"Is it Strange that My Boss Invites Me to Lunch Once a Week?" - 08/14/19 Edition
Stephen Says Column
Dear Stephen:
I am not sure if this is a weird question or even out of the norm, but here it goes. I’m an outside sales rep for a medium-sized manufacturer in a major city calling on end users and dealers. I report to a regional manager in our local office. About nine of us are in this region, including sales reps, showroom managers, assistants and some A&D people. All pretty standard, Furniture 101 stuff. We have been consistently at goal for all three years I have worked here. I am 29, and I certainly see a future at my current company. I like my boss, but at least once a week, he asks me out to lunch.
At first, this didn’t seem like a problem. My boss has long had a habit of taking his employees to lunch on a rotating basis. It seems like a good way to build rapport and get to know the people working under him. Lately though, it seems that his efforts in this regard have been focused directly on me.
To be clear, I am very sure this is not any kind of sexual or Me-Too scenario. Both my boss and I are straight males. He is married with kids, and I have been in a committed relationship for two years now. His interest in me seems entirely professional, if not social. It is a bit odd, though. At first I was flattered but now we are a few months in, and I find myself being asked to lunch more and more. My boss is a good guy, he has always been fair and compassionate with the employees. I just can’t seem to figure out what he wants.
Here is my question: I am concerned he has some kind of ulterior motive. I think maybe he is looking for gossip on other employees in our team and has somehow pegged me as the guy to mine for that sort of information. Do you think this is possible? Should I be concerned my coworkers think I am brown-nosing the boss to their detriment? Should I find a way to make the lunches stop? Please help me out.
Signed,
Is There Really a Free Lunch?
Dear Free Lunch,
My gut reaction is that you are overthinking it, and this is one big, fat nothing burger. (All lunch puns intended!).
My experience is that regional sales managers and VPs who are smart often take employees out for lunch or breakfast. It reminds me of a book by one of my friends and a fellow author, “Never Eat Lunch Alone” by Keith Ferrazzi.
Bosses want to keep in touch with what is going on in their division, and it is true they might at times select one or two salespeople who might end up telling them exactly what is happening behind the scenes without even knowing it. You seem to think this isn’t you but the next time you go to lunch, act as you normally would and then afterwards, take a moment to reflect on the conversation and consider what information you may have revealed.
Bosses want to keep in touch with what is going on in their division, and it is true they might at times select one or two salespeople who might end up telling them exactly what is happening behind the scenes without even knowing it.
Here is my suggestion, why not casually suggest to your boss that some colleagues are jealous of your exclusive lunches and then see if you can get one or two of them invited in for the next time? It simply may not occur to him that he is playing favorites. Or it may just be that he feels the two of you may have a good relationship and what I call “similareating” patterns. For instance, I’m a fast eater and like to eat with other fast eaters as well. A vegan might want to eat with another vegan, and nobody wants to eat with people who make a thousand special requests and augmentations to their order. You get the idea.
The bottom line: Don’t overthink it. That being said, having lunch with your boss once a month is normal, once a week is a lot. You are in sales, how in the world do you have time with your boss once a week! The next time your boss asks you to come with him down the street for a bite, you better tell him you’ve already got a Lunch & Learn scheduled with a client. If not, one of these lunches is going to end with you getting kicked out the door because you’re not selling enough and over lunching with your boss!
Best,
Stephen
You can send your workplace questions to Stephen at: StephenSays@bellow.press
Questions selected to be answered, will appear in this column. Please use the Subject: Stephen Says for all emails. Stephen Viscusi is a bestselling author, television personality, and CEO of The Viscusi Group, global executive recruiters located in New York. Follow Stephen on Twitter @stephenviscusi. Like Stephen on Facebook and follow him on LinkedIn.

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