Open questions – the key to better customer insights

Deep customer feedback and understanding the voice of the customer depend on asking good, open questions. But there are challenges around asking the questions you need to in order to get the valuable feedback you need to develop and grow your business. Here are some reasons to ask good questions of your customers.

What happens when you ask someone an open question (as opposed to a closed yes/no type of question)?

🤷🏻 You don’t know.

And that’s the beauty of open questions and why you ask them.

You might have an idea of what they will say but they could say something that surprises you, that is new to you, that is shocking, provocative…

The point is you probably don’t know what’s going on for people, even the ones closest to you. Unless you ask open questions.

👂And then stop and listen.

And if they say something interesting, ask more open questions.

👂And listen.

This is an age old, simple process to finding out what’s going on for people, how they feel, what they are thinking etc. As long as you listen, that is.

📖 A career spent asking questions and listening to answers has told me one thing – people have incredible stories to tell. If you let them tell them.

And that brings me to my work and why listening to customers and stakeholders is so important.

If you run a business, you may well say that you know what your customers are thinking – sales, account managers and customer success do that for you.

But what are you asking?

⦿ Are you using the product?
⦿ Is it working for you?
⦿ Do you need help with it?

Are these questions useful if you want to find out how your product fits today? 👏 Yes.

Are they good for understanding customers’ future challenges and plans and how you might support them?
⛔️ No.

Asking good questions sounds deceptively simple. It is. But in business there are barriers that get in the way. Here are some common ones:

Fear – “What if they raise something we can’t fix?”
Reaction: stick to safe topics and miss signs of deeper issues.

Lack of skill – “Our teams aren’t trained to ask or probe.”
Reaction: miss what’s unsaid — the real goals and frustrations.

Time pressure – “We’ve only got 30 minutes — let’s stick to the agenda.”
Reaction: don’t pause to explore what matters most.

Misaligned metrics – “We’re measured on usage and renewals.”
Reaction: focus on outputs, not outcomes.

No system for insight – “Even if we learn something useful, where does it go?”
Reaction: valuable intel gets lost or stays in someone’s notebook.

Why this matters
When you ask deeper questions, you build real understanding — of your customer’s world, not just your product. That brings big advantages. You can:

✅ Spot risks and opportunities earlier
✅ Align your offer to what really matters
✅ Earn trust, which drives retention and referrals
✅ Become part of strategic conversations, not just operational ones
✅ Create insight that fuels innovation, not just account plans
✅ Elevate your relationship from vendor to trusted partner

You can achieve these benefits surprisingly quickly.