Blunt questions to ask as a seller

or you'll lose deals more than you'd like to admit.

Author

Troy Munson
January 23, 2025

I’ve listened to 400+ Gong calls for reps. Almost all of them avoid blunt questions.

A post by yours truly, Troy Munson.

Before we jump in: Did you know every single deal I’ve closed over $208,000 started with a cold email? I’m 100% bullish on cold email - I truly believe if you can get someone to convert via email, you’ve got someone drowning in pain. Check out some of these tools that can help. I’m a fan of Lavender, Scout, and Mailforge, but there are many more incredible tools that can help. Now, let’s get into blunt questions.

Here’s what you’re in for:

  • Why blunt questions are important

  • Examples of blunt questions to ask

Let’s get into it.

I was obsessed with Criss Angel as a kid

FYI - you can practice these questions with AI role play tools.

Why should you even ask blunt questions?

For starters, most reps struggle with landing the plane. What does this mean? They’ll ask a question, pause for a split second, then follow up with a reason to the question before the other person answers. STOP. This is an easy trap to fall into, but you need to let the prospect talk. 

Secondly, blunt questions get you the answers you and your leadership needs. More often than not, reps don’t really know the answers to if a deal will close or not. The reason for his is because:

  1. You’re not digging deep enough

  2. You’re not asking questions to get the answer

So, I’ve compiled a handful of blunt questions you can ask on your next call.

Blunt questions you can ask:

ps - I love asking “do you mind if I ask you a blunt question?” This will help lower their zone of resistance.

1. If we land on a price, what needs to happen on your end to get a signature?2. What's preventing you from signing this week?
3. If we miss your timeline, what happens?
4. Who ultimately signs the paper and why would they say no?
5. Sounds like things are fine... why do you need to do something now?
6. Have you quantified the problem? What does that look like?
7. If [pain] continues for the next 6 months, who's on the hook?
8. What are we competing against?
9. How would you justify this internally to leadership?
10. What do you like about X competitor? What are they missing? Why haven't you decided to go with them?
11. What's the overall business initiative our solution would solve for?
12. What needs to happen for you to feel comfortable moving forward?
13. How is [pain] impacting the business? Would the executives agree?
14. Who can shoot down this project at the drop of a pen?
15. Why do you think [your solution] is the best fit?
16. What have you done already to try and solve this?

There are 100+ I can think of, but here are a few you can start implementing tomorrow… or.. today!

What other tips would you like to hear about? Respond and I’ll try my best to help :)

Thanks for spending part of your day with me! See you next time — Troy

P.S. i luv you