Before my current position, I would have said no. It is not only not possible, but ill-advised.
Now, I work in a two person department. My supervisor and I regularly (at least every couple of months) go to lunch together. Sometimes we talk about work, but mostly we talk about other things. It is an opportunity to connect without the prying eyes and eavesdropping ears of our co-workers. It’s relaxed.
Knowing this was an anomaly from my previous experiences, I asked around about how other people view going to lunch with the boss.
On friend had two very different stories to tell.
“I was working for a women’s lifestyle magazine in St. Louis. It was very about looks, and appearances, etc. I was broke, a graphic design graduate, and definitely not looking “the part” at a women’s lifestyle magazine where everyone looked like this. One day my boss (the guy) came and asked if we could go to lunch (out of the ordinary). He took me to a super healthy restaurant and proceeded to pick out my meal and stare at me as if to say “are you going to eat ALL of that?” It was the most torturous experience and I felt horrible about myself for the remaining four months I worked there. I was broke and hungry all the time.”
Yikes! I have no idea how I would handle that situation. Luckily, the other lunch with the boss situation was much better.
“I was hired for my current job over lunch with my boss. He took me out to offer me the job and it was the best lunch I’d ever had (it was just McCallister’s). We talked about my ideas for the position and what we thought we could do to expand. It was really great having someone actually interested in what I thought I could do, and what my experiences were. It was a great preview of my position and what was to come.”
I think the takeaway from the above situations is that a lunch with your boss can give you insight unavailable in the every day office setting.
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