What to Ask in a B2B Buyer Interview

You want better messaging. You want a stronger value prop. You want a website that actually converts. You can have everything you want if you ask your customer what they want.

At Borrowed Pen, buyer interviews are at the heart of our market research process. We use them to help clients see their brand through the buyer’s eyes, unfiltered, unpolished, and exactly what we need to build messaging that resonates. Here’s what we’ve learned about what to ask, what not to ask, and how to get answers that shape real strategy.

Why Conduct B2B Buyer Interviews

B2B buyers rarely tell you the full truth in sales calls. Not because they’re hiding it, but because the dynamic is different. You’re selling and they’re evaluating. They don’t want to offend you, get pitched harder, or share internal context with a stranger. However, in a third-party interview, especially one designed for insight rather than sales, they open up.

They tell us:

• Why did they really choose Vendor A over Vendor B

• What your sales process felt like from their side

• What they thought when they read your website

• What helped them say yes, and what almost made them say no

These insights are gold, but only if you ask the right questions. Below are some questions to ask and some to skip:

Example questions to ask in a B2B interview:

1. “Tell me about the moment you realized you needed help.”

Their answer gives you the trigger. The pain point. The conditions that started the search.

2. “What did you Google first?”

Their answer reveals search intent and what terms they used, what content they found, and what they were hoping to see.

3. “What stood out about our client/solution?”

Their answer helps you uncover what makes your brand actually different in their eyes, not what your team hopes they’ll say.

4. “What almost made you walk away?”

Their answer gets to friction points like pricing, tone, process, or gaps in clarity. You won’t get this in a win/loss email.

5. “What advice would you give someone in your shoes now?”

Their answer reveals how buyers self-identify and how they talk about your category to others.

The types of questions we skip in a B2B interview:

1. “What do you think of our brand?”

Too broad. Too abstract. You’ll get polite, vague answers. Instead, ask about experiences and feelings, not labels.

2. “Would you recommend us?”

If they’re on the call, the answer is likely yes. It’s not useful. Better to ask, “Have you recommended us?” or “What did you say when you referred us?”

3. “What features do you want?”

This question turns the interview into a product feedback session. Stay focused on buying behavior, not product wishlist.

Our favorite unexpected question?

• “What’s something you wish vendors like us would stop doing?”

The questions always get a laugh and then a goldmine of insights. We learn what annoys them, what makes them tune out, and what makes them trust someone new.

Buyer interviews aren’t about flattering your brand. They’re about finding the gaps between what you think you’re saying and what your buyers are actually hearing. Want us to run your buyer interviews? We handle outreach, guide the questions, analyze the data, and turn it into a messaging strategy that actually makes sense. Let’s dig in.