[Ian Investor]

Hello — I’m exploring simple ways AI might help with follow-up emails after meetings or introductions. I’m not very technical and want to save time while still sounding personal.

My main question: Can AI reliably draft follow-up emails that include useful, value-add resources (links, short tips, or attachments) without sounding generic?

Specifically, I’d love practical input on:

• What tools or services work well for this for non-technical users?
• How do people ensure the suggested resources are accurate and appropriate?
• Tips for keeping tone warm and personal when using AI?
• Any privacy or workflow concerns to watch for?

If you’ve tried this, please share what worked, what didn’t, and any example prompts or templates you’d recommend. Thanks — I’m eager to learn from real experiences.

[Jeff Bullas]

Yes — and you can do it without being technical. AI can draft follow-up emails that genuinely add value by recommending helpful resources, but success comes from the right inputs, review, and clear rules.

Why it works

AI excels at summarising, matching resources to needs, and writing clear, friendly copy. Combine that with a simple automation trigger (e.g., “no reply in 3 days”) and you’ll have timely, useful follow-ups that feel human.

What you’ll need

• List of recipients and basic context (name, company, prior convo snapshot)
• Goal for the follow-up (reminder, share value, book a call)
• Short resource library (3–6 vetted links or attachments)
• An AI tool (ChatGPT, other LLM) and a simple automation platform (email tool with templates)
• Human review step before sending

Step-by-step

1. Gather context: paste the last email or meeting note and the recipient’s role.
2. Pick the objective: help, nudge, or close. Keep it singular.
3. Choose 2–3 high-quality resources relevant to that objective.
4. Use the AI prompt below to generate 2 subject lines and 2 body variations (concise and resource-first).
5. Human-edit for voice and accuracy; personalise one detail (company name, recent win).
6. Set the automation trigger (e.g., 3 days no reply) and add an embargo for manual review for high-value prospects.
7. Measure opens, clicks on resources, replies, and refine monthly.

Copy-paste AI prompt (primary)

Act as a helpful business follow-up writer. Based on this context: [paste last email or meeting note], recipient name: [Name], role: [Role], company: [Company], and objective: [help / nudge / book call]. Suggest 2 subject lines and write 2 short email versions: Version A (concise, 3–4 sentences) and Version B (resource-first, 6–8 sentences). Include 2–3 suggested resources relevant to the objective with one-sentence explanation for each. Use friendly, professional tone, no jargon. Include a clear single call-to-action (reply or schedule). Keep each email <150 words. Flag any missing info needed for personalization.

Variants

• Short variant: ask for a one-line reply instead of a call.
• Resource-first variant: lead with a useful link and short explanation, then a CTA.

Example output

Subject: Quick resource on [topic] — thought you’d like this

Hi [Name],

Thanks again for your time last week. I promised a couple of useful resources on [topic] — here they are:

• Guide: How to [do X] — practical checklist for immediate steps.
• Case study: [Company] cut costs by 20% using [method].

If any of these help, reply with the best time for a 15-minute call and I’ll book it. If not, tell me what you’d prefer and I’ll adjust.

Common mistakes & fixes

• Too-salesy: fix by swapping pitches for “helpful” resources and a low-friction CTA.
• Irrelevant resources: fix by maintaining a small vetted library by topic.
• No human review: always scan for factual errors and tone before sending.

7-day quick action plan

1. Day 1: Collect 20 recent follow-ups and 10 resources by topic.
2. Day 2: Run the prompt on 5 samples and pick best outputs.
3. Day 3: Create templates and subject lines in your email tool.
4. Day 4: Set automation triggers and manual review for priority leads.
5. Day 5–7: Monitor opens/clicks, refine prompts and resources.

Start small, measure, and iterate. AI speeds the writing — your judgement keeps it valuable.

[aaron]

Good point — the trigger + human review combo is the backbone. I’ll add the KPI focus and a clear, non-technical rollout you can run this week.

The gap

Many teams automate follow-ups but measure only sends and opens. That hides whether you’re actually moving deals forward or building trust with useful resources.

Why this matters

If your follow-ups increase replies and resource clicks, you shorten sales cycles and reduce wasted outreach. If they don’t, you’re just sending noise and training people to ignore you.

My experience in one line

Start with a tight loop: AI drafts → human reviews → automation sends → track 3 KPIs → iterate weekly. That takes the guesswork out and protects relationships.

What you’ll need

• Recipient list + last message or meeting note (paste the last exchange).
• Objective per recipient: help / nudge / book call.
• Resource library: 3–6 vetted links or attachments by topic.
• An AI tool (ChatGPT or equivalent) and your email tool with template/trigger capability.
• A reviewer for high-value prospects (1 person, 10–15 minutes per email).

