The Sound Piece of Dating Advice You Should Also Apply to Your Job Search

published Jul 9, 2023
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Credit: Photo: Sidney Bensimon; Prop Styling: Carla Gonzalez-Hart

After going through a tough breakup, hardly anyone would fault you for being hurt and maybe even a little resentful. One way of dealing with unresolved feelings is venting about your ex or comparing new dating partners to your past relationships. The problem is, complaining about your ex isn’t going to help you move on. At least this is what I recently said to a friend who was struggling after a breakup. As soon as the words left my mouth, I realized I was also talking about me. I had just gone to a job interview still fuming about my last employer (and it showed).

No surprise — I didn’t get the job. While it may seem obvious that you shouldn’t complain about your old job while looking for a new one (or talk about your ex while on a first date), you might not even realize that you’re doing it. To help you avoid the same mistakes I made, I rounded up expert advice on how to handle a job search when you’re still stewing about your ex-employer.

Complaining about your old job is a red flag to hiring managers.

A little venting session with a friend or family member can be a healthy way to deal with your emotions. However, if you’re a prospective hire, complaining about a previous job to a potential employer “comes across as unprofessional and negative,” says Ashley Samson, chief of staff at National Business Capital. She still remembers an interview early in her career with a job candidate who had some harsh words about their current employer.

“It felt more like a therapy session than an interview,” Samson says. “The person vented about how toxic the company was, the high turnover rate, and the lack of appreciation as an employee.” She explains that focusing on the negative detracts from the opportunity to discuss your potential for growth within the new organization.

Andrew McCaskill, a LinkedIn career expert and creator of The Black Guy in Marketing newsletter, agrees, saying that a job interview should focus on “how you can bring value and impact to the company.” It’s OK to describe the pros and cons of a previous job when discussing your work history. At the same time, you should “try to speak positively or at least respectfully about your former employer to make a good impression,” he adds.

Credit: Chinasa Cooper

Mistakes happen, but you can still turn things around.

Go easy on yourself if the conversation starts shifting to complaints about your old boss. In my case, I was grieving the death of a family member and wasn’t thinking clearly. When this happens, Samson will politely redirect the conversation to the current job. “Most of the time, job candidates get the hint and shift gears,” she says.

If your interview gets off to a rocky start, “Take a deep breath and focus the conversation on why you’re drawn to this specific company and role,” says Dr. Kyle Elliott, founder and career coach at Even though a job interview isn’t the right place to air your grievances, bear in mind that “most people have had a bad boss and can relate to a difficult work environment,” he says. His advice is to be honest about why you’re looking for a new job without getting into too much detail. Make it clear to the recruiter or hiring manager that you’re committed to personal learning and career growth.

Another strategy to help turn things around during an interview is to match every negative point with a positive statement. “Rather than focusing on what your past employer did wrong, reframe the experience as an obstacle you had to overcome,” McCaskill says. For instance, you can talk about communication skills you developed to solve a problem or time management skills you used to meet a big deadline. “Make sure you’re presenting solutions, rather than just looking back,” he says.

Credit: Tessa Cooper

Negative experiences shouldn’t ruin your chance at a fresh start.

When you’re searching for a new job, consider the skills you’ve gained rather than “focusing only on what went wrong the last time,” McCaskill says. Speaking poorly of a past employer can backfire — especially if they belong to the same professional network as a potential employer. Plus, you might also need them as a reference for future opportunities.

Spend some time reflecting on your last job and what aspects didn’t work for you. “Examine your values, work must-haves, lifestyle priorities, and passions, and outline a plan that includes exactly what you want in a new job — whether it’s more flexibility, higher pay, or remote work,” McCaskill says. He suggests going to the company’s website or LinkedIn page to see if their values and commitments align with yours.

Because you only get one crack at a first impression, “Channel your attention toward the good,” Elliott says. He recommends journaling about positive experiences with your last employer or finding someone outside of your organization to help you process negative feelings. Bad job experiences can stick with you, but they shouldn’t dictate your career path.