If You Don’t Like Your Boss’s Answer to These 5 Questions, It’s Time to Quit

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.

Here are five questions to ask your boss for more clarity — minus any awkwardness.

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.

1. In your opinion, what was the best part of the project I just completed?

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.

2. Where do you see me in the next 5 years?

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.

3. What’s next for you?

You can also gather facts in a subtle way by asking your boss hiring-related questions.

4. What do you think the company will look like after we ramp up our hiring?