There’s nothing quite like finding out you’re wrong.

I’ve shared previously about the research I was able to take part in as a designer at Automattic. Meeting Small Business Owners from across the United States on video calls, learning about their lives, their fears, their challenges, and the kind of work they do. I pored over transcripts after these interviews. I wrote lines and lines of notes. I took part in workshops with our team to synthesize all this information. To say I learned a lot would be an understatement.

But I have a confession to make: I was pretty sure I knew a lot about Small Business Owners going in.

At Automattic I’ve had the chance to be on the front lines with our WordPress users for years. I’ve participated in usability studies. I’ve done yearly customer support. I’ve worked in our forums. I’ve met with users of our products in person. Many of these people have been small business owners.

Prior to Automattic I had done the same with my work in WordPress theming. And prior to that I’d had years of experience in providing print design work directly for, working directly with, Small Business Owners. These were people running 1 or 2-person operations that were just starting up. Sometimes Small Business Owners with dozens of employees who had been “doing this for years” or “since before I was born.”

I thought that was a pretty decent amount of experience.

I was wrong.

I hadn’t yet really talked to Small Business owners who hadn’t used our product yet. People that weren’t quite sure what they wanted. I’d never listened to the hopes and fears of those Small Business Owners. I didn’t know what their day was like, how they managed their time, how they thought about technology in general, or how they viewed other products they needed for their business.

I came away from that effort further convinced of some ideas about Small Business Owners and with fresh set of eyes on our product. I definitely learned a lot more about how a Small Business Owner actually thinks. But what I really learned, maybe the most important thing, was the location and substance of one more thing I didn’t know I didn’t know. I found out I was wrong. There’s nothing quite like that.

Posted by Ian Stewart

Canadian, designer, dad, and dork. I work at Automattic on WordPress.com .

One Comment

  1. >I didn’t know what their day was like, how they managed their time, how they thought about technology in general, or how they viewed other products they needed for their business.

    Senior designers in tech face a critical moment right now. Because they’ve spent most of their lives defining the genre around folks who are just like themselves, so it’s almost impossible to imagine how to step out of that comfortable bubble. It’s such a pleasure to observe leaders like yourself out there — similarly at companies like the Googles, Adobes, and even the Airbnbs — who ask the difficult question of themselves, “Do I really know as much as I believe I’m SO smart to already know?”

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