11 non-obvious questions to ask when you’re interviewing for estate manager jobs

Finding the perfect estate management role for your passions and skillset can be like finding a needle in a haystack. It might take setting dozens of job alerts and sifting through hundreds of job descriptions to find one potential role that really gets you excited.

If you land the interview, it’s easy to focus on how to position yourself as the right fit for the role. But, it’s just as important to remember that you are interviewing your future principals, too.

So, how do you make the most of the interview process? How do you learn as much as you can about an estate management role, before you take it?

We asked the experts in our Easemakers community to share their go-to questions to ask during the interview process, beyond the obvious questions around basic responsibilities, schedule, salary, etc.

Check out their answers below, and join the conversation in Easemakers, the leading community for private service professionals!

1 – How long was the employee in this position? What was one thing they did you liked or did not like?

Nashville EA-PA and House Manager Ian Garcino suggests asking your predecessor’s tenure, what they did well and what they didn’t. Asking how long the former estate manager spent in the role will help you spot a job with a high rate of turnover — a red flag mentioned by several of our Easemakers.

2 – What is the 2.0 version of the person leaving the role? If you could improve upon my predecessor, what would that look like?

This question from Bay Area Chief of Staff and Estate Manager Tina Luther is another great way to ask about your predecessor, while keeping the conversation very positive.

It should also help you uncover two of the red flags Tina watches for when talking with potential principals: speaking disparagingly of former employees and setting unrealistic expectations.

3 – Tell me about your team dynamics. How is success gauged? How do you support employee development?

San Francisco Estate Manager Aline Urkumyan says asking these questions help her gain insights into the work environment and the principals’ commitment to long-term employee growth.

She looks for principals who invest in their staff, who can demonstrate a track record of team empowerment, and whose current team members are happy with their work environment.

4 – What do you want your employee culture to look like?

John Laverman, a Ranch Operations Manager in Montana asks this question about culture, along with these followup questions:

• What do you do to promote that culture?
• How successful do you feel about reaching that goal?
• How would you like your employee culture to change?

This is a great way to ask potential principals about not only their existing culture, but also where they aspire to be, and how you can help them get there.

5 – What is the salary increase criteria?

This question from Ian Garcino gives you an opportunity to get specific about performance metrics. It’s important to understand what success looks like in a role, as well as the concrete steps you’d have to take to qualify for a promotion or a salary increase.

6 – Where do you see myself in your organization / family in 5-10 years? 

Often, both private service professionals and the families they’re interviewing with are looking for a long-term fit. Staying in a role for years or decades can offer incredible career opportunities — as long as you choose the right household in the beginning.

Asking this question from Ian Garcino will help you understand where the family wants to go over the next 5-10 years, and how your role could change. They may want to add dozens of properties and staff members, or they may plan to downsize to one property, and having an idea of their plans will help you choose a role that aligns with your career goals.

7 – What is your preferred method of communication?

Tina Luther explains that the answer to this question could be different for every principal, for example, “give me the reader’s digest version, put post-it notes on the counter, write me an essay, text me hourly.”

Asking this question early on will help you identify anyone whose communication style isn’t a good match for you, and set you up for success if you take the job.

8 – What do you perceive the average work week being like? How many hours do you expect the average work week to be?

This question from John Laverman will give you a sense of the principals’ expectations and gauge whether they’re realistic.

“I once had a position offered to me in which I was told the average work week would be about 50 hours and I knew beyond a shadow of a doubt it would be 65-70,” John explains. “They simply wanted to justify underpaying, or they clearly didn’t understand the time it would take to perform the tasks in a professional manner (red flag on both counts).”

9 – What non-traditional benefits do you offer?

Estate management roles can come with a lot of perks.

John Laverman has been offered private property hiking, fishing, hunting, and use of the principals’ watercraft. Once, a principal leased a large parcel of land for him to hunt, and even paid for him to put in food plots.

