You just hired someone to work in your home. Now what?
The first month is weird for everyone. They’re learning your house, your routines, your preferences. You’re learning how they work, what they need from you, whether this is actually going to work out.
Some families over-manage this period. They hover, micro-correct every little thing, and drive their new employee crazy. Others under-manage it. They assume the person will figure everything out and then get frustrated when things aren’t done the way they wanted.
At Seaside Staffing Company, we’ve walked hundreds of families through the first month with new household staff in Miami and across the country. There’s a pattern to what works. Week one looks different than week two. What you should worry about at day ten is different than what matters at day thirty.
Here’s what the first month should actually look like, and what you should be paying attention to along the way.
Week One: Orientation and Information Overload
The first week is all about information transfer. You’re showing your new house manager or housekeeper or chef everything they need to know. Where things are, how systems work, what your preferences are, who to contact for what.
It’s overwhelming. For both of you.
You’re trying to remember everything you should tell them. They’re trying to absorb everything you’re saying. Everyone’s on their best behavior and slightly uncomfortable.
This is normal. Expect it to feel awkward.
Start with the basics on day one. House tour, keys, alarm codes, wifi password, where the cleaning supplies are, where the coffee is. Show them their workspace if they have one. Introduce them to anyone else in the household.
Don’t try to cover everything the first day. Their brain is full after a couple hours. You can continue the orientation over the next few days.
We worked with a family in Miami’s Coral Gables who tried to cover everything in the first three hours with their new house manager. Security systems, vendor contacts, property management details, family preferences, household procedures. The house manager left that day exhausted and couldn’t remember half of it. The family had to re-explain everything the second week.
Better approach: cover the essentials day one. Add more detail each subsequent day. Let information sink in gradually.
What to Cover in the First Few Days
By the end of the first week, your new household staff member should know:
How to get into the house and any security protocols. Where things are located that they’ll need regularly. Basic household routines and schedules. How you prefer to communicate and when. Who they should contact for questions or problems. Any immediate priorities or urgent tasks.
For specific roles, there are role-specific things to cover. A housekeeper needs to know your preferences about cleaning products, what areas are off-limits, how you like things organized. A private chef needs to know dietary restrictions, favorite meals, kitchen equipment, grocery shopping procedures. A house manager needs to know your vendor relationships, how you handle bills and expenses, what decisions they can make independently.
Write things down. Give them a household manual if you have one. If you don’t have one, create a basic reference document with important information. Phone numbers, wifi codes, alarm instructions, vendor contacts, preferences.
Don’t expect them to remember everything you say. They won’t. You didn’t when you started your job either.
A family in Miami Beach hired a housekeeper through Seaside Staffing Company and created a simple one-page sheet with all the basics. Where the vacuum was stored, what day trash went out, how to work the washer and dryer, which rooms to clean which days. The housekeeper kept it on her phone and referred to it constantly the first two weeks. By week three, she didn’t need it anymore. But having it made week one so much smoother.
The Stuff You Forget to Mention That Matters
There are things you won’t think to mention because they’re so automatic to you. Then your new employee does something differently and you realize you never told them.
The coffee maker is finicky and you have to hit the button twice. The front door sticks and you have to pull it hard to close it. The dog is scared of the vacuum. The alarm system randomly beeps and you just ignore it. You like the throw pillows arranged a certain way on the couch.
You won’t remember to mention these things until they become relevant. That’s fine. Just be patient when they don’t know something you never told them.
Some families get frustrated during week one because things aren’t being done “right.” But right according to who? If you never explained your preference, how would they know?
A house manager we placed in Miami’s Pinecrest got scolded for putting groceries away “wrong” on her third day. She’d put canned goods in a different cabinet than the family preferred. The family was annoyed. But they’d never shown her where things went. They just assumed she’d figure it out.
If something matters to you, say it. Don’t expect people to read your mind.
Week Two: They’re Finding Their Rhythm
Week two is when people start to relax a little. The newness is wearing off. They’re getting comfortable with the house, the routine, your communication style.
This is when you should start to see some independence. They should be able to handle basic tasks without constant direction. They should know where things are and how systems work.
