Recently a client challenged me to help them amp up their sales meetings. They wanted to spark creative thinking and identify blindspots regarding their offers, sales process and culture. They wanted 10 questions to ask their sales team that weren’t just “out-of-the-box” thinking, they wanted “box-isn’t-even-in-the-building” thinking.

Intrigued? You should be.

You see, a study from CSO Insights showed that companies asking the right questions and having dynamic, adaptable sales processes saw a 28% higher win rate. When my client saw that statistic, they took it to heart, and had me add a twist. Together, we created a cheeky decathlon for a year’s worth of monthly meetings (they had a plan for July & Dec). In the end, I gave them a set of 10 questions to keep their sales team on their toes and their sales soaring.

With permission from the client I created them for, here are the 10 Questions to Ask Your Sales Team:

  1. “If our product was a superhero, what would be its superpower?”
    • This question sparked creative discussions about unique selling points and how to present them to prospects and clients.
  2. “What’s the most unexpected benefit our customers have discovered?”
    • This question digs into customer feedback, unearthing golden nuggets of real-world product benefits and a great opportunity for the sales team to collect and share success stories.
  3. “If our sales pitch was a movie, would it be a blockbuster or a flop?”
    • This fun question encourages a critical look at their pitch. A fun follow up activity was to present their pitch as a movie genre… get the popcorn ready for that meeting!
  4. “Who’s the most formidable competitor on your radar, and why?”
    • A question that keeps a keen eye on the competition. They even looked at their competitor’s superpowers and that sparked even more ideas about differentiating.
  5. “What’s the weirdest objection you’ve ever received from a prospect?”
    • This quirky question led to stories that helped the team better prepare for out-of-left-field objections. This was especially helpful for the newer people on the sales team. I had them record this conversation on video and they now include it in their new hire training program.
  6. “If you could change one thing about our sales process, what would it be?”
    • An invitation for constructive criticism and process improvement. This highlighted not only what could be streamlined, but also revealed insights about the parts of the sales process the team wasn’t fully comfortable with… naturally, I was able to help with that.
  7. “What was the last sales book or podcast that had a real impact on you?”
    • This question promotes a culture of continuous learning. This lit a fire under the tushies of people on the sales team who were not continuously sharpening their saw. Let’s face it, if the last book you read was How To Win Friends And Influence People, it’s probably high time you renewed your library card.
  8. “If you had to sell our product in the Sahara desert, how would you do it?”
    • This quirky question encourages creativity and out-of-the-box thinking… like the idea of offering a bottle of water with every purchase… lol… they didn’t really do that.
  9. “What’s one thing you wish our product could do that it currently doesn’t?”
    • This insightful question gathers feedback for product development. For this particular meeting, the sales team invited members of the operations team to listen to ideas. It was such a productive meeting, the operations team invited some salespeople to attend one of their meetings to share ideas. Now, the department heads meet regularly and include team members from sales and operations to exchange ideas which was a true culture shift.
  1. “If our target market was a party, are we the life of it, a wallflower, or not even invited?”
    • This light-hearted question allows the sales team to evaluate the company’s position in the market. They did this meeting in November and paired it with a thank you party for the team which energized them before the end of the year push toward their stretch goals.

Each week, their sales meeting transformed into a lively game show with these 10 questions to ask your sales team. Sales reps would answer one, sparking discussions that were as enlightening as they were entertaining.

And the results? Spectacular.

After a year of this unorthodox method, the company witnessed a staggering 35% growth in sales. Even more impressively, their employee satisfaction shot up, which made sense based on a Harvard Business Review study revealing a 20% increase in job happiness among sales reps who felt their input was valued.

So there you have it, folks. The tale of ten cheeky questions that show the power of asking the right questions, in the right way.

As you ponder your sales strategies, remember that you can accomplish serious results without having to be too serious. Throw in a dash of creativity, a spoonful of cheekiness, and whip up your own set of 10 questions to ask your sales team. Who knows? Your sales team might just surprise you with their answers.

After all, the right question can unlock a world of potential.

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