How To Ask Sensitive Sales Questions Without Upsetting Prospects [Roleplay]

Last week, I wrote about how "off-the-wall" sales questions can be used to take control of your sales call. While you can see example questions in that post, today I'd like to illustrate the effectiveness of these questions through a roleplay.

Oftentimes, as a sales rep, you need to be the one to ask a sensitive question or tell someone that they’re really wrong or simply say something really critical. Here's how this might play out ...

[Sales] “How can I say this without upsetting you?”

[Prospect] “Say what?”

[Sales] “Never mind. I don’t know you well enough.”

[Propsect] “What are you talking about?”

[Sales] “I have a question, but it’s very sensitive and I really don’t know you well enough to know how to ask it.”

[Prospect] “Just ask.”

[Sales] “I don’t want to upset you.”

[Prospect] “I won’t be upset.”

[Sales] “Okay. Let’s do this. I’ll say it as best I can and if you’re upset with the way I said it, you promise to tell me how to say it so that I won’t upset you. Promise?”

After they promise, tell them whatever you need to tell them in a halting voice. When you finish, pause and say ...

[Sales] “You’re upset.”

[Prospect] “Darn right.”

[Sales] “I understand. How could I have said it without upsetting you?” 

And now the real conversation will begin!

Try using off the wall questions in your calls, and let me know if you need any help along the way. I even list some of my best sales questions here.