How to Do Customer Interviews From Someone Who Does it For a Living

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Your customers can provide a wealth of insights. 

They can tell you if your idea truly excites them, if they’d pay more for a specific feature, how satisfied they are with your service—the list is practically endless. 

You can’t get this kind of information anywhere else. That’s why customer interviews are a must for both new and established businesses.

There’s just one catch: These interviews only yield valuable results if you know how to conduct them.

That’s why I chatted with Chris Bennett

As the Product Manager for LivePlan, Chris has conducted dozens and dozens of interviews and has a successful track record of translating customer insights into impactful product recommendations.

Here’s what he had to say about conducting customer interviews that get truly valuable results.  

Key Takeaways:

  • Remember, you’re just talking to people.
  • Come prepared but follow the conversation.
  • Work with a partner if you can.
  • Formalize your notes as quickly as possible.

1. Prepare your questions

The questions you ask should act as guidelines for your interview. You likely won’t get through them all, and that’s OK. The real goal is to get unique first-hand insights from each customer. 

Don’t just stick with a template

It can be tempting to try and standardize what you ask. Chris warns that this can make your interviews less effective.

“It makes it feel too much like a task. Really, the work is talking to the person.”

So, should you just skip preparing questions entirely? 

No. Come prepared with a handful of must-ask questions to help you get your desired answers. Just don’t get too hung up on repeating a rigid verbal survey.

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Opt for open-ended questions

You want the interviewee to think about how they felt, what they were doing, and what did or didn’t work. You won’t get any of that by asking questions that lead to a ‘yes’ or ‘no.’

“I try to use questions like, ‘Tell me about the last time you came to the LivePlan forecast.’ And they may respond with, ‘Well, I just finished the working day, I needed to hop in, and I wasn’t sure whether I was going to make it to the end of the month.’ 

This gives me a little more context around why they’re coming to us, the problems they’re trying to solve, even the emotion behind it.”

Have follow-up questions in mind

Before you start talking with people—prepare some simple follow-up questions. 

These are great to have ready and can help you dig deeper and keep the conversation going. 

“It can be something simple like ‘and then what happened?’” says Chris. “These are not about the product, but about helping flesh out their story.”

The more you interview, the better you’ll get at naturally following up. But at the start, it’s not a bad idea to be a bit more prepared. Even if the follow-ups you have down are simple reminders. 


  • Come in with a few critical questions.
  • Avoid asking things that lead to a yes/no answer.
  • Don’t stress about hitting every question on your list.
  • Prepare follow-up questions to keep the conversation going.

2. Begin reaching out

Remember, connecting with customers is about practice, figuring out what gets results, and doubling down. Every conversation, email sent, call, and DM is a step in the right direction.

Pick an incentive

You may not need to compensate every customer. Depending on how you ask and the number of questions—someone may just be willing to quickly chat with you. 

But if you need more than a few minutes of their time, it’s worth giving them something in return. 

“We usually offer people a small gift card as a sign of our appreciation,” says Chris. “It may not compensate them fully, but it does convey that we value their time and input.”

You don’t have to offer a crazy amount, either. A cup of coffee or a discount on your product may be enough. Set a budget, start small, and only increase if you still can’t land conversations. 

Do your homework

A little research can go a long way in sparking a connection and securing an interview. While you may already have some information on current customers, a deeper dive can help you personalize your outreach.

“I’ll do simple stuff like look them up on LinkedIn and see what I can find,” says Chris. “If I have an email, I’ll load their domain name and see if they have a website.”

This extra effort often translates to a higher response rate. “It’s more labor intensive, but we get a higher response rate because it’s personalized.”

Researching your interviewee also streamlines the interview itself. As Chris explains, “It allows me to dispense with some of that introductory stuff. If I already know what industry you’re in, we can get right to the core of the conversation.”

Related Reading: Why you need to conduct market research

Just have conversations

Ideally, the people you interview represent potential customers. But you can’t always be picky. You just need to have conversations and get reactions.

So, set up shop somewhere public and ask people to talk with you.

“Back in the old days (of LivePlan), they’d go down to a local coffee shop and just sit there,” says Chris. “And as people would walk in, they’d say, Hey, I got this thing. Will you take a look and tell me what you think?”

The point is that you don’t have to be formal or fancy. Anything you do is a chance to practice, work on your questions, and hopefully gain useful insights. 

I left this last because, yes, you should try to speak with people who fit the profile of your target customers. But again, if you’re spending hours and hours on outreach and can’t get people to talk with you, don’t be afraid to broaden your reach


  • Know what you will offer people for their time.
  • Research before you reach out and before the interview.
  • Don’t be afraid to broaden your interview base.

3. Running the interview

Heading into the interview, be sure to verify the following with the customer:

  • Date, time, and length of the interview.
  • If it will be in person, over the phone, or via video call.
  • If the individual needs special accommodations to participate.
  • Consent to be recorded or use the information gathered.

Lastly, I want to reiterate the importance of researching the person beforehand. As Chris mentioned, it helps you ask more specific and relevant questions.

