How to Structure (and get the most out of) Your Customer Development Interviews

Running a startup puts a ton of responsibilities on your plate. From marketing to sales, hacky-HR to accounting, development to project management, you’re wearing a million hats.  

The same can be true for Product Managers. You can find yourself involved in many projects, tons of meetings, and more competing priorities from your stakeholders than you’d like.

Yet, through all this busy-ness, whether you’re an early stage founder, or a product manager, you need to make time to talk to customers. It’s the lifeblood of building something people want, getting to Product-Market Fit, and launching successful new products and features.

As you commit yourself to “getting outside the building” to talk to your customers, it’s essential you make the most of those discussions.

Talking to customers…but how?

One of the hardest things for newcomers to customer development and product management to get right is the questions they ask in their interviews.

Done well, you can learn priceless insights that help you prioritize and build the right things, while descoping things that turn out not to matter. Done poorly, you fail to get sufficient signal across interviews, and waste you and your customer’s time.

Fortunately, I’m here to help you today.

I’ve taught dozens of product managers and founders this process hands on (and thousands more through posts like these), and it’s led to fantastic results for them. By using this structure, you avoid biasing your customers or putting them on the defensive. You also maximize your learning so that you can get the best insights in the fewest number of interviews.

With that in mind, let’s dive in, so you can learn how to have great customer interviews, too.

How to Structure (and get the most out of) Your Customer Development Interviews

The biggest mistake I see otherwise well-intentioned founders and PMs make is that they come to their customer interviews with no preparation.

Showing up and just saying, “Tell me about…” or “What do you think of my demo/product?” is a huge missed opportunity; you don’t know what you don’t know at that point, and lose out on a lot of great insights you could learn if you asked the right questions, in the right order.

Ask the right questions at the right time.

You can make a great impression and learn a lot more by following this simple, 3-step process I share below: 1) People, 2) Problems, and then 3) Your Solution. 

A few quick notes before we break those down:

  • Timing: Depending on the person, this question flow generally takes 30-45 minutes to go through. If you can get a customer to agree to a 1 hour call, that’s ideal, but you can prioritize the best questions if you have only 30 minutes.
  • Business Model: This structure is best suited to B2B customer development, but with a little creativity, you can definitely adapt this for B2C interviews, especially if the B2C product involves the customer making a direct purchase (i.e.- subscription or e-commerce).
  • Order: This order (People -> Problems -> Your Solution) is extremely intentional. You must go in this order, or it will hurt your results of your interviews. More on why later in this post.

With that in mind, let’s take a look at the 3 sections, in order:

1) People – Aka – Who Are You Interviewing?

Before you get into anything about problems, or your solution, you need to figure out who you’re actually talking to. This both warms up your interviewee with some softball questions and gives you an opportunity to build some rapport with them.

It also helps you get to know them and the parts of their life around the edges of the problems you’re potentially solving for them.

Important: Do not shortchange this opening section of questions!

You don’t need a novel on their daily life, but you *do need* enough to be able to understand their role within their company, who key players are, and a general baseline of their sophistication.

All of this will help you later pattern match who the user type that is most receptive to the problem you’re solving and the solution you offer, as well as who is not a fit. This is priceless for your product, your marketing, and your sales processes.

Some example questions you can ask:

  • What is your name and role at your company? (If you can find this out in advance, always look it up to save asking the question)
  • How do you fit into your company’s department structure? Overall in the company?
  • How do you discover new products for work? Do you need any approval to try them?
  • Have you tried anything new recently? How did it work for you?
  • What is a typical day like on your job? What are you main routines?
  • What is your budget like? Who has to approve your purchases?
  • How much time do you spend doing [task X]? (Task X being anything they mentioned in their typical day that stood out to you or related to your product/business)

Pro Tip: When you’re preparing for your interviews, give yourself a section before your People questions to fill in things you can look up on your own.

This can be things like: Their name, Job Title, Company Website, Linkedin profile, Company name/size/industry, location, internal analytics profile from your company, and anything else you can find out about them that shows context about who they are and their behavior in your product.

Then, add any questions to your script that come to mind as you gather this info to really make the most of your interviews like their usage of parts of your product, unusual things in their profile, etc.

Going into these interviews, I never know which aspects of getting to know them will be the key, which is why adding the extra notes beforehand helps; you’ll be looking back at all your interviews to figure out what common patterns and differentiators are.

2) Problems – Aka – What are your greatest pains?

This section is where you try to find out whether the person has the problem you believe you’re solving.  Your goal is to not lead them to your problem. The less you lead them while still hearing your problem being mentioned, the more validation you have!