He adds, “a follow up question may be, can my wife or children participate in these perks with me?”

Meanwhile, Bay Area Estate Manager Aimée Moreault says non-traditional benefits can show a principal’s commitment to work-life balance. She says offering benefits like a gym membership or a ski pass shows that they genuinely support you and value your time away from work — a green flag.

10 – How common is it that employees use all their PTO each year? How is PTO to be used?

Speaking of work-life balance, John Laverman also likes to ask how commonly employees use their PTO.

“This is often a sign of how much freedom you have to use it and how the principal values employees having time away from work,” John explains.

He adds that some families may have rules around how paid time off can be used, for example, some may require you to use it in blocks, or a week at a time.

“I like to use mine around weekends — it extends a vacation without using as much PTO,” explains John Laverman. “This is not allowed in some situations.”

11 – How are you on your worst day? 

This question from Tina Luther can give you insight into a principal’s leadership style. How do they handle challenges and stressful situations? Are they able to maintain a positive environment and remain kind and respectful, even on their worst day?

Asking this question may also help you build a rapport with a future principal and show that you want to get to know them as a person — but at the same time, because it’s a fairly personal question, you should use your intuition and only ask this question if it feels right in the context of the conversation.

What to watch for in the interview process

Beyond asking the right questions, certain signals during the interview process can show you whether a role is a good fit for you.

John Laverman looks for a base compensation package that is truly aligned with the value of the position and a job description that is well-defined and stays consistent throughout the interview process.

“A red flag is a role that seems to grow and evolve as you go through the interview process,” John explains, adding that he saw the opposite during the interview process for his current role. “I spent 11 weeks interviewing seven times with different people prior to coming out and seeing the property, meeting the principals, and getting an offer. Fortunately, the job description stayed the same throughout it.”

He gets truly excited about a role when the principals’ vision for the job aligns with his skillset, and he can connect with the job, principals, fellow employees, and location.

For Aimée Moreault, a green flag is when the interviewers move through the interview process quickly, respecting everyone’s time. 

She is even more drawn to a role when she learns that the principals are good decision makers who don’t micromanage employees and allow for trust to be built.

“And, do they stick with what they said, or do the ‘I never said that’ dance,” she adds.

Tina Luther gets excited about the opportunity to build processes and systems, and the potential for impact.

“For me, moving the needle is very important,” says Tina. “If they have pain points that I can solve, that is exciting.”

Aline Urkumyan looks for a culture that values integrity, the big picture, people and teamwork, community, and innovation.

“Seeing how the role contributes to a larger mission or positively impacts society is a powerful motivator,” she says.

More resources for estate managers and private service professionals

Want to learn more from other estate managers and experts in the private service industry? Check out some of our other favorite resources.

• On-demand household management workshops — No matter how many years of experience you have managing high end residential properties, these workshops will help you level up your estate management skills. Start with the foundational workshop to streamline your household operations, then dig into intensives on housekeeping, maintenance, and home systems.
• Household staffing guides — Check out our guides for hiring household staff, packed with tips from Easemakers on how to hire and retain great staff members. Whether you’re hiring a housekeeper to live onsite or a part-time private chef, deciding between hiring for a full-time property manager job or working with a property management company, or looking for a detail-oriented household manager, these guides have the tips you need to create a job post, ask the right questions, and find the perfect fit.
• Easemakers Podcast — Hear from fellow estate managers and private service industry experts from New York, California, Florida and everywhere in between, and explore a range of estate management topics, including construction project management, collections and high end asset management, job searching, career growth, and more.
• Easemakers Community — Looking for an electrician in Los Angeles, a vintage furniture repair shop in Miami, a restaurant recommendation in Chicago, or a personal assistant in Washington? Need advice about budgets, sustainability, leasing a yacht, or gauging new pricing from a vendor? No matter your question, the expert private service professionals in Easemakers have an answer. This community is your place to turn for connection and support.

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