Your Secret Interview Question is Bullshit

Zachery Moneypenny
4 min readApr 24, 2017

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If you‘ve been performing technical interviews for your software group for any non-trivial amount of time I’m sure you delight in The Question. The one you stumbled upon by accident perhaps. Or maybe was handed down to you from a senior engineer long gone. Or possibly is the ultra-concentrated pure logical residue to a devious problem you encountered long ago. For many years I had my very own version of The Question and here’s why I came to understand that it was bullshit.

I was tapped to perform my first interview three weeks after I graduated from college and moved to the Bay Area. I was a QA Engineer at Intuit, and my Test Tools & Automation team was staffing up to start automating much of the daily acceptance testing for QuickBooks for Windows builds. My boss asked me to go interview some intern candidates and I was flummoxed and terrified. I don’t remember what, if any, technical questions I asked, but I do remember thinking that I had no moral authority to sit in judgement of a candidate when I had been in the job (and industry!) for about five minutes.

Later, when I started doing on-campus screening and interviewing for Software Engineers, my nervousness found some kind relief when I realized that I could have one or two questions that I knew inside and out, and whether I was fresh or exhausted from interviewing 12 candidates in a row I could talk reasonably about it from many different angles. My deep knowledge of all of the possible angles a candidate could approach my few questions lessened my anxiety that I was a fraud who shouldn’t be interviewing people in the first place.

For me, The Question was about coping with my insecurities. For others, it’s about the nature of being thrown into an interview unprepared.

Many folks pulled in to conduct technical interviews are almost literally that: pulled away from their desk on short notice, with a resume thrust into their hands and a hearty “See you in the calibration session afterwards!” For those that conduct an interview only once in a great while, The Question is a defense mechanism. When put on the spot to evaluate talent in others, its difficult to pull a Goldilocks question from thin air: not too hard, not terribly easy, exercises certain brain muscles the company values, etc. If after a few attempts they stumble upon a question that, wonder of wonders!, allows for varied levels of discussion, allows for different approaches, and presents an infinite onion-skin of a problem that can be ratcheted up to challenge even the most senior of candidates, then its status as The Question solidifies.

I have met engineers that delight in the deviousness of their Question, while others readily admit it’s a crutch in approaching an activity they actively despise or resent being made to participate in.

I don’t know that anything I write here can convince engineers to care about doing something if they resent it, but for those that have developed The Question as a defensive or coping mechanism, here’s my advice to you: throw them all away.

At a memorial for George Carlin, Louis CK recounts listening to Carlin talk about how he developed his shows: he would throw away his material every year and start over building something new . Louis was terrified to throw away the shitty material he’d built over 15 years of standup, but he also realized that he hated that shitty material. It was getting him nowhere close to where he wanted to go.

So Louis started throwing out his material every year, and he’d write a new show. It forced him to move away from jokes about dogs and examine deeper things about himself, his relationships and his fundamental views and thoughts on things.

Throw away your material

This then, is my task to you. To become a better interviewer, to be get out of your comfort zone and engage with candidates beyond giving them a pop quiz, I implore you to throw away your 15 year old act and try something new. And once you’ve done that for awhile, throw that away and try something new still.

Every few months, ask around your team, group, or organization: “What exactly are we looking for in a new developer?” Beyond a short-list of buzzwords fit for recruiter’s unsolicited email, what kind of skills does the group need at that time? Does your Question address that skillset? Maybe it’s time to retire That Question and find something new to talk about; something that exercises the skills you’re currently looking for.

I also believe heartily that the best way to find your new material is to engage other folks that interview regularly. What has worked for them? What hasn’t? I’ve learned a lot about everything from the correctness of what I’m even trying to test for, to ways that I can be knowledgeable about my bias and limit how that affects my interview style.

So, throw away your Questions. Invite uncertainty by searching for the best conversation you can have with this candidate, right now.

This is the first in a series of posts about how to approach and improve the skill of technical interviewing. To learn about how we arrived at the current feel of the site, see the inimitable Kelly Rauwerdink’s post about doing 0–60 Brand Design.

Zachery Moneypenny is a Principal Developer at adorable.io. He’s been conducting interviews of software engineers for over a decade, and is currently the Mock Interview Coordinator for the YWeb Career Academy as well as the Organizer of the Technical Interviewing Meetup in Madison, WI.

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Zachery Moneypenny

engineering manager at cars.com | opinions on tech interviewing | woodworking | song-and-dance man