Send Past Clients Something, Not a Check-In

Imagine a specialist realtor named Owen Calloway who sells old houses. Two years ago, he sold Julia and Mark Harcourt an 1890s farmhouse with a slate roof. At the closing, Mrs. Harcourt told him two things. The roof worried her, and she wanted to plant an orchard behind the barn.

Owen wants their next sale, and he wants their friends. So every couple of months, he texts her. “Hi Julia! Just checking in. How are you loving the house? Let me know if you ever need anything, and if any friends are thinking of moving, I’d love to help!” He sends the fourth one in a slow spring, when he has two listings and no offers.

Mrs. Harcourt answers the first two with “All good, thanks Owen!” Each time, she stops what she is doing to find something friendly to say. She leaves the third and fourth unanswered, and she feels rude about it. At a dinner in June, a friend says she is thinking of selling and asks about Owen. “He was good,” Mrs. Harcourt says. “He does text a lot.” The friend calls another agent.

Suppose instead that Owen writes twice a year, in March and September, and only with something for the Harcourts. In March, he texts, “Hi Julia, the county is selling heritage apple trees on April 12. The details are below.” In September, he writes, “The roofer who repaired the slate on the Mill Street house is booking autumn work. His name is Tom Reilly, and his number is below.” Neither message has a question in it.

Mrs. Harcourt plants four apple trees in April. In October, Tom Reilly replaces 30 slates before the first frost. She writes back to Owen both times, because she wants to. When her friend asks about selling, Mrs. Harcourt says, “Call Owen. He found me my roofer.”

Owen kept in touch both times. What changed was what each message asked of Mrs. Harcourt. The check-ins asked her to reply, to say the house was fine, and to send him a friend. The messages in March and September asked her for nothing, and each one handed her something she could use. Here is why the first kind feels like a debt, and how to send the second kind on a rhythm.

A gift that comes with a hint of payback earns less thanks

In 2006, Philip Watkins and three colleagues published two studies in the journal Cognition and Emotion. People read short descriptions of a gift being given. The descriptions differed in how clearly the giver expected something back. The more the giver expected, the more people felt they owed, and the less grateful they felt.

People also said they would be less willing to help that giver in the future. The researchers concluded that feeling grateful and feeling in debt are two separate feelings. A gift can produce either one, depending on what comes attached to it.

Those were people reading about a gift on paper, and the step to a client is the course’s own. Here is the step. A message to a past client is a small gift of your attention. “Just checking in” attaches an expectation to it. The client has to reply and has to say the work is holding up. In Owen’s text, she also has to find him a friend. So Mrs. Harcourt felt that she owed him an answer, and she felt rude when she did not send one. The roofer’s name came with nothing attached, so what she felt was thanks.

The last finding matters most for a service business. The people in the studies were less willing to help a giver who expected something back. For a professional, help from a past client usually means the next job or a friend’s name. When Mrs. Harcourt’s friend asked about Owen, the answer was, “He does text a lot.”

A designer in Palm Beach Gardens stays in her clients’ orbit instead of following up

In January 2026, Business of Home asked seven designers how they stay in touch with clients after a project is over. Krista Watterworth Alterman, a designer in Palm Beach Gardens, began with what she does not do. “I don’t ‘follow up’ with old clients,” she said. “I stay in their orbit.”

What she sends is meant for one client at a time. “I’ll text you when I see a chair you’d love, send a note when your kid graduates, or DM you a house I know you’d buy.” Her clients also get her emails and watch the studio grow. What they do not get, she said, is “awkward check-ins” or “sales energy.”

She described what comes of it. “When years go by and I get the call that starts with, ‘So … we’re moving.’ That’s when you know you did it right.”

Measured against this lesson, every message on her list carries something and asks for nothing. The chair, the note at graduation, and the house each need no answer, and none of them asks for work. The call about the move came from the client, years later.

A check-in usually goes out to settle the professional’s worry

Owen sent his fourth check-in in a slow spring, and that timing is common. The course’s own explanation is short. A “just checking in” message usually goes out when the professional is uneasy. The month is thin, or a client has gone quiet, or the fear is that the client has forgotten you. The message asks the client to settle that unease by replying, by saying the work was good, or by sending someone new.

That is why the client feels it as a request. “How are you loving the house?” sounds like a question about Mrs. Harcourt. What it asked her for was a sentence that would make Owen feel better. The same pull shows up in a follow-up before the sale, when the job starts to matter. After the sale, the pull is quieter, and it can go on for years.

