How to Re-Engage Stalled Deals in HubSpot (Before They Die)

You know that deal sitting in "Proposal Sent" for 3 weeks? It's not coming back on its own.

Every sales rep has a graveyard of deals that just... stopped. No rejection, no commitment—just radio silence. They sit in your HubSpot pipeline like abandoned shopping carts, dragging down your forecast and mocking your follow-up attempts.

The hard truth: a deal that goes quiet for 7+ days rarely closes without intervention. But here's the good news—most stalled deals aren't actually dead. They're just waiting for the right nudge.

Here's how to identify which deals are worth saving and exactly what to say to bring them back to life.

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Why Deals Stall (And Why It's Not Always Your Fault)

Deals don't usually stall because your product sucks or your price is too high. They stall because:

Internal chaos at the buyer's company

• Their champion got pulled into a fire drill
• The CFO put a freeze on new purchases
• Three executives need to sign off and two are on vacation

Your deal isn't urgent enough

• It solves a real problem, but not a right now problem
• They're comparing you to 2-3 competitors
• Budget got reallocated to something shinier

Communication fell through the cracks

• Your last email got buried
• They meant to respond but forgot
• No one owns the decision internally

The key insight: most of these are fixable. But you need to know which deals to prioritize.

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Step 1: Identify Stalled Deals in Your HubSpot Pipeline

Here's how to find deals worth re-engaging:

Create a "Stalled Deals" view in HubSpot

Filters to use:

• Deal stage: NOT "Closed Won" or "Closed Lost"
• Last activity date: More than 7 days ago
• Close date: Within the next 60 days (or past due)

Sort by deal amount (descending). Focus on your biggest fish first.

Red flags that a deal is truly stalled

Not just slow-moving—actually stuck:

• No response to your last 2+ emails (they're ghosting you)
• Scheduled call got cancelled and not rescheduled (they're avoiding you)
• "Will get back to you next week" was 3 weeks ago (classic stall)
• Last note in HubSpot says "waiting on their end" (you're blocked)

If a deal checks 2+ of these boxes, it's stalled. Time to act.

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Step 2: Figure Out Why This Specific Deal Stalled

Before you fire off another "just checking in" email (please don't), dig into the context.

Review your HubSpot activity timeline

Look for:

• What was the last real conversation? (not just an automated email)
• What did they say was the next step? (check call notes)
• What blocker did they mention? ("need legal to review", "waiting on budget approval")
• Who's involved in the decision? (just your champion, or are there other stakeholders?)

Example from a real stalled deal:

Last call (Dec 15): Prospect loved the demo. Mentioned CFO needs to approve anything over $10k. Said "I'll talk to her this week."

12 days later: Silence.

Why it stalled: CFO approval is blocking it. Your champion probably tried, got pushback or delay, and now feels awkward telling you.

What NOT to do: "Hey, just following up!"

What TO do: Address the CFO blocker directly (more on this below).

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Step 3: Write a Follow-Up That Actually Gets a Response

Here's the framework that works:

The anatomy of a re-engagement email that converts

1. Reference the last real interaction

Show you remember the conversation. No generic "hope you're doing well."

Bad:

"Hi Sarah, I wanted to circle back on our proposal."

Good:

"Hi Sarah, following up on our December 15th call where you mentioned getting CFO sign-off."

2. Address the likely blocker

Make it easy for them to tell you what's really going on.

Bad:

"Are you still interested in moving forward?"

Good:

"I know budget approvals can be tricky in Q4. Is that what's holding things up, or is there something else I should know about?"

3. Offer something valuable

Don't ask for their time without giving something first.

Examples:

• "I put together a one-pager showing ROI for companies your size—happy to send it over for your CFO meeting."
• "I found a case study from a company in your industry that had the same compliance concerns you mentioned. Want me to forward it?"
• "Our VP of Sales did a webinar on exactly this use case last week. The recording might be useful for your team—I can share the link."

4. Make the next step stupidly easy

Remove all friction. Don't make them think.

Bad:

"Let me know if you'd like to schedule a call."

Good:

"I have 15 minutes open Tuesday at 2pm or Wednesday at 10am—does either work for a quick sync?"

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Real Example: Before vs. After

Let's see this in action.

Context

Deal: ACME Corp - Sales Automation Platform - $45,000
Stage: Proposal Sent
Last interaction: Call on Dec 15, prospect (VP Sales) said CFO needs to approve
Stalled: 12 days, no response to 2 follow-up emails

Bad re-engagement email (what most reps send)

Subject: Checking in

Hi John,

I hope you're doing well! I wanted to circle back on the proposal we sent over a couple weeks ago.

Do you have any updates on your end? Happy to jump on a call whenever works for you.

Let me know!

