Beyond the Check-In: The Questions Top CSMs Use To Build Authority With Customers

CLICK PLAY TO HEAR THE FIVE POWER QUESTIONS TOP CSMS ASK TO BUILD AUTHORITY WITH CUSTOMERS:

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Here’s what you can expect from this episode:

What if the only thing standing between you and a six-figure expansion deal is just one question you haven’t asked yet?

If your customer check-ins feel like awkward small talk and surface-level updates, this episode is going to change the game.

Because here’s the truth: the difference between being seen as “just another vendor” vs. a trusted strategic partner? It comes down to the questions you ask.

In this episode, I’m walking you through five power questions that top-performing CSMs use to uncover pain points, unlock expansion opportunities and measurable success metrics, all without feeling salesy or forced. One of these questions? Helped a client close a six-figure deal after months of stalled conversations. (Yeah… you’re gonna want to steal this one!)

You’ll hear a real before-and-after scenario that shows exactly how these five questions turn a flat, forgettable check-in into a conversation that builds credibility and authority with customers and positions you as a trusted advisor, not a glorified support rep.

If you’ve ever felt like your customers aren’t opening up, you’re not getting looped into strategic initiatives, or your “QBRs” are just you presenting slides to a bored audience, then this episode is your tactical blueprint to change that without adding anything new to your plate. No extra prep. No deep product knowledge. Just five simple questions that flip the script completely.

This isn’t theory. It’s a script you can start using today! And once you hear it in action, you’ll never run a “check-in” the same way again.

Hit play and let’s make your next customer convo your most impactful one yet!

Topics covered on the five power questions top CSMs use to build authority with customers:

• When to ask the one question that instantly reveals your customer’s real priorities and why skipping it keeps you stuck in the “vendor” zone
• What to say instead of “any issues?” so customers start opening up and see you as a strategic partner, not a box-checker
• The five power questions I teach my clients to use in EVERY customer convo (one of them led to a six-figure deal after months of silence)
• How to pull meaningful business context from even the most vague customer updates (with tons of real-life examples)
• How to use silence as a secret weapon to increase your authority
• The simple follow-up question that makes you sound like a seasoned strategist, even if you’re brand new to CS
• How to get in the habit of doing discovery all the time so hitting your adoption, expansion, and retention goals feels way easier

Resources Mentioned:

• Optimize your resume for Customer Success jobs to land consistent interviews: Watch the FREE Training here
• Learn how to sell yourself as the best candidate and walk into your next Customer Success job interview with confidence: Watch the FREE Training here
• Learn how to MASTER Behavioral Interviews: Watch the FREE Training here
• Actively looking for a job in Customer Success or plan to in the near future? Apply for 1:1 Coaching with me

Connect with Carly:

• Connect with me on LinkedIn 
• Email me at [email protected] 

Related Episodes:

• Episode 50: How Top CSMs Nail Customer Value
• Episode 35: Driving Customer Adoption: The Career-Killing Mistake Most CSMs Make

More about Customer Success Career Coach:

Customer Success Career Coach is the must-listen podcast for current and aspiring Customer Success pros. Join Carly and her guests as they spill the secret strategies and tips for building your Customer Success career. This isn't your typical snooze-fest – they’re diving deep into the world of Customer Success careers. Whether you're starting from scratch (hey career transitioners!) or eyeing that next big promotion, they’ve got the playbook for you. Every Wednesday, join Carly and her amazing guests as they dish out practical advice and real-life steps you can actually use. No fluff, just stuff you can apply ASAP to score that dream job, snag that promotion, or become the team rockstar.