Keep Calm and Close
By Whitney Littlewood
Like everything in business (and life), Customer Success is evolving fast.
One of the biggest shifts we’re seeing at The Success League is this: post-sales teams are now carrying growth revenue quotas. That means many CSMs are being asked to sell without ever having been trained in sales.
So here’s a critical tip for any CSM responsible not just for retention, but for expansion: stop jumping straight to the solution.
Yes, everyone is busy. Yes, customers are distracted. Yes, the world feels chaotic and when a customer mentions a problem you know you can solve, it feels like hitting the jackpot.
“We’ve got a feature for that!”
Totally natural.
Also…usually ineffective.
The moment you rush to solve before fully qualifying the problem, you lose leverage. Our advice? Pause your excitement and get curious first.
If you’ve ever confidently offered the “perfect” solution only to watch your customer nod politely and move on, it’s usually because of one (or more) of these truths:
People don’t like change - even when they know they need it.
The cost of the solution feels bigger than the cost of the problem (time, money, effort, process disruption).
They haven’t fully connected the problem to real business impact.
So next time you get a bite… slow down.
Ask. Don’t tell.
Why is this a problem?
What’s the impact on the business?
How much time does it waste?
What does it cost them financially, operationally, and emotionally?
Quantify it. Make it real.
When you ask the right questions, something powerful happens: both you and the customer start to see the true size of the problem. And once that’s clear, the math flips. The cost of the problem suddenly outweighs the cost of the solution.
That’s when you hear:
“Send me the addendum.”
Boom. Growth revenue for you. A solution they actually care about for them.
A real win-win.
This is the beauty of CSMs selling in the post-sales journey. It’s not smoke and mirrors. It’s not pressure. It’s value-based, targeted, incremental growth rooted in genuine customer outcomes.
So slow down. Ask better questions. Qualify before you solve.
Your customers, and your CRO, will thank you.
The Success League is a boutique customer success training and consulting firm focused on building extraordinary CS programs. For more on our comprehensive suite of certification series for both CSMs and CS Leaders, visit our Learning page or TheSuccessLeague.io.
Whitney Littlewood - Whitney is a passionate customer success leader that believes a healthy mix of data and empathy drive exceptional customer outcomes. She most recently led customer success teams at high-growth startups including UserTesting and Optimizely. Before that, she held roles in consulting, product development and marketing at companies including Adobe and Travelocity. She loves teaching and helping people grow both professionally and personally.
