Your new family assistant starts Monday. You spent weeks interviewing, checking references, negotiating terms, and now you’re relieved to finally have someone hired. But here’s something most Chicago families don’t realize until they’ve been through this a few times: the first week with a new family assistant tells you almost everything about whether this placement will succeed long-term or crash within a few months.
We’re not talking about whether they remember where you keep the kids’ snacks or whether they’ve mastered your coffee maker by day three. We’re talking about patterns of behavior, communication style, problem-solving approach, and how they handle the inevitable confusion and mistakes that come with learning a new household. These patterns show up immediately, and they rarely change after the first week.
After twenty years placing family assistants with households across the country, we know exactly what to watch for during those first five days. Some signs predict years of excellent partnership. Others predict conflict, frustration, and eventual turnover regardless of how much you try to make it work. The difference isn’t usually about skills or experience. It’s about work style, communication patterns, and whether their approach actually fits what your household needs.
Let’s talk about what you should be watching for, what matters and what doesn’t, and how to tell the difference between normal adjustment and genuine red flags.
How They Handle Not Knowing Things
Nobody expects your family assistant to know everything about your household on day one. Your systems, your preferences, your kids’ routines, where you keep things, how you like things done – all of that takes time to learn. What matters is how they handle the inevitable gaps in knowledge.
Watch whether they ask questions proactively or wait for you to notice problems. The family assistants who succeed ask constantly during the first week. “Where do you keep extra paper towels?” “What’s your preference for organizing the kids’ art supplies?” “Do you want me to check with you before scheduling the car detailing or just handle it?” They’re building a mental map of how your household operates and they’re not embarrassed about needing information.
The ones who struggle either don’t ask and then make mistakes you have to correct, or they ask you to make every tiny decision rather than using judgment. Both patterns are problems. The person who reorganizes your pantry without asking because they “thought it would be helpful” and the person who texts you six times during their first morning asking permission for basic tasks are both showing you concerning patterns.
Pay attention to how they respond when you correct something they did wrong. Do they get defensive and explain why they did it that way, or do they take the feedback, ask clarifying questions, and adjust? The family assistants who last are the ones who can hear “actually, we prefer the kids’ lunch packed the night before, not morning of” without making it a whole thing.
Notice whether they’re taking notes. Seriously. The ones who write things down during the first week remember your systems. The ones who insist they’ll remember and then ask you the same questions repeatedly aren’t retaining information well. You shouldn’t have to explain your morning routine structure five times in five days.
Their Communication Style Emerges Immediately
How your family assistant communicates during week one is how they’ll communicate permanently unless you address it directly.
Watch how they update you on what happened during the day. Do they give you enough information without overwhelming you with unnecessary detail? Or do they either barely tell you anything, leaving you to piece together what actually happened, or send you paragraph-length texts about every minor event throughout the day?
Notice how they handle schedule changes or unexpected situations. Do they flag issues early enough that you can actually respond, or do they wait until something’s already a crisis? If they’re supposed to take your daughter to soccer but she’s running a fever, does your family assistant text you at 8am when she notices the fever, or do they wait until 3:45pm when they’re supposed to leave and now you’re scrambling?
Pay attention to tone in all communication. Are they professional and warm, or does something feel off? Some family assistants are overly familiar right away, texting you like you’re their best friend. Others are so formal and stiff that you feel like you’re communicating with a robot. Neither extreme is great. You want someone who can be appropriately professional while still being a real person.
Watch whether they read situations appropriately. If you’re clearly in the middle of something stressful, do they recognize that’s not the time to ask about organizing the garage? If there’s genuinely an urgent issue, do they interrupt appropriately? The ability to gauge context and communicate accordingly matters enormously.
See how they handle disagreement or pushback. If you say “actually, let’s do it this way instead,” do they accept that smoothly or do you sense resistance? During week one, everyone should be in learning mode. Family assistants who act like they know better than you about your own household during their first week are showing you a problematic pattern.
How They Interact With Your Kids
Family assistants aren’t nannies, but they’re still working closely with your kids. How they handle those interactions during week one tells you a lot.
