Hypercritical taste is a gift the world resents.

I frequently feel like an asshole.

I’m hypercritical. I have strong opinions about the products I work on and the ones I use. These opinions come from years of evaluating products for why they succeed and fail.

My career started in QA where I discovered a knack for breaking things, bringing up weird edge cases, and pointing out inconsistent design. Since then I’ve moved into a hybrid role of development and design and my ability to identify flaws in design, architecture, or even strategy has only sharpened.

My biggest issue with being in QA was that I constantly felt like a teacher marking red ink all over other people’s work. This feeling was my primary driver to move on to development.

You might think this means that the things I create are near perfection. But, that is very much not the case.

The reality is that building things is an iterative process. We have to design and build and then find flaws with what we have. This brings us to another round of designing and building. In modern software there is never a done state.

The ability to rapidly find flaws is truly a gift. The sooner they are brought up the faster the iterative process of improvement goes. The downside is this skill is often perceived as negativity.

People I work with know me as hypercritical. Some see it as great taste and some see it as being a nay-sayer.

A lot of this comes down to the culture of the team. Some teams are more open to criticism than others. I’ve worked on projects where whatever leadership says is what gets built. Those projects are all dead.

People often tie the products they’re selling to their egos. It’s a dangerous situation because it makes you willfully ignorant to the product’s problems.

I have to choose battles carefully because sometimes I need to bring up critical product flaws. These need to be clearly separate from minor design and brand risks.

All criticism can feel like an attack. A deluge of criticism feels like a war.

A hypercritical person needs to be careful with how they present their thoughts. If you use vague language and derogative phrasing your criticism is going to raise defenses instead of consideration. I find it’s often best to open these discussions with questions rather than statements.

This is a part of the skill that can be learned. Observing reactions to criticism is a wonderful teacher about approach. When you see guards go up, back off and try a different tact. I often see people try to deliver criticism without specificity or context and it’s not productive.

The eye for problems is harder to learn. There’s a required combination of system knowledge and context awareness. You need curiosity to prod things from every angle.

Curiosity for problems is more a thing you develop and less something you teach.

This is why some people see criticism as negativity. It’s an approach to looking at a product that not everyone engages with. To avoid being an asshole, critical people need empathy for others that don’t see this way.