Step-by-step rollout (what to do, how to do it, what to expect)

1. Choose 20 priority prospects. Export names, companies, last message.
2. For each, select one objective and 2–3 relevant resources from your library.
3. Run the AI prompt below to generate 2 subject lines and 2 email variations.
4. Human-review: check facts, add one personal detail, approve or edit (5–10 mins).
5. Set automation: trigger = 3 days no reply; embargo manual send for top 20% value.
6. Expect: first batch sent Day 3, measurable replies within 48 hrs of send.

Copy-paste AI prompt (primary)

Act as a helpful business follow-up writer. Using this context: [paste last email or meeting note], recipient name: [Name], role: [Role], company: [Company], objective: [help / nudge / book call]. Produce: 2 subject lines; Version A (concise, 3–4 sentences) and Version B (resource-first, 6–8 sentences). For each version include 2–3 suggested resources with one-line value statements and a single clear CTA (reply or schedule). Keep tone friendly, professional, under 150 words. Flag missing personalization fields.

Variants

• Short variant: ask for a one-line reply instead of a call.
• Resource-first variant: open with the most relevant link and why it matters.

Metrics to track (start here)

• Reply rate (primary): target +10–20% lift vs current baseline.
• Resource click rate: target ≥25% of opens click a link.
• Meetings booked: measure closed-loop from reply → booked call.

Common mistakes & fixes

• Too many resources — fix: 2 max, ranked by likely relevance.
• Auto-send without review — fix: manual embargo for top-tier prospects.
• No CTA or confusing CTA — fix: one clear action (reply or schedule).

7-day action plan

1. Day 1: Collect 20 prospects + 10 resources by topic.
2. Day 2: Run prompt on 5 samples and review outputs.
3. Day 3: Finalize templates and subject lines in your email tool.
4. Day 4: Configure automation triggers and manual embargo rules.
5. Day 5: Send first batch (with review). Monitor replies/clicks.
6. Day 6: Tweak prompts/resources based on early data.
7. Day 7: Roll to next 50 prospects or adjust cadence.

Clear, measurable steps — minimal tech required, maximum control. Your move.

[Fiona Freelance Financier]

Nice callout — the trigger + human review loop plus KPI focus is exactly the foundation. To reduce stress, layer simple, repeatable routines on top so the process scales without you feeling on-call 24/7.

Quick checklist (do / don’t)

• Do: Keep two ready templates (concise and resource-first), limit resources to 1–2, and require a 5–10 minute human review for high-value prospects.
• Do: Set a fixed trigger (e.g., 3 days no reply) and a weekly 15-minute metric review to close the loop.
• Don’t: Auto-send everything without a manual embargo for top 20% accounts.
• Don’t: Overload the email with more than two links or a long pitch — keep it helpful and short.

What you’ll need

• Recipient list with last message or meeting note
• Clear objective per recipient: help / nudge / book call
• Small vetted resource library (3–6 items) organised by topic
• An AI drafting tool and your email platform with template + trigger capability

How to do it — simple routine (step-by-step)

1. Pick a daily 30-minute batch window: draft, review, queue. Routine reduces decision fatigue.
2. For each prospect: choose one objective and 1–2 ranked resources from your library.
3. Use your AI tool to produce two short variations; don’t skip the human quick-check (5–10 mins): verify facts, add one personal line.
4. Queue the message in your email tool with trigger = 3 days no reply; apply manual embargo for top-tier accounts.
5. Weekly: review three KPIs (reply rate, resource click rate, meetings booked) and tweak templates/resources.

What to expect

• First batch: replies often arrive within 48 hours of send.
• Small iterative gains: aim for a measurable +10–20% reply lift over a month.
• Less stress: fixed daily batch time and short review windows keep work predictable.

Worked example (one prospect, low-friction routine)

Context: Prospect asked about a pilot but hasn’t replied to pricing details. Objective: nudge + add helpful resources.

• Chosen resources: 1) Short checklist for running a 30-day pilot (one-page), 2) One-page case summary showing time-to-value.
• Two subject line options: “Quick checklist for a 30-day pilot” or “Short case: how others ran a fast pilot”

Version A (concise):

Hi [Name],

Following up on the pilot details — I thought this one-page checklist might make planning easier, and this short case shows typical timelines. If helpful, reply with one good day for a 15-minute check-in and I’ll confirm availability.

Version B (resource-first):

Hi [Name],

Sharing two quick items to speed setup: a 30-day pilot checklist for immediate tasks, and a one-page case that shows how peers measured impact. If either looks useful, reply with a preferred time for a brief call or tell me the main blocker and I’ll tailor next steps.

Expect to spend ~7–10 minutes preparing this email (pick resources + quick review). Over a week, use the KPI check to decide whether to adjust messaging or resources.

[aaron]

Sharper, lower-stress version: keep your routine, but don’t hard-code a 3-day trigger for everyone. Enterprise buyers often prefer 5–7 business days and local business hours. Segment your cadence by account tier to lift replies and protect deliverability.

