My Boss Told Me To Train My Replacement Then Joked In Japanese To The CEO That They’d a Fire Me Right After. Pity No One Told Him I Studied In…
My boss told me to train my replacement while pretending it was just vacation backup, but every strange question from the new guy made it clearer that something much bigger was happening behind my back.
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My boss told me to train my replacement, although he certainly didn’t describe it that way. I knew something was wrong the moment Dylan swaggered into my cubicle fresh out of college, wearing a smug grin and announcing that I was the employee he’d be shadowing. My boss Greg had already cornered me in the breakroom that morning, claiming the company simply needed a little “redundancy” in case I ever took a vacation—but I hadn’t taken one in four years.
I’d barely taken time off at all. I’d worked through a double ear infection and even a sprained wrist because payroll doesn’t stop simply because someone’s having a bad week. So Greg’s sudden concern about vacation coverage didn’t make sense. Dylan wasn’t sitting beside me because management had suddenly become worried about my work-life balance. He was there to learn what I knew.
Dylan made the situation even stranger by narrating practically everything I did as though he were recording a tutorial. When he discovered the macros and reconciliation process I’d built myself, he seemed impressed. What he didn’t understand was how much work had gone into automating the company’s outdated expense-routing system—or how much knowledge existed behind the processes he was casually trying to absorb.
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Then Greg started appearing behind us.
He asked what access level I’d given Dylan for vendor management. I told him read-only.
Greg wasn’t happy.
He suggested I might as well give Dylan full access because he was “gonna need it eventually.”
That single word told me plenty.
Eventually.
I smiled and changed nothing.
If my boss told me to train my replacement, I could cooperate without blindly handing over every key to the company’s financial systems. So I continued teaching Dylan while paying much closer attention to what was happening around me.
And the more carefully I watched, the stranger things became.
Dylan somehow knew where the vendor authorization templates were before I’d shown him. Greg kept checking the timestamps of our training sessions on Slack. Then Dylan casually asked whether we still maintained legacy payroll backups dating back to 2020—and actually winked at me as though the two of us shared some private joke.
We didn’t.
But that question stayed with me.
I continued playing the role Greg apparently expected: helpful, dutiful Ava, patiently guiding the new employee through the company’s accounting systems.
I showed Dylan formulas, approval flows, and the places inside the system that nobody should touch unless they were prepared to answer uncomfortable questions from auditors.
Meanwhile, I watched Greg.
He seemed convinced he was several moves ahead of me.
Then came the company lunch.
Greg chose an upscale sushi restaurant decorated with minimalist styling and bonsai trees, the kind of place he could proudly describe as “authentic.” I arrived early, and CEO Mr. Takahashi followed a few minutes later.
His longtime assistant and translator had been delayed by a flight problem.
Greg saw an opportunity.
He joked that he’d have to rely on his language-app skills and began showing off the little Japanese he knew.
As the meal continued, Greg became increasingly confident. He drank sake, stumbled through simple Japanese phrases, and talked about modernizing the company’s legacy systems.
I stayed mostly quiet, drinking tea and listening.
Greg apparently believed that because I wasn’t participating in the Japanese conversation, I couldn’t understand it.
He was wrong.
And as lunch continued, he leaned toward the CEO and prepared to say something he clearly believed would remain safely beyond my understanding.
