Turn Customer Conversations into Gold by Asking Better Questions
Getting the right people in your Customer Advocacy Group is step one.
Step two is getting the right words out of their mouths.
That means asking better questions.
Not longer ones. Not more impressive ones. Just better.
I’ve sat in too many CAG sessions where a great customer was in the room, ready to give gold, and someone from the product team lobbed in a vague, open-ended softball like:
"So... what do you think about the new design?"
You can guess what came back.
"Yeah, it’s good. Pretty smooth."
Useless. Unless you only wanted to spend the time, effort, and money to put together a CAG just so you could get an insincere compliment.
These are smart, experienced users. They’re not being difficult. You’re just asking them to do your work for you. If you want feedback you can act on, you need to change the way you ask.
Start With a Real Goal
Before you walk into any CAG session, ask yourself:
What am I trying to learn?
What decisions are on the table?
What will I actually do with this feedback?
If you don’t know the answer to those, you’re not ready to ask questions yet.
Skip the Survey Language
Surveys are fine for NPS and basic sentiment. But, scales and ranges should be kept to quantitative research. Right now, you’re talking to real people to get real-world feedback. Don’t ask: “On a scale from 1 to 10, how would you rate…”
That’s a number. Not a conversation. “A scale of 1 to 10,” immediately turns off the customer ‘s interest and sullies the interaction.
Instead ask: “The last time you used the DirtRipper 3200, where did it slow you down the most?”
Now the user knows how to answer and you’ve got a story to work with. You could have a few different areas to explore deeper.
Avoid “Yes” Traps
Whether they are conscious of it or not, every customer falls in the same traps when offering feedback. Your customers are going to be biased to telling you what they think you want to hear. It is natural for every human to do this. Don’t be upset with them for, but also don’t blindly let it happen. Carefully craft the way you ask questions, and how you respond as the conversation continues, to avoid simple echo-chambers. Closed-ended questions are the fastest way to make someone say what they think you want to hear.
“Would you say it’s easy to maintain?”
“Does it feel better than the last version?”
These give you a polite “yes” or a nervous “uh… yeah, I guess.” These responses tell you nothing.
Try this instead:
“Walk me through your last maintenance check. Are their any tools required on our machine that you don’t use anywhere else?”
or
“If we handed you the previous model and this one side-by-side, which would you use, and why?”
Look for the Story, Not the Soundbite
People don’t always know how to answer directly, especially if they’re unsure what you want. But they do know how to tell stories.
So ask for them.
“Tell me about the last time something went wrong with your machine and you had to improvise.”
“Can you tell me about a situation when you were impressed with how it handled a rough job site?”
Stories have friction. Emotions. Workarounds. Those are the clues you use to uncover what needs fixing and what should never change.
Ask About Tradeoffs
Every good product involves tradeoffs. Good feedback should surface them.
“If we added an automatic greaser, would you be okay with the added cost and complexity?”
“We made the undercarriage tougher, but it added 70 pounds. How does that change your operation?”
Get specific. Make the tradeoff clear. Then listen hard to what gets prioritized and why.
Make Them Choose
People love to be agreeable. So give them structured conflict.
“You can only pick one: better cooling performance or easier access to the radiator panel. Which one saves you more pain?”
They’ll pause. They’ll think. They may even try to argue that the engineers should be able to provide both. Stick to your guns and insist that, at least for this exercise they must pick only one. Eventually they’ll usually say something like:
“Look, that option would be nice, but I’d rather have this option because...”
That’s insight. That’s design guidance. That goes on the spec sheet.
Keep Questions Specific and Grounded in Use
Here’s a cheat sheet of better questions you can steal:
What’s the first thing you change when you buy a brand new unit?
Is there some way you use this machine that is different from how you think the engineers expected it to be used?
If you had five minutes to explain this machine to a new operator, what would you skip?
When you’re annoyed with this machine, what is the most common cause?
Are there parts of this machine where you wonder, '“what the heck were they thinking when they designed that?”
The Most Powerful Question You Can Ask
Want a secret weapon? Try this one, every time:
“What’s something about this machine that most people wouldn’t notice, but you do?”
This question cuts straight to the seasoned operator’s instinct. It gives them permission to share the kind of insight that makes your product actually better, not just statistically improved.
Quick Tips for Better Questioning
Don’t wing it. Come in with a plan.
Don’t ask how they feel. Ask what they do.
Don’t ask for praise. Ask for stories.
Don’t ask yes/no. Ask them to choose.
The End Goal: Usefulness
The purpose of a CAG isn’t validation. It’s clarity.
The questions you ask should give you something specific enough to write into a product requirement — not just a quote for a sales deck.
And when you get that right, you stop guessing what the field needs.
You start building with confidence. And your customers start noticing.
Want help designing the questions that turn feedback into specs?
Reach out and we’ll help you ask the kind of questions that get answers worth building around.