Checklist (do / don’t)

• Do: Use two short templates (concise, resource-first). Keep 0–2 links; a zero-link nudge often wins for the first follow-up.
• Do: Segment triggers: SMB (2–3 days), Mid-market (3–4), Enterprise (5–7 business days). Send within recipient time-zone business hours.
• Do: One human review for top accounts (5–10 mins): verify facts, add one personal detail, sanity-check tone and length (<120 words).
• Do: Maintain a vetted resource library tagged by topic, persona, and stage; rank a single “best next” item.
• Don’t: Attach files on cold or early follow-ups; use a short description and offer to send on request.
• Don’t: Stack CTAs. One action: reply with a time or answer one question.
• Don’t: Resend identical copy. Keep two variations in rotation to avoid fatigue.
• Don’t: Send into out-of-office loops; filter OOO replies before the next step.

What you’ll need

• Prospect list with last interaction, role, industry, and value tier.
• Resource mini-library (3–6 items) with tags: topic, persona, stage, one-line value statement.
• AI drafting tool and an email platform with templates, triggers, and basic analytics.
• Reviewer for top-tier accounts (one person is enough).

How to run it (step-by-step)

1. Segment: Assign SMB/Mid/Enterprise; set the trigger window and quiet hours by segment.
2. Define objective: help / nudge / book call. Choose one.
3. Select resource: pick the single best-fit item (or none for the first nudge).
4. Draft with AI: use the prompt below to generate two versions and two subject lines.
5. Review: confirm facts, personalize one line, check length, remove jargon. Approve or adjust.
6. Queue + embargo: schedule by segment; keep manual send for top 20% value accounts.
7. Log outcomes: categorize replies (positive/neutral/objection/OOO/no response) for weekly analysis.

Copy-paste AI prompt

Act as a business follow-up specialist. Context: [paste last email or meeting note], recipient: [Name, Role, Company], segment: [SMB/Mid/Enterprise], objective: [help / nudge / book call]. Constraints: 1 personalized line tied to the context; 0–1 resource for first follow-up, max 2 afterward; one clear CTA (reply with a time or answer one question); 75–120 words; plain language, no buzzwords. Produce: 2 subject lines, Version A (concise), Version B (resource-first). Include a one-sentence value statement per resource. Flag any missing details for personalization. Ensure the content reads naturally if no resource is provided.

What to expect

• Most replies land within 24–48 hours of send; set a 72-hour check for next steps.
• Baseline targets: +10–20% reply lift; 20–35% click rate when one resource is included; 30–50% of replies positive when resources match the stated need.
• Lower stress: fixed batch windows and segment-based triggers prevent “always on.”

Metrics that matter

• Reply rate by segment (primary).
• Positive reply rate (booked, qualified interest).
• Meeting conversion (replies → scheduled).
• Resource engagement (when used).
• Health: bounce <2%, spam complaints <0.1%, unsubscribes <0.5%.

Common mistakes & fixes

• Generic resources → Tag by persona and stage; surface one “best next” item only.
• Overlong emails → Cap at 120 words; remove adjectives, keep one CTA.
• Too many links → Start with zero-link nudge, add one resource in the second touch.
• AI inaccuracies → Always human-scan names, numbers, and claims.
• Uniform cadence → Use segment-based triggers; avoid Fridays for Enterprise follow-ups.

Worked example

Scenario: Enterprise CFO hasn’t replied after reviewing pricing. Objective: nudge with one helpful resource.

• Resources: 1) One-page ROI checklist (CFO-focused), 2) 30-day pilot milestones (optional second touch).
• Triggers: 5 business days, send between 9–11am recipient time; manual embargo enabled.

Subject options: “ROI checklist CFOs use before green-lighting pilots” or “Short next step to stress-test ROI assumptions”

Version A (concise, zero-link first touch):

Hi [Name], quick nudge on the ROI questions. I have a one-page CFO checklist that helps pressure-test assumptions before a pilot. If you want it, reply “send the checklist” and I’ll forward it. If timing’s off, what week should I circle back?

Version B (resource-first, second touch):

Hi [Name], sharing a one-page CFO ROI checklist that highlights the 5 assumptions that usually decide a pilot. If it helps, reply with one assumption you’d like to validate first and I’ll tailor a quick plan. Happy to send a 30-day pilot milestone outline next.

1-week action plan

1. Day 1: Tag your resources (topic, persona, stage) and nominate one “best next” per scenario.
2. Day 2: Build two templates and a 5-line voice guide (tone, reading level, sign-off style, length, CTA).
3. Day 3: Segment 30 prospects (SMB/Mid/Enterprise). Set triggers and time windows by segment.
4. Day 4: Generate drafts with the prompt for 10 prospects; human-review and queue with embargo for top accounts.
5. Day 5: Send first batch. Label outcomes as replies arrive.
6. Day 6: Review KPIs by segment; adjust resource choice and subject lines.
7. Day 7: Scale to the next 50 contacts; introduce the zero-link first nudge for Enterprise if not used.

Segment your cadence, limit links early, and measure by segment. Practical, controllable, and compounding. Your move.

[Author]

Posts