So the test before you send is one question. What does this message ask the client to do? If it asks them to reply, to reassure you, or to do something for you, the message is for you. If it asks for nothing and hands the client something they can use, the message is for them.

A London designer sees her old clients at least twice a year

In the same Business of Home roundup, Venetia Rudebeck, a designer in London, gave a rhythm. “We try to do something intimate and special with old clients at least a couple of times a year,” she said. She and her business partner know each client’s taste. So they invite old clients to “an exclusive art preview, exhibition opening night or an event we know they’ll genuinely enjoy.” She and her partner believe in a phone call and “a proper chat” over relying only on email. She also counts many former clients as friends.

Measured against this lesson, her rhythm is the part to keep. An invitation to an event is a different step. Many of her old clients are friends. With a client who is not, an invitation is a step closer, and the client sets that pace. Send something close to the work instead, the way Owen sent a roofer.

The course takes twice a year as the floor, from Rudebeck. It adds one suggestion of its own, which is to tie the two dates to the client’s year, not to yours. Owen wrote in March, before planting, and in September, before the frost. The reason is that a message timed to the client’s year arrives when what it carries is useful. Two messages a year, every year, also answer a question the client has about you. It is whether you will be the same next time.

Between the two dates, send something whenever you come across it, as Alterman does with a chair. What you do not send is a message on the date with nothing in it. That is the course’s own rule, and here is the reason. An empty message sent because the date came round is the check-in again, with a calendar behind it.

Why a gift with a request at the end goes wrong

Imagine a caterer named Priya Anand who cooked for Mrs. Osei’s 50th birthday dinner in May. During the evening, Mrs. Osei told her that her son loved the lamb and was leaving for university in the autumn. In September, Priya sends a card with the lamb recipe written out for one pan and a student kitchen.

Under the recipe, she adds a sentence. “If any friends are planning a party this winter, I’d be so grateful if you passed on my name!” Mrs. Osei is about to text her thanks. Instead, she sends the recipe to her son, puts the card in a drawer, and does not write back. In November, a friend asks her for a caterer, and Mrs. Osei gives three names. Priya’s is one of them.

Priya did the hard part well. The recipe was meant for one family, and it came from something Mrs. Osei told her. The last sentence turned the gift into a request, which attached the expectation of something back that the Watkins studies tested. The version that works is the same card without that sentence. Then the card is a gift, and whatever Mrs. Osei does next is her own choice.

Asking for nothing does not mean being forgotten

Many professionals worry that a client they ask for nothing will forget them. The check-in can feel like the only way to stay in the client’s mind.

Owen’s two messages put his name in front of Mrs. Harcourt twice a year, every year. Each time, his name came with a roofer or an apple tree. Alterman’s clients called her years later, about a move, without a single check-in in between. The Watkins studies point the same way, because the expectation made people less willing to help the giver. When her friend asked about Owen, Mrs. Harcourt talked about the roofer.

How to stay in touch with a past client

1. At the end of each job, write two dates for the coming year on the page you keep on the client. Tie each date to something in the client’s year, not to a quiet month of yours. For example, a florist who did a June anniversary dinner might write May 15. Her second date is in December, before the family’s holiday party.
2. A week before each date, look at the client’s page and find one item for them. It might be a name, a date, a place, or something they can buy. Use only what the client told you, not what you found. For example, a music teacher’s former student wanted to play in a quartet. The teacher can send her the date of a chamber music workshop.
3. Write the message so that it ends on what you are sending. Leave out any question, any “let me know,” and any request. For example, an event planner can write, “The garden at Hollins House takes private bookings again from April. The booking page is below.”
4. If you find nothing for a client by the date, send nothing, and move the date a month on.
5. Between the two dates, send something whenever you come across an item meant for one client. For example, a dog walker whose former client’s spaniel swims in the Elm Park pond can text, “The Elm Park pond is drained from May 3 for two weeks. The lake at Fenwick is open to dogs.”
6. Before you send any message to a past client, ask what it asks them to do. Take out every sentence that asks them to reply, to reassure you, or to do something for you. If nothing for the client is left, do not send it. For example, a coach who wrote, “Hope the new role is going well! Let me know if you ever want to catch up,” has nothing left to send.

Next: You will see why a client who trusts you stays, and what leaving you would cost them.