Follow-Up Sequences

Most sales happen on the follow-up — here is the exact sequence that closes deals without being annoying

Most sales happen on the follow-up. Not on the first call, not on the proposal, not when you first say the price. Later, in the follow-up.

Research consistently shows that over 80% of sales require five or more contacts. Most people give up after one or two. Which means the follow-up is not a nice-to-have. It is the majority of where the yes comes from.

The reason people avoid it is the fear of being annoying. This lesson shows you how to follow up in a way that adds value instead of applying pressure and gives you the Claude prompts to write every message in the sequence.

The Follow-Up Mindset

You are not chasing someone. You are serving them.

A good follow-up adds something: a new piece of relevant information, a question that moves the conversation forward, evidence that directly addresses something they expressed doubt about, or a specific next step when the last one went quiet.

A bad follow-up is a reminder that you are still waiting. Those are annoying. Those should not be sent.

Every follow-up you write should be able to answer the question "what value does this add for the person reading it?" If the answer is "nothing, it just reminds them I exist," do not send it.

The Proposal Follow-Up Sequence

This sequence starts after you send a proposal and covers the typical timeline from initial send to close or clean exit.

Day 0: Proposal sent with a short covering email.

Day 3: First follow-up if no response.

Write a short follow-up email sent 3 days after I submitted a proposal.

Proposal was for: [PROJECT DESCRIPTION]
Prospect: [NAME]
One thing from the discovery call that seemed most important to them: [THEIR PRIORITY]

Write a follow-up that:

• References that specific priority showing I have been thinking about their situation
• Offers to answer any questions on the proposal
• Optionally includes one short piece of new information relevant to their decision

such as a relevant result, something I thought of after the call, or a relevant example

• Ends with a specific question or a suggested time to reconnect
• Is under 100 words
• Uses my voice from @MARKETING.MD

Day 8: Second follow-up if still no response.

Write a second follow-up sent 8 days after the proposal after one unanswered follow-up.

Prospect: [NAME]
Project: [DESCRIPTION]

This message should:

• Acknowledge that they may be busy or the timing may not be right
• Change the angle — ask a question or offer something different rather than repeating
• Be even shorter than the first follow-up — 3 to 4 sentences maximum
• Suggest a very short call of 15 minutes just to make sure the proposal answers

their questions

• Not drop the price or change the offer

Day 21: Long-pause follow-up.

Write a long-pause follow-up sent 21 days after the proposal with no response.

Prospect: [NAME]
Project: [DESCRIPTION]

This message should:

• Not apologise for following up again
• Reference that it has been a few weeks
• Re-ask whether the timing is still relevant
• Be 2 to 3 sentences only
• End with an easy out: "If the timing has changed or you've gone a different

direction, just let me know and I'll close out the conversation"

Day 60 or whenever relevant: Circumstance-change follow-up.

This is not a "still thinking about it?" message. It is a relevant trigger where something changed and you thought of them specifically.

Write a circumstance-change follow-up for a prospect who went quiet after a proposal.

Prospect: [NAME]
What they were working on or their problem: [DESCRIPTION]

What changed or triggered this message: [NEW INFORMATION — something you built,

a result you got, something relevant happening in their industry, a new offer you have]

Write a follow-up that:

• Leads with the new thing and not the old proposal
• Does not say "just checking in" or "following up on my proposal from X months ago"
• Is short — under 80 words
• Makes it easy for them to re-engage without embarrassment about the silence

The "Closing the Loop" Message

This is the final message in any sequence. Sent when you have followed up multiple times with no response or when a timeline has clearly passed.

This message works better than you expect. Many prospects who seemed dead reply to this one.

Write a "closing the loop" final message for this prospect.

Prospect: [NAME]
Project or proposal: [DESCRIPTION]
Last contact: [DATE OR TIMEFRAME]

Write a message that:

• Is very short — 3 to 4 sentences
• Explicitly says I am closing out the conversation
• Makes it easy for them to say "actually wait" if the timing has changed
• Does not guilt or pressure — just states clearly that I am moving on
• Leaves the door open for them to come back whenever it makes sense
• Sounds human and not like a CRM drip sequence

Example tone: "I haven't heard from you in a while — I'm going to assume the

timing isn't right. If that changes, I'll be here."

This message converts a higher percentage of seemingly dead leads than any other follow-up. The explicit closure creates a reaction: some prospects realise they have been stalling and decide. Others genuinely reach back months later. Either way you get resolution instead of open loops.

Building Your CRM (Simple Version)

You do not need CRM software. A simple leads.md file works:

# Active Leads
## [PROSPECT NAME] — [DATE OF FIRST CONTACT]
- Project: [DESCRIPTION]
- Proposal sent: [DATE]

• Last contact: [DATE + WHAT WAS SAID]
• Next follow-up: [DATE]
• Status: Proposal sent / Awaiting decision / Negotiating / Dead / Won / Lost

Use Claude to help you manage this:

Here is my current leads list: [PASTE LEADS.MD]
Today is [DATE].

Tell me:

1. Which leads have a follow-up due today or this week?
2. Which leads have gone cold with no response in 14 or more days?
3. For each follow-up due, suggest which type of message to send

(proposal follow-up, long-pause, circumstance-change, or close the loop)

Based on the follow-up type use the appropriate prompt from my @SALES.MD

to write the message.

Adding to SALES.md

## Follow-Up Sequence

After proposal:

• Day 3: Short follow-up, reference their top priority from the discovery call
• Day 8: Second follow-up, different angle, suggest 15-minute call
• Day 21: Long-pause, ask if timing is still relevant, offer easy out
• Day 60+: Circumstance-change only triggered by something new and not just time
• Final: Close-the-loop message sent when I am genuinely moving on

Rule: every follow-up adds something. Never send a "just checking in."

Your Action Right Now

List every proposal you have sent that is still open, anywhere from last week to six months ago. For each one determine which follow-up is due based on how long it has been. Run the appropriate prompt above. Send the messages today.

If you have never followed up on a proposal after sending it, start now. The deal you think is dead might not be.