Here’s something we see all the time: nannies walk into interviews focused entirely on making good impressions, answering families’ questions thoughtfully, and proving they’re qualified for the position. All of that matters, absolutely. But what gets overlooked is using the interview to assess whether the position will actually work for you, whether it supports the work-life balance you need for a sustainable career, and whether the family’s expectations align with what you can realistically provide long-term.
After twenty years helping nannies navigate interviews throughout Chicago and beyond, we’ve learned which questions actually reveal whether positions support healthy work-life balance versus which ones will slowly grind you down through constant boundary violations, unpredictable schedules, and expectations that bleed into every corner of your personal life. The families worth working for don’t just tolerate these questions, they appreciate them. They recognize that nannies asking thoughtful questions about work-life balance are professionals thinking seriously about long-term sustainability rather than just accepting any job offer.
Chicago families often work demanding careers in finance, healthcare, law, consulting, and other intensive fields. Many value work-life balance in their own lives and extend that value to household employees. But not all of them. Some expect nannies to constantly accommodate their unpredictable schedules, be available whenever convenient for the family, and treat personal time as negotiable rather than protected. The interview gives you the opportunity to figure out which type of family you’re dealing with before you accept positions that will damage your wellbeing.
The questions we’re suggesting aren’t confrontational or demanding. They’re straightforward inquiries that any professional should ask when evaluating whether jobs fit their lives. How families respond tells you volumes about whether they view you as a professional deserving respect or as someone whose needs don’t really matter as long as their childcare gets covered.
“What Does a Typical Week Look Like?”
This seems like a basic question, and it is, but listen carefully to how families answer it. You’re not just gathering scheduling information, you’re assessing whether they have realistic understanding of what they need and whether the “typical” week they describe actually exists or is aspirational fiction.
Good answers provide specific details about daily schedules, variations between different days, and honest acknowledgment of how often the typical week actually happens versus getting disrupted by work demands or other factors. They might say something like “I usually need you Monday through Friday, 8am to 6pm. Tuesdays and Thursdays I work from home so I’m around more. Mondays tend to run a bit later, closer to 6:30 or 7pm. The schedule’s pretty consistent, though maybe once or twice a month something comes up where I need to stay late at work.”
That’s honest, specific, and gives you real information to work with. You can assess whether that schedule works for you, whether the occasional late days feel manageable, and whether their definition of “typical” aligns with reality.
Red flag answers sound vague or overly optimistic. “Oh, it’s pretty flexible, we’ll figure it out as we go.” Or “It really varies week to week, depends what’s happening with work.” Or “Well, we’re hoping it’ll be regular hours but my job can be unpredictable.” These responses suggest families who don’t actually know what they need, who haven’t thought through logistics carefully, or who are hoping you’ll just constantly accommodate whatever comes up.
Also pay attention to whether they mention their own schedules and how that affects your work. Families working from home some days need to address how that affects your work environment, whether you’ll have private space to work with children, and how interruptions get managed. If they’re traveling frequently, does that affect your schedule or create expectations you’d travel with them?
Chicago’s mix of industries means schedule patterns vary widely. Finance and law families might have more intense but somewhat predictable schedules. Consulting families might travel extensively. Healthcare families might have irregular hours. Understanding their specific work patterns helps you evaluate whether the position’s rhythms match what you can sustain.
Ask follow-up questions if initial answers raise concerns. “You mentioned the schedule varies, can you give me a sense of the range? Are we talking occasional 7pm days or frequently not knowing when you’ll be home?” Push for specifics that help you make informed decisions.
“How Do You Handle Schedule Changes?”
This question gets at how families manage the inevitable disruptions to planned schedules and whether they respect your time or view it as infinitely flexible to accommodate their needs.
Strong answers acknowledge that schedule changes happen but describe clear processes for managing them respectfully. “If something comes up and I need to work late, I try to give you as much notice as possible, at least by lunchtime. I totally understand if you can’t stay, and I have backup options. If you can stay, we’d pay overtime and really appreciate the flexibility.”
That response shows they understand your time has value, they plan ahead when possible, they have backup systems rather than relying entirely on you to solve their problems, and they compensate appropriately when asking for accommodation. They’re treating you like a professional with legitimate boundaries rather than someone who exists purely to serve their convenience.
Warning sign responses blame their work’s unpredictability as if that makes imposing on you reasonable. “My job’s really unpredictable, I never know when I’ll get stuck late, so I’d need you to be flexible.” Or “We’d really need someone who can roll with last-minute changes.” Or “In this position, you’d need to be available when we need you.”
These answers reveal families who expect you to absorb all the chaos their work creates without acknowledging that you also have a life requiring some predictability. The unpredictability of their work doesn’t obligate you to accept constant disruption of your personal time.
Ask directly: “When schedule changes come up, what kind of notice do you typically give?” And “How do you handle situations where I can’t accommodate schedule changes because of personal commitments?” Their answers reveal whether they view your personal time as equally legitimate to their work needs or as something that should always bend to accommodate them.