People love to talk about themselves, so let them go nuts here and really rant about their problems (i.e.- Shut up 🤐 and listen!).  Generally, people are terrible at proposing solutions, but you want to hear generally what they envision as solutions or see what they’ve cobbled together themselves.

Some sample questions you can ask:

  • What are your biggest initiatives and goals right now? How are they going so far? (To understand their priorities and which they need help with most)
  • What are your top 3 challenges you face in your job right now? Why did you choose those? Why that order?
  • What are your top 3 challenges you face in your job related to [industry X]? (Industry X being the one your startup/business is in)
  • If you could wave a magic wand and instantly have a solution to any of those problems…what would the solution be?
  • Dig deeper into their typical day on anything that sounds painful or expensive. (You can add some hyperbole here to get them to rant a bit by saying things like “that sounds inefficient…” or “that sounds expensive…”)
  • How have you dealt with or solved [Problem X] so far? (You’re looking to find out if they’ve hacked a solution together themselves. If they have…ask for a copy of it!)
  • How does your work in this area interact with your coworkers? (Look for collaboration problems, needed features, and others you should interview)
  • What do you have to report to your manager or other teams related to this? (Look for reporting needs, buyer expectations, and how this problem may impact others)

Notice, you haven’t mentioned your solution, nor problem yet. If they don’t mention your problem specifically, then as you finish this section of questioning, you can directly ask them if what you think is a problem is a problem for them. Whether they agree it’s a problem or not, you want to then probe why it wasn’t one of their top problems.

The beauty of this approach is that you’ll learn a lot about their day to day, and what they perceive as their most pressing problems. This can often help refine what you’re working on, or reveal a pivot that can change the fate or trajectory of your business.

3) Your Solution – Aka – See if your idea survives customer interaction

In your discussions in part 2, if your interviewee brings up your problem you think you’re solving, then you’re on the right track! Bonus points if the way they describe solving it with their “magic wand” remotely resembles what you’re doing.

No matter what happens in part 2 you should discuss with them what you thought the problem was and what your solution is. Getting validation that they wouldn’t be interested in the idea is just as helpful as finding out they love it; either they’re not a customer, or you are learning what your customers want instead.

Some sample questions you could ask:

  • Walk them through the problems you believe your solution solves. Do they agree?
  • Does [your solution] solve any of your problems? Why or why not?
  • What looks most helpful or important to you? How will that help you?
  • What’s missing from what I’ve shown you to help solve your problems? Why is that important to you?
  • How do you see this fitting into your routines? What would be important to make it fit well for you?
  • Who else on your team, or at your company, would be interested in this? How do you think it would help them?
  • Would you be willing to pay for our solution? What budget do you have for something like this? (Don’t be afraid to probe for the pricing you know you want…”Would [X] be reasonable?” It’s imperfect but gets you started.)
  • If they’re willing to pay for your product and like the idea then… “Would you be willing/ready to start right away?”

If all goes well and you really are solving a pain, then your customer should want access to your product or new feature right away. More likely, you’re going to learn a ton about what they do and do not want and your idea will begin evolving. You’ll also find out others at the company you may want to talk to that have needs if your customer will start using your product.

Keep in mind: The way you present the solution can be flexible for the state of your business or the development of this feature:

  • Describe it in words: Tell them what you have in mind, or sketch it on a napkin or paper.
  • Show them mockups: Share your screen or turn your laptop/tablet towards them to show what you have in mind.
  • Send them a clickable prototype: Especially if you’re interviewing them on video, sending a prototype link is a great way for them to see and feel what you have in mind. (In that case ask them to share their screen and narrate their thoughts as they go through it)
  • Give them staging or feature-flagged access: Once you’ve launched, this is the most powerful because they can try it exactly as you intended. (And again, have them share their screen and narrate.)

In all cases, the goal is to give them something they can react to. Don’t let the simplicity of what you have stop you from learning.

In fact, you can learn a ton in these interviews when you literally have nothing to talk about in the Solution section; I’ve launched products and new features multiple times where the first round of interviews had little to no solution discussion, and we only followed up later for solution-focused feedback built on what we learned in the People & Problem sections.

Making the most of your customer interviews

This basic structure can carry you a long way towards some great validated learning about your idea and your market’s desire for it. It can help refine your idea or feature, help you determine if you should pivot, and reveal new opportunities that can help you grow faster.

There’s a few more things to keep in mind that I’ve learned over time. Applying these tips can help you become a real pro at interviewing customers.

1) Take good notes and record everything!

