for me and showed just how reps being judged in live roleplays can easily be mis-scored. It’s honest. It’s innocent. Nonetheless, it’s wrong – and it doesn’t help us understand the rep’s ability to apply sales skills and judgment in selling situations.

Lessons Learned: 7 Limitations of Live Roleplays

Here are some of the problems inherent in live roleplays. The players – both sellers and buyers – have to be super serious and professional or else the whole thing becomes a “joke fest” and nothing is gained. Let’s face it, it’s a fairly expensive and a very time-consuming proposition:

  • get a bunch of reps in a room to do roleplays,
  • find willing and able buyers, and
  • a third party filling the role of judge (which rarely ever happens).

This means the buyer is usually the scorer as well – so they really have their hands full.

Let me net out what I’ve learned about roleplays:

  1. Salespeople hate them. Roleplays don’t make the top 250 things salespeople like to do at work. They put people under a spotlight, which is uncomfortable. It’s actually a distraction to learning for many.
  2. Live roleplays rarely represent a real world situation.
  3. Live roleplays are not scalable. How many reps, “buyers,” and judges can you take off the floor? And the judges and buyers require experience and certain talents to be effective.
  4. Someone inevitably gets so uncomfortable they usually leave their role and the whole scene collapses. (Perfect moment for reality TV, but not for developing sales reps.)
  5. Judges – whether independent or also playing the role of the buyer – are biased, inconsistent, and can do more damage than good. A sales enablement professional who was conducting roleplays during his company’s onboarding process once told me that he brought a seller to tears – literally. It was a disaster that neither of them ever recovered from.
  6. Scoring is inconsistent – even when the same buyer is involved. (This could be an article on its own. Just think about the drama that ensues with each Olympic competition where medals are awarded by judges.)
  7. We all have biases. And in many cases we have no idea we are biased. This is a factor.

Let me acknowledge that live roleplay can be very effective. But only under the best of circumstances. And that rarely happens – pretty much never. I use live roleplay to focus on a specific aspect of a conversation – e.g., overcoming resistance in a particular area of an anticipated conversation.

Before I conclude, a moment of full disclosure: my company develops simulations for sales practice, which puts salespeople in an automated, unbiased, scalable roleplay simulator. So, some would call me biased and self-serving on this topic. Maybe. But for sure, I’m informed about the dos and don’ts of live roleplay and alternatives that work better in most cases.

Drop me a note if you’d like to discuss.


Nick Rini
Author: Nick Rini

Nick Rini, with an extensive tenure in tech as an entrepreneur, has led three companies as CEO, and served as an advisor to several tech company CEOs. Nick’s experience includes raising venture funding, mergers and acquisitions, sales forensics consulting, sales, marketing, and sales management.