Sales reps and customer success folks: you’re busy. You don’t need another tool promising “total automation” while leaving you buried in manual follow-ups. This guide is for anyone who actually uses Outreach and wants to cut the busywork out of their follow-up process—without handing over control to clumsy bots.
Below, I’ll walk you through how to use Outreach workflow features to automate follow up tasks that actually save you time. No fluff, no magic. Just practical steps, honest takes, and a few “things to skip” so you don’t get lost in the weeds.
Why Automate Follow Up Tasks?
Let’s be real: following up is where deals are won or lost, but it’s also where most sales teams drop the ball. You forget, you get busy, and suddenly that hot lead is ice cold.
Automating follow up tasks in Outreach helps with:
- Consistency: No more forgetting to check in.
- Speed: Cut the lag between replies.
- Scale: Handle more leads without working nights and weekends.
But—automation done badly can annoy prospects and make you look robotic. The goal isn’t to become a spam machine. It’s to take repetitive tasks off your plate so you can focus on the real conversations.
Step 1: Map Your Follow Up Process (Don’t Skip This)
Before you touch a workflow, sketch out your actual follow up process. Automation is only as good as the process it’s built on.
Ask yourself:
- How many follow-ups do you typically send after an initial outreach?
- What channels do you use (email, calls, LinkedIn, etc.)?
- What triggers a follow-up? (No response after X days? Opened but didn’t reply?)
Pro tip: Write it out on a whiteboard or notebook first. If your process is messy, the automation will be messy.
Step 2: Get to Know Outreach Workflow Features
Outreach workflows are mostly built around “Sequences,” but there’s more to it:
- Sequences: Pre-built series of emails, calls, or tasks—set it up once, Outreach handles the rest.
- Triggers: Automate actions based on things like email opens, replies, or task completion.
- Tasks: Reminders for manual actions (like “Call this person”).
- Rulesets: Control when and how sequences or tasks fire (think: “only send this email if they didn’t reply in 2 days”).
If you haven’t poked around in Outreach’s workflow automation menus, spend 10–15 minutes clicking through. Don’t worry about breaking anything—you won’t.
Step 3: Build a Simple Sequence for Follow Ups
Start small. Here’s how to automate a basic follow up sequence:
1. Create a New Sequence
- Go to “Sequences” in Outreach.
- Click “Add Sequence.”
- Give it a clear name (e.g., “Demo Request Follow Up V1”).
2. Add Steps to the Sequence
- Step 1: Your initial email (manual or automated).
- Step 2: Wait 2–3 days, then send a follow-up email if no reply.
- Step 3: Wait another 3 days—add a task to call or message them.
- Step 4: Wait 5 days—final follow-up email or task.
Tips: - Keep your follow-up emails short and to the point. - Always include a manual step for at least one follow-up—don’t trust automation to handle every scenario. - Don’t overcomplicate things with 7+ steps unless you know it works for your audience.
3. Set Up Conditional Logic (Optional)
Outreach lets you do things like:
- If the contact replies, remove them from the sequence.
- If the email bounces, stop the sequence.
- If they open but don’t reply after 2 days, queue up a call task.
You can set these rules in the sequence editor. Don’t get lost in the weeds here—start with basic “reply = stop sequence” logic, then add more rules as you go.
4. Test the Sequence
- Enroll yourself or a test contact.
- Watch how tasks and emails trigger.
- Make sure tasks show up in your “Tasks” panel when expected.
What to skip: Don’t bother with every Outreach feature right away (like A/B testing every email or complex branching). Get the basics working first.
Step 4: Automate Task Creation (Beyond Just Emails)
Email isn’t everything. Lots of follow-up still requires a human touch—calls, LinkedIn messages, research. Outreach can automate these too.
How to Add Automated Tasks
- In your sequence, add a step: “Create Task.”
- Choose the type (call, manual email, custom action).
- Set the timing (e.g., “3 days after last step”).
When the time comes, Outreach will remind you with a task in your dashboard. You get the nudge, but you control the execution.
What works: This keeps you from dropping the ball on non-email follow-ups, while still keeping things personal.
What doesn’t: Don’t try to automate everything. Prospects can tell when you’re phoning it in—literally.
Step 5: Use Triggers and Rulesets to Get Smarter
Once your basic sequence is humming, you can start using Outreach’s triggers and rulesets for more advanced automation. This is where most people overcomplicate things, so tread carefully.
Triggers you can set up:
- Auto-enroll new leads: When a contact is added, automatically add them to a sequence.
- Branch logic: If a prospect opens an email 3+ times but doesn’t reply, create a “high interest” task.
- Status changes: If a lead replies with “not now,” move them to a nurture sequence.
How to Do It
- Go to “Triggers” in Outreach.
- Create a new trigger.
- Set your conditions and actions.
Keep it simple: Start with 1–2 triggers that clearly save you time. Ignore the urge to automate every edge case. Too many triggers = chaos.
Step 6: Review, Refine, and Avoid Common Pitfalls
Automation isn’t “set it and forget it.” Here’s how to keep things running smoothly:
- Review your sequences monthly: Look for steps with low reply rates or tasks you keep skipping.
- Ask your team for feedback: If tasks are stacking up, something’s off.
- Stay human: Personalize when it matters (first emails, key accounts).
- Don’t automate apologies: If you mess up, handle it yourself.
Pitfalls to avoid:
- Over-automation: Don’t try to replace all human touchpoints with bots.
- Ignoring reporting: Outreach gives you data on what’s working—use it.
- Letting tasks pile up: If you ignore your Outreach task list, the automation is pointless.
Real Talk: What Actually Works (and What Doesn’t)
Works:
- Automating repetitive “check-in” emails.
- Reminding yourself to call or research a lead.
- Auto-pausing sequences when people reply.
Doesn’t Work (in the real world):
- Fully automated, multi-channel cadences for every lead. Prospects spot mass automation a mile away.
- Overly complex logic trees. You’ll spend more time fixing than selling.
- Ignoring the manual tasks—automation should serve you, not the other way around.
Summary: Keep It Simple, Iterate Often
Automation in Outreach isn’t about replacing you—it’s about supporting you. Start with one or two basic sequences, use triggers sparingly, and let the data tell you what to improve. Don’t fall for the hype that says “set it and forget it.” The best automation is the stuff you barely notice because it just works.
Keep things simple, review your setup every month, and don’t be afraid to delete what isn’t working. You’ll save time, follow up more reliably, and, honestly, have fewer headaches.