Document or partner up

You really want to be present in these interviews. To participate in the conversation, listen to their responses, and follow up with the right questions. 

The easiest way to do this is by working with a partner. Chris mentioned that this allows each person to take on specific roles.

  • One does most of the talking
  • The other documents the conversation

Unfortunately, this isn’t always possible. 

You may be running your business solo or, like Chris’s case, expanding the number of interviews you conduct, meaning you must split up the work.

So, if you’re running interviews yourself, just record the conversation. “It’s a no-brainer because you might want to refer back to it—especially the one call that’s just gold.” 

Doing interviews online makes this really easy, but even in person, you can just use your phone to record a voice memo (which is actually what I did when interviewing Chris for this article). 

Really, anything that keeps you in the moment is worth doing.

Adapt as you go

Remember, you should come in with specific questions to ask. Just be prepared to make adjustments.

“It’s about listening to what they say and then being able to adapt,” says Chris. “Some people you have to redirect. Others, you’re like, oh, I’m trying to talk about this, and they really want to talk about that.”

If you have a talkative customer, give them a chance to guide the conversation without cutting them off. Sometimes, the best insights come from questions you wouldn’t have thought to ask before they started talking.

Related Reading: Why growth planning is essential for your business

Don’t force validation

One trap interviewers (and business owners) often fall into is only looking for reasons why their business, product features, or marketing messages work. 

You want the answer to be yes

The issue is that you can’t speak to just a few people; have them tell you something is good and assume it represents everyone.

“If you talk to eight people who say, ‘yeah, I like milkshakes,’ that doesn’t prove that you should open a milkshake business,” explains Chris.

However, speaking to one person can help you identify critical problems you may otherwise overlook. 

“You talk to one person who says, ‘I’m lactose intolerant,’ and you’ve identified a problem to solve—a market segment you’ll miss without non-dairy milkshake options.”

Basically, come into these interviews looking to poke holes in your ideas. It may hurt to hear that someone doesn’t like what you offer, but spending money on an idea and having no one want it will hurt even more. 

Related Reading: How to validate your business idea

Stick to your time limit

Remember, these people have taken time out of their day to speak with you. Even if the conversation is going really well, stick to the time allotted.

“I really try to respect the time the person has made available. At half an hour, I say, we’re at time. Is there anything else you want to mention?”

Chris mentions again that this is another area where having a partner can be helpful. Someone who can keep track of time and make sure you hit everything you want to.

“Doing these conversations in pairs allows me to step back from the conversation and to flag things we should revisit before the end of the call.” 

If you’re running things solo, have a timer handy and create obvious notes about points you want to revisit. If you’re running short on time, it never hurts to ask if they have a few more minutes to wrap up a couple of questions.


  • Do your homework!
  • Focus on poking holes in your business.
  • Record or work with a partner.
  • Stick to your scheduled time.

4. What to do after the interview is over

The first thing to do post-interview is review your notes and add any lingering thoughts. 

“Get the top-line bullets down when they’re fresh. You know what’s important right now and won’t struggle with remembering when you reflect on it.”

You can even develop a summary template to make it easier. Chris did this for a while, and at first, “it helped simplify some of the project management.” 

But like anything with these interviews, don’t force yourself into a structure that doesn’t work. Chris mentions, “The template just got to be a little too much and I didn’t end up filling everything out every time.”

Additionally, if you were having a good conversation with the person and want to follow up, mention that during the interview and immediately send an email. 

Even if you aren’t scheduling a follow-up, make sure to close the loop, thank them for their time, and leave the door open for another conversation.

One last tip from Chris: If you can drop an image of the person into your notes, do it. 

“Having that visual cue of who this person is will often bring back a lot of the wealth of that conversation without even having to read the notes. Oh, this guy! He was the restauranter who lived in Ohio struggling to understand his financial statements. I talked to him three months ago!” 

All of that came flooding back just by having a picture attached.

Related Reading: How to create a customer persona


  • Formalize your notes right away.
  • Send a follow-up request or thank you message.
  • Add imagery to help you remember the customer.

Prepare to interview with your business plan

Whether you’re exploring an idea, just starting out, or looking to grow—first-hand research can help you know if you’re on the right track. 

You want to speak with real people who reflect your current (or possible) customers. Focus on having them poke holes in your work and try to tap into their wants and pain points. 

While everything here will help you set up and run effective interviews, writing a one-page plan will help you turn the insights you get into actionable steps to improve your business. 

Download our free one-page plan template to get started. Or, for a plan that grows with you, try LivePlan.

With LivePlan, you get:

  • An AI-powered planning assistant.
  • Access to up-to-date industry benchmarks.
  • The ability to share and collaborate on your plan.
  • Robust financial management tools to track and review performance.

Get LivePlan today, risk-free. 

It’s the perfect tool for testing your business idea, making quick adjustments, and identifying growth opportunities.

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Kody Wirth
Kody Wirth
Kody currently works as the Inbound and Content Marketing Specialist at Palo Alto Software and runs editorial for both LivePlan and Bplans, working with various freelance specialists and in-house writers. A graduate of the University of Oregon, he specializes in SEO research, content writing, and branding.
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