Not every job or employee is meant to last forever. The hardest part? Recognizing when it’s time to move on—whether you’re the one considering leaving or the leader realizing it’s no longer a fit. Staying too long in the wrong situation doesn’t serve anyone. So, how do you know when it’s time?
For Individuals: Signs You Should Leave
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You’re Not Meeting Expectations. If you’re consistently struggling to meet the role’s demands despite effort and feedback, it may not be the right fit.
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You’re Not Excited by the Work. A bad week is one thing. But if you’ve lost all motivation and no longer care about what the organization is working towards, that’s a red flag.
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You Disagree With the Vision. If you fundamentally don’t believe in where the company is headed, it will be hard to stay engaged.
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You’re Unwilling to Engage. If you’ve stopped asking questions, seeking feedback, or working on professional growth, it might be time to move on.
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Your Gut Says It’s Time. If you wake up dreading work daily and feel more relieved than uncertain at the thought of leaving, listen to that instinct.
For Companies: Signs an Employee Should Leave
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They Can’t Meet Expectations. If someone continuously underperforms despite continued support, they may be in the wrong role or company.
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They’ve Checked Out. A disengaged employee who no longer contributes meaningfully affects morale and productivity.
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They Don’t Align With the Vision. If they regularly challenge or resist the organization’s direction after several conversations, it may not be the right fit.
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They Refuse to Grow. When an employee isn’t willing to take feedback, learn, or develop, they’re choosing to remain stuck rather than progress.
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The Team Is Carrying Their Weight. If others are constantly compensating for their lack of performance or engagement, it’s time to re-evaluate their place in the company.
Reflection Questions
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For individuals: If nothing changed in the next six months, would you still want to be here?
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For companies: If this person applied for the role today, would you be excited to (re)hire them?
Recognizing when it’s time to leave—or let someone go—is tough. But the longer you hold on to something that isn’t working, the more it costs everyone involved. It holds the individual back from using their talents to the best of their ability and it blocks the organization from finding someone ready to invest in the mission. Consider where you can create more freedom for everyone.
