Sort your contacts into three tiers by how likely they are to refer you, then give each tier a different monthly rhythm: personal notes for the closest 25 or so, a quarterly touch for the middle group and a few seasonal messages for the rest. Use AI to draft each month's messages from a calendar, and edit every one.
"Keeping in touch" fails for a simple reason: it is a vague intention with no calendar attached. An agent who sells 20 homes a year may have 300 past clients, relatives and neighbours in a phone and a CRM, and no way of deciding who deserves a message this week. A touch plan removes that decision. Each month you open the calendar, see who is due, ask an assistant for drafts, add the personal line and send.
Sort the list into three tiers before drafting anything
Export your contacts into a spreadsheet with these columns: first name, relationship (past buyer, past seller, family, friend, neighbour, referral partner), year of last transaction, home purchase month, tier, last touch date, and a "personal fact" column for one detail you know. A phone number and email stay in your CRM; you do not need them in the sheet you show an assistant.
Tiers decide effort, so define them by behaviour, not by income.
| Tier | Who | Rough size | Rhythm | Style |
|---|---|---|---|---|
| A | People who have referred you, close friends and family, repeat clients, referral partners | 20 to 30 | Most months | Personal note, call or coffee |
| B | Past clients from the last three years and warm neighbours | 50 to 80 | Every quarter | Short email or text with one useful item |
| C | Older clients and acquaintances | Everyone else | Two or three times a year | Seasonal email, newsletter |
Let the AI help sort once, with your rules. Paste the sheet without contact details and ask: "Apply these rules and give each person a tier and a one-line reason. If a row lacks the information to decide, write 'ask me'." Review the 'ask me' rows yourself. Judgement about who is a friend and who is a business acquaintance belongs to you.
A worked example, with illustrative numbers. Say an agent has 160 contacts. After sorting there are 26 in tier A, 64 in tier B and 70 in tier C. Touches per year: tier A gets about ten (26 times 10 is 260), tier B gets four plus a home anniversary note (64 times 5 is 320) and tier C gets three (210), so roughly 790 touches a year, or about 66 a month. That sounds a lot until you notice that each tier B quarterly touch and each tier C touch is one shared email, and that only about 27 of the 66 a month need individual wording: the tier A notes and the tier B anniversaries. Those 27 messages are what AI helps draft.

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A calendar works if every month has one theme and a type of touch for each tier. Here is a twelve-month version. Edit the themes to suit your market and your seasons. Home anniversary notes sit outside the table: each tier A and B client gets one in the month they got the keys. For tier A it replaces that month's touch; for tier B it is the one extra message of the year.
| Month | Tier A touch | Tier B touch | Tier C touch |
|---|---|---|---|
| January | Personal check-in: "how is the year looking?" | None | Market update: what moved last year |
| February | None | Home maintenance checklist for late winter | None |
| March | Invite to coffee or a call | None | None |
| April | Personal note on something they mentioned | None | None |
| May | Short note with one useful local item | Spring market note | None |
| June | Personal note | None | Seasonal email |
| July | Summer check-in or a small event | None | None |
| August | None | "What is your home worth?" offer, soft | None |
| September | Back-to-routine check-in | None | None |
| October | Personal note on something they mentioned | Home-prep checklist before winter | None |
| November | Thank-you note for referrals and loyalty | None | None |
| December | Personal greeting | None | Season greeting |
Notice the rules built into the table: in tiers B and C no more than one touch in three is a market update, tier A never gets one, and apart from one referral note a year for tier A (covered below), no touch asks for business outright. Only tier B hears a "what is your home worth?" offer, once a year in August, framed as something they can take or leave; with tier A that conversation comes up naturally over the March coffee. Everything else is about them or is useful to them.
Put the calendar into your CRM as recurring tasks, or into a spreadsheet with a column for the date you sent each message. If you do not have a CRM yet, the realtor CRM comparison shows what small teams pay and which tools include tasks and templates.
Prompts and sample drafts for each touch type
The prompts have one thing in common: they supply a real fact and cap the length. Without a fact, assistants invent a warm but empty sentence.
The home anniversary note (tier A and B)
Write a 40 to 60 word message from a real estate agent to a past client on the anniversary of their home purchase.
Facts you may use: first name [first name]; they bought a [type of home] [number] years ago; one detail I know: [e.g. "they were planning to redo the back garden"].
Do not mention the price they paid, the current value of their home, or any offer to sell. Do not ask for a referral. Warm, brief, no exclamation marks. End with one easy question about the detail.
An illustrative output:
Hi [first name], it is three years this month since you got the keys to the house. I hope it feels more like home every year. Did the back garden project ever get started? I would love to see how it turned out if you feel like sharing a photo. [your name]
What to fix: nothing structural, but confirm "three years" against the purchase date and delete "I would love to see" if that is not how you speak. The asked-for photo is a gentle prompt for a reply, which is the point of the touch.
