Working With Assistants and House Managers

Imagine a photographer named Tobias Wynn who takes family portraits in people’s homes. In November, Ruth Abara writes to him. She is the house manager for the Kerrigans, and Mrs. Kerrigan wants a portrait of the family for the holiday card. The family can give him 45 minutes at four on a Sunday, in the garden if it is dry.

That Sunday, Tobias is finishing a christening across town. He sends his assistant, Kit, ahead at two to set up the lights, and he does not think to tell Ruth. At the service door, Ruth finds a young man she has never seen, with a car full of stands. The children are in the house. She keeps him waiting on the step while she calls Tobias to check who he is.

At four, Tobias takes the portrait in the garden, and the photos are lovely. Mrs. Kerrigan sends the card to 200 people. In March, she asks Ruth to book “the photographer from Christmas” for her son’s graduation. Ruth says she will. Then she mentions the stranger at the door, and the phone call she had to make while the children were home. Mrs. Kerrigan says, “Find someone else, then.”

Suppose instead that Tobias asks Ruth a question when she books him. “What would make Sunday easy for you?” Ruth tells him to use the service door and park by the garage. The housekeeper finishes the front hall at three, so nothing should come through the front before then.

On Friday, Tobias writes to Ruth. “My assistant, Kit Moreno, will arrive at two to set up in the garden. He drives a gray van, and he’ll come to the service door.” On Sunday, Ruth lets Kit in and shows him the garden. In March, Mrs. Kerrigan asks about the photographer from Christmas. “He was no trouble at all,” Ruth says, and she books him for the graduation.

Tobias took the same portrait both times. What changed was what Ruth saw on that Sunday afternoon, and what she said when Mrs. Kerrigan asked. In a household that runs itself, the person who books you is usually the person you serve. In a larger household, the one who calls you may be an assistant or a house manager. That person stays on the job after you are booked. Here is why what they see reaches the owner, and how to work with them.

A house manager in Toronto tells his employers about problems as they happen

In 2017, the recruiter Scott Munden interviewed a house manager in Toronto for Estate & Manor. He calls the man “Sam,” to keep the family private. Sam has worked for the family for 12 years. His employers trust him, he said, to hire and let go of staff, to pay the household’s bills, and to “organize repairs.”

So the trades and suppliers who come to the house deal with Sam. He said that he has “a great relation with all our trades and suppliers.”

Sam’s employers are closely involved in their household. “I report issues as they occur,” he said. He gave a project that costs more than planned as an example. “I don’t hesitate to bring it to my employers’ attention so that a decision can be made.”

Measured against this lesson, Sam’s job has two sides. To people outside the house, he is the house manager who sees everything and says nothing. To his employers, he passes on what goes wrong, as it happens. So when a professional causes a problem in Sam’s house, the family hears about it from Sam. So a professional who works in that house is, first, one of Sam’s own working relationships.

House managers say they watch the people they bring into a house

In 2015, the estate management firm Celebrity Estate Management asked members of its network for tips on working with vendors. “Vendors” is their word for the trades and services a house hires from outside, such as a painter or a landscape crew. “Respect, communication and relationship-building were a common theme,” the firm wrote.

One answer came from a house manager at a private home in Palm Springs, California. The house manager passed on the boss’s rule, that vendors will “Do what you INSPECT, not what you EXPECT.” Then the house manager explained what that looks like. “It’s common that you will walk through the work in detail with the owner or manager when he’s trying to get the contract, then you will never see them again. A totally new guy will show up to do the work.”

So the advice to other house managers is to walk through the job again and “watch them carefully.” The reason came last. “At the end of the day, their work is a reflection of your service.”

Measured against this lesson, an employer judges a house manager by the people that house manager brings in. So the house manager notices who turns up and how the work goes, on days the owner may never see. The stranger at the Kerrigans’ service door was the surprise this house manager warned about. Some professionals are pleasant to the owner and careless with the staff. In a house like this one, the carelessness happens in front of the person whose job is to notice.

An estate manager and a designer kept their disagreements to themselves

Peter Van Ryder teaches a course on household and estate management. In 2022, he and the designer English Minter talked on the Easemakers podcast about why estate managers and designers clash. His firm’s write-up of the episode tells it in his words. He calls the owner of the household the principal.

