How To Tell Your Boss You’re Quitting When You're Friends

As many employees seek better job opportunities, you might be considering spreading your wings and growing your career elsewhere. But what happens when you’re working under a great manager you really like? Kathi Elster and Katherine Crowley of K Squared Enterprises, a career coaching service, have some insight into why you might want to quit your job if you like your boss and how to go about it so that all parties are content.

Why leave if you like your boss?

The Great Resignation has given employees the means and motive to take a leap and search for a new role. However, Elster and Crowley say that for many, hopping on the quitting trend has very little to do with your boss.

“The great resignation was more about individuals realizing they wanted a job that was permanently remote, or they were seeing opportunities for more money,” Elster says.

“We all learned that working remotely and designing a work-life to fit our personal lives was actually possible,” Crowley adds. And now, employees want to continue building a life where they put their needs first.

“Also, the idea of remote is a big one for people,” Elster continues. “If your current job does not allow remote and that is your preference or you have moved, and it’s necessary, then your boss or friend will understand.”

Elster says that, for the most part, employees who are happy with their bosses don’t want to leave their jobs. However, ambitious employees who don’t see a future for themselves in their companies might want to look elsewhere.

Crowley adds that even if one’s boss is their friend or they get along well, employees might realize that they need to grow. And that growth stems from a shift into unfamiliar territory.

“You may like your boss but feel stagnant in your job. Or you may like your boss and realize – as Kathi said — that you want a different work-life, one that allows for remote work or a more flexible schedule,” Crowley continues. “You may also like your boss and decide to go into a different industry or pursue further education.”

Should I really quit?

If you see your boss as a friend or mentor, you could consider staying at your company. But to feel like you’re not being taken advantage of, you need to take a couple of steps to ensure that your needs will be met in your current role.

Step 1: Talk it out

Elster says that if you’re considering quitting your job and having a good relationship with your boss, bring it up with your boss as soon as possible – even if it’s a complicated conversation.

“Let them know that you are thinking about making a change but didn’t want to do anything before speaking to them,” Elster says. She stresses the importance of voicing your preferences with your boss and seeing if they can accommodate you.

“The big challenge here is clarifying what you want and taking the risk of asking for it,” Crowley adds. “It can be challenging to ask for what you really want if you are worried about sounding unappreciative or demanding.”

Step 2: Decide on your final straw

Elster says that the tipping point for many is when you don’t feel like you have a seat at the table or don’t enjoy the work you’re doing anymore. You may also have been dismissed by someone above your manager, making your job more difficult to accomplish.

“This decision can take many people a while – up to six months,” Elster says. “But some people are quick decision-makers, and when they know, they know.”

To Crowley, this process of deciding to quit involves several phases. The first is contemplating quitting, the second is investigating options, and the third is bargaining with yourself.

“Usually, it’s a process where you first try to make the current job work for you,” Crowley says. “ “Maybe this isn’t so bad,” or “maybe I can’t find anything better.” Then you realize that it’s not enough (last straw), then you generate options, then you quit.”

Step 3: Have the conversation

Once you’ve spoken to your boss and are sure that you want to quit, you need to have a formal conversation where you talk about termination. Crowley explains that you shouldn’t see quitting as a negative thing. It’s a natural evolution of one’s career, and your boss will understand that if you’re on good terms.

“Frame your departure in a positive light,” Crowley says.

Unfortunately, regardless of your relationship with your manager, they might be someone whose self-worth is tied to employee retention. They could be hurt, saddened, or even angered by your departure. But don’t be dissuaded from quitting – you’ve got to do what’s best for you.

“Some bosses are offended by anyone who resigns and quickly marginalizes the individual,” Crowley says. “The best you can do is create systems for the person who will replace you and complete as many parts of your unfinished work as possible.”

Step 4: Have an exit strategy

Finally, if you want to know how to quit your job without tarnishing the relationships you’ve built, you should bow out gracefully. On a practical level, Elster recommends giving appropriate leave time, anywhere from two weeks to three months, depending on the job. In that time, she says, create a solid exit plan.

“It’s important to not burn bridges when leaving a job,” Elster says. “Have a plan on how you are going to complete all your work and how the next person can pick up where you have left off. Make yourself available to assist the new person.”