Q: I’m a director-level operations and HR leader at a small start-up. My boss, whom I have known for many years, is currently pulling triple duty as COO, CFO and general counsel. Thanks to his diligence over the past few years, we are finally making solid revenue with lean operating expenses, and we have started adding new hires.

I love my job and my co-workers overall, and I make decent money, but I hate interacting with my boss on certain financial matters.

We have a small-items expense policy that allows employees to purchase certain low-cost items with fast reimbursement. Larger expenses are generally charged to our corporate card after an approval process. Over the past few years, my boss has repeatedly tried to have me expense larger purchases, recently as much as $1,500, using my own credit card — presumably to simplify bookkeeping.

I always push back, but the conversations leave me feeling humiliated. I’m a Black man with not the greatest credit score, living on a tight budget, and although my boss is an ally who tries to drive diversity and inclusion, it feels like a “white privilege” issue that he assumes I somehow have liquidity to cover these purchases.

I’m also worried about how this affects new employees. Some senior employees are fine with charging an $800 purchase for reimbursement, but it could be a hell of a hit to a junior hire. And that’s not the culture I want to build for this team.

We have performance reviews coming up, including upward feedback. I’m thinking it’s time to have a hard talk with my boss about this, and I’m terrified. This expensing issue is the one thing that has ever made me consider leaving this company.


A: “Come on, you know I don’t mix business expenses with personal ones.” Delivered firmly, with a smile, every time.

Employers should not be floating operating expenses on their employees’ backs, no matter how much those employees earn, or how they spend it. Your paycheck is not a slush fund for your employer to dip into to keep its books balanced.

If a start-up’s founder chooses to take on a hefty business expense, that is one thing. But no employee should be asked or even subtly pressured to do the same for management’s convenience. What if reimbursement is delayed and the employee has to pay interest? What if the expense isn’t approved for reimbursement, or the company suffers a catastrophic (cough-pandemic-cough) setback?

Fortunately, your company’s expansion plans offer the perfect opportunity to discuss tighter policy enforcement, for everyone’s protection: “Now that we’re ramping up hiring, I think we should firm up our expensing policy and small-items limit to make sure everyone’s going through the appropriate approval and documentation channels.”

If that policy is too restrictive and cumbersome, you might discuss broadening access to the company card to a wider group of managers — but always in conjunction with formal policies that ensure everyone is operating under the same rules.

You don’t need to reveal your personal financial situation, but you can use it to help you express and inspire empathy for others in similar straits: “We need to ensure all our managers and employees have equal access to the equipment and resources they need to do their jobs. We don’t want anyone feeling pressured to spend their own money, or concerned they or their team will be at a disadvantage because they can’t afford big-ticket items outside the approval process.”


Incidentally, if your boss is truly open to hearing upward feedback, it might be worth asking whether some of his planned hires should be at the executive level.

Start-up leaders frequently wear multiple hats to stay nimble and avoid making the company top-heavy with highly paid executives. But as the company becomes more established, so should the boundaries between its finance, operations and legal departments – to avoid overloading your boss, and to prevent the temptation to cut corners and fudge numbers.

Finally, you should not feel shame or any need to justify being unable or unwilling to cover your employer’s expenses. People with spotless credit scores and fat savings cushions are the exception in this country, and while poor money management is a popular scapegoat, many other causes are beyond individual control, including medical expenses; unemployment; rising cost of living; and decades of redlining, predatory lending, and other economic practices that have disproportionately targeted and depleted the wealth of generations of Black and Latino communities. Those of us with the luck or resources to have avoided or overcome those obstacles can still empathize with those who have not, but sometimes we need a nudge from someone in a position to speak truth to privilege.