Terrible Questions

Jonathan Maimon
3 min readDec 11, 2018

I started a new job a few weeks ago, and with a new job, comes a new team and new people. With new people, sometimes you haven’t worked out exactly how you work best with them, and this is especially true while brainstorming.

We were having trouble coming up with good interview questions to ask our users, in this case, junior employees at the company.

I proposed an idea to my two teammates. It’s called “terrible questions”. It works the way you’d think it would.

Set a timer for four minutes. Then ask each member of the team to take a couple post-it notes and write out what they think is a terrible question to ask a junior employee. Like what would just be an awful, awkward question? It’s much easier to come up with terrible questions than it is to come up with good ones.

For example, “What do you hate most about your job?” That’s a kind of terrible question. It’s overdramatic. It’s awkward and uncomfortable to ask to someone you just met for an interview. Or consider, “What do you really want to tell your boss that you’re afraid to ask?” That’s again a terrible question. You’d never ask that in a real interview with a junior employee. These terrible questions are easy to come up with and fun as well.

It’s much easier to come up with terrible questions, than it is to come up with good ones.

Once we each came up on our own with terrible questions on post-it notes, we put them on the wall to compare. My teammates were quite good at coming up with terrible questions, and we all laughed as we read each other’s questions. Not only was it a good exercise for brainstorming, but it also helped break the ice with the new team.

Once we had the terrible questions, we realized, some of them weren’t so terrible. I’m not going to go into details of our specific questions or scope, but for example, the question I gave earlier as an example, can easily be made into a good question.

For example, “what do you hate most about your job?” could be re-phrased as, “Is there anything you find frustrating in the work you do?” This is a good question to get a participant to open up about pain points, which makes our job as UX designers easier once we understand the employee’s system and process. Or take the second question in my example, “What do you really want to tell your boss that you’re afraid to say”, made me think of a good question just now, “What would you like to know about from your boss that you haven’t asked before?” That not-so-terrible question might get a participant to open up about what unsaid things might make an impact for an employee but he or she is afraid to ask or find out from their supervisor.

Some of the questions my teammates thought were terrible actually ended up being pretty good. One person’s terrible question is another person’s treasure, and we ended up incorporating a couple of terrible questions into our interview script, with slight modifications. But once we came up with a bunch of terrible questions, it was much easier to come up with good ones. It’s like how it’s much easier to critique a design once you have a design in front of you, rather than trying to critique an abstract concept you cannot see.

Some of the questions my teammates thought were terrible actually ended up being pretty good.

Terrible questions proved to be an easy-to-do exercise that helped us get through a rut in brainstorming and gave the team a fun activity to generate new ideas during the design process.

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