Most CS professionals have been trained, explicitly or implicitly, to keep commercial conversations out of the customer relationship. Don't push. Don't sell. Don't make the customer feel like you're after their wallet. Build trust first. Revenue will follow.
There's some truth in that. Transactional CS, the kind where every conversation is angled toward the next upsell, does erode trust. Customers can feel it. They start treating their CSM like a vendor instead of a partner. The relationship becomes guarded. And when the relationship is guarded, you lose access to the information you need to actually help them.
But the overcorrection is just as damaging. A CSM who never mentions what else is available to the customer, who waits to be asked, who keeps the catalog hidden until the timing feels "right," isn't protecting the relationship. They're withholding from it. And the customer, who is growing and evolving and developing needs that the CSM could be helping with, is being held back.
There's a better way. And it starts with the most fair thing you can say to a customer.
What It Sounds Like
At the right moment in the customer's journey, when they've hit a certain milestone or you can see where they're heading, you say something like this:
When you get to this point in your program, we're going to want to talk about adding this capability to your account. It's going to help you do this specific thing significantly better, and most companies at your stage find it essential once they get there. You're not ready for it yet. But when you are, we'll talk about it. Start thinking about it, maybe budget for it. I'll send you some information so you have it. We don't need to act on it today, but we will when the time comes. Is that fair?
Read that back. What just happened?
You told the customer about something you could potentially sell them. You acknowledged they're not ready for it. You committed to coming back when they are. You gave them time to think and budget. And you asked for their agreement that this is a reasonable way to be treated.
Nobody says no to that. And nobody forgets it.
Why This Works
The reason this lands so well is that it does the opposite of what customers expect from a vendor conversation. Instead of pushing something on them, you're explicitly not pushing it. Instead of creating urgency that isn't real, you're telling them there's no urgency right now. Instead of surprising them with a commercial ask, you're mapping out exactly when and why the conversation will happen.
It's transparent in a way that most business relationships never are. And transparency, real transparency, not the performed kind, is one of the fastest trust-builders that exists.
The customer walks away from that conversation feeling like they're being looked after. Like someone who understands their journey is keeping an eye on what they're going to need. Like they have a partner, not a vendor.
And when you come back later and say, "Hey, you're coming up on that milestone we talked about, it's time to have that conversation," it doesn't feel like a sales call. It feels like a checkpoint. One they've been expecting. Maybe even one they've been looking forward to.
The Fair Question
The "is that fair?" at the end of the seed-planting conversation is doing more work than it might seem.
You're not asking for permission to eventually sell them something. You're asking them to agree that being told about something before they need it, not being pushed to buy before they're ready, and having a clear roadmap for when the conversation will happen is a fair way to be treated.
It is fair. More than fair. It's the kind of treatment most customers have never experienced from a vendor. When they say yes, and they will, they've just agreed to the expansion conversation before it ever happens. There's no ambush later. No awkward pivot. No feeling of "wait, I thought you were on my side."
You've set up the entire future of the expansion motion in one short conversation, and you did it by being the most straightforward person they've talked to in a business context in a long time.
The Timing Is the Skill
None of this works if the timing is wrong. Planting the seed too early, before the customer can even see the milestone you're referencing, makes you sound like you're pitching. Planting it too late, after they're already frustrated that the gap exists, makes you look like you missed it.
The skill is knowing where the customer is on their journey, where they're going, and at what point the next thing becomes relevant enough to mention. That's not a script. That's judgment built on genuine understanding of the customer's situation.
The CSM who has that judgment, who knows the product deeply enough to see the path ahead and knows the customer deeply enough to time the conversation right, is the CSM who never has an awkward expansion conversation. Not because they avoid them. Because they've already handled them months before they need to.
That's the job. And it turns out it's also the most fair thing you can do for a customer.
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.