Write a quarterly check-in that delivers value, not small talk
Writes a check-in email built around one piece of repeatable intelligence instead of 'hope all is well' filler — plus a lighter variant for weaker ties. It keeps you present with customers, past prospects, and displaced champions each quarter in a way that builds credit rather than spending it.
You are a relationship-led sales advisor who believes the quarterly check-in is the most squandered email in B2B. 'Hope all is well — anything we can help with?' is a chore for the reader. A great check-in works like a micro-briefing: one piece of intelligence the recipient is glad to have received, one light personal thread, and an ask so small it's frictionless — or no ask at all.
Write my quarterly check-in email. Rules:
- Under 110 words.
- Structure: (1) one insight worth their time — a market shift, a benchmark from what we're seeing across similar companies, a specific idea for their situation; (2) one line that shows continuity with our last interaction, referenced naturally; (3) either no ask, or a feather-light one ('want the full data?' / 'worth a coffee next time I'm nearby?').
- The insight must be concrete enough to repeat in a meeting — 'we're seeing reply rates on old-school sequences drop about 30% this year' — not vibes.
- Banned: 'hope all is well', 'just checking in', 'it's been a while', quarterly-business-review formality, and any hidden pitch dressed as a question.
Also produce a light version under 60 words for contacts I know less well.
Before you write anything, interview me. Ask me these questions ONE AT A TIME, waiting for my answer each time:
1. Who is this contact — customer, past prospect, partner, champion who changed jobs — and what's the relationship history?
2. What happened in your last interaction, roughly when?
3. What do you know that they'd find genuinely useful — data you're seeing, market changes, a relevant idea?
4. What do you sell (so I keep the insight adjacent to it without pitching)?
5. Do you want a soft ask included, or purely value this quarter?
Once you have my answers, write both versions. If I can't name anything genuinely useful in question 3, help me find one by asking what patterns I've seen across my customers this quarter.How to use it
- 1
Copy the prompt into Claude, ChatGPT, or any LLM.
- 2
Before answering question 3, skim your last quarter for one pattern worth sharing — win rates, reply benchmarks, a market shift you're seeing.
- 3
Use the full version for real relationships and the sub-60-word version for lighter ties.
- 4
Batch this quarterly: run 10 to 20 contacts through the same chat in one sitting while your insight is loaded.
- 5
Log each send in your CRM so next quarter's question 2 has an answer.
Best practices
One insight per email — two makes it a newsletter, and newsletters get skimmed while notes get answered.
Champions who changed jobs are the highest-ROI recipients on your list; a valuable check-in at their new company often becomes an opportunity within two quarters.
Skip the ask entirely at least every other quarter — pure-value touches are what make the eventual ask feel natural.
If your 'insight' would work for any recipient in any industry, it's not ready; sharpen it against their situation first.
Example: what this looks like in practice
A founder of a 10-person outbound consultancy runs her quarterly check-in batch: 14 contacts including past prospects and two champions who changed companies. For question 3 she offers what she's seen across clients: reply rates on 5-touch generic sequences down sharply, while trigger-based sends held steady. The model produces a 98-word check-in leading with that benchmark, referencing each last interaction naturally, no ask. One past prospect replies 'this matches what we're seeing — can you look at our sequences?'. One displaced champion answers 'perfect timing, new team here has nothing built'. Two conversations from 14 emails, neither of which contained a pitch.
Best fit
This prompt is one gear in a bigger machine. We orchestrate 20+ tools into outbound systems our clients own — and guarantee the results.
Apply for a Pilot Spot → →Frequently asked questions
Lead with something useful to them: a benchmark from across your customer base, a market shift you're watching, or a specific idea for their situation. Add one natural line of continuity from your last interaction, then either no ask or a tiny one. The test: would they be mildly glad this email arrived? 'Hope all is well, anything we can help with?' fails that test every time.
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