Chicago’s professional culture tends toward directness and efficiency, so asking these questions clearly usually gets honest responses. Families who bristle at questions about respecting your time are telling you something important about what working for them would actually be like.
“What Are Your Expectations Around Communication During Off-Hours?”
This question addresses whether families respect boundaries between work time and personal time or whether you’re expected to be constantly available mentally and digitally.
Healthy responses establish clear boundaries. “During work hours, text or call anytime with questions or if something comes up. Outside of work hours, I’ll only contact you for genuine emergencies. If I need to discuss something that can wait, I’ll bring it up when you’re next working.”
That establishes appropriate limits where you’re accessible for urgent matters but not fielding routine questions, requests, or family updates during your personal time. It recognizes that constant work-related communication during off-hours prevents you from truly disconnecting and recharging.
Concerning answers blur these boundaries. “I might text you questions that come up in the evenings or weekends, nothing major, just little things.” Or “I like staying in touch about how the kids are doing, so I might check in even on your days off.” Or “We’re pretty casual about work-life separation, we’ll probably text back and forth about various stuff.”
What sounds like casual friendliness is actually constant low-level work intrusion that prevents genuine time off. Those “little” evening texts or “just checking in” messages during days off keep you mentally tethered to work, unable to fully relax or focus on your personal life.
Be direct: “How do you typically handle communication during my off hours or days off?” And “Are there situations beyond genuine emergencies where you’d expect me to be responsive outside of working hours?”
Some families try to frame constant communication as relationship-building or staying connected rather than recognizing it as boundary violation. Trust your instincts about whether their communication expectations feel respectful or invasive.
“How Do You Handle Sick Days and Personal Time Off?”
This reveals whether families provide appropriate paid time off and respect your need to use it, or whether they view your being unavailable as major inconvenience they’ll subtly or not-so-subtly punish.
Good answers specify clear PTO policies and backup plans. “You’d get two weeks paid vacation, five paid sick days, and seven paid holidays. For vacation, I’d choose one week and you’d choose the other, we’d figure out timing a few months ahead. For sick days, just text me in the morning and we’ll handle it. I have some backup care options and can work from home in a pinch, so don’t worry about leaving us stranded.”
That shows they’ve thought through how to handle your inevitable absences, they’re providing reasonable PTO, they have contingency plans rather than making your absence a crisis, and they understand humans get sick sometimes without viewing it as personal failing.
Red flags include vagueness about PTO or framing your absences as problems. “Well, we’d really need someone reliable who doesn’t call out often.” Or “We’re pretty flexible, but we’d need advance notice if you’re taking time off.” Or “Sick days aren’t really planned, so we’d have to figure it out when it comes up.”
These responses suggest families who haven’t actually planned for your completely normal, inevitable need for time off, who view your using PTO as inconveniencing them, or who conflate normal sick day use with unreliability.
Ask specifically: “What PTO would I have?” And “What’s your backup plan if I’m sick or need to take time off?” Families who’ve thought this through have answers ready. Those who haven’t are telling you they expect you to basically never be unavailable.
Chicago’s brutal winters mean sick days happen more frequently due to weather, illness spreading through schools, and general seasonal challenges. Families who haven’t planned for this reality in a Chicago context aren’t being realistic about employment here.
“What Happens During Your Vacations?”
Family vacation expectations vary wildly, and this question reveals whether you’re expected to travel with them, whether you’ll be paid during their absence, and whether their vacation creates stress or opportunity for you.
Ideal answers respect your needs while being clear about expectations. “We usually take two weeks vacation as a family in summer and a week around the holidays. We wouldn’t need you during those times, and you’d be paid for those weeks. Consider it your vacation time too, or you can use your own PTO for different timing if you prefer.”
That’s generous and clear. You’re not expected to travel with them, you’re not losing income during their absence, and you have flexibility about whether to use that time as your vacation or schedule your own time off separately.
Middle-ground answers involve some negotiation but are still reasonable. “We take about three weeks of family vacation annually. Usually we’d want you to come with us for one of those trips, and you’d be off during the other two weeks. We’d pay your regular rate for the travel week plus cover all expenses, and you’d be paid for the other two weeks as well.”
That’s more complex but still fair. You’re getting paid, the travel expectations are clear, and they’re covering expenses rather than expecting you to subsidize their vacation.
Problematic answers create financial or schedule hardship for you. “We travel quite a bit, so you’d be off during those times. That’s usually about six weeks a year.” No mention of payment during those absences means you’re expected to go without income for over a month annually, which isn’t sustainable. Or “We’d need you to come on most family vacations to help with the kids.” Without clear boundaries, compensation structure, or acknowledgment that travel is work not leisure for you.
Ask directly: “When you take family vacations, what are expectations around my schedule and compensation?” And if they mention wanting you to travel with them: “Can you tell me more about what that would look like, how it would be compensated, and how often it happens?”
