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This article builds on a core idea from the Foundations of Customer Success series: being strategic is not about sounding impressive — it’s about applying judgment with clarity. If you haven’t already, start with: “Being Strategic Is Vague - and How to Make It Real” which defines what strategy
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Why the advice CSMs hear most is also the least actionable At some point in their career, every Customer Success Manager hears the same feedback: “You need to be more strategic.” It’s often well-intended. And almost never explained. CSMs are left to interpret it on their own, which usually
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Why disengagement is usually a design problem, not a customer problem Quarterly Business Reviews have a reputation problem. They’re often described as: * Necessary but painful * Important but poorly attended * Strategic in theory, transactional in practice When QBRs fall flat, the default explanation is usually: “The customer just isn’t
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And why most expectations go unspoken Enterprise Customer Success looks impressive from the outside. Large contracts. Complex organizations. Executive stakeholders. Strategic conversations. But once you’re inside those relationships, a surprising truth becomes clear: Enterprise customers rarely tell you what they expect - they assume you already know. That gap
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Why so many capable CSMs feel behind, burned out, or unsure of their impact Most Customer Success Managers didn’t choose this career because there was a clear, well-defined path. They landed here. From support. From implementation. From sales. From project management. From “you’re good with people, can you
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Why disengagement is usually a signal - not a failure You’ve scheduled the review. You’ve prepared the materials. You’ve sent the invite. And still, the signs are familiar: * Attendance is minimal * Engagement is polite but thin * The conversation stays surface-level * Nothing meaningful changes afterward At some point,
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Why confusing the two quietly undermines Customer Success Adoption is often treated as the north star of Customer Success. Logins go up. Feature usage increases. Engagement looks healthy. And yet; renewals still stall, executive sponsors disengage, and expansion never materializes. This isn’t a tooling problem. It’s a definition