How To Talk About Work With Your Family

We’ve all been there. Usually, sometime after turkey and before the game starts, when the uncomfortable silence starts to descend upon a living room full of people who want to believe they know each other better than they really do, we ask the question, “How’s work going?” Because hey, we’re family, and we’re desperate to pretend we have a handle on or even care about what our second cousins do for a living. Also, we don’t really know what else to talk about. The most common response is “good,” followed by an excruciating 20-second pause before some innocuous detail is thrown in to either shut the conversation down or open the door for more meaningful interaction. 

I am advocating for the latter and here to show you the way. Here are some quick pointers that can help you make conversations about work with your family just a little bit less awkward. 

  1. Take An Inventory: Prior to arriving at grandma’s house (or logging onto zoom) think through each of your family members and take a pulse on how much you know about what they do for a living. Do you know their occupation? Who their employer is? How long they have been there? Whether or not they like their job? It’s a simple exercise that will show you how much or how little you actually know about your extended family. 

  1. Ask Open-Ended Questions: “How’s work going?” No. Get more specific. For example, “What do you love about your job?” or “If you could make a career change, what would you do?” Stay away from questions that will remind them of their disappointed parents like, “What’s your plan for the next five years?” Most people don’t have a plan and, this year more than ever, are just plain exhausted. Bonus tip: be careful not to ask questions that you really just wish everyone would ask you. 

  1. Don’t Discriminate: So cousin Johnny is building rockets for Space Force and uncle Greg is managing a Dairy Queen. I get it. You really want to hear about how the rocket building is going and are less interested in how to make a blizzard. Do your best to give everyone equal attention, regardless of how sexy/unsexy their job is. The reason behind asking genuine questions about work is to show your family members you care about who they are, not so much what they do (or don’t do). 

  1. Underpromise and Overdeliver: Don’t make a promise you can’t keep. If your nephew is looking for a new job don’t volunteer to help if you’re not sure you can. Otherwise, you can bank on daily text messages just checking in for an update for the next 6 months. If your sister-in-law is raising money for a start-up don’t give her any indication that you’d back it if you’re not confident she can execute. It’s better to surprise someone with help than for them to be waiting around for you to deliver.

When the conversation turns to how things are going for you on the work front, stay humble if things are going well and stay positive if things are not. During the holidays, families parachute into each other’s lives and fight like hell to make up for lost time. For many of us, the holidays are the only time we will see our extended family in a given year. Because it is impossible to give someone a full picture of your work life, be wise in what you share and what you don’t. You could be coming off a rough week in the office and share something as harmless as, “things have been tough recently,” then your grandma immediately assumes you’re homeless. Or, you could tell folks that it’s been a great year only to get shaken down at the dessert table for a personal loan to your Aunt. Be wise and keep the focus on other people. That’s a pretty good way to show anyone that you care. Go get ‘em.