"Just checking in" is the email customers learn to skip. It asks for their time and gives them nothing back, so after the second or third one they stop opening it.
The problem usually isn't the wording. It's that the check-in has no purpose. When there's no rhythm behind it either, two things happen: the friendly customers hear from you every week, and the quiet ones don't hear from you until they cancel.
Below are seven checking in email samples that each carry a reason to reply, some subject lines, and a simple way to decide how often to send them. Swap in your own names and details. (Names in the examples are made up.)
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The rule: every check-in needs a reason
A check-in earns a reply when it does one of these:
- Asks about their side: what's changed, what's coming up.
- Shares something from their account they'd want to know.
- Saves them time with a tip that fits how they actually use the product.
- Asks one question that matters, and makes it easy to answer.
If you can't name the reason before you write, don't send it yet.
Seven checking in email samples
1. The everyday check-in
For when there's no special news. Ask about their side, not yours.
Subject: Anything changed on your side?
Hi Ines,
What's changed on your side since we last talked? Anything coming up
in the next couple of months I should know about?
If something's getting in the way, tell me and I'll pick it up.
Theo
2. Proposing a regular check-in
Use this when you start working with an account, or when you set up a rhythm for the first time.
Subject: A monthly 20 minutes?
Hi Ravi,
I'd like to check in with you about once a month, 20 minutes, to make
sure you're getting what you need. If that's too often or not enough,
tell me.
Would the first Wednesday of the month work?
Theo
3. Sharing a result
Lead with one number from their account. Fill in the real figure; don't round it up.
Subject: Your [month] numbers
Hi Ines,
One number from your account this month: [the number and what it
means, in one line]. Thought it might be useful for your next team
meeting.
Is there anything you'd like us to focus on next quarter?
Theo
4. A tip based on how they use it
Only send this if you've actually seen something in their usage.
Subject: A quicker way to [the task]
Hi Ravi,
I noticed your team [what you saw in their usage]. There's a quicker
way: [the feature or setting, in one line]. Here's a short walkthrough:
[link].
Happy to show your team live if that's easier.
Theo
5. The quiet account
For the customer you haven't heard from in a while. Make the reply as small as possible.
Subject: Still getting what you need?
Hi Ana,
It's been a while since we spoke, and I want to make sure you're
still getting value. If anything's changed, like new people or new
goals, I'd like to hear it.
Would a short call be useful, or is email easier?
Theo
6. When they've said no to regular check-ins
Some customers don't want a monthly call. Agree a lighter touch and keep to it.
Subject: Once a quarter, then
Hi Marcus,
No problem at all. I'll send you a short email once a quarter instead,
and you can reach me any time in between if something comes up.
Theo
7. Following up when they don't reply
One question, and a yes or no is enough.
Subject: One quick question
Hi Ana,
Bumping this in case it got buried. Just one question: is anything
getting in the way for your team right now? A yes or no is fine. If
it's yes, I'll take it from there.
Theo
Subject lines that say why you're writing
- Anything changed on your side?
- Your [month] numbers
- A quicker way to [the task]
- Still getting what you need?
- One quick question
"Just checking in" as a subject line tells the reader you don't have a reason.
If they say yes to a call
Keep it short and keep it to four questions:
- What's changed on your side?
- What's next for you?
- Is anything blocking you?
- What's one thing I can help with?
Afterwards, write down two things in your account list: the date of this last real conversation, and the next step. That list is what makes the rhythm below work.
How often to send a checking in email
A rhythm per tier works better than treating every account the same. Here's a starting point:
| Tier | Who's in it | Check-in | Booked as |
|---|---|---|---|
| One | High value, or high need, such as a complex setup | A monthly call | A recurring invite |
| Two | Standard accounts | A quarterly call or email | A calendar reminder |
| Three | Small or self-serve | A monthly update email | A calendar reminder |
A few notes on making it stick:
- Tier by need, not just size. A small account with a complicated setup can belong in tier one. A big account that never needs help may not. Two or three tiers is plenty, and two if you have fewer than 30 accounts.
- Check the hours. Add up what each tier's rhythm costs you in a month, with prep and follow-up. If it doesn't fit your calendar, the promise is too big.
- Sort every Monday. Sort your accounts by the date of the last real conversation and reach out to anyone past their rhythm. Twenty minutes is enough.
- Skip once, never twice. A quiet, happy account can miss one check-in. Not two in a row.
- Risk means now. If a check-in turns up a risk, act on it. Don't wait for the next scheduled one.
- If you keep falling behind, the rhythm is wrong for your hours. Lower one tier's rhythm and tell your manager, rather than quietly missing check-ins.
How do you know it's working? A starting target: no more than two overdue accounts in tier one for two weeks running.
Let AI make the Monday list
If your account list lives in a spreadsheet, an AI assistant can find who's overdue and draft the first lines for you. Use only a tool your company approves, and follow your company's data policy before you paste anything. Taking names out isn't always enough.
Here's my account sheet with tier and last real conversation date.
Today is [date]. Rhythm: tier 1 every [n] days, tier 2 every [n],
tier 3 every [n].
List accounts past their rhythm, sorted by how overdue. For each,
draft a two-line, friendly outreach message that doesn't sound
automated. Use only the sheet. Draft for me.
[paste sheet]
Read each draft and add the reason for writing yourself. That's the part an AI can't see in a spreadsheet.
Where to start this week
Delete "just checking in" from your templates, give every account a tier and a rhythm, and put the Monday sort in your calendar. That alone catches the quiet accounts before they go silent for good.
If you want to see a full play in this format, with its prompt, a fill-in list for every bracket, guardrails and a made-up sample result, the free sample is one complete play from The CS Agent Playbook: the Escalation Brief for Leadership, as a 3-page PDF. Get the free sample play.
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