Q&A Should I Get Drinks With My Boss?

Over the course of the next few months, I’m going to be answering specific questions that come into to me. This week’s question came from Instagram (@nikgold) from Alicia. She wrote me, “my boss asked me to get drinks with her after work and I don't know the context of the meeting so I'm not sure what to do and I feel uncomfortable about it. Do you think I should go? By the way, my boss is a female so I'm not worried about anything sexual.”  Listen or read below for my answer.

The tl;dr:

  1. Figure out the intention of the drinks. That will put you at ease. Usually a boss will want to get drinks to get to know you outside of work better.

  2. Building a personal relationship with a boss is a really good thing. It builds trust.

  3. Make sure you act professionally. It’s still work! Don’t drink too much and don’t gossip.

  4. Never feel pressured to drink. You can suggest taking a walk and grabbing a coffee instead.

  5. From my experience as Head of People, sometimes this comes up and there are questionable intentions (i.e. sexual). To test the waters, first give your colleague the benefit of the doubt but make sure to avoid any activity that has drinking involved or is associated with nightlife. Take a yoga class or a walk.

My Full Answer:

So Alicia, you feel uncomfortable about this situation. Let's talk about why you feel that way. It seems to me that you feel uncomfortable because you don't know why your boss wants to have that meeting. You don't know her intention behind asking you for drinks. When we don't know someone's intentions, we get that feeling of uncertainty, which leads to anxiety. Anxiety is simply not knowing what's around the corner and operating in the unknown.

So let's answer this question for you. In my experience, it's a really good thing to have a personal relationship with your boss outside of work. It builds trust and it allows you to work in ways that you might otherwise not be able to. Think about it, if you don’t have a personal tie the context of your relationship is just about projects around the corner. So it can be a really good thing.

I say go out with her and get to know her a little bit more outside of the walls of your office. Now when you're out, it's really important that you keep it professional. Definitely don't drink too much and you know, don't gossip, don't talk about anything that you wouldn't really otherwise it's just a chance to get to know each other more. Don't bring anything or anyone else into that conversation. And if you don't drink that's totally fine. You never need to feel pressure to order a drink and if you don't even feel comfortable going to a bar, which maybe sometimes I wouldn't either! Try saying something like, Hey, do you mind if we just take a walk? I'd love to buy you a coffee instead. Simple as that.

Putting on my Head of People hat, it would be remiss not to mention that sometimes the reason we feel uncomfortable about going drinking with a boss or a coworker is because there may be sexual undertones. Answering a question like that requires much more context, but a really good rule of thumb to live by is to make sure that any first interaction definitely, definitely doesn't involve any nightlife or alcohol, just so that we can understand intention a little bit more before proceeding with any sort of workplace relationship.

If you have a question that you want me to answer comment below or DM me over Instagram.

Nikki Goldman