Question three of the six: for everything on your expansion inventory, do you know what each item is worth per customer?
Most people hear that as a pricing question and reach for the rate card. That's the mistake. Value per item isn't a list price. It's a function of who's buying and when they're asked.
The Same Item Doesn't Have One Value
Take one add-on from your inventory. On your starter tier it might be worth one price. On your mid tier, another. For enterprise, a third. Same item, three values, because the value was never in the item. It's in what the item does for that segment.
A flat-fee service might genuinely carry one price everywhere. Fine. But you only know which items flex and which don't after you've priced them per segment on purpose, instead of letting one number flatten all of them.
Timing Is a Price
Here's the version of this almost nobody prices: the same item, offered to the same customer, is worth dramatically different amounts depending on when it shows up.
Stuff it into the initial sale as a discounted one-click and it's a $50 line item the customer barely registers. Hold it back and present it at month six, after the milestone that makes its value obvious, and it's the $500 offer they say yes to without blinking. Same item. Ten times the value. The only variable was when.
That difference never shows up on a dashboard, because nothing failed. The item sold. Revenue was booked. Nobody logs what it would have been worth presented properly, so the discount is invisible and it repeats on every deal.
The Largest Silent Discount in Your Business
Answer question three and your inventory stops being a list and becomes a priced list: this item, this segment, this moment, this number. That's the difference between knowing what you have and knowing what it's worth, and it's what makes the arithmetic in question five possible at all.
Until then, mispriced timing keeps running as the largest silent discount in your business. No approval process, no sign-off, no line item. Just full value quietly marked down to whatever the front door would take.
Most executives can answer two of the six questions. This one is shortest to explain and slowest to see, because nothing about it looks broken. Price the inventory, then price the timing. The markup was always yours to take.
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.