How I Make Customer Development Interviews Less Weird and More Natural

Summary:  Most people expect us to give them sales pitches about our products.  When we instead start asking Customer Development questions about their habits and problems, the conversation can seem really weird to them.  I’ve found that framing the meeting by (1) asking for advice, (2) keeping the meeting short, (3) giving them unique industry insight, and (4) framing the background questions all make the conversation more natural.    Listen to me talk about this post on SoundCloud.

Recently a number of startups have been asking me during my startup help office hours why Customer Development interviews can seem so weird and what they can do about it.  As part of my commitment to writing about the practical side of Lean Startup in 2013 I’ll share my own experiences.

What Works in Silicon Valley Doesn’t Work Everywhere

Most of the ideas around Customer Development came out of startup experiences in Silicon Valley. Unfortunately many of us are experiencing that the rules and guidelines don’t always translate well to other regions and cultures.

In the Valley you can walk into someone’s office and talk conceptually about changing the world. Startups are part of Silicon Valley’s culture.  People share ideas, people are curious about startups. People want to help entrepreneurs and are happy to talk about fixing problems. This isn’t true for most of the world.

This past week at AcceratorHK demo day I had the chance to help a few Hong Kong startups. The founders are following Steve Blank’s advice for doing Customer Development interviews and finding that people won’t talk about their problems.  Some even say, “we have no problems”.

This is particularly true in Asian cultures where “saving face” can be important for people. Customer Development interviews can seem very weird outside of Silicon Valley.

Why Customer Development Interviews Seem So Weird

So…why are you here in my office?

99.999% of the world – including almost all of your customers – are going to assume that you’re trying to sell them something. Most sales pitches are terrible and we’re all sick of being sold to. From the minute you start talking they are trying to find the fastest way to tell you “this isn’t for me because…”

So when we don’t start with a pitch but instead start asking questions like “what are your biggest problems”, “what is your budget”, or “how does your workflow in X process happen”, most people are instantly on guard. They are expecting a pitch and you’re asking probing questions.

Sometimes people will interrupt with a dialog like the following:

Customer: So…what exactly do you guys do?
Me (thinking, I’m actually wondering that myself): We’re working on a solution to make X problem easier for people like you.

Customer: Oh. So what’s the product/what are you selling?
Me: Well…nothing yet but maybe in the future we might….

At this point the Customer glances at his watch and starts thinking about his next meeting and I’m not likely to get much out of the conversation. Worse yet, he or she starts to worry that I’m going to tell their boss about the problems.

Customer Development interviews can seem weird because it isn’t what people expect.   I’ve found that properly framing the meeting can make is less weird.

Tip 1: Genuinely Appeal to People’s Egos and Ask for Advice

The best way I’ve found to frame these meetings is to – genuinely – ask for advice. People love to give advice and by simply asking for it you’ve already demonstrated you respect their opinion.

It sets the expectation that the Customer will be talking and that you’ll be listening, asking more detailed questions.

Rob Fitzpatrick suggests in this video (minute 14)  an explicit message about seeking industry advisors for your company1

Tip 2:  Keep it Casual and Short

Whenever possible I try to buy people lunch, coffee, or drinks. Lunch meetings are great because they have a natural start and end.

If you meet in someone’s office, plan for 20 minutes. Of course be prepared to stay longer if they want to keep chatting. Planning for 20 minutes also forces me to identify the top 2-3 questions since I won’t have time for more than that.  I try to start the conversation with a connecting question about the person who introduced us, their favorite sports team, or their family.

Sales people are pros at this and can give you great advice.

Tip 3:  Give Them Some Unique Insight

Simply by working on your startup idea and talking to lots of people you have something valuable for potential customers: insight from a macro level that they don’t have.  Customers spend their days fighting fires, being bored in meetings, and answering email.  An informed, outsider discussion can be a welcome respite.

If you can offer people white papers, information changing regulation, links to blogs, or insight from other meetings, you’ve suddenly turned the meeting into a dialog between colleagues and not someone there to sell them something.

