How to Answer the “Why did you Leave your Last Job?” Question when you Left under Questionable Circumstances

By Jack J. Kelly


You gave the new job your best shot, but ultimately felt the need to cut your losses. The opportunity seemed great, the boss was charismatic and charming, the company is well-respected, and the rest of the team appeared like good people to work with and learn from.  Unfortunately, over time, it turned out to be a highly toxic environment.


The once seemingly good-natured boss turned out to be an overbearing, bullying, micromanaging, vindictive, mean-spirited, and downright awful person.  The manager attracted the worst sorts of employees; they gossiped, talked behind everyone else’s backs, thwarted each other’s internal growth, and generally created drama and misery. So, rather than ruin your health and become trapped in a horrible situation, you tendered your resignation. For the first day, it was liberating and you felt that the weight of the world was lifted off your shoulders. After another day or so, you started to get anxiety attacks over how you can tell this story to future hiring managers without sounding bitter, angry, or ungrateful. You may even start thinking that you were the problem and no one will want to take the chance of hiring you.


Hiring managers and human resources professionals are curious about those who leave a company without another job, as it raises a red flag. They think that if someone walked away from a steady salary, there must be more to the picture. Maybe the person left before he was fired? Perhaps, he was fired, but not telling the truth? Was the applicant really the bad guy in the story? Will you be a high-maintenance employee and start complaining about everyone at the new company?


Similarly, employees that were terminated for cause, laid off for various reasons, permitted to resign or left under a cloud of questionable circumstances all need to take time to prepare a game plan on how to tell their story. You can’t just walk into an interview and blurt out that you were let-go without offering some color, context, or putting a positive spin on the situation. You need to be properly prepared with talking points.


Here is an example of what you could say to a perspective employer:


“I’d like to share with you why I left my last firm. As you can see from my resume, I have been with only a couple of companies and have been with each place for over an average of six years.  I consider myself a loyal, dedicated, and hardworking employee. If I were to receive an offer from you, I would love to plant roots and stay here for the long term. I would like a home and the ability to learn and grow.

While it started out well at my last company, I soon realized that it was not the right cultural fit. Given that I worked at several other places prior to, I was fortunate enough to have something to compare this experience with.

The manager and team’s style and manner of interacting was different than the way it was described to me during the interview process. Sensing that this would not be a long term viable situation, I thought the fair thing to do was to leave.  I felt that, although it would put me in a tight financial situation and making interviewing difficult, it was a more ethical thing to do rather than go through the motions at the company only to show job stability. I thought that would be unfair to the company and its employees if I stayed, even though I knew my leaving would create challenges like the conversation we are having now.

I view this as a positive development, as I am now free to interview.  I’ve learned to be very careful and cautious about choosing my next position.  That’s why I’m so excited about this opportunity. Everyone seems smart, nice, caring and the position is perfectly tailored to my background. If I didn’t leave my last job, I never would have known about this great job.”


This is only an outline and you would need to massage your message based upon your own specific situation.


Be forewarned, you will be scrutinized more closely by everyone you interview with.  The interviewer will know that you have a prepared speech to explain what happened at the last company, so they will probe, dig deep, and try to catch you in a lie. Don’t take it personally or get offended. They are protecting their own butts. Nobody wants to be the person who gave the go-ahead to hire an employee with alleged issues- out of fear that they are bringing aboard a headache.


Be prepared that hiring managers will ask you about the terms of your departure in an empathetic and sympathetic manner. They will appear genuinely sincere and caring. You’ll feel the need to open up and vent about how much of a jerk your boss was.  Don’t fall into that trap. I have watched this movie play out a ton of times. The candidate feels comfortable, let’s down their guard, and becomes way too chatty about everyone and everything that happened at the last job.  You may feel a temporary relief that you got it off your chest and think that the interview went well. The feeling is short-lived, as your recruiter gets a call from the hiring manager saying, “I liked your candidate. He seems like a nice guy, but he couldn’t stop trash talking his last boss. If he did that to her, he’ll do that to me next. Thanks, but no thanks.”


The good news is that once you obtain the next position, if you stay there a while, it will be easier the next time you move. If you were only at the prior firm for a very short time period you could potentially leave it off the resume.


If this helps, as an Executive Recruiter with over 20 years of experience, this scenario happens very often. You may not realize it because people don’t like to talk about it. They brush it under the rug and pretend it never occurred. I would venture to say that if someone has been in the workforce, especially in a pressure cooker field such as Wall Street (with big swings in the ups and downs), the overwhelming majority of people with 15-plus years of experience have experienced a layoff, been restructured out of job, fired, left before they were fired, quit due to a toxic situation, or for some other miscellaneous reason.


If you stay positive, motivated, and refuse to let one bad break derail you, you will ultimately succeed.  Once the wound heals, it will be a good learning experience to critically judge others before you join a company and conduct extensive due diligence on all the people that you will be working with.



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