The Strategic Customer Success Manager Book Club Discussion Questions
- Chad Horenfeldt
- Jul 2
- 11 min read
Welcome Book Clubs!
This guide is designed to help customer success teams, leaders, and individuals explore the core ideas in The Strategic Customer Success Manager through structured, conversation-driven reflection. Whether you’re reading the book together as a team, hosting a formal book club, or simply using it to spark internal discussions during lunch-and-learns or team offsites, these questions will help you:
Connect real-world experiences to the book’s key lessons
Strengthen your strategic thinking and communication skills
Share different approaches and challenges with your peers
Align on best practices for engaging customers and internal teams
Build a shared language around what it means to be a strategic CSM
Each chapter includes 5–7 open-ended questions designed to spark conversation—not just about what the book says, but how each team member might apply it. The questions work best when answered in dialogue, but can also be used individually for self-reflection or journaling.
Suggested Ways to Use This Guide:
📅 Use 1–2 chapters per meeting in a weekly or biweekly cadence
🧠 Assign “highlight moments” for team members to bring real customer examples
🎯 End each session by choosing one takeaway to apply in your work that week
🛠️ Pair the guide with optional worksheets or team exercises (available in the resources area)
Most of all—use this space to grow. Strategic Customer Success isn’t just a title. It’s a mindset, a muscle, and a movement. And this guide is here to help you build it—together.
Chapter 1: What Exactly Is a Strategic CSM?
In your own words, how do you define a “strategic” CSM? How does that differ from being helpful, responsive, or knowledgeable?
Reflect on a time when you were operating tactically versus strategically with a customer. What triggered the difference in your approach?
What actions, behaviors, or conversations signal to a customer that you’re more than just a product expert—that you’re a long-term partner?
The chapter describes common CSM archetypes (like firefighter, fixer, or entertainer). Which one have you found yourself defaulting to under pressure? What might a strategic alternative look like?
What internal or external challenges make it difficult to consistently operate as a strategic CSM—and how do you personally work through them?
Chapter 2: How to Quickly Build (and Lose) Trust
Think of a time when you quickly gained a customer’s trust. What did you do in that first interaction that helped build credibility?
When inheriting an account, what steps do you take to prepare and signal that you're a strategic partner, not just a new name on an email?
What are some common ways CSMs unintentionally damage trust early on—especially during onboarding or handoffs?
Have you ever had to repair trust with a customer after a misstep or miscommunication? How did you approach it, and what was the result?
What signals tell you that a customer trusts you? How do you build on that momentum to deepen the relationship?
What can you do in your next customer meeting to establish or reinforce trust—especially if the relationship is new or strained?
Chapter 3: Skills and Behaviors that Strategic CSMs Need to Master
Of the four capability areas outlined—Emotional Intelligence, Ownership & Growth, Teamwork & Influence, and Entrepreneurship & Leadership—which one feels like your superpower? Which one needs more focus?
Think of a situation where emotional intelligence helped you turn around a difficult customer or internal conversation. What did you do, and what was the result?
What does taking true ownership of your book of business look like in your day-to-day work? Where are you succeeding - and where are you still reactive?
How do you influence without authority across cross-functional teams or with senior stakeholders? Share a time when your influence shaped a decision or outcome.
What habits or behaviors have helped you grow from a task-oriented CSM into a more strategic partner?
When have you demonstrated entrepreneurial thinking in your CS role - such as solving a complex customer challenge, improving a process, or spotting a new opportunity?
What’s your plan for strengthening the skill area that’s most uncomfortable or unfamiliar for you right now?
Chapter 4: Starting Your CSM Role with the Basics
When you started your current or most recent CSM role, what felt overwhelming - and what helped you feel grounded in the first few weeks?
How did you go about learning your product, customers, and company culture? What worked well, and what do you wish had been different?
What do you believe are the top three foundational skills or focus areas for a new CSM? How do you assess whether you're strong in them?
Describe a moment in your early days when product knowledge or customer context helped you build credibility. How did you prepare for it?
How do you stay focused on long-term outcomes while ramping up and absorbing large amounts of information?
If you were mentoring a new CSM today, what advice would you give them for the first 30–60 days to build confidence and strategic presence?
Chapter 4: Starting Your CSM Role with the Basics
Think back to a time you were new in a CS role. What onboarding processes helped you feel most prepared or helped you ramp the fastest when joining an organization?
How do you currently learn about your customers’ industries? What could you do better?
What’s your approach to product mastery? Do you learn by doing, reading, or observing others?
What are the “unwritten rules” of your current organization that new people should know?
Share an experience where knowing the customer’s value metrics (what metrics were important to them) made a difference in how you served them.