Tip 4:  Properly Frame the Background Questions

If you’re asking good Customer Development questions you’ll want to start asking about their behaviors, problems, and world views.  I find it necessary to necessary to explain why before starting.  Recently I’ve been saying, “Well before I tell you about my idea I’d like to ask you a few background questions about how you work today.  Is that ok?”.

They always say “yes” and I have their permission.

All Together – A More Natural Customer Development Interview

Me: Hey Tom, thanks for making the time to give me some advice. So how do you know Peter?
Customer: Sure, no problem. Peter and I….

Me: Awesome. I know you’re busy so I’ll try to wrap up by 2:30. Before I start ask you for advice on my idea, can I ask a few background questions about how you work? I don’t want to bias your response with my ideas.
Customer: Sure, go ahead.

Me: Great. So how long does it typically take companies in your industry to process data…
Customer: Well, it depends on the company. For us…

Me: Wow, that’s interesting. When I talked to X, Y, Z company they told me
Customer: Really? No way that would happen here. I’ll bet X, Y, Z…

Better Yet – Become a Thought Leader and Know Lots of Customers

While framing the meeting correctly can make it easier for people to open up, there is simply no substitution for having lots of relationships in the industry and being seen as a thought leader and a connector.

In fact, I now start any new project by first thinking about how I can start building an audience and being seen as an expert; for instance my Helpful Marketing Newsletter. It is just too hard to get people to talk to me if I don’t give them a good reason.

Most entrepreneurs start with a blog, but I’ve actually had more success with other tactics such as creating meetups, having office hours, creating directories, and office hours.  Different tactics work depending on your industry.

If you would like me to cover these in a future post, please leave a comment below or ask me on Twitter.  Make sure you Subscribe to my posts so I can deliver it to your inbox.

Need Help?

And – as always – understand that everyone’s situation is different and sometimes it is just easier to talk through your challenges in Customer Development. I’m happy to help you out, just grab an open slot on my office hours.

Photo Credit: insk0r

  1. I actually think this is a bit over-the-top and wouldn’t mention this, at least not on a first meeting unless I was quite sure I planned on asking them – most people in large company are terrible advisors. If I decide not to ask them I’ve already disappointed someone, not a good way to start making influence.  In my experience, asking for advice is enough.


  1. Sean Murphy February 12, 2013 at 1:20 am #

    Customer development is sales: you sell complex products with your ears and your questions not provocations and assertions.

    I would encourage you to consider revising Tip 1 from “appealing to ego” (or flattery) to “use appreciative inquiry”, which requires that you legitimately value and explore what someone has accomplished and the strengths they have demonstrated. In this formulation you may be encouraging folks to be insincere or manipulative. Alternatively open with your tip 3: you offer them information that’s relevant to their situation and ask if they have a few minutes to explore the implications.

    I think you are conflating celebrity with thought leader or connector (e.g. see “Six degrees of Lois Weisberg” by Malcolm Gladwell at for a good description of a connector. I think Phil Agre outlines a good model for how to become a thought leader at

    I worry that you are striving for celebrity over accomplishment with the focus on collecting tweets and e-mail addresses. Daniel Boorstin penned a succinct observation in “Who Are Our Heroes” in 1995 about the difference between celebrity and real accomplishment:

    “The hero is known for achievements, the celebrity for well-knownness. The hero reveals the possibilities of human nature. The celebrity reveals the possibilities of the press and the media. Celebrities are people who make news, but heroes are people who make history. Time makes heroes but dissolves celebrities.”
    Daniel Boorstin

    • kevindewalt February 12, 2013 at 2:37 am #

      Hey Sean! Great insight as always.

      WRT “revising Tip 1 from “appealing to ego” (or flattery) to ‘use appreciative inquiry’,” I’m in complete agreement.

      I phrased it as “Genuinely Appeal”, but the logic is the same -> cheap flattery isn’t going to get anyone anywhere. Your phrasing is probably better.

  2. jalil wambuzi August 25, 2013 at 4:19 am #

    hey Kevin,i really appreciate what have read from your site and it has helped me but I would like to know how to phrase questions on customer interviews on agribusiness.thanks.

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