Most small companies spend their marketing effort on new customers and leave past ones alone. Yet a person who has already bought from you knows your work, has your contact details in their records and does not need to be convinced that you exist. Often they stopped ordering for a dull reason: a change of staff, a busy season, a forgotten reorder. A short, polite routine can find out which it is.
This article is for an owner or sales lead of a small company with at least a few dozen past customers and an order history that can be exported from an invoicing or booking system. It describes a routine that fits into one afternoon a month.
Decide who is "inactive"
"Haven't heard from them in a while" is not a list. Write a rule from your own records. A practical version: a customer is inactive when the time since their last order is more than twice their usual gap between orders. A customer who orders monthly and has been silent for three months is inactive. A customer who orders once a year and has been silent for fourteen months is not.
Export customers with their last order date and number of orders, apply the rule and look at the list. Remove anyone with an open complaint, an unpaid invoice or a request not to be contacted. Those people need a different conversation, not a sales message. If you hold customer data under the GDPR, check that you may contact them for this purpose; the data retention schedule is a good place to see what you keep and why.
Keep the first batch small, for example ten to twenty customers. You want to read every reply.
The three messages
Each message has one job and one question. Send them as plain email from a real person, not a mass mailing tool template, and leave about a week between them.
Message 1: a check-in (day 0). Say who you are, when you last worked together and ask one simple question: is there anything you needed that we did not provide, or has the need simply gone away? No offer yet. Two or three sentences are enough.
Message 2: something useful (about day 7). Share one thing that has changed since they last bought: a new option, a shorter delivery time, a fixed price for a common job. Link to the page where it is described. The aim is to show that the relationship is worth resuming, not to push.
Message 3: a clear, limited offer (about day 14). Make a specific, honest offer with an end date: a first order at a fixed price, a free review of their current set-up, or a short call. Say that this is the last message in the series and that they are welcome to ignore it.
Keep the tone of a colleague, not a campaign. Avoid urgency you cannot honour, and do not offer a discount you would not give to a current customer; regular customers who find out will be unhappy, and the article on announcing a price change shows why consistency matters.
What to offer
The offer should lower the effort of coming back, not just the price. Options that work for small companies:
- A fixed-price first job, so they know the cost before replying
- A short call to review what they use today, at no charge
- A simple restart: you prepare the order based on their last one and they only confirm
If you do give a discount, make it modest, tied to a specific order and written down. A discount offered to everyone teaches customers to wait for it.
When to stop
Stop after message 3. A customer who has not replied to three polite messages has told you something; sending a fourth and a fifth turns a courtesy into noise and can damage the relationship you wanted to repair. Mark them "not now" with a date, and consider a short note again in six to twelve months, for example inside your regular customer newsletter.
Stop immediately for anyone who replies "no thanks" or asks you not to write again. Record this and respect it.
What to record
A simple sheet is enough, with one row per customer:
- Name and last order date
- Dates of messages 1, 2 and 3
- Reply (yes, no, later, no reply) and the date
- The reason they gave, in their words, if any
- Next action and owner
The reasons are the most valuable column. After one or two batches, read them together. If several customers say a product was too slow, too expensive or replaced by a competitor, that is information for your offer, not only for this routine. If you also ask customers for feedback after delivery, as described in asking customers for feedback after delivery, you can compare what leaving customers say with what current ones say.
Measuring whether it works
Count three numbers per batch: how many customers you wrote to, how many replied, and how many placed an order within, say, 30 days of message 3. Small batches give rough figures, so do not judge the routine on a single round. Run it monthly for a quarter, then compare. If replies are frequent but orders are rare, the offer is the problem. If replies are rare, check the list: perhaps the e-mail addresses are old or the inactive rule is too wide.
Also watch the other side: what share of new customers become inactive after the first order? If it is high, the better fix may be earlier, such as the first two weeks checklist, rather than a later win-back routine.
Common mistakes
- Writing to everyone who ever bought, instead of customers who match a rule
- Contacting customers who have an open complaint or unpaid invoice
- Opening with a discount before asking what went wrong
- Sending more than three messages
- Not recording replies, so the same customer is written to again next month
- Treating the routine as a one-off campaign instead of a monthly habit
Checklist
- A written rule for "inactive", based on your own order rhythm
- A list of 10–20 customers, with exclusions removed
- Three short messages with a week between them
- One honest offer with an end date
- A stop after the third message and a "not now" date
- A sheet with replies and reasons
- A monthly time slot and a named owner
Sources
- Common practice for customer re-engagement in small companies, offered as a practical guide. The inactivity rule, message timing and batch size are starting points to adapt to your own business. No client results or market figures are claimed in this article.
