It's a pain to administer your bonuses on an excel sheet.  It's time consuming for your admin staff, and if they're being honest, it's easy to forget if someone has left the organization, meaning hundreds of thousands of dollars of unearned bonuses walks out the door every year. 

If your team is honest, they'd rather not spend valuable time managing, tracking, and trying to collect on outstanding debts owed by ex-drivers.  There's a lot of other time-sensitive tasks they'd rather focus on

Even in situations where your team remembers to ask for a signing bonus back if an employee leaves early, you have no recourse if the ex-employee decides not to repay the obligation. 

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It's generally not worth it to pursue these debts in small claims court individually - but collectively, these losses can be substantial. 

For an industry that is increasingly scrutinized for taxes related to owner-operators, firms need to conform tightly to tax and regulatory requirements.

If you want to be able to deduct signing bonuses from other wages owing to the departing employee, you will need to document the bonus as forgivable “loan” to comply with Employment Standards restrictions on deductions from wages. Chances are you aren't doing this, due to the complexities of managing this process.