But they’ll still have questions. Lots of questions. That’s appropriate. They’re clarifying, double-checking, making sure they understand expectations.
Let them ask. Answer patiently. Don’t treat questions like incompetence. Questions mean they care about doing things right.
At Seaside Staffing Company, we tell families to expect heavy communication during week two. Your new estate manager is going to text you a lot. Your housekeeper is going to check in frequently. This is good. It means they’re engaged and want to meet your standards.
The families who struggle are the ones who get annoyed by questions. “Why don’t they just figure it out?” Because they’re two weeks in and still learning your specific household. Give them time.
When to Step In, When to Let Them Figure It Out
This is the balance everyone struggles with. You don’t want to micromanage, but you also don’t want things done wrong. So when do you correct and when do you let it go?
Correct when something matters or could cause a problem. If your housekeeper is using the wrong product on a delicate surface, say something. If your house manager is handling vendor communications in a way that doesn’t work for you, address it.
Let it go when it’s just different, not wrong. If they organize the pantry differently than you would have but it still works, fine. If they take a different approach to a task but get the same result, that’s okay.
You hired them for their expertise. Let them work the way they work, as long as the outcome is what you need.
We worked with a family in Miami who hired a private chef and then tried to dictate every step of meal prep. How to chop vegetables, when to start cooking, what pans to use. The chef was miserable. She felt like she couldn’t do her job. Eventually she quit.
The family thought they were being helpful. They were actually being controlling. They hired a professional and then wouldn’t let her be professional.
Unless something is actually wrong, step back.
Week Three: The First Questions and Adjustments
By week three, your new employee has opinions about how things could work better. They’ve noticed inefficiencies or have suggestions for improvement.
This is where good household staff distinguish themselves. They don’t just do what they’re told. They actively think about how to improve systems and make suggestions.
Welcome this. Listen when they have ideas. You hired someone with experience and expertise. Use it.
A house manager we placed with a family in Key Biscayne suggested changing the grocery delivery schedule after three weeks. She’d noticed they were running out of certain items mid-week and over-stocked on others. Her suggestion saved the family money and reduced waste. They were glad they listened.
But this is also when minor tensions can emerge. Maybe your communication styles aren’t quite meshing. Maybe expectations weren’t as clear as you thought. Maybe there’s a task they’re struggling with.
Address these things early. Don’t let small frustrations build into big problems.
If something isn’t working, have a conversation. “I’ve noticed you’re doing X this way. Can we talk about that?” Most issues at week three are easily fixable if you address them directly.
Normal Concerns Versus Real Problems
How do you know if what you’re seeing at three weeks is normal adjustment stuff or a sign this isn’t going to work?
Normal concerns: they’re still asking a lot of questions, they’re not as fast as you’d like, they’re still learning your preferences, minor miscommunications happen, they seem nervous or tentative.
Real problems: they’re consistently late or unreliable, they’re defensive when you give feedback, they’re not following basic instructions, they’re disrespectful to you or family members, their references check out but their actual work doesn’t match their experience.
One family in Miami almost fired their housekeeper at week three because she was “too slow.” But when we talked to them, it turned out she was being thorough, not slow. She was doing deep cleaning in addition to surface cleaning. Once the family understood that, they appreciated her approach.
Another family had a personal assistant who was charming in the interview but by week three was missing deadlines, forgetting tasks, and making excuses. That wasn’t adjustment. That was incompetence. They let her go.
Trust your gut, but give people a real chance to learn your household before you decide it’s not working.
Week Four: Evaluating Whether This Is Working
By the end of the first month, you should have a pretty good sense of whether this is going to work long-term.
Not a perfect sense. One month isn’t enough to know everything. But you should know if the foundation is solid.
Ask yourself: Is this person reliable and trustworthy? Do they communicate well? Are they improving as they learn? Do they take feedback well? Do you feel comfortable with them in your home?
If the answer to all of those is yes, you’re probably fine. Keep going.
If the answer to any of those is no, you have a problem that likely won’t fix itself.
At Seaside Staffing Company, we do 30-day check-ins with families. We ask how it’s going, what’s working, what’s not. Most of the time, families are happy or have minor adjustments to make. Sometimes, we hear that it’s not the right fit.
