If you’re managing sales, projects, or deals, you already know the pain of tracking pipeline stages. Spreadsheets get messy. CRMs get ignored. People “forget” to update the status. If you want to keep your pipeline honest—and actually useful—Winn can help, but only if you set it up right. This guide is for anyone who wants to actually trust what’s in their pipeline, not just check a reporting box.
Why bother with pipeline stages at all?
First, let’s be real: pipeline stages aren’t magic. They won’t close deals for you. But they do show you where things are stuck, what’s working, and what needs attention. Without clear stages and consistent tracking, your pipeline is just noise.
Too many folks obsess over getting the “perfect” workflow or adding a dozen micro-stages. Don’t fall into that trap. Your workflow should be just detailed enough to show progress, but simple enough that people actually use it.
Step 1: Map out your actual process (not the one you wish you had)
Before you touch Winn, sketch out how deals really move through your pipeline—not how the textbook says it should work.
Ask yourself: - What are the 4–7 big milestones every deal hits, no matter what? - Where do things commonly stall out? - Are there any “dead zones” where activity drops off and deals disappear?
Pro tip: If you can’t remember the last time a deal stalled in a certain stage, you probably don’t need that stage.
What works:
- Fewer, clearer stages (think: “Contacted,” “Qualified,” “Proposal Sent,” “Won/Lost”).
- Honest names. If you call a stage “Commit,” but nobody commits there, change the name.
What doesn’t:
- Vague stages like “In Progress” or “Pending.” They don’t tell you what’s actually happening.
- Overcomplicating. More stages = more chances for things to get stuck or skipped.
Step 2: Set up your Winn workflow to match your real-world stages
Now, bring your process into Winn. Winn’s workflows are flexible, but that just means you need to be disciplined about what you set up.
How to do it: 1. Go to the workflows section and create a new pipeline. 2. Add your stages in the actual order deals move (not what looks prettiest). 3. Use clear, action-based names (“Demo Scheduled” instead of “Discussing”). 4. Set up default fields or checklists for each stage—only if they’re actually needed.
Pro tip: Less is more with required fields. If you make every field mandatory, people will make up answers just to move things along.
What to ignore:
- Fancy automations you “might need later.” Start with basics; you can always add triggers or reminders once the workflow is actually working.
Step 3: Make it dead simple to update stages
No matter how slick your workflow, if it’s a pain to update, people will skip it. Winn’s UI is pretty clean, but you still want to make things as frictionless as possible.
Tips: - Put the most common actions front and center. - Use bulk update if you’re moving several deals at once. - Train your team to update the stage while they’re on the call or sending the email—don’t let it pile up. - Set up smart notifications for deals that sit too long in one stage, but don’t overdo it (notification fatigue is real).
What works:
- Quick, one-click moves between stages.
- A shared team norm: “If it didn’t get updated, it didn’t happen.”
What doesn’t:
- Guilt-tripping people for missing updates. Instead, make it easier and show why it matters.
Step 4: Review and clean up your pipeline regularly
Pipelines rot if you don’t clean them up. Deals get stuck, people leave, and your “hot” list becomes a graveyard.
How to stay honest: - Set a recurring calendar event to review the pipeline every week or two. - Use Winn’s filters to find deals with no activity for X days. - Close out dead deals—don’t just drag them along for “pipeline coverage.” - Review stage definitions with your team. If people are confused, change the wording.
Pro tip: Celebrate when someone closes out a dead deal. It keeps your numbers honest and makes wins feel real.
Watch out for:
- “Zombie” deals that live in limbo for months. They mess up your forecast and waste everyone’s time.
Step 5: Use Winn’s reporting—just don’t chase vanity metrics
Winn’s built-in reports can show you where deals are moving, stalling, or falling out. Use these to spot problems, not to pat yourself on the back.
Best uses: - Track average time in each stage. If something’s always slow, dig in. - See which stages have the most drop-offs so you can fix leaks. - Compare activity across team members (to spot process issues, not to blame).
Ignore: - Total pipeline value if half your deals are fake or outdated. - “Activity counts” if they don’t tie to real outcomes.
Step 6: Iterate based on what actually happens
No workflow survives first contact with real users. Expect to tweak your stages, rename things, or even cut steps.
How to adapt: - Get feedback from folks actually using Winn—not just managers. - Watch for stages nobody uses, or where everyone enters “miscellaneous” notes. - Don’t be afraid to drop or combine stages if they’re not adding value.
Remember: Your pipeline is a tool, not a trophy case. If it isn’t helping you close more deals or spot problems faster, change it.
Common pitfalls (and how to avoid them)
1. Overengineering the workflow - Keep it simple. If you’re debating between two stages, start with one.
2. Tracking for tracking’s sake - If nobody acts on a field or stage, ditch it.
3. Chasing “perfect” data - Good enough is good enough. You’ll never have 100% up-to-date info.
4. Letting the pipeline get stale - Schedule regular reviews—otherwise, your “pipeline” is just a junk drawer.
Final thoughts: Keep it simple, keep it honest
Pipeline stages are there to help you see what’s really happening—not to look busy or impress your boss. With Winn, you’ve got the tools to track your deals, as long as you don’t get lost in the weeds. Start simple, focus on what’s actually useful, and be ready to adjust as you go. The best pipeline is the one your team actually uses.