Awkward Interview Questions

A: I like groceries

Someone asked me, You said you hadn’t had a job in over ten years. How did you address that in your interview?

This is what I said on the phone:

“I’m a radical candor person, so I’ll just tell you. I haven’t had a regular day job in over ten years.”

They already had my resume, which was of course an accurate reflection of how I have spent my time over the past twenty years. If I got an offer, they were going to do a full background check. They’d “find me out” one way or another, if they hadn’t already. I figured, if they’re talking to me, they’re interested. I have their attention.

Might as well be myself.

What I never realized when I was younger is that employers don’t care what you did in the past. They don’t even care what you’re doing today.

They want to know what you’re going to do for them going forward.

(And can you convince them that you will?)

It’s really hard to be future-facing when you have doubts, guilt, shame, or mixed feelings about your past performance. This is just as true in the workplace as it is in academia, family relationships, or even clearing out your closets. If you want to move forward, you have to figure out a way to integrate your experiences with your identity.

A fixed mindset will say, Failure is permanent, absolute perfection is mandatory every single microsecond, the way we have been is the way we always will be.

This never made sense to me because it’s unclear where that fixed set of attributes starts. After high school? Because surely we all remember a point when we did not know something that we know today. We were all completely incompetent at something, from tying our shoelaces to driving a car to filing a tax return.

If you learned one thing, you can learn another thing.

That right there is your growth mindset.

Not only CAN you constantly learn new things, but... why wouldn’t you? Why would you ever stop?

Another thing that I said during my interview is that “I’m challenge-driven. I’m motivated by curiosity.” I can’t let it rest with not knowing how to do something. As soon as I realize there is something more to know, I’m going to dive deeper.

This was actually a significant liability in some of the lower-level jobs I had as a young person. What those employers wanted was someone obedient who could be tasked and would cover shift changes or skip breaks with no notice.

This type of organization usually starts out interviews from an adversarial position. They are trying to hide their dirty secrets, usually including high turnover, low or no opportunities for advancement, unappealing benefits, uninspiring corporate culture, demands for unpaid overtime, and at least one supervisor who drives people out the door. Because they have to lie about what they are offering, they naturally assume that new hires are hiding things too.

What are you hiding??

I’ve been asked on interviews:

What is my worst flaw (almost every time)

How I would describe myself in one word (??)

Why I left my last position (almost every time)

Where I see myself in five years

These are ‘gotcha’ questions, as is the sneak-attack “Do you have any questions for me?” Nobody is expected to tell the truth about these lame questions; they’re expected to wear a good social mask and give the expected answers in the acceptable way.

My worst flaw? I’m excessively punctual! I’m such a perfectionist!

How would I describe myself in one word? Dedicated!

Why did I leave my last position? I’m looking for new challenges. 

Where do I see myself in five years? Working here, I hope!

It doesn’t really matter how you answer the “do you have any questions for me” thing, as long as you actually have a question. This time, my question was, “How supported did you feel during the transition to telecommuting?”

What did I do over the ten years that I stepped out of the traditional workplace? I realized that no employer defined who I was or what I could do. I had “F.U. money” and the incredible luxury of never having to take a job that I didn’t want. I started to learn how to think like a professional (someone with a profession) rather than an employee or, worse, a servant.

(What does someone in customer service do? Serve. And what do you call someone who serves? Right).

To be transparent, I am emotionally attuned toward service no matter what I am doing. I don’t really mind doing scutwork or waiting on people. I don’t even care if I have to wait on Rude People because I think it’s funny to return their behavior with gracious courtesy.

Two things change everything about your outlook and your appeal as a prospect:

Whether you internalize the organization’s goals as your own, and

Whether you are very clear about what you bring to the table.

I’m not *asking* for a job from anyone. I am *offering* the option to bring me on board. Nobody wins if it’s a poor fit, if either of us on either side pretend to be something that we are not.

I was an obvious choice for my new job for a bunch of reasons. One was that I had taken the initiative to do a long-term project on spec, and after nearly two years, it demonstrated a great deal about my work ethic, creativity, and ability to adhere to a production schedule. There is simply nobody like me, and nobody else who can do exactly what I can do.

NB: That’s true of you, too (I’m certain of it), but it’s up to you to demonstrate whatever that is.

Another reason I was an obvious top candidate is that I spent my ten years off doing things that did not fit in my prior job descriptions. I built my resume around a list of untraditional, non-clerical skills, including event planning, ideation, and literature search. I had years’ worth of volunteer positions of increasing responsibility, including leading a team, and I had won a bunch of awards. I had felt stymied in my earlier work life, and I had found a ladder up and out.

Your boss and your job do not tell you who you are, what you can and can’t do, or what you have to offer. You do that. If you feel limited in any way, you’re already prepared to launch straight through the roof. You’ve already outgrown what you were doing. Now it’s up to you to decide what you’d rather be doing, and start figuring out how to get there.