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The second e-mail matters more than the first. Here is when to send it.

When to follow up after a proposal
  • KindPlaybook
  • DateSep 18, 2026
  • Read4 min read

Playbook

The second e-mail matters more than the first. Here is when to send it.

When to follow up after a proposal
  • KindPlaybook
  • DateSep 18, 2026
  • Read4 min read

Playbook

The second e-mail matters more than the first. Here is when to send it.

When to follow up after a proposal
  • KindPlaybook
  • DateSep 18, 2026
  • Read4 min read

Most deals that go quiet after a proposal were never lost. They were waiting for a reason to answer. The second e-mail you send is often the one that gets the reply, so it is worth timing it well.

Watch the opens, not the calendar

When you send a proposal from Leadline through Gmail or Outlook, you can see when it was opened and how often. That tells you more than any fixed rule about how long to wait.

  • Opened several times, no reply: they are reading it closely, probably with someone else. Call the same day. Ask what questions came up, not whether they have decided.
  • Opened once: they have seen it. Wait until the next working morning, then send a short note with one useful thing, such as an answer to a question they raised on the call.
  • Not opened at all: it may be buried. Resend it with a single line on top that says what is inside and what you need from them.

Write the second e-mail for a busy reader

Keep it short enough to read on a phone. Name one decision you need and one date. Do not attach the proposal again unless it was never opened; a link back to it is enough.

A good follow-up gives the buyer something to forward, not something to apologise for.

Avoid "just checking in". It asks the buyer to do the work of remembering. Mention the problem they described, in their own words, instead.

Put the next step on the card

Before you send the e-mail, set the next follow-up as a reminder on the deal. It appears on your list for that day, and if it slips, it moves to the top as overdue. Nothing depends on memory, and a colleague covering your deals can see exactly what was promised.

When to stop

If a buyer has opened nothing and answered nothing after a few honest attempts, move the deal back a stage or close it as lost with a reason. A clean pipeline is easier to forecast than a hopeful one, and you can always reopen the card if they come back.

Written byMaya Brookscustomer success at Leadline

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E-mail it

Most deals that go quiet after a proposal were never lost. They were waiting for a reason to answer. The second e-mail you send is often the one that gets the reply, so it is worth timing it well.

Watch the opens, not the calendar

When you send a proposal from Leadline through Gmail or Outlook, you can see when it was opened and how often. That tells you more than any fixed rule about how long to wait.

  • Opened several times, no reply: they are reading it closely, probably with someone else. Call the same day. Ask what questions came up, not whether they have decided.
  • Opened once: they have seen it. Wait until the next working morning, then send a short note with one useful thing, such as an answer to a question they raised on the call.
  • Not opened at all: it may be buried. Resend it with a single line on top that says what is inside and what you need from them.

Write the second e-mail for a busy reader

Keep it short enough to read on a phone. Name one decision you need and one date. Do not attach the proposal again unless it was never opened; a link back to it is enough.

A good follow-up gives the buyer something to forward, not something to apologise for.

Avoid "just checking in". It asks the buyer to do the work of remembering. Mention the problem they described, in their own words, instead.

Put the next step on the card

Before you send the e-mail, set the next follow-up as a reminder on the deal. It appears on your list for that day, and if it slips, it moves to the top as overdue. Nothing depends on memory, and a colleague covering your deals can see exactly what was promised.

When to stop

If a buyer has opened nothing and answered nothing after a few honest attempts, move the deal back a stage or close it as lost with a reason. A clean pipeline is easier to forecast than a hopeful one, and you can always reopen the card if they come back.

Written byMaya Brookscustomer success at Leadline

Share this post

E-mail it

Most deals that go quiet after a proposal were never lost. They were waiting for a reason to answer. The second e-mail you send is often the one that gets the reply, so it is worth timing it well.

Watch the opens, not the calendar

When you send a proposal from Leadline through Gmail or Outlook, you can see when it was opened and how often. That tells you more than any fixed rule about how long to wait.

  • Opened several times, no reply: they are reading it closely, probably with someone else. Call the same day. Ask what questions came up, not whether they have decided.
  • Opened once: they have seen it. Wait until the next working morning, then send a short note with one useful thing, such as an answer to a question they raised on the call.
  • Not opened at all: it may be buried. Resend it with a single line on top that says what is inside and what you need from them.

Write the second e-mail for a busy reader

Keep it short enough to read on a phone. Name one decision you need and one date. Do not attach the proposal again unless it was never opened; a link back to it is enough.

A good follow-up gives the buyer something to forward, not something to apologise for.

Avoid "just checking in". It asks the buyer to do the work of remembering. Mention the problem they described, in their own words, instead.

Put the next step on the card

Before you send the e-mail, set the next follow-up as a reminder on the deal. It appears on your list for that day, and if it slips, it moves to the top as overdue. Nothing depends on memory, and a colleague covering your deals can see exactly what was promised.

When to stop

If a buyer has opened nothing and answered nothing after a few honest attempts, move the deal back a stage or close it as lost with a reason. A clean pipeline is easier to forecast than a hopeful one, and you can always reopen the card if they come back.

Written byMaya Brookscustomer success at Leadline

Share this post

E-mail it
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Import your contacts this afternoon. Your team drags its first deal before the coffee goes cold.

Free for 2 seats. No card.

Leadline

A free CRM for small sales teams: leads, a pipeline board, follow-ups and forecasts.

An office at dusk, the city lights coming on

Start free

Import your contacts this afternoon. Your team drags its first deal before the coffee goes cold.

Free for 2 seats. No card.

Leadline

A free CRM for small sales teams: leads, a pipeline board, follow-ups and forecasts.

An office at dusk, the city lights coming on

Start free

Import your contacts this afternoon. Your team drags its first deal before the coffee goes cold.

Free for 2 seats. No card.

Leadline

A free CRM for small sales teams: leads, a pipeline board, follow-ups and forecasts.

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