Once you feel you’ve almost managed to convince your boss, he might need an extra push to be convinced that there is no risk to the company or him.
To put his mind at rest, suggest that you be allowed to do it on a trial basis for anywhere between 2 weeks to a month and let him reassess you once the trial period is over.
If at the end of the trial you don’t meet performance standards, then he has the right to revoke your teleworking rights.
At this stage, you are putting all the pressure on yourself to perform and any failure of the teleworking agreement will be your own.
If you boss accepts this, pack your stuff and head on home.
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