When it comes to HubSpot automation, there’s a fine line between “working perfectly” and “I have no idea why this isn’t firing.”
We’ve audited dozens of HubSpot portals, and nearly every single one had at least one workflow error causing friction, missed leads, or messy reporting. Sometimes it's a broken trigger. Sometimes it's a chain reaction that breaks everything.
Here are the three most common automation mistakes we see — and what to do instead.
What’s going wrong:
You’ve built the workflow, set up the email, turned it on… and nothing happens. The problem? Bad enrollment criteria.
A common issue is trying to trigger off a field that never actually gets updated, or building a workflow that conflicts with another one.
How to fix it:
Use “Test Contact” to simulate enrollment before turning it live
Make sure your trigger property is actively being updated by a form, integration, or another workflow
Check your workflow history to spot blocked enrollments or skipped actions
What’s going wrong:
Multiple workflows are updating the same property or sending similar emails, leading to a confusing customer experience.
This happens a lot in marketing-to-sales handoffs, where lead status, lifecycle stage, or owner assignments get overwritten.
How to fix it:
Create a workflow map or audit sheet to document what each workflow does
Use Goal steps to prevent unnecessary automation if a contact has already converted
Use “Re-enrollment” rules wisely — don’t let contacts get stuck in loops
What’s going wrong:
You’ve set up a follow-up email or internal task… but the contact moves stages before the action happens. Or worse — they get hit with conflicting messages.
How to fix it:
Add delays and if/then branches to ensure your workflow reacts to real-time changes
Use “Contact has not been contacted in X days” filters to keep things clean
Avoid automation that assumes perfect timing — build in wiggle room
We offer free HubSpot portal audits that include a full automation review. We’ll show you what’s working, what’s broken, and what’s possible — no strings attached.
Or if you’re not ready for that, start with our free Data Hygiene Audit Checklist to clean up the messiest parts of your CRM.
Need help fixing a specific workflow?
Book a free audit here and we’ll take a look.