This was written as part of the rough draft for Deploy Empathy, a practical guide to interviewing customers.
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I suppose this should start out with why I’m doing this.
I talk to founders and prospective founders and help them work through their business problems fairly often: in my capacity as a mentor for Earnest Capital, on my podcast Software Social, through the various communities I’m part of, and sometimes just because people I’ve never met DM me on Twitter and we find time for a call. It’s something I love doing, and make time for even at times when I don’t even have time for other more critical things. (People tell me I should do consulting, but I don’t want to, and that’s a whole ‘nother topic we’re not going to get into.) When customer research comes up, and people ask for more information, I don’t have one good solid place to send them that approaches it from an approachable, high-level-yet-nitty-gritty perspective. It’s a mix of books, blog posts, and podcasts, many of which are only partly relevant to people trying to start or grow businesses, or are written for UX people. So my idea here is to try to create that place I can send people. And maybe this turns into something, and maybe it doesn’t, but at the very least, it’ll be a helpful resource for me as I help founders.
Helping founders and prospective founders is a guiding motivation for me. We’ve seen ourselves the benefits of running a bootstrapped B2B SaaS. The liberation that comes from being your own boss and the freedom that comes with being able to work from anywhere. We’ve built a $1M+ ARR company, and I feel a responsibility to help others do the same. And a huge part of our story is how listening to our customers is embedded into everything we do. It is the cornerstone, foundation, and pillars of how we make decisions. There’s no guarantees it will work the same for you, of course. But from my experiences helping founders, I can tell you that in the worst case, it will be accretive to your existing efforts, and in the best case, save you months or years of spinning your wheels, trying to launch things only to have them fall flat.
I want to help you avoid launches that fall flat because I’ve been through a lot of them myself, and they aren’t fun. Learning how to do customer research, and then seeing how it can clarify strategy and increase motivation and alignment was a revelation for me when I was a product manager. I was exposed to some of the underlying concepts somewhat haphazardly when we launched Geocodio and were buried under hundreds of feedback emails for the first few months, and carried from that an interest in feedback, though without any systematized way or with frameworks guiding me. But while I was more interested in feedback than most other product mangers I met at the time, it was still only marginally more, and I’d say I was somewhat of a skeptic. I remember the first time someone from the UX team suggested the idea of user testing our products before we launched them – how the heck were we supposed to find time for that within our already-hectic release schedules? A week of testing and then another two weeks of tweaking just wasn’t in the cards for the 4-6 week product launch timelines we were doing. It was only later, as my mind started to be more open to more rigorous research, that I learned that it is absurd to start customer research the week before launch – because it needs to happen much sooner, as part of guiding the development of the product. But that took me a long time, so I try to keep that in mind whenever I’m talking about this stuff, and recognize that it’s a mental leap for a lot of people. If you’re new to this area, you may not believe me until you start seeing the results for yourself, and I accept and welcome that.
I also write this from the perspective of someone who really had to learn how to listen to people. My default social position tends to be feeling like an outsider, and combine that with a sprinkle of ADD and you get someone who is very enthusiastic when other people share my interests or experiences. For a long time, this made me someone who would excitedly share my own experience or perspective whenever someone said something that I related to… which also made me not a very good listener. Over the past five or so years, I’ve really focused on becoming a better listener in general. So much of customer research is learning how to listen to people in a structured way, and doing so empathetically. I recently learned that our ability for empathy doesn’t fully develop until 25, and this is another area that I’ve focused on. I’ve really had to intentionally focus and learn both of those concepts, concepts we aren’t really taught in school. The key to good listening is doing so empathetically, really Being John Malcoviching yourself into someone else’s shoes, understanding their processes, their motivations, their struggles.
So my goal here is to teach you those things. Teach you to listen better, how to talk so people will talk, and how to turn all of that into actionable information you can use to make business decisions. I can’t promise it will be in a remotely sensical order; I’m going to write as topics strike me, and the frequency will be irregular. Sometimes it’ll be high-level frameworks, and sometimes it will be super nitty gritty. It won’t all be relevant to you, and I accept and embrace that up front.
I’m very much writing from my own perspective (former product manager, now bootstrapped founder), and I recognize that my perspective is not all-encompassing, so I genuinely and enthusiastically hope that you will reply with your thoughts on the topics I bring up (and ones I don’t – suggestions are fair game). If this ever becomes anything more than a newsletter, it will be because of the thoughtful additions and proddings of people like yourself, so I do hope you will be an active participant in this. I want you to ask me to elaborate on things more, to tell me when I’m making leaps of reasoning without showing my work, to tell me about times you tried things and they didn’t work out (or they did!), or whatever it is that comes to your mind as you read this.