Once you’ve interviewed 8-10 people, you should be going back over all of your notes and look for patterns. This includes especially looking for patterns in the Part 1 section to see what all the people that agree you are solving their problem have in common.

Summarize your notes then and share with your team, so everyone benefits from what you learned, and you can iterate together on your solution based on what you learned.

In particular, having a recording (and more recently, AI transcription) can really help here, because then you can re-listen to and review great interviews, as well as share snippets or the whole interview with your colleagues.

2) Have other team members sit in on some interviews

A good customer development focused company will have everyone involved in the process. Performable, pre-HubSpot acquisition, had their engineers spending 30% of their time on the phone with customers. Nothing helps someone do their job better like understanding who they’re building/selling/marketing for.

Equally important, when you have colleagues join, you have a buddy who can help you take notes. (More advice on note taking here)

3) Be conversational

Using a script like this should not feel like an interview! They should feel like they’re just having a conversation with a friend about their problems at work. The more comfortable they feel with you, the more they will open up. This is part of the value and intention of the People section of questions.

By preparing your interview script in advance, you can more confidently run your interviews knowing exactly what you want to talk about. Be sure to use language that feels comfortable and natural to you, and don’t be afraid to iterate on any questions that aren’t getting the response you hoped.

4) Go off script

The best insights comes when you dig a little deeper on something that strikes a chord in the discussion.  The script is there to be your roadmap, but there’s no reason you can’t return to it after a 5 minute digression about a specific pain, or discovery about how the company operates.

5) If they’ve made an MVP…ask to see it!

Nothing gives you more insight to a customer than what they’ve hacked together themselves to solve a problem. The best thing you can do is ask to see it, which will give you an idea of what they’re hoping your solution will provide. These people are also the strongest candidates to be great, helpful early adopters of your product.

If the hacked solution is actually a competitor’s product they’re frustrated with, ask them to share what they love and hate about it; that’s just as valuable as any hacked or cobbled together solution.

6) Always follow up

It’s common courtesy to thank people for their time and help. It also opens the door to follow up with them in the future if your product changes and is a fit for them, or to invite them to try it out when it’s live/launched.

Also, if you promised a free gift card (or other compensation) for their time, be sure to keep your promises and send it to them promptly. And if you hear about any bugs they report, be sure to fix them and then let them know.

All of these things score major points and make a great impression, which will make it easier to get people to interview in the future as well as build good will with current and future customers.

7) End with an ask

Always end your interviews by thanking them and asking them for something. It may be to get a copy of their MVP, or even better, ask for an intro to someone they know that might be interested in what you’re working on.

In my experience, these intros have an 80-90% success rate in becoming new customer development interviews, whereas cold emails asking customers you’ve never spoken with only have a roughly 10% success rate.

8) Be open to new problems! That’s how great products are born.

As Steve Blank has said, No idea survives first interaction with a customer. Don’t be afraid to shift your focus from your first idea to what you’re actually hearing customers want.  If you probe in part 2 and find a burning problem…find out how they currently solve it and what they’d pay to solve it.

Sometimes these shifts are subtle, because what you thought was most important is secondary to a bigger problem. That’s when you tell marketing and sales about a shift in positioning.

Other times, this is a huge shift and you need to change what you’re building significantly. That’s when you should have a bigger team-wide discussion.

Either way, having detailed notes, recordings of your calls, and some examples from customers of what they want instead can be the difference between what you found falling on deaf ears, or being embraced as strong evidence of a change in focus or full blown pivot being necessary.

In the end, you want to find a “hair on fire” problem, not a “nice to have problem.”  Think about it this way: If my hair is on fire (literally), and you’re selling buckets of water, I’m definitely going to buy your product. But if I’m cold and wet, I’m not likely to buy your bucket of water right now, but might consider it in the future.

Find customer pain and a solution they desire and will pay for. Rinse. Repeat.

From launching your first product, to adding the nth feature to your company’s product suite, interviewing customers is an essential skill. By using the People -> Problem -> Solution framework and being well prepared for each interview, you can spend more time building the right things and less time adding things that no one cares about.

Further Reading:

Looking to truly master the art and science of interviewing customers? Read these other posts:


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Don’t build that feature! How to use the 5 Why’s to learn what your customer really is saying

Are you sure we should build that?

Whether you interview customers regularly, watch support requests on HelpScout or use a feedback app like UserVoice, your company is inundated with feature requests from your customers.  

It’s great to talk to your customers, but can lead to the dreaded “feature creep” that creates bloated, unusable products.

What’s a product manager to do?

