The Cheshire Cat Gave the Best Onboarding Advice I've Heard All Year
The best onboarding advice I've heard all year came from the Cheshire Cat.
I heard it while scrolling TikTok before my morning coffee, so make of that what you will. Someone was telling a story that had absolutely nothing to do with Customer Success. Somewhere in the middle, she brought up the scene where Alice is lost in Wonderland and asks the Cat which way she should go.
“Would you tell me, please, which way I ought to go from here?” “That depends a good deal on where you want to get to,” said the Cat. “I don’t much care where...” said Alice. “Then it doesn’t matter which way you go,” said the Cat. “...so long as I get somewhere,” Alice added.
We've all heard that line a hundred times. It's on coffee mugs and motivational posters in offices everywhere. But this morning it hit different, because I realized I've been sitting across from Alice for most of my career.
She shows up to every onboarding kickoff.
Every kickoff has an Alice
In 85 to 90% of our kickoffs, customers struggle to define their goals.
They have a broad sense of what they want. They want to "be more efficient" or "get better visibility" or "scale the team." But when you ask them what that looks like in six months, or how they'll know it worked, you get a long pause and a lot of looking at each other on the Zoom.
They want to get somewhere. They just can't tell you where. Tell me that's not Alice.
And listen, I get it. Nobody bought software because they were dying to sit through a kickoff deck. They bought it because something hurts, and they're hoping we're going to make it stop.
The problem is what happens next. Without a destination, we can't design a plan to get them there. So the engagement fills up with the only things we know how to give them: features, trainings, configuration sessions and a lot of busy work. Everyone feels productive. The calendar is packed. And then six months later we're sitting in a QBR trying to explain value to someone who never told us what value meant to them in the first place.
That's how you end up with a customer who is technically onboarded and completely unclear on why they're paying you. I promise you, that customer shows up on your churn report eventually.
Customers bring pain, so walk them backwards
Customers rarely show up with a clearly defined goal. They show up with a pain, and they need our help turning it into something they can actually work toward. That translation is our job, and it's one of the most valuable things we do in the entire relationship.
When a customer can't tell me where they're going, I walk them backwards from the pain:
What problem are you actually trying to solve? Get underneath the first answer. "We need better reporting" is a symptom. Why do you need better reporting? Who is asking for it, and what are they trying to decide?
What bigger business goal is sitting behind it? Every pain connects to something the business cares about, like revenue, retention, cost or growth. If you can't find the connection, keep asking.
What happens if nothing changes, and what changes if it does? This is where the stakes show up. It's also where you'll usually find the number you need to measure against.
Where does our product fit in getting you there? Notice this one is last. If you lead with the product, you'll get a feature wish list instead of a goal.
Once you have a few goals on the table, don't let them keep all of them. At one company I led, we built out a set of seven core business objectives that pretty much anyone buying our product would want. And guess what happened on intake? Customers said they wanted all seven.
So I told them, "We're not going to hit all seven right away. Pick three and stack rank."
Onboarding focused on number one so the customer got to a clear first value moment.
Then the CSM who picked up the account after onboarding went to work on number two. The customer had a destination, and the CSM had a roadmap. You don't keep a customer in onboarding purgatory just because they have three goals.
Leaders, this one is on you too
Unfortunately, a lot of CSMs don't know how to have this conversation, or they don't think it's part of their job. Some of them were hired to be product experts and trainers, so that's what they default to. Some of them are worried that pushing a customer on their goals will feel uncomfortable or rude. So they ask once, write down whatever vague answer they get, and move on to the configuration checklist.
I don't blame them for that, because most of them were never taught how to do it. That part is on us.
Telling your team to "go capture their goals" is about as helpful as the Cat's directions. It sounds like guidance, but it doesn't tell anyone how to get anywhere.
And it's rarely a one-time miss. When I ask CS teams when they last captured goals for their customers, the answer is very often "at onboarding," even for customers who have been with them for three years on a product that deploys in three months. So the one conversation that was supposed to anchor the entire relationship happened once, probably went sideways, and never got revisited.
If you want your team to get this right, they need more than a field in the CRM. They need to know which questions to ask and in what order. They need to know when to keep probing, when to stop, and when to redirect a customer who keeps steering back to features. That takes real coaching:
Give them the questions. Write them down. Put them in the kickoff guide. Don't make every CSM invent their own version.
Show them what good looks like. Share examples of strong goals and weak ones from your own book of business, so they can hear the difference between "improve efficiency" and "cut onboarding time for new reps from six weeks to four."
Model the conversation first. Get on the call and run it yourself while they watch. Then let them run it while you watch. Then debrief.
Inspect it after kickoff. Review the goals your team captures the same way you'd review a forecast. If you can't measure it, send it back.
It's more work up front, and it's absolutely worth it. A CSM who can run this conversation well is a CSM who can prove value at renewal, and that's the whole game.
Pick a destination
The Cheshire Cat was being brutally honest with Alice, and I kind of love him for it. If you don't care where you're going, any road will do, and you'll definitely get somewhere. It just might not be anywhere worth going.
Our customers deserve better than that, and so do our teams. If our customers don't have a destination, then we're just traveling.
So I'm curious. What's the question you ask when a customer is struggling to define their goals, or how do you guide them there? I'd love to hear what's working for you.
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