A designer, he wrote, often grows close to the principal while the work is going on. The staff do not have that closeness. So the designer “feels a deep responsibility to the Principal’s vision.” The designer often tries to carry it out “at all costs without considering how it affects the operation of the household.” The estate manager, meanwhile, has to keep the house running and make the finished work last.

The write-up names one question that changes the tone between the two, whichever side asks it. “What do you need me to do to help you?”

Van Ryder and Minter worked on a project together, in what he called “one of the most difficult environments I have been involved with.” He wrote, “Did we disagree on things? Yes. Did we let it stop us or let our principal/client know? No!” He counts that as a small help to a principal in the middle of a stressful job. The principal can see “that we are all on the same page for THEIR benefit.”

Measured against this lesson, the designer who works “at all costs” treats the owner as the only relationship on the job. Van Ryder and Minter treated their own working relationship as one more. They disagreed, they settled it between the two of them, and their principal saw two people on the same side.

Why asking a house manager to keep a slip quiet goes wrong

Imagine a dog walker named Bram Kessler who walks the Fairleys’ two spaniels every weekday. Lucia Ferraro, the Fairleys’ house manager, hired him in the spring. One afternoon in the park, the younger spaniel slips her collar and runs off. Bram catches her ten minutes later, muddy and unhurt.

Bram is behind on his afternoon walks. When he brings the dogs back, he tells Ms. Ferraro what happened. “Could we keep this between us?” he asks. “I don’t want Mrs. Fairley worrying over nothing.”

Ms. Ferraro does not promise anything. That evening, she tells Mrs. Fairley about the dog and about the request. Reporting a loose dog is part of her job. Mrs. Fairley is less upset about the collar than about the request. She wonders what else has not reached her. Before the month is out, she asks Ms. Ferraro to find another walker.

Bram was right to tell Ms. Ferraro. His mistake was asking her to keep it from her employer. Part of a house manager’s job is to report problems as they happen. So his request asked her to choose between him and her employer. The version that works gives her the whole story to pass on, with the fix in it. “Poppy slipped her collar in the park today. I had her back in ten minutes, and she’s fine. I’ve ordered harnesses for both dogs, and they come Thursday.”

Asking a house manager what they need is not serving the wrong person

Asking a house manager what would make your visits easy can feel like taking orders from someone who is not your client. The owner hired you, and the owner pays you.

The owner also asked the house manager to run the house you work in. Van Ryder’s question, “What do you need me to do to help you?”, set the tone between an estate manager and a designer on a hard job. Their principal got the two of them on the same side. So asking the house manager what they need is part of serving the owner.

How to work with an assistant or a house manager

1. When an assistant or a house manager books you, ask what would make your visits easy for them. Then ask when the house needs its rooms back, because they have to keep the house running around your work. For example, a personal trainer can ask, “What would make my mornings here easy for you? And when is the gym cleaned?” Write the answers on the page you keep on the client.
2. When anyone else from your business will come to the house, tell the house manager the day before, by name. Say when they will arrive and which door they will use. For example, a home organizer can write, “My assistant, Dana Ruiz, will come with me on Thursday. She’ll park by the garage and use the side door.”
3. When a job will cost more or take longer, tell the house manager first. Give them what they will need to pass on, which is what changed, why, and the choice. That is the course’s suggestion. Its reason is that a house manager like Sam brings a higher cost to the family for them to decide. Your note gives the house manager what the family will ask. For example, a travel adviser can write to a client’s assistant, “The villa in Positano has gone up by $2,000 for August, for a new cleaning fee. I can hold it until Friday, or book the one next door at the old price.”
4. When something goes wrong in the house, tell the house manager the same day, with what you will do about it. Do not ask them to keep it from the owner. For example, a music teacher can say, “I scratched the lid of the piano with my ring today, and I’m sorry. A restorer can come next week, at my cost.”
5. When you and the house manager disagree, settle it with the house manager. Do not take it to the owner to win it. For example, a private chef can say to the house manager, “The fish has to go in at seven, so the kitchen won’t be clear until nine. Could the cleaning start at nine if I leave the counters bare?”

Next: You will see why a partner who missed the meeting is a common reason a decision stalls.