We’ve all been in that awkward situation in which the person we’re talking to has something unpleasant (disgusting) about their person. The question is, do you say something?

First, you have to figure out if someone can handle truth. Let’s face it, there are a lot of fragile egos out there and even the most delicate comments can sour a good rapport if you don’t tread lightly. But if you’re not sure, put yourself in the other guy’s spot. Chances are, 9 times out of 10 you’d want someone to tell you what’s wrong rather than walk around like a jerk all day. You just don’t want to be embarrassed in the process. Suffice it to say, as with anything, it’s all in the execution.

I write this coming off a lunch exactly where the best and worst examples happened. I swear, you can’t make this up.

I finally get a lunch with this whale. Scratch that, the guy is his own ecosystem. And I get the lunch because, as usual, somebody knows somebody who sets it up for me. I decide to bring not just my boss, but also my boss’s boss, figuring this is someone who needs to know he’s got top dog attention.

Anyway, we’re in Boston at one of those places you don’t even know unless you know. Everything is perfect. And then it happens: Keiko has practically got a garden growing in his jaws. It’s actually to the point of distracting. So I wait until my boss is looking down at his food and without saying a word I point to my mouth and nod my chin upwards at him. He takes the cue, excuses himself and comes back groomed as a whistle, looking happy and confident.

A few cocktails later, our man has got some of the blueberry dessert blacking a gaping whole into his front tooth. My idiot boss, feeling too comfortable, interrupts the conversation bluntly and points to the guy’s mouth (practically touching him) and says, “You gotta little something there friend.” Mortified, our man throws his napkin on the table with a “for Chrisssake” guffaw and storms to the men’s room. When he comes back, he looks at my boss like a wasted homecoming queen and says, “You get the check yet?”
From there on out you’d think it was all me and him, my boss effectively on the sidelines. Remember: Networking is about respect. You have to show it in even the smallest gestures if you mean it, no matter how many cocktails into the deal you are.