Deals rarely die in a dramatic “no”. They die quietly. A proposal goes out, nobody follows up, and three weeks later the buyer has signed with someone else. Two automations fix most of this. First, every time a deal moves stage, HubSpot creates the next task for the owner. Second, if a deal goes 14 days without activity, the owner (and you) get a nudge. Here’s how to build both.
What you need
- For stage-based tasks: Sales Hub Starter, Professional or Enterprise. HubSpot’s pipeline automations, including “Create and assign a task”, work from Starter up.
- For stalled-deal alerts: Sales Hub Professional or Enterprise, because they need a full workflow with custom filters.
- Permissions: Super Admin or workflow edit permissions.
- One custom deal property for the alert, which I’ll explain in step 5.
- Optional: the Slack integration, if you want alerts in Slack instead of email.
Step by step
1. Write down your stages and the one task for each
Before you click anything, write a table. One stage, one task, one due date. For example:
| Stage | Task created | Due |
|---|---|---|
| Discovery booked | Send agenda and confirm attendees | 1 day |
| Discovery done | Send recap email with next steps | 1 day |
| Proposal sent | Call to walk through the proposal | 3 days |
| Negotiation | Confirm decision date and signer | 2 days |
| Closed won | Hand off to onboarding | same day |
If you can’t name the task for a stage, the stage probably isn’t a real step. That’s worth fixing too.
2. Add the stage tasks with pipeline automation
Open your deals board view. Hover over a stage, click Automate, and choose Create and assign a task. Fill in:
- Task name: “Call to walk through the proposal: {Deal name}”
- Assigned to: the deal owner
- Due date: 3 days after the task is created
Click Create workflow. HubSpot builds a small workflow behind the scenes. Repeat for each stage in your table. You can also do this from the pipeline settings: in Settings, go to Objects > Deals, open the Pipelines tab, choose the pipeline, and click Automate.
3. Add a reminder into the task body
Tasks get read on phones between meetings. Put the “why” in the description:
Proposal went out. Ask: did they review it, who else needs to see it, what would stop them signing by {Close date}? Log the call and update Next step.
4. Decide what “stalled” means
HubSpot gives you several date properties on deals. The useful ones here:
- Last activity date: the most recent note, call, logged email, meeting, or message on the deal.
- Next activity date: the next scheduled activity.
- Date entered current stage and Time in current stage.
My rule for most small teams: a deal is stalled if it’s open, has no activity in 14 days, and has no upcoming activity scheduled. That last part matters. A deal with a call booked next Tuesday isn’t stalled, just quiet.
Adjust the 14 days to your sales cycle. If deals usually close in 3 weeks, use 7 days. If they take 6 months, 21 days is fine.
5. Create a “Stall alert sent” property
Go to your deal properties and create a Date picker property called “Stall alert sent”. The workflow will stamp today’s date on it when it fires. This does two things: it stops the same deal triggering every day, and it gives you a clean field to re-enroll on.
6. Build the stalled-deal workflow
Go to Automation > Workflows, create a workflow from scratch, and choose Deal. Enrollment filters (all must be true):
- Pipeline is Sales pipeline
- Deal stage is none of Closed won, Closed lost
- Last activity date is more than 14 days ago
- Next activity date is unknown
- Stall alert sent is unknown, OR Stall alert sent is more than 14 days ago
Note from HubSpot’s docs: relative date filters like “more than X days ago” are checked at the start of each day, so a deal can take up to a day to enroll after it qualifies. That’s fine for this use.
Turn on re-enrollment in the workflow’s Settings tab and tick the trigger on Stall alert sent. Check the re-enrollment options in your portal, because HubSpot doesn’t allow every property type for re-enrollment.
7. Add the actions
- Create task for the deal owner. Title: “Stalled: {Deal name}, no activity in 14 days.” Due: today. Priority: high.
- Send internal email notification (or Send a Slack notification) to the deal owner:
{Deal name} ({Amount}) has had no activity since {Last activity date} and nothing is scheduled. Either book the next step, or move it to Closed lost with a reason.
- Edit record: set Stall alert sent to the date the action runs.
8. Add a manager escalation (optional)
After the actions above, add a Delay of 3 days, then a Branch: if Last activity date is still more than 17 days ago, send a notification to the sales manager. If the rep has acted, the deal falls through with no message.
9. Test on old deals first
Before you turn it on, filter your deals board with the same criteria and see how many match today. If it’s 60 deals, turning the workflow on sends 60 alerts in one morning. Clean up the obvious dead ones first, or start with a stricter filter (say, 30 days) and tighten it over a few weeks.
Common mistakes
- Alerting without a “nothing scheduled” check. Reps get nagged about deals they’ve already handled, and start ignoring every alert.
- No stamp property. Without “Stall alert sent”, you either get one alert ever or one every day.
- Too many stage tasks. One task per stage is plenty. Five tasks per stage get bulk-completed without being done.
- Forgetting the closed stages filter. Closed lost deals have no activity forever. They will all trigger.
- Flooding on day one. Count matching deals before switching on.
When it’s worth getting help
The stage tasks are a good first project to do yourself. The stalled-deal alert is simple in principle, but the details (which activities count, how to handle multiple pipelines, when to escalate) depend on how your team actually sells. If you’d rather talk it through, my HubSpot page explains how I work, and the B2B CRM niche page lists the other automations I usually set up alongside this one.