Question four of the six: which observable milestones tell you a customer is ready for their next purchase?
Notice the word observable. Not which customers seem happy. Not which accounts have good health scores. Observable moments, things that either happened or didn't, that signal a customer has arrived somewhere real and the next thing has become relevant.
If you can't name those moments, then readiness is invisible in your business. And when readiness is invisible, there's only one motion available: present everything to everyone and hope. The batch blast isn't a strategy. It's what's left when you can't see who's ready.
What a Readiness Milestone Looks Like
Four kinds, and most businesses have all four without tracking any of them.
Progress milestones: the customer achieved something real with what they bought. First result shipped, first workflow live, first quarter of numbers. Events: something changed on their side. New funding, new leadership, a hiring wave, an acquisition. Triggers: usage crossed a line. Seats maxed, capacity strained, a feature ceiling hit. Calendar moments: renewals, budget cycles, planning seasons, the moments money is already in motion.
Every one of these is observable. Every one is a fact, not a vibe. And each item you're holding back in your inventory attaches to the specific milestone that earns it: when this happens, that becomes relevant. Not before.
The Alternative Has a Name
Most companies run what I call thoughts-and-prayers expansion. Everyone agrees the customers will grow. They love us, they'll buy more. And nothing in the company is built to notice when a specific customer is actually ready for a specific next thing. No milestones defined, no offerings attached, no signal watched. Just sentiment, and a quarterly blast when the number gets tight.
Milestones are the difference between believing expansion should happen and knowing when it happens. The blast dies the day readiness becomes visible, because you never again present something to someone who isn't ready for it.
The Part Customers Can See
One more thing milestones do, and it's the piece almost everyone misses: milestones work in both directions. You see who's ready. But the customer sees the path.
When the next milestone and what it earns are on display, staying stops being inertia and starts being aspiration. There's somewhere to get to. That has consequences for lifetimes, not just purchases, and it's a big enough subject that it gets its own piece.
Random Timing Produces Random Revenue
Answer question four and timing stops being a guess. The catalog is priced, and now each item has a moment. What's left is knowing how many customers are approaching those moments right now, which is question five, and it turns out to be the most predictable pipeline you've never looked at.
Most executives can answer two of the six questions. The companies that can answer this one have stopped blasting and started noticing. Because random timing produces random revenue, and the milestones were sitting in your customer data the whole time, waiting for someone to name them.
Lincoln Murphy formally named and popularized Customer Success starting in 2010 and has spent 15 years connecting it to expansion revenue and commercial outcomes. Read The Premise.