Dear Crabby,
I’ve been managing credit and collections for many years and generally feel confident handling difficult customers. But I’m currently dealing with a situation that leaves me unsure where professionalism should end and discomfort begins.
One of our past-due long-time customers, an older gentleman, always pays, but never on time. Over the years, he has also become increasingly personal in his communications. Most recently, he sent me a box of chocolates for Valentine’s Day. While the gesture was polite and not overtly offensive, it did make me feel uneasy. I’m trying to keep things friendly so the payments continue, but I’m not sure where the red line should be. How do I manage this without jeopardizing the business relationship?
Feeling Uneasy
Dear Uneasy,
You are not alone, and you’re not overthinking this. Situations like yours live in a gray area that many credit professionals quietly navigate but rarely discuss. When a customer consistently but reliably pays late, they often lean on familiarity and goodwill to soften accountability. Sometimes that shows up as extra friendliness, emotional openness, or mild flirtation. It’s not enough to file a complaint, but it’s still enough to blur professional boundaries. The chocolates are a symbol, not the problem. The real issue is whether personal gestures are being used, consciously or not, to deflect from late payment behavior.
Credit managers often feel pressure to “roll with it” because the payment eventually comes in. That instinct is understandable, but it comes with a risk. Over-personalized communication can quietly shift the power dynamic, making it harder to enforce terms later. The moment you feel hesitant to press for payment because you don’t want to seem rude, ungrateful, or dismissive, the line has already started to move, and not in your favor.
Some common signs that a customer relationship is drifting into uncomfortable territory include:
- Gifts or gestures that go beyond standard business courtesy
- Compliments unrelated to work performance
- Repeated references to personal life, loneliness, or emotions
- Humor or flirtation that feels one-sided
- Payment conversations that quickly pivot away from dates and amounts
Individually, these behaviors may seem harmless. Collectively, they can undermine clarity and control.
So how do you respond without escalating the situation? One approach is gentle redirection. A light, professional response, even with a touch of humor, can reset the tone without embarrassment. For example, thanking the customer for the gesture but immediately pivoting back to the invoice and payment date sends a clear signal. Humor works best when it reinforces boundaries, not when it avoids them. A brief line such as, “The chocolates were kind and now let’s make the payment just as sweet,” keeps things friendly while refocusing the conversation.
In some cases, however, honesty is more effective than humor. If the personal comments continue or begin to make you uncomfortable, it’s entirely appropriate to state your preference clearly and calmly. You don’t need to accuse or explain. You simply reinforce that you need to keep all communication professional and payment focused. Most customers will adjust once boundaries are articulated. Those who don’t are often the ones most dependent on blurred lines to maintain late-pay behavior.
Bottom line: professionalism is not coldness, and boundaries are not hostility. You can be courteous, empathetic, and effective without allowing personal discomfort to become the cost of getting paid.
Stay firm, stay professional, and don’t let chocolates replace cash.
Crabby
Dear Crabby is a credit, collection, and human resources advice column by Nancy Seiverd, President, CMI Credit Mediators Inc. Your thoughts and comments (nseiverd@cmiweb.com) are most welcome!
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