Chapter 5: Beyond the Basics: Customer Journey, Processes, and Tech
How is your current customer journey defined? What’s missing or unclear?
What was the most confusing internal process you had to figure out on your own? How would you improve onboarding around it?
How do you manage customer data today? Where does it fall short in helping you show value?
What is one way you’ve used technology to work more efficiently or scale your efforts? How have used various AI tools or features?
Have you ever had to advocate for a clearer handoff between teams? How did you approach it?
Chapter 6: How Best to Align Yourself with Other Teams, Departments, and Partners
Think of a time you had a strained relationship with another internal team (e.g., sales, support, product). What happened? How did it affect your work with customers?
Which internal department do you most often collaborate with? How do you ensure alignment?
What’s your strategy when priorities between your team and other teams or departments clash?
Share a win where cross-functional collaboration led to a great (customer) outcome.
How do you handle differences in incentives across teams (e.g. CS vs sales)?
Chapter 7: The First 90 Days and Beyond
In your first 90 days, what activities helped you ramp fastest? What would you prioritize differently next time?
How did you set up your “daily rhythm” when you were new to the role? Has that rhythm evolved? Why or why not?
Which of the four CSM “focus zones” (customer engagement, internal alignment, strategic planning, professional development) do you spend the most time in? Which one is currently underinvested?
Share a time when you felt overwhelmed in your early days. What helped you refocus and find clarity?
As you moved beyond your first 90 days, how did you shift from learning mode to owning outcomes? What signaled that you had hit your stride?
Chapter 8: Building a Proactive Client Risk Management Strategy
Share a time you turned around an at-risk customer. What specific steps made the biggest difference?
Think back to a time when a customer churned unexpectedly. What early signals might you have missed, and how would you approach it differently today?
What’s your current process for proactively identifying risk? How do you balance intuition with data?
How do you categorize risk—product fit, executive alignment, usage drop-off, competitive threats, etc. - and which area do you feel least prepared to address?
What role does your health score or CRM platform play in risk management? Is it accurate?
When a customer shows signs of risk, how do you escalate internally and communicate externally to regain trust?
How can you build a more scalable risk strategy across your team - especially if you manage a large or fast-changing book of business?
Chapter 9: Building Unbreakable Customer Relationships
What habits do you practice consistently (e.g., proactive reach outs, executive updates, value recaps) that help you stay top of mind and trusted?
What’s your approach to building relationships beyond your primary contact? How do you identify and nurture other champions or stakeholders?
How do you balance responsiveness with boundaries, especially when customers treat you like support or expect 24/7 availability?
Have you ever been blindsided by a churn despite having a “great relationship” with a customer? Why do you think that happened?
How do you get meetings with elusive executives? What’s worked—or flopped—for you?
What are some of your tactics when a client champion or decision-maker has left?
Chapter 10: How to Cultivate Strong Connections With Your Colleagues
Think of a time when strong internal relationships helped you deliver a better customer outcome. What was the key to that collaboration?
When have you seen internal silos hurt the customer experience? How might stronger colleague relationships have changed the outcome?
What are you currently doing (or could start doing) to intentionally build stronger internal relationships, especially with teams critical to your success (e.g., engineering, finance, product)?
Have you ever had to repair trust with a colleague or team? What steps did you take, and what did you learn from the experience?
How do you advocate for your customers while still supporting your internal teammates? What does “customer-centric, team-aligned” look like in action?
What rituals, habits, or team norms help build a culture of connection in your organization?
Chapter 11: How to Forge Internal Relationships with Key Cross-Functional Teams
Think about your strongest internal partnership—what makes that cross-functional relationship effective, and how did you build it?
What strategies do you use to advocate for your customers' needs without creating tension with internal priorities?
How do you stay informed about what other departments are working on so that you can better align and support shared goals?
Share an example of a time you influenced a cross-functional initiative or decision. What approach helped you gain buy-in?
When have you seen internal silos hurt the customer experience? How might better collaboration have changed the outcome?
Chapter 12: How Improved Productivity Leads to Customer and Career Success
What tools or habits help you stay organized and efficient day to day?
Share a time when automation or a process saved you hours of work.
How do you avoid context switching across accounts and tasks?
What’s your approach to managing a large book of business without sacrificing quality?
Have you tried implementing time blocking or deep work practices? What was the effect?
What's something from this chapter that you will look to implement to help you with your productivity? What's something you're doing today or an app you are using that is making you more productive?
Chapter 13: How to ACE Client Meeting Preparation and Follow-Up
How do you typically prepare for client meetings? What part of your prep feels most essential - and what do you sometimes skip?
