Customer Journey Questions for CSMs

CSM Strategic Questions Guide

Asking the Right Questions Across the Customer Journey

Great Customer Success isn’t about having all the answers. It’s about knowing which questions to ask, when to ask them, and why they matter.

The CSM Strategic Questions Guide is a comprehensive, ready-to-use resource designed to help Customer Success Managers lead more effective, confident, and outcome-driven conversations at every stage of the customer journey.

This guide removes guesswork and equips CSMs with thoughtful, practical questions they can use to uncover goals, risks, blockers, and opportunities — without sounding scripted or transactional.

What’s Included

CSM Strategic Questions Guide (Document)
A complete, curated collection of strategic questions organized by:

Customer Journey Stages

• Onboarding

• Adoption

• Maturity & Growth

• Renewal

• Post-Renewal & Advocacy

Key Partnership Events

• New executive or stakeholder changes

• Churn risk or intent to cancel

• Evaluating other solutions

• Mergers & acquisitions

• Reorgs and leadership turnover

• Company growth, IPOs, and expansion

• Feature requests

• QBRs

• Account transitions

• Lack of product adoption

• Loss of executive sponsor or power user

• Poor NPS scores

• Product gaps

• Customer exit interviews

Each section includes light context on when to use the questions, followed by clear, practical prompts that help drive better conversations.

How to Use This Resource

• Prepare for customer meetings with confidence

• Guide strategic discovery conversations

• Navigate high-risk or high-change moments

• Ask better questions without relying on scripts

• Build trust, alignment, and long-term value

This is a working guide — meant to be referenced before calls, during planning, and throughout the lifecycle.

Who This Is For

• Customer Success Managers (ICs & Senior CSMs)

• CSMs onboarding into new accounts or segments

• CS teams standardizing discovery and value conversations

• Leaders enabling consistent, high-quality customer engagement

Why This Matters

Most customer risk, churn, and missed expansion opportunities stem from misalignment that went unspoken.

This guide helps CSMs surface the right insights early — and revisit them often — so they can lead proactive, strategic partnerships instead of reactive support.

Format & Access

• Digital document

• Easy to reference and share internally

• Instant access upon purchase