A reader writes:
I’m hoping you can help me with this conundrum. This situation is complicated by the fact that this is a family business, and all employees are my relatives and/or their romantic partners, but we have virtual assistant team members (independent contractors or third party services) who are party to these conversations.
Background: I’m the main operator, but not the owner, of our family business, which leans more informal than most workplaces. We have some on-site operations, but significant “back office” admin occurs virtually. It’s my responsibility to set the tone and culture, and I believe I should change some things. One problem is my younger sister, Amanda, overshares about breaks and sick time in the primary team communication channel. I think it creates a problematic impression for everyone, but especially for our virtual team who aren’t family members.
For example, when taking breaks, Amanda doesn’t say, “I’m taking my 15 minute break, back soon.” She includes details like “I’m walking my dog, be back after feeding him lunch.” Or when taking personal time: “I’m taking my dog to the vet for throwing up, might have to get his stomach pumped, wish me luck it’s nothing serious.” She also has intermittent chronic illness that the family all agreed means she can be flexible with her work hours, but she overshares this to the team also. Instead of saying “taking a sick day” or “out on sick time for a few hours,” she provides excessive details like “Have a major migraine, must go lay down for a while, don’t know when I’ll be back or if I can make the weekly team meeting,” or “My stomach is really bothering me, stuck in the restroom, please don’t contact me unless it’s an emergency.” Similarly she overshares her doctors’ visits, such as “Leaving for my appointment with my gastroenterologist, if the tests they run hurt too bad I might not be back online today.”
Her role is functionally entry-level, but she’s not a recent college graduate. She’s in her early 30s.
Oversharing about her dog, doctors, and symptoms happens nearly every day. Symptom-related sick time overshares occur two to three times per week, and she has one to three doctor appointments per month. Over time, this creates a broad impression that she is constantly taking frivolous breaks or what feels like an unusual amount of sick time, both in general and compared to other employees and team members. Family members have commented as much and, although no virtual team members have explicitly said so, I suspect they also feel this way. I’m concerned about the impact on company culture and morale. She’s privately told me and other family members that previously, both corporate and mom-and-pop employers have punished her when she clocks in late or needs to take sick time due to her symptoms or have been unsupportive of her needs for medical appointments
From an operating perspective, our solution has been to give her flexibility for start times, end times, and breaks, and not assign her projects or tasks that require specific hours. For example, she doesn’t open or close the office or answer phone calls, but she does set up and updates customers in our CRM, process submitted applications within 24 hours, create and schedule invoices, pay bills, collect and label receipts from purchases, review security footage, initially categorize expenses for our bookkeeper, etc. These tasks largely don’t have an difference if they’re completed at 9 am, noon, or 3 pm, as long as a backlog doesn’t build up. She works 35-40 hours a week, and quality of those tasks isn’t a concern.
Can you provide some guidance about how to approach this conversation? She‘s previously been upset and resistant to feedback that she perceives is critical of her chronic illness, both from family and from previous employers. Her actual taking of breaks is within the guidelines we agreed upon, but the nature of if and how she shares with the team needs to change. I don’t think she’s aware of the impression this creates. She’s also expressed interest in raises and moving up into a position of higher responsibility, and I want to be clear about what would need to change for that to happen without coming across as judgmental or unsupportive of her medical needs.
It sounds like she’s talking to you as family rather than as colleagues … because you are in fact family.
This can be a hard boundary to draw in businesses where nearly everyone is family (and especially where those who aren’t are remote).
But that doesn’t mean you can’t address it!
I’d frame it as, “When you’re out sick or for a break or an appointment, we don’t need to know any details — only that you’re out and when you expect to be back. I want you to stop including details beyond that, because it creates the impression that we expect people to justify their time away. I don’t want other people to feel pressure to provide personal details about their own time away. We’re happy with your schedule and your work, and we trust you to manage your time well. Going forward, please just announce you’ll be out for X amount of time, no reason needed.”
Also, does she need to alert you to 15-minute breaks at all? Ideally you’d tell her that she doesn’t need to alert anyone to those dog-walking breaks at all (just like you presumably wouldn’t expect people to message “I’m going to zone out for 15 minutes”). If she truly needs to keep people that updated on her availability, that’s different — but based on the work you describe her doing, she doesn’t need to. Again, you trust her to manage her own schedule and get her work done. She doesn’t need to provide a minute-by-minute narration.
If framing it as “this is sending problematic signals to others about what’s expected of them” doesn’t work, then you could say, “As the business is growing, we need to professionalize the way we operate. Nothing needs to change about your schedule. The system we came up with for breaks and time off is working well. However, I want you to move from sharing details about why you’ll be out (like taking care of your dog or the details of an illness) and just say that you’ll be out and when you’ll be back. That’s what we’d ask of non-family employees, and I want to move us in that direction now.”
You could say, “Sharing this level of detail is making people feel like you’re constantly away, whereas they wouldn’t notice it at all if you gave less info. And some of it’s an overshare that people prefer not to hear, like details about GI symptoms.” But since she’s previously been upset and resistant to feedback that she perceives as connected to her health, just go with the more business-focused reasons above. Those aren’t about her; they’re about the business and what it needs, and you’re on solid ground taking a firm stance.
