Should you stay or should you go? Before deciding, it’s a good idea to go on a (subtle) information-gathering mission to determine whether quitting your job is the best decision for you. You’ve probably spoken to a trusted work friend or two about it — but picking the brain of your boss is the best source of insights.
Why? Because if you’re craving a change, it’s important to understand why you’re craving it in the first place, as well as whether your current job situation can fulfill your needs. And your boss holds some answers that can help clarify the latter.
“Before considering quitting your job, it’s crucial to identify why you’re unhappy or what you’re seeking elsewhere. Is it wanting a higher income, a different team environment, a better work-life balance? Knowing the root of your questioning about whether to stay in your current job will allow you to develop important questions to ask before quitting,” says Mason McSpadden, Vice President of WELD Recruiting.
“If it’s a factor that can be changed, then it’s worth taking the risk to ask for that change. Chances are, if you’ve performed well, the company and team won’t want to lose you, so they’ll be willing to negotiate to keep you on board. If you’re confident in knowing what it is you want, then if you ask respectfully to help your decision of staying or looking for a new job, it can only help you.”
In other words, you don’t know what you don’t know, and knowing more can only help inform your choice to stay in your current job or jump ship. However, think twice before marching into your boss’ office and making your intentions of potentially leaving known.
If you do end up staying, it might change the dynamic of your relationship and even lead your boss to consider your commitment.
And if you leave, you’ll want to make sure the transition is smooth. So it’s best to ask your boss subtle questions that will support your decision-making process, without being blatant about where you’re at.
Here are five questions to ask your boss for more clarity — minus any awkwardness.
1. In Your Opinion, What Was the Best Part of the Project I Just Completed?
Asking this question is basically asking for feedback, so it won’t betray your intentions of potentially quitting. And it’s particularly insightful because it’s a specific, qualitative way to gauge where you stand in the eyes of your boss.
“The more clarity you have about your unique value-add to your company, the easier it is to make the decision to stay or to leave. If your contribution is being celebrated and respected, especially by upper management, then you may opt to continue to rise within your existing organization,” says coach Randi Levin, who specializes in life transitions and reinventions such as career switches.
2. Where Do You See Me in the Next 5 Years?
Switching jobs is a big decision — and it should be based on your longer-term vision. To avoid falling into the trap of short-sightedness, it’s crucial to wrap your head around the paths that may or may not be available to you in the future.
“This type of question is valuable because it clarifies your position within the organization and helps you plan your future with/without your current company,” says Damian Birkel, Founder & Executive Director of Professionals In Transition®.
“Ask your boss questions that fine-tune how you can best grow within the organization. Part of your stay or go decision-making should circle around how much you like and support your current company and company culture, and, in turn, how they best support you. Where will your best opportunity be?” says Levin.
3. What’s Next for You?
Flip the script by prompting your boss to reveal more information about her own plans, which can reveal a lot about any interesting opportunities coming down the pipeline.
“Ask your boss what they are planning next. People love talking about themselves and likely, your boss is no exception. If your boss has an exit strategy, perhaps you should too. Or perhaps you should be building a plan to take their place when they leave,” says executive coach Erica McCurdy.
4. What Do You Think the Company Will Look Like After We Ramp up Our Hiring?
You can also gather facts in a subtle way by asking your boss hiring-related questions.
“If your boss can’t give you a viable commentary on their hiring plans, you may be stagnating in your career. The options you have outside of the company could be more fruitful, compared to staying in a company that doesn’t have a vision for its employees’ futures,” says Brad Touesnard, Founder & CEO of SpinupWP.
“On the other hand, realistic plans that involve you, particularly in a managerial or department-building role, are a more positive sign. Essentially, you want to know that your boss has plans for growth, and where you’re located within them.”
Besides giving you a better idea of advancement opportunities ahead, this question can also help you figure out whether you’ll get more support anytime soon if you’re overworked.
“One of the most common reasons for quitting is feeling like you have too many responsibilities. While delegating is a great option, sometimes it is impossible to do so, most especially when there is no one to delegate it to,” says Stacey Kane, business development lead at EasyMerchant.
5. Are You Planning to Shift To In-person Work Again?
Are you considering remote-work arrangements in your decision-making process? If so, you might want to ask pointed questions to find out more about your organization’s plans post-Covid.
“As situations bounce back to normal, a lot of companies are planning to reinstall the workforce at the office. If you’re comfortable with remote work, this information will help you crystallize the decision to switch to a job that is entirely remote,” says Jon Buchan, CEO of Charm Offensive.
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Anouare Abdou is a career expert, writer, and entrepreneur who started her career as a lifestyle journalist before stepping into leadership roles at publications like AskMen and Goalcast. From managing editorial teams to producing video content and leading business operations, she has tackled various challenges in digital media and discovered her passion for management in the process.
She believes your Mondays should feel as exciting as your weekends and has helped dozens of people pursue their dream careers through mentoring and writing.
Abdou loves to offer her expertise in writing about career-related news, advice, along with helpful tips and tricks in business. Her work has been featured in Ladders News, Business Insider, Thrive Global, and more.