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Interviewing in text

Deploy Empathy
Deploy Empathy
This was written as part of the rough draft for Deploy Empathy, a practical guide to interviewing customers.
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I’ve had a lot of people ask me how to interview someone in text: over email, via DMs, and whatnot.
It seems like this comes from two places:
  • Greater comfort with text. There’s less of a chance you’ll say the wrong thing and offend someone or make it awkward if you can read what you said before sending it. (And if they don’t like what you said, they can just not reply, making the underlying feared rejection invisible.)
  • No need to schedule a call and deal with the logistics. A call feels like work, whereas replying to an email or DMing someone on Twitter or Reddit feels more efficient.
Interviewing over text feels like lower effort, and thus more approachable.
So it makes sense if your instinct is to start (or stay) in text.

A quick reminder
Let’s recap for a moment what you’re looking for when you interview someone:
  • The overall goal they’re trying to accomplish (“file my expense reports so accounting doesn’t get mad at me”)
  • All of the steps of that process
  • Which of those steps require a lot of time, money, or complexity
  • How often they undergo the whole process and each step in it
  • Where they are now in that process
  • Where your product/problem you’re trying to solve fits in that process
  • What they’ve already tried
Diving into their process helps you find where the problems are, whether they might articulate them as such or not.
In addition to the process-based perspective, you also want to find the three dimensions of the process:
  • Functional elements (“I need to be able to upload a copy of the receipt”)
  • Social elements (“I don’t want to get tsked-tsked by accounting for filing my expense report late”)
  • Emotional elements (“I feel guilty when I file them late, and the process to reconcile all of the receipts is a drag”)
What interviewing over text will give you
Interviewing over text can be helpful for getting a high-level view of the process and for getting a glimpse at the functional dimension.
Unfortunately, I’ve found that people just aren’t as open over email.
…Largely for the same reasons that you might be more comfortable with it.
They can read their response before they reply, leading them to edit themselves. People tend to be more formal in email than they would in speech.
Mentally, you’re asking them to do all of the work of uncovering a process they probably haven’t consciously broken down before. (You know you’re doing an interview right when someone says, “Well I never really thought about it, but…”) So they skip to the high level.
It can be helpful for some of the questions. Ones I’ve had particular success with over text include:
  • What did you use before [current product]?
  • Can you give me the big picture of what leads you need this in the first place?
  • How did you come across us? (People are so used to the “how did you find us” question that it’s the textual equivalent of a banner ad, and gets skipped over. I’ve found this version gets better responses.)
What interviewing over text won't give you
Interviewing over text won’t give you the nitty-gritty of someone’s thought process and functional steps, and it won’t surface the emotional or social elements.
I’ve found that people are more willing to be open on the phone. (I say on the phone intentionally. People can be much more guarded on Zoom or in person.) Responding and following up shows that you care and are listening, which is feedback they wouldn’t get over text, and you can get them talking. Especially when it comes to more sensitive topics, like how they feel about the tools they use or whether they need signoff to use a new tool.
Those emotional and social elements may sound fluffy… but they’re critical.
Who has the purchasing power in an organization is a social element. How the restrictive terms of service of their previous vendor made them frustrated and want to find something new is an emotional element. Social and emotional elements can be make-or-break.
Mike Rogers, a reader of this newsletter, found this out recently. In an honest blog post this weekend about shutting down his service Typo CI, he wrote:
When I first started Typo CI, I didn’t reach out & talk to my users. I only talked to a small handful of people I knew quite well.
Recently I followed the advice from Michele Hansen & I started talking to my users. I found out I had a lot of faults with Typo CI which would require a lot of work to fix.
The big discovery I’ve had was “the users who want to use Typo CI, often don’t have the right level of permission within their organisation to install it”. For example, a developer may want to help improve the spelling within their codebase by adding Typo CI, but to do this they need their boss to install it. This extra bit of friction would lead to the idea of installing Typo CI being suggested, but just never actioned.
The developers loved what he made. But they didn’t have the permission to install it—only their boss did (a social dimension). And this led them to not use it, and ultimately, for Mike to have to shut it down.
(I give Mike huge kudos for sharing this story and allowing others to learn vicariously through his experience.)
What to do? Both.
Some information may be gleaned over text, especially surface-level functional elements. This is helpful for some purposes, like pulse-checks for why new people are signing up.
But to find all of the dimensions, you need to talk to people. Maybe that seems overwhelming or time-consuming. That’s okay. My goal is to get you comfortable with it and reaping the rewards.
I promise you it’s worth it. Your time is too valuable to spend it working on things people won’t buy.
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Deploy Empathy
Deploy Empathy @mjwhansen

A practical guide to interviewing customers

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