Watch whether they’re building rapport at an appropriate pace. The ones who try too hard to be the cool favorite person immediately often struggle with maintaining boundaries later. The ones who barely engage with kids even when the situation calls for it might not be comfortable in family environments. You want someone who’s friendly and warm with your kids while still maintaining appropriate professional distance.
Notice how they handle kid-related tasks. Are they annoyed when they have to deal with something child-related that wasn’t explicitly in the job description? If your assistant is supposed to run errands and ends up taking your six-year-old along because your nanny called in sick, do they roll with it reasonably or act put out?
Pay attention to how they talk about your kids when updating you. Do they notice things – “Emma seemed really excited about her science project today” – or do they treat your kids as objects in the house they have to work around? Family assistants who genuinely like families do better in these roles long-term than people who prefer working in households without kids.
Watch how they handle kid chaos. If they’re trying to organize the playroom and your toddler is “helping” by pulling everything back out, do they handle that with patience or frustration? Nobody expects them to love the chaos, but they should be able to tolerate normal kid behavior without getting visibly irritated.
See whether they follow your parenting guidelines when they’re in charge for a moment. If you’ve explained that screen time is limited and they stick your kid in front of the TV the second you leave the house, that’s telling you something about whether they’ll respect your preferences when you’re not watching.
Their Judgment Calls Show Problem-Solving Style
The first week inevitably involves situations where your family assistant needs to make decisions without checking with you first. How they handle those moments predicts future success.
Watch what kinds of things they decide independently versus what they bring to you. Family assistants who ask permission for every tiny decision will drive you crazy long-term. “Should I use the blue sponge or the green sponge?” is not a question adults should need answered. But family assistants who make major decisions without consulting you – like throwing away something they assume is trash but isn’t, or scheduling service appointments during times that don’t actually work for you – are also problems.
Notice whether their judgment aligns with your priorities. If they spend two hours organizing a closet you barely use while urgent tasks sit undone, they’re not assessing importance well. If they keep choosing to do the most visible tasks rather than the most important ones, they’re prioritizing wrong.
Pay attention to how they handle mistakes. Everyone messes up during the first week. Did they shrink your favorite sweater in the wash? Forget to pick up the dry cleaning? Schedule two things at the same time? What matters is whether they own it immediately, apologize appropriately, and figure out how to prevent the same mistake from happening again.
Watch how they respond when systems aren’t working. If the way you’ve always organized your kids’ school papers isn’t actually functional, does your family assistant either suffer through it or mention that there might be a better approach? The good ones notice inefficiencies and suggest improvements respectfully. The ones who struggle either never mention problems or criticize your systems in ways that feel judgmental.
See how they handle unexpected situations. Your dryer breaks during their first week. Do they panic and call you immediately, or do they look up repair services, get a couple quotes, and present you with options? The level of autonomy and competence they show when things go wrong during week one is the level you’ll get permanently.
Work Pace and Style Becomes Clear
Some family assistants move through tasks efficiently. Others are slower but extremely thorough. Some can juggle multiple priorities simultaneously. Others need to focus on one thing at a time. None of these styles is inherently wrong, but it matters whether their natural pace matches what you need.
Watch whether they’re getting through a reasonable amount of work in the time available. If they’re working full days but accomplishing what seems like two hours of actual tasks, either they’re very slow or they’re not working efficiently. If they’re racing through everything but the quality is poor, speed without quality doesn’t help you.
Notice whether they understand how to prioritize when they can’t complete everything. If they have six tasks and only time for four, do they choose the four that actually matter most? Or do they complete the easiest ones and leave the urgent items undone?
Pay attention to their energy level throughout the day. Do they start strong but fade significantly by afternoon? Are they consistent? Understanding their natural rhythm helps you structure their responsibilities in ways that work with rather than against their patterns.
Watch how they handle downtime. If there’s a gap between tasks, do they find productive things to do, take appropriate breaks, or scroll their phone for thirty minutes? You’re not expecting them to invent work when there isn’t any, but you also don’t want to walk in and constantly find them on social media.