The market note (tier B)
Market notes are riskier because they carry figures. Pull the numbers yourself from your local statistics and paste only those into the prompt. The full method for building a market update that you can verify, with a figure register, is in the monthly market-update newsletter tutorial. For a touch plan, keep the note to two sentences: one figure for the neighbourhood and one plain implication. Example: "The typical home in our neighbourhood took 27 days to sell last month [median from your report]. If you have wondered whether now is a sensible time to sell or whether to hold, I am happy to talk it through." Check the figure before sending; the assistant must not supply it.
The useful-item message (tier B)
Tier B gets something to keep: a home maintenance checklist for the season, a short guide to a rule change you have confirmed, the date of a community event. Ask the assistant to turn your notes into a short email of 80 to 120 words with a heading and five bullets. Verify any date and any technical claim, and avoid giving tax or legal advice; point to a qualified adviser instead.
The "I was thinking of you" note (tier A)
This is the one AI should draft least. Ask it for three alternative openings from your note, such as "saw their daughter's name on a local fixture list" or "they mentioned a new job", then write the rest yourself. If a tier A message could have been sent to anyone, it is not a tier A message.
How to make an assistant do twenty drafts in ten minutes
Once a month, batch the work. In a spreadsheet filter to the people due this month. Copy first name, tier, touch type and personal fact (no contact details) into one prompt:
Here is a table of people due a message this month. For each row write the message type named in "touch", 40 to 70 words, using only the "personal fact" for that row. If the personal fact is blank, write a generic seasonal line and put "NEEDS A DETAIL" at the start. Number the messages to match the row numbers. Do not invent any fact, date or event.
[paste table]
The "NEEDS A DETAIL" rule matters. In an illustrative run of 20 rows, 14 might have a fact and 6 might not. The six blank rows are where a generic message would sound like spam, so they come back to you for one line of your own. Spend your time there, not rewriting the 14.
Then edit. Read each message aloud once. If it sounds like you, send it from your own email or phone, not from a mass-mailing tool, because tier A and B messages should look like individual notes. Update the "last touch" column with the date, or have your CRM log it.
Keep it from sounding like spam
People forgive a message that is clearly personal and a little clumsy. They do not forgive one that is polished and hollow. A few checks catch most of the problems.
- One purpose per message. If it contains greeting, market stats, a referral request and a promotion, split it or cut.
- The reply test. Ask: would a reasonable person be able to reply in one line? If not, simplify.
- The asking ratio. Aim for at least four touches that ask for nothing for every touch that asks for something.
- A named sender. Messages come from you, in your voice, signed with your name. Avoid "Dear valued client".
- Easy exit. In email, include a one-line way to stop: "If you would rather I did not write, just reply and I will take you off." Honour it the same day.
- No surprises about data. Do not mention things the person never told you. If you learned something from their social media, do not quote it.
Rules on texting and calling are stricter than on email, particularly for automated or prerecorded messages. If you plan to text, read the guide to AI voice follow-up and call-consent rules first and keep consent records in your CRM.
Catch anyone who slipped through with one formula
The calendar says what to send each month; the sheet should also tell you who has slipped through, such as a tier A contact you skipped in a busy spell. With the columns in the order listed above (tier in E, last touch date in F), add column H for "days since last touch" with =TODAY()-F2, then a column that compares it with the longest gap the calendar ever leaves for that tier: about 65 days for tier A, 130 for tier B and 190 for tier C. A formula such as =IF(H2>IF(E2="A",65,IF(E2="B",130,190)),"overdue","") marks anyone past it. Filter on "overdue" at the start of each month and add those people to that month's list, whatever the theme. This takes five minutes to set up and means the plan runs from the data, not from your memory on a busy Friday.
Two edge cases to handle in the same sheet. A person who replies "please stop" gets the tier "Do not contact" and a date, and the filter excludes them. A person who has just bought or sold with you should have their "last touch" set to the closing date, and a thank-you and a 30-day check-in already scheduled. Otherwise a client who closed last week may receive a generic tier B email.
Asking for referrals without spoiling the relationship
A touch plan earns the right to ask, but the ask has to be rare and specific. A vague "do you know anyone who is buying or selling?" is easy to ignore. A specific one is easier to answer: "I am working with more first-time buyers this year. If you know someone renting and wondering whether to buy, I would be glad to give them an honest, no-pressure conversation." Ask the assistant for three versions at 40 words, then choose the one that sounds like you, and send it to tier A only, once a year, from your own email.
Before and after, in an illustrative case. Before: "Hope you are well! Remember, I rely on referrals, so please think of me if you know anyone looking to buy or sell!" After: "Hi [first name], a quick one. This year I am helping a lot of people who have outgrown a flat and want a first house. If you know someone in that spot, I would be glad to give them a straight conversation with no pressure. If not, no worries at all." The second version names a situation the reader can match to a person, and it releases them from obligation.
Thank every referral, whether or not it leads to a sale, within a day. Send a handwritten card for tier A and an email for tier B. Check your brokerage's and your area's rules before offering any gift or fee for a referral, since some arrangements must be disclosed or are not permitted; do not let an assistant draft a referral incentive without your broker's sign-off.