If you realize at 30 days that you made a mistake, it’s okay to acknowledge that. Better to cut your losses now than drag out a bad situation for six months.
But if things are generally good with some rough edges, give it more time. Most household employment relationships take three to six months to really smooth out.
What Good Performance Looks Like at 30 Days
You shouldn’t expect perfection at one month. You should expect competence, reliability, and improvement.
A good house manager at 30 days should be handling routine tasks independently, communicating proactively about issues, and showing good judgment about what needs your input versus what they can handle alone.
A good housekeeper should know your preferences, clean thoroughly, manage their time well, and ask when they’re unsure rather than guessing.
A good private chef should be comfortable in your kitchen, accommodating your preferences, and producing consistently good meals.
For any role, you want to see: consistency, good communication, follow-through, and a genuine effort to meet your standards.
You also want to see that they’re comfortable. If someone still seems nervous and unsure at 30 days, that’s a flag. By now they should be settling in.
Communication Patterns to Establish Early
The first month is when you establish how you’ll communicate going forward. Do it intentionally.
Decide how you want to be contacted. Text? Email? In person? For urgent things versus routine updates?
Decide on check-in frequency. Daily? Weekly? As needed?
Decide on how feedback will be given. Regular sit-downs? Real-time as issues come up?
Be clear about this. Don’t assume. Different people have different preferences and habits.
We worked with a family in Miami who preferred minimal communication, while their new house manager was used to frequent check-ins. They kept missing each other’s expectations until they finally had a direct conversation about it. Once they aligned on “weekly email updates unless something urgent comes up,” everyone was happier.
Some families want daily texts about what’s happening. Others find that intrusive. Know what you want and communicate it clearly.
The Boundaries Conversation You Should Have
Sometime in the first month, have a conversation about boundaries.
What rooms are private? What times are off-limits for communication? What personal information is appropriate to share and what isn’t? How do you handle mistakes or problems?
This feels awkward to talk about, but it prevents bigger awkwardness later.
A family in Miami’s Coconut Grove didn’t have this conversation with their live-in estate manager. By month two, the estate manager was helping himself to their wine collection and using their home gym without asking. The family was uncomfortable but hadn’t set boundaries, so they couldn’t really complain.
Set expectations early. “Please don’t go into our bedroom unless you’re cleaning it. Don’t eat our food unless we offer. Don’t have visitors over without asking.”
Most professional household staff appreciate clear boundaries. It makes their job easier.
When 30 Days Isn’t Enough
For complex roles like estate managers or chiefs of staff, 30 days might not be enough time to fully evaluate.
These positions involve relationship-building with vendors, learning complex systems, understanding nuanced family dynamics. That takes longer than a month.
If you hired someone for a role like this, give them 90 days before you make a final judgment. The first month is just the beginning.
But for more straightforward roles like housekeepers or personal assistants, 30 days should give you a good read on whether it’s working.
Red Flags at One Month That Mean Trouble
Some warning signs at 30 days shouldn’t be ignored.
Chronic lateness or unreliability. If they’re still struggling to show up on time consistently, that’s not going to improve.
Inability to follow basic instructions. If they’re still doing things you explicitly asked them not to do, that’s a problem.
Defensiveness about feedback. If they can’t hear constructive criticism without getting upset, working together long-term will be hard.
Lack of initiative. If they only do exactly what you tell them and never think ahead or suggest improvements, they’re probably not the right fit.
Poor communication. If they’re not telling you about problems, mistakes, or important information, that creates bigger issues down the road.
These things rarely get better with more time. If you’re seeing them at one month, consider whether this is the right person for your household.
At Seaside Staffing Company, we encourage families to trust their instincts at the 30-day mark. If something feels fundamentally off, it probably is. If things feel generally good with normal adjustment bumps, keep going.
The first month is about building a foundation. If that foundation is solid, you can build a great working relationship from there. If it’s shaky, you’ll keep struggling.
Pay attention to what you’re seeing. Give people a fair chance to learn and adjust. But also trust what you’re observing. Your first month tells you a lot about what the next year will look like.
