The perfectionism problem
coping with learned failure to prioritise 2025-08-19 #product
Imagine a fictional job interview, with participants acting out a contrived role-play. The interviewer sticks to the script, and asks:
‘What is your biggest weakness?’
‘I’m a perfectionist!’ beams the disingenuous candidate, happy to use one of their prepared answers. One of two things happens next.
Or perhaps the candidate’s clichéd lack of originality shocks the interviewer awake, and they actually consider the implications of what they just heard.
Learned perfectionism
I first encountered perfectionism at school, aged nine or ten, when we learned to write with italic-nibbed fountain pens. Our headmaster decreed that we all use a particular style italic handwriting, full of straight lines and sharp corners, probably based on some book.
A few of my classmates produced beautiful script, and I remember the disconnect with my awkward scrawl when I saw the winning entries in a competition. To me, they looked beautiful, but also looked like a waste of time.
Throughout my later school years, we never talked about the trade-off between a result’s perfection, and the time that takes to achieve. Our teachers certainly never encouraged us to spend less time on schoolwork. Teachers and parents, if they care, probably wish teenagers would spend more of their time on schoolwork.
In general, school doesn’t teach everything that we need later in life. In particular, we shouldn’t assume that school aims to prepare people for jobs, knowledge work especially.
The enemy of good
Someone who recently finished university in the UK told me that they were happy with their less-than-perfect ‘upper-second’ degree classification. They reasoned that they still got a good result, and wouldn’t have had as much fun if they’d got a first. They probably went to more parties than I did.
The phrase ‘perfect is the enemy of good’ captures this idea of making trade-offs to get good results. If you don’t learn that at school, you certainly learn it in most jobs. And while you might forgive naïve perfectionism in a job applicant applying for their first professional graduate job, you can also expect that they still have some tough lessons to learn.
Perfect never ships
In software product development, perfect is the enemy of good becomes perfect never ships. Experimentation and incremental delivery mean shipping imperfect products. But perfectionism leads people to value right first time over learning, and trying to deliver perfection before getting feedback. Perhaps we should blame schools for waterfall software development as well.
The software industry has adopted enough manufacturing metaphor to understand the economics concept of diminishing returns, and apply it to software development. In product management terms, the pursuit of perfectionism ignores additional work’s product impact.
The curse of perfectionism
Let’s return to the fictional interview. The interviewer decides not to accept the candidate’s trite answer about their perfectionism. With a mischievous smile, they respond:
‘Ah, I find your self awareness of the curse of perfectionism… refreshing’. The interviewer then pauses, to give the candidate time to realise that they didn’t get away with it.
‘I’d like to know more about that’, the interviewer continues, hoping to sound encouraging.
‘When was the last time perfectionism made you fail to prioritise?’