See whether they can shift gears when priorities change. If you text midday that actually the grocery run can wait but you need help with a last-minute party prep, do they adapt smoothly or get frustrated that the plan changed?
Red Flags That Show Up Week One
Some concerning patterns emerge during the first week that rarely improve without direct intervention.
If they’re consistently late or leaving early without asking, that’s not adjustment period behavior. That’s showing you they don’t respect the schedule.
If they’re on their phone constantly for personal reasons, that’s not going to magically improve in week two. Some personal phone use is reasonable, but if they’re texting friends, scrolling social media, or taking personal calls frequently during working hours, that’s the pattern you’ll get.
If they talk negatively about previous families during casual conversation with you – “my last family was so disorganized” or “I couldn’t stand how picky they were about everything” – file that away. Eventually, they’ll talk about you that way too.
If they seem to have an excuse for every mistake or issue – nothing is ever their fault, there’s always a reason why something didn’t get done or didn’t get done right – that victim mentality doesn’t change. You need someone who takes ownership.
If they ignore instructions you’ve given clearly, that’s not confusion. That’s either not paying attention or deciding they know better. Either way, it’s a problem.
If your gut tells you they’re not being fully honest about something – maybe they said they completed a task that clearly isn’t done, or their explanation of what happened doesn’t quite add up – trust that instinct. Integrity issues that show up in week one are dealbreakers.
Green Lights Worth Celebrating
On the flip side, some first-week behaviors predict years of successful partnership.
If they ask thoughtful questions that show they’re thinking about how to do things well, not just how to get things done, that’s someone who cares about quality.
If they notice things that need doing without being told and then either do them or mention them appropriately, they’re observant and proactive.
If they handle feedback gracefully and you see immediate adjustment based on what you’ve said, they’re coachable and want to meet your standards.
If they’re building genuine rapport with your family while maintaining professional boundaries, they understand the unique nature of household employment.
If they’re reliable – showing up on time, doing what they said they’d do, following through on commitments – that consistency is gold.
If they communicate proactively and appropriately, keeping you informed without overwhelming you, they’ve got the judgment this role requires.
If you feel lighter and less stressed after their first week rather than more anxious, that’s telling you something important about whether this is working.
What To Do With What You’re Seeing
If week one reveals mostly green lights, tell them. “You’re doing great, I appreciate how you handled X, keep doing what you’re doing.” Positive feedback reinforces good patterns and helps new employees understand what’s working.
If you’re seeing some concerning patterns but they’re not dealbreakers, address them directly now. Don’t wait and hope they’ll figure it out. “I’ve noticed you’re checking your phone pretty frequently during work hours. Personal phone use needs to be limited to breaks.” Clear feedback during week one can course-correct issues before they become entrenched habits.
If you’re seeing serious red flags – integrity issues, major judgment problems, disrespect, inability to follow clear instructions – you’re probably looking at a mismatch that won’t improve. It’s kinder to both of you to acknowledge it’s not working rather than dragging it out for months.
The first week is still feeling-each-other-out territory, but it’s not too early to see patterns that matter. Trust what you’re observing. Your family assistant is showing you exactly who they are and how they work. Believe them.
After twenty years placing family assistants with Chicago families and households nationwide, we’ve learned that successful long-term placements almost always have positive first weeks. Not perfect – everyone’s adjusting and there are always hiccups. But fundamentally positive, where both parties feel like this is probably going to work out well.
The placements that fail usually show warning signs immediately. Maybe families ignore them because they’re desperate for help or hopeful things will improve. But week one patterns typically intensify rather than disappear. The family assistant who’s defensive about feedback in week one will be defensive about feedback in month six. The one who communicates beautifully during adjustment will keep communicating beautifully once they’re settled.
Pay attention to what week one is telling you. It’s giving you almost everything you need to know about whether this placement has what it takes to succeed long-term. Trust what you’re seeing, address issues promptly, and celebrate when you realize you’ve hired someone excellent who’s going to make your household run better for years to come.
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