Best,
[Your name]

Why this fails:

• Generic subject line (gets ignored)
• No reference to the actual blocker (CFO approval)
• Asks for their time without offering value
• Vague next step ("whenever works")

Good re-engagement email (what actually works)

Subject: Quick ROI breakdown for your CFO meeting

Hi John,

Following up on our December 15th call where you mentioned needing CFO approval for the sales automation platform.

I know budget approvals can be tricky in Q4. Is that what's holding things up, or is there something else I should know about?

I know finance teams want to see hard numbers, so I put together a one-pager showing the ROI breakdown for companies your size. The short version: most teams see payback in under 4 months from time saved on manual follow-ups alone.

I'm attaching it here—feel free to forward it to your CFO or use it however's helpful.

Also, totally fine if the timing isn't right or if this got deprioritized. Just let me know either way so I'm not bugging you.

If you want to discuss before your CFO meeting, I have 15 minutes open Tuesday at 2pm or Wednesday at 10am: [calendar link]

Thanks,
[Your name]

Why this works:

• References the specific blocker (CFO approval)
• Offers immediate value (ROI one-pager)
• Gives them an out ("totally fine if timing isn't right")
• Makes next step easy (specific times + calendar link)
• Professional but conversational

Result: 70%+ response rate on emails like this (vs. <10% for "just checking in").

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Step 4: Know When to Let It Go

Not every stalled deal is worth chasing.

Cut your losses if:

• You've sent 3+ personalized follow-ups with no response (they're ghosting on purpose)
• They explicitly said "let's revisit in Q2" (respect the timeline, set a reminder)
• Your champion left the company (and you have no other contacts)
• They went with a competitor (move on)

Mark it "Closed Lost" in HubSpot and free up mental space.

But before you do, send one last email:

"Hi [Name], I haven't heard back and I don't want to be a pest. I'm going to assume the timing isn't right and close this out on my end. If things change down the road, you know where to find me. Good luck with [specific thing they mentioned]!"

You'd be surprised how often this gets a response. People feel less pressure and sometimes reply with "Actually, sorry for the delay..."

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Step 5: Automate the Boring Parts

Here's the reality: if you're manually tracking every deal that goes cold, you're going to miss some.

What you should automate

Stalled deal detection

• Set up a workflow in HubSpot: "If last activity > 7 days AND deal not closed, send me a Slack notification"
• Or use a tool that does this automatically (Flux tracks every deal and flags the ones going cold)

Follow-up reminders

• HubSpot task: "Follow up on ACME deal" with due date 7 days after last touch
• Google Calendar reminder: "Check in on stalled Q1 deals" every Monday

What you should NOT automate

The actual follow-up email.

Please, for the love of closed deals, do not send automated drip sequences to stalled deals. They can tell. And it's insulting.

Use automation to remind you to follow up. Write the email yourself (or use AI to draft it, then edit heavily).

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The Follow-Up Timeline That Works

Here's the cadence we've seen convert best:

• Day 0: Deal goes cold (7+ days since last activity)
• Day 1: Send re-engagement email #1 (reference last conversation, offer value)
• Day 4: If no response, send email #2 (different angle—maybe share a case study)
• Day 7: If still no response, send email #3 (the "breakup" email)
• Day 14: If STILL no response, mark Closed Lost and move on

Total: 3 touchpoints over 2 weeks. If they don't respond to that, they're not coming back.

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The Bottom Line

Stalled deals aren't lost deals—they're just deals you haven't followed up on correctly yet.

The difference between a 30% close rate and a 50% close rate often comes down to how well you re-engage deals that go quiet.

Here's what works:

• Identify stalled deals early (7+ days = act now)
• Understand WHY each deal stalled (check your notes)
• Write personalized follow-ups (reference the blocker, offer value)
• Make next steps stupidly easy (calendar links, specific times)
• Know when to let go (3 touchpoints, then close it)

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Frequently Asked Questions

How many times should I follow up on a stalled deal?

3 times over 2 weeks. After that, if there's zero response, mark it Closed Lost and move on.

What if they said "I'll get back to you" but never did?

Your next email should acknowledge this: "I know you said you'd get back to me last week—totally fine if priorities shifted. Should I close this out on my end, or is there still interest?"

Should I call them instead of emailing?

If you have their cell number and a good relationship, yes. But most buyers prefer email for re-engagement. Test both.

What's the best subject line for a re-engagement email?

Specific and valuable. Examples: "Quick ROI breakdown for your CFO meeting", "Case study you asked about", "Following up on [specific thing they mentioned]". Avoid: "Checking in", "Following up", "Just touching base".

Can I use AI to write my follow-up emails?

You can use it to draft, but edit heavily. AI emails sound generic. Reference specific details from your notes that AI wouldn't know—or use a tool like Flux that reads your deal context.