Customer Interviews: A Guide to Perfecting B2B Messaging

There are basic marketing principles we all know we should follow, but let’s be honest—we often don’t. Customer interviews fall into that category. Try Googling how often B2B marketers actually conduct them, and you’ll find vague claims like a “significant minority” (which is code for “we have no idea”).

Instead, marketers convince themselves that listening in on customer calls or chatting at events is a sufficient substitute. But according to Dentsu, 68% of buyers feel that B2B brands all sound the same and fail to differentiate. Clearly, winging it isn’t working.

Great messaging isn’t an accident. No one wakes up magically understanding what keeps a Chief Security Officer at a healthcare conglomerate up at night. It’s time to stop assuming and start interviewing.

Why bother with customer interviews?

If you’re interviewing the right ICP (not sure who that is? Learn how to define them here), you’ll uncover insights like:

• Why customers chose your product
• Whether their expectations match reality
• What keeps them using it (or what’s pushing them away)
• How smooth (or painful) their buying process was
• What objections they had to overcome internally

These insights should inform your brand strategy, go-to-market motion, audience targeting, and product evolution. This isn’t just about identifying popular features—it’s about unlocking:

• Customer motivations and pain points
• The exact language they use
• Emotional triggers that drive purchasing decisions
• Blind spots in your messaging and sales approach
• How competitors may be positioning themselves differently

How often should you conduct customer interviews?

We recommend conducting customer interviews when there are major changes in the market, a change in product strategy is on the horizon, a new product offering is being developed, or if brand momentum is showing signs of slowing down.

Ideally, customer interviews aren’t an emergency tactic – but they are a great tool if you have a suspicion something has changed for the worse. Sometimes customer messaging no longer resonates because the market has become more mature or pundits are providing contraindicative advice to using your product.

Signs that your brand messaging might need work include:

• Lower-than-benchmark conversion rates
• Weak website engagement
• Declining lead volume
• Complaints from sales or customer success

A bad quarter (or two) is an excellent excuse to run some customer interviews!

Preparing for Effective Customer Interviews

Here’s how to make sure your interviews are actually useful:

1. Set a Clear Goal – What are you trying to solve? Align your messaging goals and aim for at least eight interviews within a set timeframe.
2. Choose the Right Segment – Start with your largest and most loyal customer profile.
3. Identify Who to Interview – Align which persona you choose with your core objectives for the project.
4. Pick the Right Interviewer – Never let sales or CS conduct the interview (bias alert). Choose a neutral, skilled interviewer who can establish rapport and remain impartial.

A neutral interviewer is critical because customers often hesitate to share honest feedback with someone they associate with the company’s revenue goals. A salesperson or customer success manager may unintentionally lead the conversation or make the interviewee feel pressured to give positive responses.

Creating a comfortable environment is also key. People share the most useful insights when they feel safe. A good interviewer should:

• Build rapport before diving into tough questions
• Reassure interviewees that their feedback will remain anonymous or only be used internally
• Use open-ended questions that encourage genuine, unfiltered responses

Pro Tip: Keep the interview 85% customer speaking, 15% you speaking (or less).

An example customer interview question set

We recommend working with your operations team to have them analyze if there are sticking points in the buyer journey by looking for slow stage velocity, disengaged leads, stalled opportunities, and poor conversion rates compared to industry standards.

Once you understand where potential stalling points are and have determined your interview project’s objective, it’s time to create a list.

These questions are built for the following scenario:

We are a marketing analytics company selling into the B2B realm in the United States. Our primary end users and champions are marketing operations professionals, however we know the sale will not be approved without CMO or CRO advocacy and existing budget. We have an array of products, but are best known for attribution. 

Our primary concern is customer churn. When our primary stakeholder churns, so does the product. How can we become more engaged directly with leadership to avoid churn and when should this happen in the customer life cyle?

Because we want to understand the interplay between operations and executives, we would target eight interviews with marketing operations and eight with the VP of Marketing, CMO, or CRO. The questions will be pretty consistent and only slightly tailored to the persona.

Example questions for marketing operations:

• Whose idea was it to purchase marketing attribution?
• How risky is it to bring in a new marketing attribution system? 
• How difficult was it to convince leadership to invest in the tool?
• Do you think your leader understands why the product was purchased? 
• What was your leader’s goal for purchasing the product? Were their expectations aligned with what you expected/wanted?
• How often do you think the leader looks at reports or actively uses the tool? When or why not?
• If you were to win the lottery and leave your company, do you think your leader would keep the product? Why or why not?
• When your CFO analyzes software spend, how do you defend this purchase? What information would you like to more easily defend the purchase?
• What did you want out of a marketing attribution tool?
• How did you feel your expectations of the product matched with what you received?
• Is there anything you would like to discuss that I haven’t asked about?
  

Example questions for a CMO, VP of Marketing or CRO:

• Whose idea was it to purchase marketing attribution?
• How difficult was it to convince your peers (CEO/CFO) to invest in the tool?
• Do you think your CFO/CEO understands why the product was purchased? 
• What was your goal for purchasing the product?
• Do you ever use the product? Why or why not?
• If your operations leader were to win the lottery and leave your company, would you keep the product? Why or why not?
• When your CFO analyzes software spend, how do you defend this purchase? What information would you like to more easily defend the purchase?
• What did you want out of a marketing attribution tool?
• How did you feel your expectations of the product matched with what you received?
• Is there anything you would like to discuss that I haven’t asked about?

Keep in mind that we’re not mapping out essential interviewer activity. Our interviewer knows they need to perform during the call like building rapport, establishing a safe place for open feedback, and using active listening skills.

Analyzing customer interview data

We’ve found that customer interviews often have obvious patterns early on in the process. However, it’s important to collect at least eight interviews to ensure you don’t have contradictions to those early insights shared by other customers. 

Reviewing conversations for patterns and identifying people who were engaged and enthusiastic about providing thorough feedback is important. It’s ok to weigh the few interviewees that openly spoke about a poor match between the expectations sales set and what customer success delivered more heavily if it was apparent the other personas weren’t involved in the sales process or were reluctant to share criticism.

Incorporating customer interview insights into brand messaging

It’s to get excited about your project findings and rush to update all of your content. Sometimes that’s a great idea – but the more cautious and data driven way to roll out these changes is to create A/B tests. 

The best practice is:

1. Test – Run A/B tests on ads, landing pages, and social content.
2. Measure – Track engagement, conversions, and lead quality.
3. Refine – If results improve, roll out updates more broadly.
4. Keep Interviews on File – Use recorded interviews to get sales and leadership excited about strategic shifts.

A successful brand messaging update will result in higher engagement on your website from your target audience, more leads, higher conversion rates, and more pipeline. 

Some final thoughts on customer interviews

Customer interviews are a great way to revamp your brand messaging and we’re huge fans of the outcomes we’ve seen from this process. While we don’t do interviews ourselves, if you feel like investing in your brand, we do work collaboratively with partners like Decode Insights. If you’re feeling brave enough to tackle a major project like this yourself, watch Yael Morris’s interview for inspiration.