"Be More Curious" Isn't a Strategy ft. Adnan Rahman (Paycor)

Adnan Rahman gave his Customer Success Managers (CSMs) a playbook for better strategic customer conversations. Then he realized the playbook was only half the answer.

Adnan Rahman, Global Head of Customer and Partner Success at Paycor, joins host Josh Schachter on the latest [Un]Churned episode, “186. Why The Best CS Leaders Start With The Boardroom, Not The Product.” He shares how Paycor structures Customer Success (CS) across a 35,000-account base, why discovery questions were crucial, and how he sees AI helping to scale their success.

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🎯 The [Un]Churned Take: Curiosity Is Infrastructure, Not Instinct

Adnan Rahman built a value realization playbook for his team at Paycor, complete with outcome categories, leading and lagging metrics, a cyclical success plan structure, and a Quarterly Business Review (QBR) process. But in building it, he learned something the playbook itself couldn’t fix. You can’t operationalize value delivery if you can’t surface what the customer actually cares about in the first place.

Inspired by a past visit from Nick Mehta, whose parting advice was to “be more curious,” Adnan dug deeper to figure out what that actually looks like in a strategic sense.

His solution was to make curiosity part of the process.

The Simplest Answer is to Ask More Questions

Health scores reward account stability. Renewal timelines reward contract closings. Escalation queues reward responsiveness. The CSM who keeps things quiet is doing their job by every measure you’ve given them. There’s no metric for the question they never asked.

To help him incorporate curiosity into the value realization framework, Adnan brought in customer discovery expert and coach Bob London. Bob shared a deceptively simple rule for discovery: stop asking questions customers can answer with a yes or no. “Do you have hiring challenges?” gets you nowhere. “Which parts of your hiring process feel inefficient?” gets you a conversation. Same topic, completely different output.

Adnan’s team put that into practice with two questions. The first: if you could sit in on your board meeting right now, what’s the one thing they’re debating? The second, which he calls the churn question: if a competitor called you today, would you answer, and what would you say?

His team was hesitant about the second one, assuming that customers would avoid answering. But the opposite happened. “Customers are very forthcoming when you give them the opportunity to tell you about the relationship and how things stand,” Adnan shared. They had opinions; they just needed someone to ask.

Why Most Frameworks Fail Before They Start

The most critical step leaders can miss when moving towards a value delivery strategy is that they define outcome categories and build frameworks, but assume their reps already know how to help customers clearly articulate priorities in measurable terms. In reality, most reps don’t, which isn’t a personality issue, but a training gap that often gets mistaken for a lack of motivation.

When CSMs get stuck in tactical conversations, it’s rarely due to a lack of care. The real issue is that nothing about their environment makes it easier to have strategic conversations instead of reactive ones. With the right questions and structure, that dynamic shifts. Customers see their CSMs differently, and CSMs start to see themselves differently, too.

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🎧 Listen for These Moments

This conversation goes places most CS content doesn’t. A few cues worth listening for:

1. The resistance before the results: Adnan’s team didn’t immediately buy in. He talks about what it took to get them there, and why the hesitation was worth pushing through.

2. The long-tail customer problem: How Adnan thinks about AI agents specifically for the accounts that will never have a dedicated CSM, and why he’s sequencing efficiency and insights first before touching automation.

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🔎 Where to Find Adnan Rahman

LinkedIn: linkedin.com/in/adnan-rahman

📎 Referenced in This Episode

• Bob London — customer discovery coach and creator of the UBR method

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📅 Coming Up

Pulse 2026 — Gainsight’s annual conference is May 27–28 in Las Vegas. CS and AI are converging faster than most organizations are ready for. Come see what leading teams are actually doing. Register at gainsightpulse.com →

New Rules of CS: Expansion — The series continues June 9th with a session on identifying early expansion signals. If your team owns any part of the revenue number, this one’s worth your time. Save your seat →

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Wrapping Up

Customer Success is in the middle of an identity shift from vendor contact to strategic advisor. If you feel like your team is still struggling through this metamorphosis, it might be time to do the unglamorous work of discovering what strategic thinking actually looks like. Not just the vision, but also the infrastructure.

See you next week 🧠