This set up a ritual, of sorts. I’d go off to one of my kid’s end of school events and I’d send Andrew a photo or a video. At least once, in my zeal, I had my kid thank him via video for letting his pops cut out of work. He called it emotional blackmail. I took this as a joke. And I joked too, telling people it was all a ploy. “If he ever tries to fire me, all he’ll be able to think about are my children crying, ‘Uncle Andrew, why!?’” That wasn’t true, of course. He’d probably have zero problems firing me if I deserved it (Editor’s Note: He doesn’t). Still, I had to wonder, was he really feeling “emotionally blackmailed”? Was I hurting my employment by sharing my family life so freely and directly? Or was I digging some terrible hole from which I could not escape. I’m a reporter, so I reached for the phone. I called Lea McLeod, career coach and creator of the 21 Days to Peace at Work program, to ask. “You never know what goes on in people’s heads,” she told me. Which means that knowing how much you should share requires understanding your boss or manager’s views on mingling work with family. But that wasn’t always the case. Midway through the previous millennium, men were expected to build a wall between family and work. A perfunctory, “They’re fine,” was the only acceptable response to the equally perfunctory, “How’re the kids?” But like everything else in the world, technology has shattered previous norms. “Social media puts everything front and center whether you wanted to hear about it or not,” says McLeod. “If they wanted information on you, it’s really easy to find out pretty much anything, unless you’ve made your accounts private.” Considering that’s the case, active disclosure may seem like over-sharing to some managers. And that could make them particularly squeamish about working closely with employees who are effusive about their family life. “There’s such a revolution happening in the workplace right now,” McLeod explains. “The first thing you need to do is suss out what is the appetite of the manager to be exposed to that information and what is their perspective on it?” On that advice, I sent my boss an email, asking exactly those two questions. “I dig that you’ve got a happy home life and I like to hear about it. I especially like when you send videos because your kids are adorable and sometimes there’s footage of you being ridiculous,” Andrew wrote back. But he was also quick to temper his enthusiasm. “I do think it’s hard to say, ‘Patrick, that’s a great video of your child singing now where is the story that was due yesterday.’” he added. “That’s my job. I have to do that to make sure we’re treating you fairly and not being giant hypocrites about work/life balance.” I understand all of this, of course. Managers have to walk a tightrope of strong, strategic guidance and care without losing employees or productivity. In some respects, it makes sense that they might be reticent to have so much insight when there is a possibility that it could off the balance of empathy and strategy. And that made Andrew’s answer to the perspective question so interesting. Because while I felt that sharing my family might make us closer, it turns out the opposite may be true. He pointed out that working closely with another person without the context of their family life allows colleagues to feel a shared experience. We can easily believe we’re more alike than different. A more open view shatters that illusion. “When you share stories and images and videos from home, I think that the unintended result—and this is sort of ironic—is the creation of distance,” he told me. “I remember that we’re very different people with very different families. The illusion of cultural homogeneity in the office is broken because you talk about church–or whatever.” While I’m glad I have this knowledge now, clearly not every employee will feel comfortable coming out and directly asking their boss for opinion on the sharing of family life. “You don’t have to say, ‘Gee, what’s your take on this? Can I share stuff about my family?’” says McLeod. “But you can observe in a very nuanced way.” She suggests that employees look for signs of openness, including whether or not their boss is open about their own family life. Look for connection and places where conversations can occur but don’t force them. Do they fill their desk with pictures of family? Do they encourage time off to do things like going to a preschool art show? On the other side McLeod says be wary of bosses who appear to encourage a culture where people are allowed to complain about parents taking time off for sick kids. Also, look for clues that what you’re sharing might make them uncomfortable—the use of the term “emotional blackmail” for instance. As for me, the first day of school is coming up. Will Andrew receive a picture of my sharply dressed kid waiting on his bus to head to first grade? Hell yes, he will. After all, I’ve got cute kids and that’s all that matters. Right? Andrew? You reading this?