The answer may surprise you in its simplicity: use the 5 Why’s.

Don’t build that feature! How to use the 5 Why’s to learn what your customer really wants

In case you’re not familiar, the concept of 5 Why’s is that by asking a person a series of “why” questions, you can get to the real root cause of an issue.

Commonly, the issue can be used to do analysis of technical failures as outlined in a great post by Eric Ries found here. 

However, this can be just as powerful when you apply it to discussions with customers about features.  The power comes from saving you from building things customers actually don’t want or need and surfacing what is really important.

This concept really crystallized for me when I had an experience talking to Chris Keller, the founder of email reminder tool, Followup.cc. I was an active user, but Chris hadn’t decided how to monetize yet.

I told him I’d pay for Followup if he provided a calendar to see all my Followup reminders.

There’s just one problem – despite the fact that Chris built that feature not long after our discussion, I’ve never used the calendar even though I was a paying customer because of the core product.

Chris could have avoided building the feature if he had used the 5 Why’s. Here’s how it may have gone.

Me: I’d pay for Followup if you provided a calendar to see all my Followup reminders.

WHY #1: Chris: Why would that make you pay for it?

Me: Because I could then see all the Reminders I’ve set up.

WHY #2: Chris: Why do you want to see all the reminders you’ve set up?

Me: So that I know when I have reminders coming up.

WHY #3: Chris: Why do you want to know when you have reminders coming up?

Me: So I’m sure I know when I should expect a bunch of reminders.

WHY #4: Chris: Why do you need to know when you should expect reminders?

Me: (long pause) …So I’m sure I get all my reminders.

WHY #5: Chris: Why wouldn’t you get all your reminders?

Me: Good question. I guess I’m worried about it not always working.

Chris: Don’t worry. I’ve built Followup to be robust and reliable. Are you sure you need that calendar?

Me: Maybe not.

Your results may vary, but the point is, customers are terrible at coming up with solutions.

What they are good at is sharing their problems, which you can solve.

The key is to interact with them in a methodical way to get to the heart of what they really need. That comes from having live, real conversations with them (not using feature voting tools), and taking the time to really dig into the underlying reasons for their request.

If you do that, you may be surprised what you learned the real problem they have is, and you might just build a better, less-bloated product.

Next time you hear from a customer that you need to build a new feature…ask them the 5 Why’s first!

The Lean Product Life Cycle

See my previous post to understand how I got here. The hypothesis is that product development is messy except for the most disciplined.

After talking to a number of great product people, I have a theory for how great product can be developed while being customer-centric.

The Virtuous Cycle of Lean Product Development

The Product Management Funnel

I think of product management as a funnel. At the top are all of the ideas your team generates. If you’re a lean startup, that’s hopefully driven by customer interviews, website and landing page behaviors and support interactions and of course the occasional green space wild idea.

As product manager, this is the most dangerous step. Once you have more than a few employees, it’s easy to have these ideas overflowing and interfering with the whole product process. Multiple teams I spoke with have been using their project management tools to capture these ideas which leads to a huge mess (one such company had over 4,000 stories in their icebox!) and a major time suck (one vp of engineering is spending an hour + each day managing these ideas).

The problem is project management != product management. The only thing that should be in your project management tool are key bugs to fix and what you’re building now or in the very near future (ie next sprint). Everything should be clearly defined and in a language and structure preferred by your engineers. All the evolution of the product from idea to customer validation to final prioritization should be done outside the project management tool.

The Rest of the Funnel

The Full Product Funnel

Going back to the beginning, you need discipline at the top of the funnel; the best product people I spoke with are requiring a shred of data tied to an idea to make it into their coveted ideas list. They also often expect a disciplined approach to what goes in by having people state, “Feature X will move Metric Y by Amount Z” so it’s clear why the feature needs added. In earlier stages that may be in a “Hypothesis vs. Metric to Invalidate” format instead.

The key of this step is effectively managing the signal to noise ratio; for every 5-10 ideas that come in, you may only make 1 or 2. Even the less disciplined product managers I spoke with have some type of hot-lukewarm-cold system for trying to rank ideas. To avoid the 4,000 stories in your icebox (or anywhere else) you have to be disciplined on dropping stale ideas and focusing on what matters now. When you’re a growing startup, where you were 3 months ago is dramatically different from where you are now so why keep those stories cluttering your system now?

After wrangling the initial feeder of ideas under control, you need to effectively refine the ideas that make it into your system and allow the most important ones to rise to the top of your list. As planning for your next sprint begins, you need to prioritize these ideas and balance with other existing projects, bugs and other demands.

