I hear yelps from the Water Cooler Area that the Boss plans to have me accompany her to a dog show in New York for fun. That means I might be out of the office for a few weeks, as I’ll need to put on the dog a bit before the big event.  So the big question is:  Can she deduct the food, grooming costs, and both our travel expenses for the trip on her tax return?

If she tried, there might be some growling from Uncle Sam’s corner, and the Boss might be commanded to sit and stay while Uncle Sam’s auditors drool over the firm’s books.

Why?  It’s true that I’m the bone-a-fide Assistant Office Manager of Law Offices of Christy Lee, P.C.  It’s also true that I’m a valuable member of the work force who regularly gets praise for my quality product.  So I’ve probably earned that first-class ticket to the Big Apple.

But it wouldn’t be wise to consider the trip totally tax-deductible because the experience wouldn’t necessarily be work-connected, even if I am her Assistant Office Manager.  So writing off the costs could trigger an audit.

How could the Boss legitimately claim at least some of the trip’s expenses without raising Uncle Sam’s hackles?  For starters, we could do the mandatory circles of paw-pressing at professional events. The Boss could, say, enroll us both in on-site training seminars for office administration, where, no doubt, she would ask the speakers to teach me that jumping on clients’ legs is a far too effusive way to greet them.

And if she can keep me from chewing up the receipts showing the fees for the training, the Boss could satisfy Uncle Sam’s appetite for evidence of expenses.  With the money she saves on tax liability, the Boss might be tempted to throw a few extra treats my way.