If you work in B2B sales, you know that deals don’t move in a straight line. There are way too many moving parts—multiple buyers, endless back-and-forth, and the constant threat of everything stalling out. If you’re sick of losing track of what’s next or who’s holding things up, you’re not alone. This guide is for anyone who wants a realistic, repeatable way to manage deal progress using Dealpad’s stages and milestones—without making it someone’s full-time job.
Why B2B deals get messy (and what to do about it)
Here’s the honest truth: most B2B deals fall through because stuff slips through the cracks. You forget who needs to sign off. A key stakeholder goes dark. Or you’re stuck waiting for legal to stop nitpicking the contract.
CRM pipelines look tidy, but the reality is way more chaotic. If you try to force a rigid process, you’ll spend more time updating fields than actually selling.
Dealpad’s stages and milestones can help—but only if you set them up to match how real deals work, not how you wish they did. Let’s break down a workflow that actually helps you move things forward (and keeps your manager off your back).
Step 1: Map your real buying process, not a fantasy one
Before you even touch Dealpad, grab a notepad or whiteboard. List out the steps your buyers actually go through. Not the idealized process from a vendor playbook, but what you see in the wild.
- Who gets involved and when? (It’s never just one person.)
- What are the real approval steps? (Be honest about the bottlenecks.)
- Where do deals stall out most often?
- What “aha” moments make buyers move forward?
Pro tip: Ask your last three closed-won and closed-lost customers to walk you through their buying journey. You’ll hear a lot you won’t get from just talking to your sales team.
Keep this list handy—you’ll use it to build your Dealpad stages and milestones.
Step 2: Set up Dealpad stages the way your deals actually flow
Now open up Dealpad. Stages are the big chunks—think of them as the chapters of your deal story. These should match the major phases your buyers go through.
Some common B2B deal stages:
- Discovery: You’re figuring out if there’s a real problem to solve.
- Solution Fit: You’re showing how you solve their pain, and they’re poking holes.
- Evaluation: Demos, trials, RFPs, security reviews—the “prove it” stage.
- Approval: Legal, procurement, final decision-makers show up.
- Closed: Deal is done (won or lost).
Don’t go overboard. Five to seven stages is plenty. Any more, and you’ll spend all day updating statuses instead of selling.
What works:
- Stages that match how your actual buyers buy, not how you wish they did.
- Clear criteria for moving a deal from one stage to the next.
What doesn’t:
- Making a separate stage for every single task (“Legal Review,” “Redlines Sent,” etc.).
- Overcomplicating things to impress your boss. (Nobody’s impressed.)
Step 3: Break stages into milestones—just enough detail, not more
Milestones are the key checkpoints inside each stage. They help you track the specifics without drowning in admin work.
Here’s how to set them up:
- In Discovery:
- Key contacts identified
- Business problem agreed
-
Budget range confirmed
-
In Evaluation:
- Demo completed
- Technical review passed
-
Reference call done
-
In Approval:
- Legal approved
- Procurement signed off
Again, only add milestones that actually matter for moving the deal forward. If you find yourself skipping a milestone half the time, it probably doesn’t belong.
What to skip:
- Fluffy milestones like “Great meeting” or “Internal sync.”
- Anything that’s really just a task for your to-do list (use your own notes or reminders for those).
Step 4: Make milestones visible to your buyers (when it helps)
One of the things Dealpad does that most CRMs don’t: you can share milestones with your buyers. That means everyone’s on the same page—literally.
- Share a mutual action plan so buyers see what’s next on both sides.
- Use clear, jargon-free language (buyers don’t care about your internal acronyms).
- Only include what’s relevant for them—skip your internal prep work.
Works well when:
- You need your buyer to do something specific (“We need a security review before we can move to the next step”).
- You want to nudge a stalled deal without nagging emails.
Doesn’t work:
- Oversharing everything and making buyers feel micromanaged.
- Treating shared milestones as a hammer for accountability (people hate that).
If buyers ignore your mutual action plan, don’t take it personally. Some will; some won’t. Keep using it for your own tracking regardless.
Step 5: Use stages and milestones to spot problems early
Once you’ve got deals moving through your workflow, use Dealpad reports to look for patterns:
- Where are deals backing up?
- Are certain milestones always skipped or delayed?
- Do certain buyers or deal sizes get stuck at the same spot?
Don’t wait for quarter-end to dig into this. Check weekly or bi-weekly. If you spot the same bottleneck over and over, it’s a process problem, not a people problem.
Pro tip:
If you see milestones no one uses, prune them. If you find yourself adding the same “off-books” step every time, make it official.
Step 6: Keep it simple—and update as you go
Here’s where most teams mess up: they over-engineer the process, then never touch it again. Instead, treat your stages and milestones like a living document.
- Review every quarter (or when something’s clearly not working).
- Involve the reps who actually use the workflow, not just managers.
- Don’t be afraid to cut steps. Less is usually more.
If your team dreads updating stages and milestones, you’ve probably made things too complex. Simplify until it’s painless.
What to ignore (seriously)
Dealpad comes with a lot of flexibility. You’ll be tempted to create a custom flow for every situation. Don’t.
- Don’t make a new stage for every big prospect or “strategic” deal.
- Don’t turn milestones into a checklist for your own admin work.
- Don’t obsess over 100% accuracy—tracking is for progress, not for show.
The goal is to help real deals move forward, not to build a dashboard that looks great in meetings but gets ignored the rest of the time.
Wrapping up: Keep it real, keep it moving
Managing B2B deals is hard enough—don’t make it worse by inventing a process nobody wants to follow. Use Dealpad’s stages and milestones to get just enough visibility and accountability, and don’t be afraid to tweak things as you learn.
Start with the basics, cut what doesn’t help, and focus on what actually gets deals across the line. The simpler your workflow, the more likely your team will stick to it—and the less time you’ll spend chasing updates. Iterate, stay honest, and don’t let the process get in the way of progress.