The anniversary note for a house they had sold
An agent uses a mail-merge tool to send "Happy home anniversary!" to everyone in the sheet whose purchase month is November. The sheet's purchase date for one contact is the date the offer was accepted, not the closing date, and another contact sold that house two years ago. Two people write back, puzzled. One asks why her old agent is wishing her happy anniversary on a house she no longer owns. That costs a client's goodwill.
The fix is a "status" column (owner, sold, moved, unknown) and a rule that only "owner" rows get an anniversary note. For every other row the anniversary touch is skipped or replaced with a general note. When the sheet is incomplete, a human note beats an automated one. It is also why the personal fact column matters: if you cannot fill it in, you probably do not know the person well enough for an anniversary message.
Privacy: what goes into the assistant and what does not
A contact list is personal data. A safe rule for the assistant is first name, relationship, a harmless personal fact and a touch type. Leave out surnames, addresses, phone numbers, sale prices, financing details and anything about health or family trouble. Use a business-plan assistant where possible, because consumer plans have a model-training setting you would need to check and switch off yourself (ChatGPT's personal plans start with it switched on). If you need to merge details into messages, draft templates with placeholders such as [first name] and let your CRM do the merging.
A before-and-after to make it concrete. Before: pasting a row that reads "[full name], [house number and street], bought for $385,000 with a 90 per cent mortgage, divorced 2025". After: "[first name], past buyer 2023, mentioned wanting to redo the kitchen." The second version still gets you a decent draft and discloses nothing that matters if it leaks.
A realistic month, start to finish
Suppose it is October. The calendar says tier A gets a personal note on something they mentioned, tier B gets the home-prep checklist, and tier C gets nothing. Of the 26 tier A contacts, three have an October purchase anniversary and get that note instead, and two spoke to the agent last week, so she skips them. She runs the batch prompt for the remaining 24 tier A rows and spends about 40 minutes adding a personal line to each before sending them from her own email. For the 64 in tier B she generates one checklist email using the prompt above, checks the five items for accuracy, and sends it through her CRM at 9am on a Tuesday, with an opt-out line.
Two days later, six people reply. One asks about the value of her home, one mentions a cousin who wants to buy, and four simply say thanks. The agent logs the two business replies as tasks, adds the personal facts from the replies to the sheet, and updates "last touch". Total time: about 90 minutes, for roughly 90 contacts. That is the practical test of the plan. If the monthly session takes more than two hours, the tiers are too big or the personal facts column is too empty to make drafting quick.
Three numbers to review after one quarter
Three numbers tell you whether the plan is working. Replies as a share of touches in tiers A and B; conversations that mention business (a referral, a valuation request, a question about a home); and the number of contacts you moved up or down a tier. You are not looking for a rise in leads in three months, only for evidence that people respond like friends and not like recipients. If replies are rare, shorten messages and ask more questions. If they are common but never lead to business, the touches may be too casual: add one clear, soft offer a year.
If you are bringing a database to a new brokerage, the plan also pairs with the first-month support covered in the agent recruiting and onboarding plan, where week three is spent on the new agent's contact list. And if replies from past clients start to pile up in an inbox, follow-up automation for buyers and vendors shows how to route them into tasks so none is missed.
Sphere-of-influence questions agents ask
How often should I contact past clients?
Match the frequency to the tier. Your closest 20 to 30 people can hear from you most months, a middle group about every quarter, and a wider group two or three times a year. Mix the types of contact so no more than one in three is a market update.
Is it spam if I email people who are not on a marketing list?
Past clients and personal contacts are a grey zone. Personal one-to-one notes are treated differently from bulk marketing, but bulk email generally needs an accurate sender identity, a postal address and an opt-out. Record consent in your CRM and offer an easy way to stop. Ask your broker if unsure.
Can AI write the messages without sounding automated?
Yes, if you give it a real fact about the person and ask for two or three sentences. It struggles when it has nothing personal to work from. Edit every message before it goes, add one detail only you know, and never let it invent a memory.
Should I paste my client list into ChatGPT?
Not as it stands. Use first names and a short note, leave out phone numbers, addresses and financial details, and use a business-plan assistant. Better still, let your CRM do the merging and use the assistant only to draft templates.
Further reads
- ChatGPT for Realtors: Brokerage Rules for Emails, Disclosures, Follow-Ups — Brokerage rules for what AI may touch in follow-up emails.
- AI Receptionist for Realtors: Cost, Call Routing and Showing Cover — Catch the calls that past clients make when they are ready.
- Follow Up Boss Pricing: What a Small Team Really Pays — What one popular agent CRM costs a small team.
- How to Get More Home Inspections: Realtor Referral Emails Written With AI — The same referral logic from the home inspector's side.
- How to Manage Your Inbox With AI: Triage, Drafts, and Follow-Ups — Keep replies from past clients from getting buried.
- AI Tools and AI Development: The Complete 2026 Guide — the AI hub, including every tutorial in the AI-for-business series.
Sources: ChatGPT Data controls FAQ and pricing page; Claude pricing page and privacy centre; the FTC's commercial email compliance guide; the reader's own CRM and brokerage rules.