Tough Interview Questions: Tell Me About The Most Boring Job You’ve Ever Had.

Tell Me About The Most Boring Job You've Ever Had

If you’re an established professional, it’s unlikely that anyone will ask you this question.  It tends to be geared toward less experienced people; after all, the interviewer doesn’t have a lot of benchmarks for figuring out whether to hire someone junior so they look for ways that you will disqualify yourself.

There are 2 ways of answering this question.  What most people actually do is talk about a job.  If you do that, you talk about something when you were much younger.  For example, in my case, I would talk about something when I was in high school and worked as a messenger.  I would talk about how boring it was to arrive at someone’s offices to pick up an envelope and bring it somewhere else.

The issue with answering the actual most boring job is that firms start to think of you in the context of being “the messenger guy” Or some other demeaning way of thinking of you.  As a result, it is an undesirable way of answering the question.  However, if you’re not comfortable using this next approach always talk about something when you were much younger.

The second way of answering this question is very slick, smart, and allows you to sell yourself In unique ways.  Thus, when you are asked about the most boring job you ever had, you respond by saying, “Huh.”  Then you start looking like you’re thinking about your answer because you have to remember that interviewing is a certain amount of theater and acting associated with it.  You never want to seem like you are so rehearsed that you have all these answers at the tip of his fingertips; you always want to make it seem like you’re thinking about things as though it is the first time you’ve heard this “brilliant question.”

You pause for a second and say, “Huh. (short pause)  When I think about it, I don’t think I’ve been bored at a job that I’ve ever had.  Maybe it goes back to the philosophy that I have that it’s kind of like being an actor where there are no small parts.  Every job has relevance and meaning to it that I have to figure out.  Even some positions that others might consider a menial job, I always found purpose and drive and determination to do it.” 

Then you give an example of a job that you had that might seem to this person much less than where you are now and how you worked hard and were diligent and putting effort and yielded a great performance, became an example for the team, yadda yadda yadda.

Always try to make “lemonade out of the lemon” is the philosophy here.   Always talk about how you did not fall prey to the prevailing wisdom of this being a dull boring job.  Instead, what you did, was put in your best effort because every job has a purpose to it.  You are hired.  You are paid.  They want your best effort and that is what you give.

Ⓒ The Big Game Hunter, Inc., Asheville, NC 2020



Jeff Altman, The Big Game HunterJeff Altman, The Big Game Hunter is a coach who worked as a recruiter for what seems like one hundred years. His work involves career coaching, all as well as executive job search coaching, job coaching, and interview coaching. He is the host of “No BS Job Search Advice Radio,” the #1 podcast in iTunes for job search with more than 1800 episodes, and is a member of The Forbes Coaches Council.

Are you interested in 1:1 coaching, interview coaching, advice about networking more effectively, how to negotiate your offer or leadership coaching? Schedule a free Discovery call.

If you have a quick question for me, you can get it answered with a 3-5 minute video at Want to do it live? offers great advice for job hunters—videos, my books and guides to job hunting, podcasts, articles, PLUS a community for you to ask questions of PLUS the ability to ask me questions where I function as your ally with no conflict of interest answering your questions.  

Jeff Altman, The Big Game Hunter
Jeff Altman, The Big Game Hunter

Connect with me on LinkedIn. Like me on Facebook.

Join and attend my classes on Skillshare. Become a premium member and get 2 months free.

Watch my videos on YouTube at, the Job SearchTV app for FireTV, Roku or a firestick or for AppleTV and 90 smart tv platforms.

You can order a copy of “Diagnosing Your Job Search Problems” for Kindle on Amazon and receive free Kindle versions of “No BS Resume Advice” and “Interview Preparation.” If you are starting your search, order, “Get Ready for the Job Jungle.”

Would you like to talk through a salary negotiation or potential negotiation you’re involved with? Order and schedule time with me.

Do you have questions or would like advice about networking or any aspect of your search. Order and schedule time with me.

Would you like me to critique your resume? Order a critique from me

Jeff’s Kindle book, “You Can Fix Stupid: No BS Hiring Advice,” is available on Amazon.




About the author

Leave a Comment, Thought, Opinion. Speak like you're speaking with someone you love.

%d bloggers like this: