A family in New York City hired an estate manager last year with 20 years of experience and impeccable references. Three months in, they realized they had a serious problem – this person could barely use email, couldn’t figure out their project management software, and was completely lost when they tried to implement a new smart home system. Every time the family introduced any kind of technology solution, the estate manager would either refuse to use it, use it incorrectly, or find workarounds that defeated the entire purpose of the technology in the first place.
The family called us asking if they should fire her, because on one hand she was failing at a pretty fundamental aspect of the role, but on the other hand she was otherwise competent and they felt guilty about holding her to technology standards she clearly wasn’t comfortable with. Here’s what we told them – in 2026, technology competence isn’t optional for household staff, especially for management-level positions. You’re not being unreasonable by expecting someone to be able to use basic tools that are standard in professional environments.
At Seaside Staffing Company, we’ve seen this situation play out dozens of times over the past few years as households have become increasingly dependent on technology for everything from home automation to vendor management to scheduling. The staff who were hired 10 or 15 years ago based primarily on their organizational skills and people management abilities are now struggling because the role has fundamentally changed. What used to be managed with paper calendars and filing cabinets now requires comfort with multiple software platforms, cloud-based systems, and constantly evolving smart home technology.
The first thing you need to figure out is whether you’re dealing with someone who can’t learn or someone who won’t learn. Those are very different problems with very different solutions. Some people genuinely struggle with technology because of learning differences, age-related cognitive changes, or just a brain that doesn’t work that way. Other people struggle with technology because they’re resistant to change, they think the old ways were better, or they don’t want to put in the effort to learn something new. The first group deserves patience and support. The second group needs a reality check about whether this role is still right for them.
How do you tell the difference? Pay attention to their attitude and effort. Someone who can’t learn but is trying will ask questions, practice on their own time, take notes, and show visible frustration with themselves when they can’t figure something out. Someone who won’t learn will make excuses, blame the technology, insist that their old system worked fine, and resist every attempt to help them improve. The estate manager in New York turned out to be in the second category – she wasn’t struggling because she couldn’t learn, she was struggling because she thought project management software was unnecessary and refused to engage with it.
Here’s what’s fair to expect from household staff in 2026 – basic email competence including attachments and calendar functions, ability to learn and use household-specific software within a reasonable training period, comfort with smartphones for communication and scheduling, and willingness to engage with smart home systems and other technology that’s integral to household operations. Those are baseline professional skills, not advanced technical expertise. If someone can’t or won’t do those things, they’re not qualified for a modern household management role regardless of how good they are at other aspects of the job.
What’s not fair to expect – that they immediately know how to use every piece of software you throw at them without training, that they’ll naturally understand complex systems without clear documentation and onboarding, or that they’ll troubleshoot technical problems that would stump most people. You can expect willingness to learn and basic competence once trained. You can’t expect them to be IT professionals unless you specifically hired them for technical skills.
The solution starts with honest assessment of what technology skills are actually essential for your household. Make a list of the specific tools and systems your estate manager needs to use regularly. Then evaluate their current competency with each one and their trajectory of improvement. Are they getting better with practice, or are they stuck at the same level of struggle they were at three months ago? If they’re improving, even slowly, there’s hope. If they’re not improving at all despite training and support, you’ve got a problem.
We worked with a family in Chicago who had a house manager who was terrible with their scheduling software when she started. The family committed to proper training – they scheduled weekly one-on-one sessions for the first month, created simple written guides for common tasks, and gave her time to practice without pressure. Six months later, she was comfortable with the system and using it effectively. She wasn’t a power user, but she could do what she needed to do. That’s a success story because both the employer and the employee were willing to invest in the learning process.
Compare that to a situation we saw in San Francisco where the family hired an estate manager who couldn’t figure out how to use their smart home system. The family tried to train him multiple times, gave him access to YouTube tutorials and the company’s support line, but six months in he was still just turning to the family and saying “I can’t figure this out” every time something needed to be adjusted. At some point, inability to learn basic technology after reasonable training and support becomes a performance issue that needs to be addressed like any other performance issue.
If you’ve determined that your staff person is willing to learn but struggling, here’s what actually helps – clear, step-by-step written instructions with screenshots for common tasks, scheduled practice time where they can work with the technology without real-world pressure, patience with the learning curve and repeated questions, and breaking complex processes into smaller pieces they can master one at a time. Technology that’s intuitive to you might not be intuitive to them, and that’s okay as long as they’re making effort.
Some families have success bringing in outside trainers or IT support people to provide technology training. Sometimes staff are more willing to admit confusion and ask basic questions to a neutral third party than to their employer. We’ve seen this work well especially for smart home systems or specialty software where the staff person isn’t going to figure it out on their own and needs real instruction.
You also need to consider whether your technology expectations are reasonable for your market and the salary you’re paying. If you’re paying at the lower end of market rate and expecting advanced technology skills, you might need to adjust either your expectations or your compensation. High-level technical competence commands higher salaries. If you want an estate manager who can seamlessly integrate multiple software systems, manage smart home technology, and handle IT troubleshooting, you need to pay for someone with those skills.
At Seaside Staffing Company, we’ve started including specific technology assessments in our screening process for household management roles. We ask candidates to describe their experience with common platforms, we have them demonstrate basic tasks like creating a spreadsheet or using a scheduling system, and we specifically ask about their comfort level with learning new technology. This has helped us identify candidates who are going to struggle before families invest time and money in hiring them.
But here’s the hard truth – some veteran household staff who were excellent at their jobs 10 years ago are no longer equipped for how the role has evolved. That’s not a moral failing, it’s just reality. The households that used to run on paper files and phone calls now run on shared calendars, cloud storage, automated systems, and digital communication. If someone can’t or won’t adapt to that, they need to be looking for positions in households that are still operating the old way, and those households are increasingly rare.
If you’ve invested in proper training and support and your staff person is still struggling significantly with technology that’s essential to their role, you need to have a direct conversation. “This role requires regular use of these specific systems, and I need to see substantial improvement in your comfort and competency within the next 60 days. What support do you need from me to make that happen?” Then actually provide the support they identify, and set clear benchmarks for what improvement looks like.
If they can’t meet those benchmarks after receiving proper support, you’re looking at a situation where the role has outgrown the person’s capabilities. That’s a legitimate reason to end employment, and it’s actually kinder to be direct about it than to keep someone in a role where they’re constantly struggling and feeling inadequate. Some people will thrive in less technology-dependent roles like housekeeping or private cooking where the core skills are more hands-on and less digital.
The families who handle this well are the ones who are clear about technology expectations from the beginning, who invest in proper training and onboarding, who provide appropriate tools and support, and who are willing to have honest conversations when someone isn’t meeting expectations. The families who handle it poorly are the ones who assume everyone should just naturally know how to use everything, who get impatient with the learning curve, or who avoid addressing the problem until resentment builds to the point where they fire someone without warning.
Technology competency is becoming as fundamental to household management roles as organizational skills or communication abilities. If your estate manager can’t handle it, you’ve got to figure out quickly whether that’s something that can be fixed with training and support or whether you need to find someone whose skills match your household’s actual needs. Your household operations shouldn’t be held back by someone who refuses to engage with basic technology that would make everyone’s life easier.