Chicago families often travel to escape winters or enjoy summer lake vacations. Understanding their travel patterns and how that affects you helps assess whether the position’s total compensation adequately covers your actual annual earning needs.
“How Do You Handle Overtime?”
This straightforward question reveals whether families understand and follow labor laws, track hours appropriately, and compensate fairly for extra time worked.
Correct answers acknowledge legal requirements. “We’d track your hours carefully, and anything over 40 hours weekly would be paid at time and a half as required. If you ever work over eight hours in a day, that’s also overtime. We’d discuss any anticipated overtime in advance when possible.”
That demonstrates they understand California wage law, they’re planning to follow it, and they’ll track hours properly to ensure correct payment. The mention of discussing overtime in advance also shows respect for your schedule.
Concerning answers include not understanding overtime requirements, suggesting work arrangements that violate wage law, or framing overtime as unusual when the position realistically requires it regularly. “We’re hoping to keep it to 40 hours, but you’d need to be flexible if we occasionally need more.” Without mention of overtime pay. Or “We’d pay a higher base rate so overtime wouldn’t apply.” That’s not how labor law works.
Ask explicitly: “How do you track hours and handle overtime compensation?” And “Based on your typical schedule, would this position regularly include overtime?” If they describe schedules that clearly involve more than 40 hours weekly but act like that’s somehow not overtime, they either don’t understand labor law or are intentionally trying to avoid paying properly.
Some families attempt to structure positions as salaried to avoid overtime obligations, but California law requires overtime for non-exempt employees regardless of whether they’re called salaried. Make sure you understand the actual compensation structure and that it complies with state law.
“What Does Work-Life Balance Look Like for Your Family?”
This broader question invites families to describe their values around balancing work demands with personal life, which gives you insight into whether they’ll respect your need for similar balance.
Thoughtful answers demonstrate self-awareness about their priorities and how that affects household employment. “We both work demanding jobs, but we try to protect family time in the evenings and weekends. That’s actually why we need excellent childcare during work hours, so we can be more present when we’re home. We think it’s important for our household staff to have good work-life balance too, because we know you can’t provide great care if you’re burned out.”
That shows they’ve thought about how their values affect employment relationships and that they see connection between treating employees well and getting quality work. They’re not just paying lip service to work-life balance, they’re extending the principle to how they treat you.
Red flag answers separate their values from how they treat employees. “We really prioritize work-life balance for our family, so we need someone who can be really flexible to help us achieve that.” Or “Balance is really important to us, which is why we need reliable childcare that we don’t have to worry about.” These responses treat your work-life balance as irrelevant to achieving theirs, failing to recognize that your wellbeing matters too.
Ask follow-up: “How do those values around balance extend to household employees?” Direct questions cut through vague statements and reveal whether their principles actually include you or just apply to their family.
“What Does Success Look Like in This Position?”
While not directly about work-life balance, this question reveals whether families have realistic expectations or whether they’re describing an impossible job that would require sacrificing your entire personal life to achieve.
Reasonable answers describe clear, achievable goals focused on children’s wellbeing and household functioning. “Success means the kids are happy and thriving, the daily routines run smoothly, you communicate with us effectively about anything important, and you feel supported in the role. We want long-term placement where you grow with our family.”
That’s focused on realistic outcomes, emphasizes partnership and communication, and implies understanding that good employees need support to succeed.
Unrealistic answers describe perfection, constant availability, or expectations that go far beyond what one person can reasonably achieve. “We need someone who’s always on, who anticipates every need before we even think of it, who makes everything run perfectly without us having to manage anything.” Or descriptions that include responsibilities spanning childcare, household management, personal assistant duties, and more without acknowledging that this is really several jobs bundled together.
When families describe success in ways that sound exhausting just hearing about it, believe them. They’re telling you what working there would actually require, and if it sounds unsustainable, it probably is.
Moving Forward With Confidence
Asking these questions during interviews isn’t being difficult or high-maintenance. It’s being a professional who takes seriously whether positions will actually work for your life and career sustainability. The families who respond well to these questions are the ones who’ll treat you with respect throughout employment. Those who get defensive or dismissive are showing you they don’t view household employees as professionals deserving appropriate boundaries and treatment.
At Seaside Nannies, we coach candidates extensively on asking the right questions during interviews because we want you making informed decisions about whether positions serve your long-term interests. We’ve seen too many nannies accept positions based on incomplete information, then struggle when the reality doesn’t match what they imagined based on families’ vague or misleading answers during interviews.
Chicago families who value household employees understand that asking thoughtful questions about work-life balance signals professionalism and self-awareness rather than demanding behavior. They appreciate candidates who think seriously about fit and sustainability rather than accepting any offer just to get a job. Trust that the right families will respond to your questions with clarity, honesty, and respect for your legitimate need to understand what you’re committing to before accepting positions.
