A family in Lincoln Park called us right after Thanksgiving last year in a complete panic. Their house manager had just reminded them she’d requested Christmas week off back in September, their nanny had family visiting for Thanksgiving week, and their private chef wanted New Year’s weekend. “We can’t have everyone gone at the same time,” the wife said, stressed. “But they all made plans already and we never actually responded to their requests. Now what do we do?”
That situation happens in some version almost every holiday season. Staff request time off. Families don’t respond clearly or quickly. Everyone assumes different things. Then November hits and suddenly there are conflicts between what staff planned and what families need, except now everyone’s made commitments that are hard to change.
After twenty years of working with families and household staff throughout Chicago and nationwide, we can tell you that holiday time-off conversations don’t have to be this stressful. But they require early communication, clear policies, honest discussions about what’s actually feasible, and real planning rather than just hoping everything works out. Here’s how to handle it properly.
Start the Conversation Early
The single biggest mistake families make with holiday time off is waiting too long to discuss it. Don’t wait until November to have conversations about Thanksgiving and December holidays. Have them in September or even earlier.
Staff are planning their own holidays months in advance. They’re booking flights, coordinating with family in other cities, making commitments. The earlier you can give them clarity about what time off is possible, the easier it is for everyone to plan successfully.
That doesn’t mean you need to have your own holiday plans totally figured out in September. It means you need to have conversations with household staff about their time-off requests and give them clear responses about what’s approved, what’s not possible, and what’s still uncertain pending your own planning.
Starting early also gives you time to coordinate between multiple staff members if you have them. Maybe your house manager really wants Thanksgiving week but is flexible about Christmas. Maybe your nanny is fine working Thanksgiving if she can have the week after Christmas. Maybe your chef would prefer New Year’s week over Christmas week. You can work out arrangements that give everyone some of what they want rather than having conflicts where everyone’s disappointed.
Chicago families often travel for holidays or host extended family, which affects what household staff coverage you actually need. Figure out your rough plans early enough that you can have real conversations with staff about timing.
Be Clear About What’s Negotiable
Some families say yes to every time-off request and then resent feeling like they have to accommodate everyone’s wishes even when it’s inconvenient. Other families say no to reasonable requests because they haven’t really thought through whether staff coverage is actually necessary.
Think honestly about what you genuinely need from household staff during different parts of holiday season and be clear with them about what’s flexible versus what’s not.
If you’re traveling for Thanksgiving week and won’t be home, you probably don’t need your house manager working that week. Let them take the time off happily rather than making them work just because you didn’t think about it.
If you’re hosting 20 family members for Christmas week and absolutely need your house manager and private chef working, be upfront about that. Don’t imply their time-off requests might be possible if you know they’re not.
If you’re flexible about exact dates but need someone working at least part of holiday periods, say that clearly. “We need you working either Christmas week or New Year’s week – your choice which one” gives staff real information to plan around.
Being clear about what’s truly necessary versus what’s just your default assumption helps everyone. Staff can plan appropriately. You’re not dealing with conflicts between what you need and what staff already arranged thinking it was fine.
Address Multiple Staff Situations
If you have several household staff members, coordinating holiday time off gets more complicated. You probably can’t have everyone gone simultaneously, but you also want to treat people fairly.
One approach is giving priority to requests based on when they were submitted. First person to ask gets first choice of dates, second person works around that, and so on. That’s simple and fair in a straightforward way.
Another approach is rotating who gets priority for different holidays. Maybe your house manager gets first choice for Thanksgiving this year while your nanny gets first choice for Christmas, and next year you flip it. That helps ensure everyone gets their preferred holidays at least some years.
Some families handle this by having conversations with all staff together about holiday coverage needs and working out solutions collaboratively. That can work beautifully if everyone’s reasonable and willing to compromise. It can also create awkward dynamics if staff feel pressured to give up time they really want.
However you approach it, the key is being transparent about your process and treating people equitably. Don’t just give your favorite staff member whatever they want while making everyone else accommodate around them. That builds resentment fast.
The Live-In Staff Complication
If you have live-in household staff, holiday time off gets more nuanced. Live-in positions often include reduced time-off expectations compared to live-out positions because housing is part of compensation. But that doesn’t mean live-in staff never get holidays off.
Be explicit in advance about what holidays live-in staff are expected to work versus which holidays they can take off like any other staff members. Don’t assume they know or that it’s obvious from how things worked last year.
Some families give live-in staff the same holiday time off as everyone else. Others expect them to work more holidays because they’re already on property. Neither approach is inherently wrong, but you need to be clear about expectations when someone accepts a live-in position.
If live-in staff are working holidays while your family’s not even home, consider whether that’s genuinely necessary or if you’re just defaulting to having them work because you can. Sometimes families keep live-in staff working during holidays out of habit even though there’s no actual reason they need to be there.
For holidays when you do need live-in staff working, think about how to make those days less isolating. Are there ways to give them special time off before or after the holidays? Can you include them in family meals if they’re comfortable with that? Small gestures make working holidays feel less punitive.
Handle Requests You Need to Decline Carefully
Sometimes you genuinely can’t accommodate staff time-off requests because you need coverage during those periods. How you decline those requests matters for how staff feel about working for you.
