Should I tell my boss I’m quitting before landing another job?

Dear Ismael,

How do I tell my boss I am quitting? I have worked for my boss for over three years now and we have a great professional relationship. Recently the company has gone through changes that do not align with my professional needs so I am looking for another job.

I am worried that this will ruin our professional relationship because I am essentially leaving her company when she needs me the most. How do I tell her I need to find another job? Do I tell her before I start applying elsewhere?

— Nothing Personal in West Loop

Dear Nothing Personal,

Trust is a dangerous belief to have in business.

No matter how great of a relationship you think you have, you should never tell your boss you are quitting point-blank until you have secured another job. And if your gut instincts are telling you she might not take the news well — because the timing isn’t great — err on the side of caution.

I’ve heard of people being walked out the door right then and there, and other stories that made me doubt if some bosses have our best interests in mind.

A professional horror story

I once had a superior who told me an interview experience that’s stayed with me forever.

She had interviewed a candidate, and they both hit it off. Her perception of the person quickly changed as soon as she called one of the references who didn’t hold back details of the nightmare it was to have the candidate on her team:

“She’s great at what she does, but no one liked working with her.”

My superior was shocked because the difference between both interactions were night and day. But she chose to believe a past supervisor with a passionate warning over a candidate who could potentially disrupt the workplace environment.

I don’t know the backstory. I don’t know if the candidate was wronged by personal feelings others felt toward her or if the previous employer felt a moral obligation to be honest, but I know this: Trust was the main culprit here.

Dropping cues to lessen the blow

While I advise you to not flat-out announce you want to quit, there are ways to let your boss know you are not happy with the direction of the company, so when the news actually drops, it doesn’t come as much of a surprise.

Voice your issues, make clear what you want from the company and follow up with solutions you and your boss can work toward that would satisfy the both of you. If your boss follows up with a proactive plan, great. If you feel like nothing came out of those efforts, that’s your cue to continue your job search.

I understand the pressures of wanting to be selfless, and waiting for your boss to be in a good place before you’re comfortable with moving on, but you really need to put yourself first.

Trust me. I’ve said no to new jobs in order to avoid disrupting my employer’s staffing or its trajectory toward success. It was stupid of me because, once I did leave, it turns out the team and company survived just fine without me. Meanwhile, I had to start from zero looking for opportunities that would get me a better title and salary.

I’ll leave you with something a friend told me, “If your boss is surprised when you say you’re leaving, they probably aren’t a good boss.”

Write to Someone in Chicago at someoneinchicago@suntimes.com.