If you’re tired of chasing down pipeline updates and your sales forecasts always seem off, you’re not alone. Manual updates are a mess—slow, error-prone, and easy to put off. If you’re using Trustworthy as your CRM or forecasting tool, there’s a better way: automate those pipeline updates so you can actually trust your numbers. This guide is for anyone who owns pipeline accuracy—sales ops, revenue leaders, even the lone wolves who wear all the hats.
Let’s get straight to it.
Why Automate Pipeline Updates in Trustworthy?
There’s no shortage of “automation will change your life” talk, but here’s the reality:
- Manual entry sucks. Even the best reps forget to update deals, or fudge numbers to look good.
- Forecasts are only as good as your data. If your pipeline is stale, your forecast is garbage.
- Sales ops are stretched thin. You’ve got better things to do than chase pipeline updates.
Automating pipeline updates in Trustworthy won’t solve all your problems, but it will:
- Cut down on manual errors
- Save time (yours and your team’s)
- Make your forecasts more believable
But let’s be clear—automation isn’t magic. It’s only as good as the process behind it. If your reps are logging junk data, you’ll just automate the spread of junk. So, get your basics right first.
Step 1: Audit Your Current Pipeline Process
Before you wire up any automation, take a hard look at how pipeline updates happen today. Otherwise, you’ll just automate chaos.
Questions to ask:
- Where are updates falling through the cracks?
- What information is most often missing or wrong?
- How often do reps update deals? Is it consistent?
- Are there “shadow” spreadsheets or side systems?
Pro tip: Don’t skip this. Automation works best on clear, repeatable processes. If your pipeline is a free-for-all, fix that first.
Step 2: Map Out What Needs to Be Automated
Not every field or update is worth automating. Focus on the stuff that affects forecasting the most.
Critical pipeline fields to automate: - Deal stage/progress - Close dates - Deal amounts - Probability to close (if you use it) - Next steps or activity logs
What to ignore (for now): - Notes or custom fields that don’t impact forecasting - “Nice-to-have” fields that just clutter the view
You want automation that updates your core pipeline without getting bogged down in details no one uses.
Step 3: Connect Trustworthy to Your Data Sources
Here’s where you start wiring things up. Trustworthy can connect with a bunch of tools—email, calendar, calls, other CRMs, spreadsheets, you name it. The goal is to capture real activity so pipeline updates happen automatically.
Common connections: - Email/calendar: Log meetings and emails to update deal activity. - Phone systems: Sync calls or voicemails to mark deals as engaged. - Other CRMs or spreadsheets: If you’re migrating or using multiple sources, set up an integration.
How to do it: - In Trustworthy, find the “Integrations” or “Connections” section (usually under settings). - Authorize connections to your email, calendar, and any other tools you use. - Map fields between Trustworthy and your data sources—be as explicit as possible. - Test each connection. Send an email, book a meeting, and see if it updates your pipeline.
Watch out for: - Permission issues: Make sure you (and your reps) have granted the right access. - Duplicate data: If you connect multiple sources, watch for double-logging the same activity. - Privacy: Only connect what you need—don’t suck in everyone’s calendar events “just in case.”
Step 4: Set Up Automated Triggers and Workflows
This is the meat of automation. Triggers are the “if this happens, then do that” rules.
Examples of useful triggers: - When a meeting is booked with a prospect, advance the deal stage. - If no activity is logged on a deal for 14 days, flag it as “stalled” or send a reminder. - When a proposal is sent (email with PDF attached), move deal to “Proposal Sent” stage. - If a deal’s close date is past and not marked “closed-won/lost,” prompt the owner to update.
How to set these up in Trustworthy: - Navigate to the “Automation” or “Workflows” section. - Use pre-built templates where possible; they save time and avoid rookie mistakes. - For custom triggers, define the input (the event) and the output (the update). - Test each workflow with dummy data before rolling out to the team.
Honest take: Don’t go overboard. Start with 2-3 high-impact triggers. Too many automations can annoy your team (think: notification overload) or confuse things.
Step 5: Roll Out Automation to the Team (Without Causing Chaos)
Automation can freak people out if you just drop it with no warning. Change creates resistance—especially from sales teams used to doing things “their way.”
How to make the rollout work: - Tell your team what’s changing and why (fewer manual updates, better forecasting, less nagging). - Show them exactly what will change in their workflow. - Be clear about what’s still manual vs. what’s now automated. - Ask for feedback—listen to complaints, but don’t let them stall you out. - Monitor adoption and tweak as needed.
Pro tip: Don’t try to flip every switch at once. Start with a pilot group or a single pipeline, then expand.
Step 6: Monitor, Measure, and Tweak
You’re not done once automation is live. Things will break. Data will get weird. That’s normal.
What to watch: - Are pipeline fields updating as expected? - Any weird gaps or duplicates showing up? - Are forecasts actually improving? (Don’t just assume.) - Are reps finding ways to “game” the system? (Someone always tries.)
How to fix issues: - Set a recurring review—weekly at first, then monthly. - Audit a sample of deals to check data quality. - Adjust triggers or field mapping as needed. - Kill automations that aren’t helping or are just noise.
Real talk: Automation is never “set and forget.” Think of it like a garden, not a factory—needs a little tending.
What Works, What Doesn’t, and What to Skip
Works well: - Automating activity logging from email/calendar—huge time saver, keeps pipeline fresh. - Automated reminders for stalled deals—gently nags reps without you chasing them. - Updating deal stages based on real events (meetings, proposals sent).
Doesn’t work so well: - Overly complex workflows—nobody remembers what’s automated and what isn’t. - Automating “gut feel” fields like probability to close—still needs human judgment. - Trying to automate literally everything—just creates more mess.
Skip or delay: - Fancy automations based on AI “intent scoring.” Most aren’t ready for prime time. - Integrating every tool under the sun—a few well-chosen connections beat a tangled mess.
Keep It Simple—And Keep Tweaking
Automating pipeline updates in Trustworthy isn’t about chasing the latest shiny feature. It’s about making things easier on your team and actually trusting your forecast. Start small. Automate the obvious stuff first. Watch what happens. Tweak what doesn’t work.
Most importantly, don’t let perfect be the enemy of good. The goal is a pipeline you can count on—not a science project.
If you keep it simple and keep iterating, you’ll spend less time chasing updates and more time actually using your data to run the business. That’s the real win.