Explain your reasoning clearly. “We’re hosting family for that week and will really need you here to help manage everything” makes sense. “We might need you” without being able to articulate why feels arbitrary.
Offer alternatives when possible. If someone can’t have Thanksgiving week off, could they take the following week instead? If they can’t have both Christmas Eve and Christmas Day off, could they pick one? Showing flexibility where you can helps soften having to say no to initial requests.
Acknowledge the disappointment. Don’t act like it’s no big deal that someone can’t visit their family for Thanksgiving. “I know this isn’t what you hoped for and I’m sorry we need you working that week” goes a long way.
Consider compensation adjustments. Some families give additional holiday pay when staff work major holidays they’d prefer to have off. Others give extra time off later. Neither is required, but both are appreciated gestures that show you recognize the sacrifice.
What About Last-Minute Family Emergencies?
Sometimes staff need emergency time off during holidays for situations nobody could have predicted. Family member gets sick. Crisis happens that requires them to travel suddenly. Genuinely unexpected circumstances arise.
Have some flexibility built into your planning for these possibilities. Don’t structure holiday coverage so tightly that any unexpected absence creates disaster. That’s as much about protecting yourself as being generous to staff.
When genuine emergencies happen, be human about it. Yes, it’s inconvenient when your house manager needs to fly home urgently because a parent had a medical crisis. But that’s life. Unless you’re dealing with someone who has “emergencies” constantly as a pattern, give people grace when real problems arise.
Chicago winters can also create weather-related coverage challenges. Snowstorms make travel difficult or impossible. Staff who live far from your home might not be able to get to work safely. Build some flexibility into holiday coverage expectations to account for weather realities.
Pay Clarity for Holiday Work
Be crystal clear about whether staff working holidays get their regular pay or receive additional compensation. Don’t leave this ambiguous.
Some families pay time-and-a-half or double-time for major holidays like Thanksgiving Day, Christmas Day, or New Year’s Day. Others provide regular pay plus comp time off later. Others just pay regular salary regardless of whether holidays are worked.
All three approaches are acceptable if they’re communicated clearly in advance and if they match what was agreed to when staff accepted positions. Problems arise when staff assume they’ll receive extra compensation for holiday work and discover they’re just getting regular pay, or when families assume staff are fine with regular pay when they were actually expecting premium holiday rates.
Put holiday pay policies in writing as part of employment agreements. That prevents confusion and ensures everyone knows what to expect before committing to holiday coverage.
The Gratitude Piece Matters
Staff who work during holidays when they’d prefer to be with their own families are making real sacrifices to support yours. Acknowledge that genuinely rather than just taking it for granted.
Thank people sincerely. Not just “thanks for working today” in passing, but actual acknowledgment of the accommodation they’re making. “I really appreciate you being here this week while we’re hosting family. I know you wanted to travel and I’m grateful you rearranged your plans” means something.
Consider small gestures that make holiday work feel less punishing. Nice meals for staff working through holidays. Special gifts beyond normal holiday bonuses. Making sure staff can participate in some holiday activities or traditions even while working. These things cost you little but matter significantly for how staff experience holiday work.
For staff who do take holidays off, wish them well genuinely. “I hope you have a wonderful Thanksgiving with your family” beats “okay, see you when you get back.” Show interest in their lives and their own holiday celebrations beyond just viewing them as coverage for your needs.
What This Looks Like When Done Well
Families who handle holiday time off well start conversations in September or October. They give staff clear information about what time off is possible. They’re honest about what they actually need for coverage. They treat multiple staff members fairly. They communicate clearly about pay for holiday work. They show real appreciation when staff work holidays they’d prefer off.
Staff in these situations generally feel respected and treated fairly even when they don’t get every single day they initially wanted off. They know families took their requests seriously and tried to accommodate them where possible. They understand the reasoning when requests can’t be approved. They don’t feel taken advantage of or resentful.
Families benefit because they have reliable holiday coverage without staff feeling exploited. They avoid last-minute conflicts and confusion. They maintain good relationships with household staff that don’t get damaged by poorly handled time-off situations.
This isn’t complicated stuff. It’s basic communication, planning, honesty, fairness, and treating people like humans who have their own lives and families to consider. But it requires actually doing those things in advance rather than just hoping everything works out.
When It Goes Wrong
We see the same patterns every year with families who handle this badly. They don’t respond to time-off requests until staff force the conversation. They’re vague about whether requests are approved. They expect staff to be completely flexible about working holidays without acknowledging that staff have their own plans. They make staff feel guilty for wanting time off during periods when families need coverage.
Then families wonder why staff seem resentful during holiday seasons or why they have trouble keeping long-term household employees. Staff who feel disrespected about time-off requests start looking for families who treat them better. Nobody wants to work somewhere they feel their personal lives and family obligations don’t matter.
The fix isn’t complicated. Start early. Communicate clearly. Be honest about what you need. Treat people fairly. Show appreciation for accommodations staff make. That’s it. But you actually have to do those things, not just intend to get around to them eventually.
Chicago’s holiday season is intense with weather challenges and family obligations pulling everyone in different directions. Making it work for both your family and your household staff requires real planning and consideration. But that investment in handling time-off conversations properly pays off in staff who feel valued and who stick around long-term rather than leaving for families who handle these basics better.