Share a time when a well-prepared agenda changed the outcome of a meeting. What made it effective?
Have you ever had a meeting go off-track or feel unproductive? What would you do differently now using the ACE framework?
How do you tailor your prep and follow-up depending on the persona you're meeting with (e.g., executive sponsor vs. daily user)?
What’s your system for post-meeting follow-up? How do you ensure it reinforces the meeting’s goals and maintains momentum?
Chapter 14: What Does It Mean to Have a Strategic Conversation?
In your own words, how do you define a “strategic conversation” versus a tactical one? What clues help you recognize which type you’re having?
Think of a recent customer interaction—was it strategic or tactical? What would you change if you could revisit it?
How do you shift a conversation from a feature or support request into a discussion about business goals or outcomes?
Share an example where a strategic conversation secured a renewal or unlocked an expansion.
What mindset shifts or habits can help you consistently lead with a strategic lens in your customer engagements?
Chapter 15: Building Trust and Gaining Influence Using the OARS Framework
Of the four OARS elements—Open questions, Affirmations, Reflective listening, Summarizing—which one do you use most naturally? Which one do you want to strengthen?
Think of a recent customer conversation—where could you have used reflective listening to build more trust or surface deeper insights?
Have you ever seen a conversation shift after simply affirming a customer’s effort or perspective? What was the result?
How do you ensure your questions are truly open and not subtly leading or closed-ended? Share an example you’ve recently used.
When summarizing conversations or decisions, what do you do to confirm alignment and avoid assumptions?
Describe a time when building trust helped you influence a customer’s decision or mindset. What specific communication techniques made the difference?
How can you begin incorporating OARS into your (or your team’s) communication playbook or onboarding for new team members?
Chapter 16: Nudging Customers to Take Action: The SOON Funnel and Assessing Motivation
Which part of the SOON funnel do you naturally use well? Which one do you tend to skip or rush?
Share a time when you successfully nudged a passive customer into action. What signals helped you gauge their motivation?
How do you assess a customer’s internal motivation or readiness to act? What clues do you listen for during conversations?
When a customer seems agreeable but never follows through, how do you adjust your approach?
Have you ever unintentionally overwhelmed a customer by making the next step unclear or too complex? What did you learn?
How could you improve your action planning in calls, emails, or follow-ups to drive better momentum?
Chapter 17: Mastering Discovery and Defining Business Outcomes
How do you handle situations where the customer only wants to talk about features, not strategic goals?
How do you help a customer connect your product to their larger company goals?
What challenges have you faced in getting stakeholders to agree on what success looks like? How did you resolve conflicting definitions?
Share an experience where a business outcome helped close a renewal or expansion.
How do you handle it when customers can’t define a measurable outcome?
What language, questions, or frameworks do you use to elevate conversations from tactical to strategic? What are some tactics you would use from the chapter?
Chapter 18: Handling Feature Requests and Rebuilding Trust with Upset Clients
Think back to a time when a customer made a strong demand for a feature your product didn’t (or wouldn’t) support. How did you handle it?
Have you ever felt stuck between your customer’s needs and your product team’s roadmap? How do you navigate that tension without eroding trust?
What language or approaches do you use when delivering a “no” that still feels like a partnership?
How do you differentiate between a feature request that’s a blocker vs. a “nice to have”? How do you communicate that back to the customer?
Describe a difficult conversation you were dreading—how did you prepare for it, and what was the outcome?
When you or your company screws up, do you apologize or not? How do you handle these situations?
Chapter 19: Fixing the Two Most Broken Meetings: Kickoffs and QBRs
Think back to a strong kickoff meeting you led or attended—what set the tone for long-term success?
What’s your current kickoff approach? How do you ensure it aligns with the customer’s business goals, not just implementation steps?
How do you prepare for a QBR or strategic touchpoint so it’s more than just a retrospective? What planning frameworks or templates have helped?
Share a time when a QBR helped reset or elevate the relationship. What specific conversation or insight made it impactful?
How do you handle it when customers don’t see the value in attending kickoffs or QBRs? What messaging or tactics have you used to engage or re-engage them?
Do you use success plans or business reviews to tell a “value story”? How do you weave product usage into a business narrative?
What are the elements from the strategic checkpoint that you would implement right away?
Chapter 20: Securing Renewals and Uncovering Growth Opportunities
What’s your role in the renewal process today? Is it clearly defined?
Share a renewal save you’re proud of. What made the difference?
What are your top signs that a customer is ready for expansion?
How do you approach value conversations in the lead-up to renewal?
Have you ever pushed too hard (or not enough) in an upsell situation? What did you learn?
Comments