As Buttondown has grown, we’ve experienced many of the typical growing pains that you’d come to expect. In particular, new customers may not fit our original customer profile, which was, for a long time, other techies like us who cared about independent software and wanted a tool that did one thing well.

If that doesn’t describe you, fair, and we’d like to figure out who you all really are and what you need. That’s where interviewing comes in.

We don’t know our customers

Admitting we don’t know our customers is a bit of a risk. You may view it as a red flag: why support us if we’re clueless about it?

But in reality, no business truly knows their customer. We think it’s a strength for us to admit that we don’t know our customers. So many businesses view their customers as an “unknown unknown”, and they succeed based on luck or guesswork.

We know we can do better. By learning what drives you, we can build the best Buttondown for everyone.

Every single customer comes to Buttondown with their own hopes & motivations. Some of them have never started a newsletter before. Others have used a spreadsheet for years and want something a little more fit for purpose. No matter your perspective, we want to know it and adapt to it.

How we interview

Every month or so, we gather a list of Buttondown users that fits a specific theme. One month we might interview veterans & power users; another month, we might ask new customers what’s holding them back from onboarding. We get a list of emails and ask them if they might have time for a half-hour call. We offer a gift card for their time, because we need to provide some form of incentive.

What we ask on that call depends on who we know we’re talking to, and what direction we find the conversation going in. We can do our best to narrow down the criteria by which we recruit new people to talk to, but at the end of the day we really have no idea who’s going to show up on the other end of the call.

As for how to guide the interview, the unfortunate answer is to spend 20 years interviewing customers before you’re asked to do it for Buttondown. Interviewing only works when you’re experienced enough to interview people specifically for design insights. It’s not enough to ask what’s broken, or what pains they felt before coming in the door. You need to listen & reflect back what the participant is saying, because you never know what will come through.

Some big things I find myself doing are:

• Create immediate familiarity & comfort. I tell all participants that we’re looking specifically for feedback that helps us grow as a business, and that I have a direct line to the CEO (true) and they cannot hurt my feelings (false, but it gets a laugh).
• Be actively listening to the customer’s response in order to guide your next question. “You said X there. Can you expand on that?” is a classic.
• Create enough silence that the customer keeps talking. That’s often where the truth comes out.
• Provide space at the end for them to ramble free-form. Every time you ask if there’s anything else they’d like to add, they say “oh, no…” and then add five things.

But the real answer is to practice by interviewing people often.

Making sense of it

I take handwritten notes on every call. Then I record & transcribe every call, and then I write up summaries of my notes. At the end of the summary, I write up some takeaways and fill our bug tracker with projects & bugs to fix. We discuss as a team, and we do it all again.

We’ll never fully understand our customers, but through interviewing we can understand more & more, and learn how to make a Buttondown that works for everyone.