Once you’ve settled on what you’re going to have engineering build next, you need to engage your team on the ideas you want to implement; you may need copy from marketing, stories from support to describe customer complaints, links or screenshots from analytics to show present activity and relevant customer development notes. All of this feeds into the project management tool you have, but now it’s uncluttered and your engineers are much happier and efficient. Unless you’re github or heroku, chances are your engineers don’t understand the customer they’re building for perfectly so all this structure makes it easier for them to see what’s going on and then adapt it to fit the project management tool they’re using to track building.

As an added bonus, there’s transparency for your other employees as they engage in more than just the initial ideation process. It also means sprint planning no longer needs to have all hands at it as they’re already well aware of what’s going on and have had opportunities to contribute as needed to the stories now being generated in the project management tool.

Completing the Virtuous Cycle

We all know this image above so well as the core of what lean startups is all about, but how often is this cycle cleanly implemented? The project management tools out today all do a great job on the build aspect, but what about measure and learn?

The funnel process I described above captures the learn aspect as you engage your team for ideas and validation. All that’s left now is to measure.

After you build something new in your project management tool, your engineers will submit it for some form of approval. Once approved, it universally ends up disappearing into the ether, because the project management tool is built to track what you are building or about to build. After building isn’t part of their process.

To close the lean loop, you need to look back and see if that feature actually moved the needle. This needs to happen within 2-4 weeks of building it; sooner wouldn’t be enough data and longer would be distorted due to other things you’ve likely built by then. This last step of learning should help you refine your instincts and feed back into what you build. This is one of the biggest challenges as Eric discusses his principle of Innovation Accounting in his book.

The amazing thing I discovered in so many of my interviews was how rare it was to do this measure step; how can you improve your accuracy without seeing if you hit the target?

The Product – Lean Opportunity

What started as an investigation of lean startup opportunities has broadened to helping teams close the loop in managing a product lifecycle. I believe there is tremendous opportunity to build a platform to aide on both sides of the project management tool and much wider than those adopting lean concepts officially (as we all know, being customer centric is not a new concept).

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Using Customer Development on the Customer Development Process

Earlier in November, I started out on a journey to see if there was an opportunity to build a product that would help companies in being a lean startup. The thought was that with Eric Ries’s book flying off the shelves and the lean startup community exploding, there would be new problems to be solved. Thanks to a nudge from Sim Simeonov and a few consulting opportunities brought my way, I felt like there was definitely something there. Like any startup, once I got outside the building, I learned some harsh realities:

1) Most people only pay lip service to lean.

Painful, but true. In both casual conversations in our community and full blown custdev interviews I found the full spectrum from strict implementers like John Prendergast and Matt Mamet (coincidentally co organizers of the local Lean Startup Circle Boston) to people who claim to be lean and think it has anything to do with how little money they spend (names withheld to protect the innocent).

2) Lean is a hands on activity.

The key to lean really is the human interaction; knowing when to ask an interviewee “tell me more” or deciding what analytics to deep dive to match up against your anecdotal discussions can’t be productized directly. It’s also risky to outsource since it’s so core to the future of your business; no amount of meetings, notes and summaries can compare to being there and doing it yourself. There’s huge opportunities to teach companies how to become lean, but I’m passionate about building a product, not a services business and I’m not sure most companies are ready to invest in lean (see 1).

3) Small startups are more likely to be lean and less likely to need process.

Part of the challenge of the adoption curve of lean is that it has most strongly permeated the zero stage entrepreneurs; they’re the ones with time and motivation to watch the videos, read the books and stay up on all the blogs (which has come a long way in the last year or two since all we had was the Four Steps to the Epiphany to go on).

Unfortunately, those people have little to no budget and because of only having a few people on their team, there isn’t much of a need for tools. Everything can be done ad hoc when you’re that small. The most common behavior when you have 5 or less people is to remove your headphones during the work day and share your findings immediately with everyone on your team.  This is effective until you grow to the point that everyone doesn’t know everything that everyone is doing (usually around 8-15 people).

So all that meant to me was time to pivot:

I’ve known all along that customer development feeds into product management. Fittingly, this is where I did find pain:

  • Managing product while being a growing, lean startup requires significant discipline. Not all companies have product leaders with this strength.
  • Many companies build up product management debt as they grow and fail to adapt to the demands of a team that passes the “take off your headphones and talk” phase.
  • Multiple challenges arise in engaging all members of a company at the right times in the right way.

My next post explains what I’ve found. Read on to see the big picture potential for a lean focused product life cycle.