Congratulations. You've built your data diet. You're tracking the metrics that matter. You're reviewing them every week. You're now officially data-driven.
But guess what? No good deed goes unpunished. So let’s talk about all the broken stuff you're going to notice now that you’re paying closer attention to your data.
You've got a $500K deal sitting in your first pipeline stage from eight months ago with zero activity.
A rep shows a crazy-high win-rate because they're only logging deals after they close.
Your average deal size is $50K but when you dig in, you've got forty $5K deals and three $200K monsters skewing everything.
Half your "meetings booked" are demos that happened six weeks ago and nobody bothered to update what happened next to them.
You see conversion rates that bounce between 8% and 47% month-to-month with no explanation.
One sales rep is creating $0 opportunities manually for free trials, another is using the lead object, and someone else is tracking theirs in a google sheet somewhere.
Welcome to the X-ray effect of data-driven leadership. Just like an X-ray reveals broken bones you didn't know were there, consistent measurement reveals broken processes you didn't know existed.
The good news?
Now that you can see them, you can fix them.
What You Might Be Noticing
We see the same broken bones in almost every company when they start paying attention to their data for the first time. Here's what to look for:
Broken Bone #1: Nobody Knows What the Stages Actually Mean
Your sales process has stages like "Qualified," "Proposal," and "Negotiation."
But when you ask three different reps what it means for a deal to be in "Proposal" stage, you get three different answers.
One rep thinks it means "we've talked about price." Another thinks it means "we've sent a formal proposal document." A third thinks it means "they've expressed interest in moving forward."
This is why your velocity metrics look insane. When everyone defines stages differently, measuring anything becomes meaningless.
The Fix: Write down exactly what has to be true for a deal to be in each stage. Not just activities from your side ("we sent a proposal - good for us") but qualifying criteria ("customer has verbally confirmed they have budget and a timeline"). Make it specific enough that any rep could look at a deal and put it in the same stage. Even better, make them customer-verifiable (e.g., “If I called the prospect and asked them, would they say X is true?”).
Broken Bone #2: Your Pipeline is Full of Fake Opportunities
Someone downloaded a whitepaper, so they're in your CRM. A rep had a good conversation at a conference, so they created a deal. A customer mentioned they might be interested in expanding next year, so that's a $100K opportunity.
When your pipeline is polluted with these fake opportunities, every metric becomes unreliable. Your win rates look terrible. Your coverage ratios are inflated. Your forecasts are fiction. And your path to the quarter becomes way more uncertain than you (or your CEO, investors, and board) want it to be.
The Fix: Create a simple checklist for what qualifies as a real opportunity. Something like: confirmed budget, identified decision-maker, business need that we can solve, and timeline for making a decision. If it doesn't meet three out of the four criteria, it's not a qualified opportunity (yet).
Broken Bone #3: Nobody Updates Anything Consistently
Your CRM is a time machine. Some deals show activity from last week. Others haven't been touched since they were created six months ago.
This kills your ability to track anything accurately. How can you measure sales cycle if half your deals have fake "last activity" dates? How can you identify stalled deals if nobody's tracking activity consistently?
The Fix: Set expectations for minimum update frequency. Every deal gets touched at least once every two weeks. Every update includes next steps and a realistic close date. Make it part of your weekly review process. Deals that haven't been updated get flagged automatically and included in a “clean your room” report that gets emailed to the entire sales org. Sounds punitive, but it’s one of the most effective levers for behavior change there is.
Broken Bone #4: Your Pipeline is a Zombie Graveyard
Opportunities that died months ago are still showing up in your coverage calculations. Deals where the contact left the company, the project got canceled, or the budget disappeared—but nobody bothered to close them out.
These zombie deals make your metrics lie to you. Your pipeline coverage looks great on paper, but half of it is imaginary.
The Fix: Build a regular pipeline scrubbing process. Every month, every rep reviews deals that are older than your average sales cycle and haven't had activity in 30 days. Either update them with real activity or close them out. Be ruthless. When in doubt, close it out. (And remember: “Always scrubbing the pipeline means you’re never actually scrubbing the pipeline.”)
Broken Bone #5: You Have No Idea How to Handle the Weird Deals
Your process works great for normal deals. But what about the enterprise opportunity that takes 18 months to close? The multi-product deal that involves three different teams? The deal that’s set to close at 11:59pm on the last day of the quarter?
These edge cases break your metrics. They skew your averages, mess up your forecasting, and make your process look broken when it's actually just incomplete.
The Fix: Create clear rules of the road for edge cases. Large deals (over $X) get their own set of rules. Create written guidelines for “how to think about close dates” (i.e., early surprises are ok, slips aren’t). Same thing for multi-product deals, partner deals, etc. Don't try to force everything into the same box. Take stock of the weird edge cases and give people guidelines for how to deal with them and how they should show up in the CRM.
Broken Bone #6: You Don't Know What "Good" Activity Looks Like
Some of your reps are activity machines—lots of calls, emails, meetings, follow-ups. Others don’t log much activity at all. You have no idea what "good" activity looks like, so you have no way to identify problems before they become quota misses. And it’s difficult to tell (a) who’s effectively working their territory and (b) which deals are getting the attention they deserve.
The Fix: Set minimum activity standards. Every active opportunity gets at least X touches per month. Every rep has at least Y customer conversations per week. Make activity visible and measurable - especially if you have an outbound-driven sales motion.
What These Problems Have in Common
These problems all have something in common: They’re the result of processes that evolved organically instead of being designed intentionally.
When you're small, you can get away with informal processes. Everyone knows everyone. Communication happens naturally. You can manage by walking around. There aren’t that many customers or prospects to keep track of.
But as you grow, informal breaks down. Without clear definitions, consistent processes, and regular hygiene, your data becomes meaningless. And without meaningful data, you're back to flying blind.
The irony? Most companies don't discover these problems until they start trying to be data-driven. The metrics force you to confront the reality that your processes aren't as solid as you thought.
The good news? Every one of these broken bones is fixable. And every weird metric can be traced back to a process problem that can be solved. It just requires the discipline to define things clearly, measure them consistently, and maintain them regularly.
So when you start seeing weird stuff in your data, don't get discouraged. Get curious.
Every anomaly is trying to tell you something. Every broken metric is pointing you towards a process that needs attention.
Your data isn't lying to you. It's showing you the truth. And the truth is that most sales processes are held together with duct tape and hope.
Now you can see the obstacles.
Great piece!
Well said.. and I feel so seen. Accountability definitely drives accountability here. Great read!