Why do deals that close on forecast still churn?

A deal can close exactly when the forecast said it would and still churn, because a forecast only measures whether the customer signs. It doesn’t measure whether they’re ready for what comes after. If your pipeline review only asks “will this close?”, you’ll find the answer to the more expensive question months later, in onboarding and then at renewal.

I learned this the hard way.

The commit that closed right on time

A couple companies ago, I was VP of Customer Success, and our sales leader and I reviewed the pipeline together regularly. I wanted to know what was coming so my team was ready to receive it.

One big deal was sitting in commit, about 90% of the forecast, and everyone felt great about it. When I read through the notes, though, I saw the customer asking a lot of questions about onboarding. They wanted to know about sequencing and cadence, what templates we had, what resources it would take, and who they’d need on their end.

Those questions told me they still didn’t feel like there was a simple plan in front of them. So I walked over to the rep and offered one of our onboarding specialists for the next conversation, just to make sure the customer felt good about what came next.

He said, “No, no, no, we don’t need that. We already have a verbal.”

The deal closed. Then we found out their data wasn’t ready and half their team was out, including someone going on maternity leave. Our onboarding usually took 3 to 4 months. This one dragged on for 8 or 9, with more than one escalation along the way. We kept trying to scope it down to one small use case so they could get some value, and they resisted every time.

That customer didn’t make it past two years with us.

Technically, that rep forecasted his deal perfectly. Every decision upstream has impacts downstream, and hi, I’m downstream.

What a commit can’t tell your CRO

A commit gets revenue into the quarter. Whether you keep that revenue gets decided in onboarding.

When onboarding runs twice as long as it should, your team burns months of capacity on one account, the customer goes most of a year without real value, and by the time renewal comes around, they’ve already made up their mind. In my experience, a rough start is one of the hardest things to recover from, because the customer’s first impression of you is everything that went wrong.

The warning signs were in the deal the whole time. The customer asked questions, and the rep answered them. What he should have done was ask, “Why are you asking? What’s happening in your organization that we should know about?” We would have found out about the maternity leave before the signature instead of after.

We met questions with answers instead of meeting questions with questions. I think that’s the difference between a good salesperson and a great one.

The question to ask in every pipeline review

When my sales leader and I went through deals, the question we cared about was how much effort a deal would take once it closed. We staffed and built capacity plans a certain way, but not all deals are the same, and some need a lot more of your team than others.

For the big or complex deals, we’d spend a few minutes on what we actually knew and what we didn’t:

• How complex is it, and how big?

• What are we integrating with?

• Who are the personas, and what are their pains?

• What’s their current setup, and how are they doing this today?

  
  

For smaller deals, we skipped the deep dive and looked at volume and close dates so we could plan.

That review only worked because the rep took great notes and wrote down what the customer was asking. This was before AI recorded every call for you. If your notes say “great call, they’re excited,” you’ve got nothing to review.

When CS should join a deal, and when it shouldn’t

CS doesn’t belong in every deal. It depends on the deal, the complexity of the product and who the customer is, and the only reason to add CS is that it adds value for the customer.

Bring CS in when the prospect is leaning into what implementation and deployment will look like, when they know they have the pain but can’t connect it to how their organization gets better, when they want to meet the team they’ll work with, or when CS could be your differentiator.

Skip it when the customer has done this before. I once sat down with an AE and we almost added a CS call to a deal that already had a verbal, mostly to keep the customer engaged through legal and procurement. They were moving off a tool like ours, knew their KPIs and had their data ready. That call would have helped us, and it would have done nothing for them, so we didn’t do it.

Take what onboarding teaches you back to Sales

About once a quarter, we went back to Sales with a review of every onboarding we’d finished: what we wish we’d known earlier, where expectations needed setting better, and what to change on our intake form.

That deal became the example we kept pointing to. Out of it, we built a question guide for Sales, sorted by deal type, stage and the questions customers were asking. Every question came with when to ask it, what to listen for, and what a good or bad answer sounded like.

Steal this: the pre-close question guide

“What other priorities are competing for the same people and timeline as this project?”

Listen for a long list. If the team is already stretched, this project is heading for the back burner.

“What other tools in your stack would our data be useful in, for teams outside yours?”

Listen for tools you’ve integrated with before. Anything outside your experience is uncharted territory, which could be an opportunity for your product team or a real challenge. A long laundry list of tools is a flag that the project could be endless, so help them anchor on which ones are core to the business.

“What does a successful onboarding look like for you? What needs to change in the next 30, 60 and 90 days?”

A good answer names one specific change or one priority, because that’s possible in the time you have together. Flag it if they expect a huge transformation by the end of onboarding. Success in onboarding means they can use your software on their own and have an early win that shows the rest is possible.

“Who are the core people on this project, and have they deployed something like this before?”

A team migrating off a similar platform has the expertise to move fast. A team doing this for the first time will move slower, so plan for it.

“Outside your team, who else needs to be involved, and how do we make sure they show up?”

Listen for borrowed resources. At a company I worked at that sold software to CS teams, the RevOps person a customer needed usually sat on the revenue team, so their time was never fully ours.

“What do you expect the next stage of this to look like? Paint the picture for us.”

Ask this one last, and don’t lead the witness. Let them say all the things out loud. If what they describe is far off from what you deliver, dial it in before the signature. If it lines up, celebrate that and lean in.

Before your next pipeline review

Pick your biggest commit and ask how much effort it will take once it closes. If nobody in the room can answer, you just found your next risk.

If you want more like this, After the Close, The Customer Revenue Newsletter, lands every other Tuesday. Subscribe here.

And if you’re still deciding whether CS belongs in your sales process at all, start with Should Customer Success be involved in the sales process?