A few years ago I noticed something uncomfortable: I was constantly hustling for new clients while completely ignoring the dozens of clients I’d already done good work for. Some I hadn’t spoken to in 18 months. The relationship hadn’t soured — I’d just stopped reaching out, and so had they.

I ran a small experiment. I picked 50 past clients, in tiers of “high quality, definitely want to work with again,” and sent each one a single email. Same email, modulated slightly for context.

Result: 30 of them re-engaged. 60%. Of those, about half turned into actual paid work within three months. The total revenue from a single round of emails was the largest sales win that quarter, and the work didn’t take any new lead generation.

I want to walk through what worked, because the email itself is genuinely simple.

The email

Here’s the structure, with the specific language I now use:

Subject: Quick check-in

Hi [first name],

I was thinking about [the project we worked on / the conversation we had at X / the brand identity we built last year] and realised it’s been a while. I hope [the result of the work / your business] is going well.

No agenda for this email — just wanted to say hello, and to mention I’m taking on a few new projects in [Q3 / next quarter / spring]. If anything’s come up that I might be able to help with, even just informally, do let me know.

Otherwise, no need to reply — happy to know things are good.

Warm regards, [Your name]

That’s it. Five sentences. No CTA, no link, no follow-up calendar invite. The deliberate looseness is the point.

Why it works

Three things I now think it’s doing right.

It assumes nothing. It doesn’t say “I noticed you haven’t worked with us recently, want to come back?” That phrasing is needy and slightly accusatory. It says “thinking about you, hope you’re well.” Different energy entirely.

It mentions capacity without pitching. “Taking on a few new projects” is a casual way to signal availability without selling. People who don’t need anything won’t feel pressured. People who do have something pending now have an opening.

It releases them from the obligation to reply. “No need to reply” is liberating. People who get an email like this don’t feel like they have to dredge up something to say. Many will reply anyway, but the absence of pressure means the ones who don’t reply don’t feel guilty either.

The combination feels professional and warm rather than salesy.

The variations that didn’t work

Before I landed on the version above, I tried other approaches. They underperformed:

The “promotion” email. “Hey, I’ve got a 20% discount on services until end of month.” Conversion rate: low. Felt like a marketing email, treated as such.

The “follow-up on our last project” email. “Hope the brand identity is still serving you well. Let me know if you’d like to expand on the work.” Slightly better than the discount version, but felt transactional.

The “long check-in” email. Three paragraphs about what we’d been up to, recent case studies, things we’d been thinking about. Good intentions, terrible response rate. Long emails to dormant relationships feel like an imposition.

The short, low-pressure version outperformed all of them. The lesson: in cold-but-not-cold relationships, less is more.

Who to send it to

Don’t send this to everyone in your contact database. The list matters.

I now have three rules for who gets this email:

Rule one: did good work end well? If the relationship soured at the end (a payment dispute, a difficult final phase), don’t reach out. They remember the bad bit, and a “thinking of you” email reopens it.

Rule two: was the client themselves a good fit? Some past clients were profitable and pleasant. Others were profitable but exhausting. The exhausting ones go on a “do not re-engage” list. Just because they paid doesn’t mean you want them back.

Rule three: has it been at least 9 months? Sooner than that and the email feels too soon. People remember finishing the project; the dormancy hasn’t really set in yet. After 9 months, it lands as a genuine check-in.

After applying these three filters, my list of 50 became my list of about 20 in the first round. Quality of list matters more than quantity. I’d rather send 20 well-targeted emails than 100 sloppy ones.

The cadence

I now do this twice a year, roughly Q1 and Q3. Not more often. The whole point of this email is its low-pressure quality, and that’s incompatible with quarterly outreach.

Each round produces some immediate work, some “we’d love to but not yet” responses (which I diary for 6 months later), and some “thanks, doing fine” replies that just maintain the relationship.

Across the year, this is consistently one of the highest-ROI sales activities I do. No new leads required. No marketing spend. Just a list, a short email, and a willingness to do this twice a year without expecting much.

The bigger lesson

Most small businesses are obsessed with the top of the funnel — getting more new leads. The middle of the funnel (existing clients, recently dormant ones, near-misses from past pitches) is usually under-tended.

The maths is interesting once you look at it. Re-engaging a past client who already trusts you converts at, in my experience, six to ten times the rate of a cold lead. The cost is approximately zero. And yet most businesses spend almost nothing on this and almost everything on lead generation.

I’m not saying don’t generate leads. I’m saying spend an hour every quarter on the people who already know you. That hour will routinely be the most productive sales hour of the quarter.

stedd.io tracks past clients and lets you filter by last-engagement date — so the list of “dormant 9+ months” is one filter away.