Why You're Stuck as a CSM (And How to Break Free)
The brutal truth about moving from tactical order-taker to strategic partner
Based on an exclusive webinar with Kristi Faltorusso of Client Success.
You're not alone if you're a customer success manager who feels stuck in tactical work instead of driving strategic impact. In a recent webinar with
, I shared a brutally honest truth: You're not strategic - and that's why you're stuck.But here's the good news: being stuck doesn't mean you suck. It means you haven't yet learned how to elevate yourself from order-taker to strategic partner.
The Turning Point That Changed Everything
My journey from tactical CSM to strategic leader began with a devastating client churn. Picture this: sitting in a basement office, getting that dreaded email from a client saying they're leaving. Most CSMs would panic, scramble, or simply accept defeat.
Instead, my VP of Marketing stepped in and demonstrated something powerful. Through strategic questioning, he uncovered that the client didn't actually want to leave - they were struggling with cost concerns, a new CMO, and hadn't properly utilized their internal team.
The result? What seemed like a lost cause became a 30-day turnaround plan that saved the account.
The lesson: Sometimes the difference between losing and winning a client isn't your product knowledge - it's your ability to ask the right questions and uncover the real problems.
The Four Roles That Keep You Stuck
I identified four common roles that trap CSMs in tactical work:
1. The Firefighter 🔥
Always in crisis mode, jumping from one urgent issue to another. You're reactive, not proactive.
2. The Entertainer 🎭
Focused on keeping customers happy through small talk and surface-level relationships. Your customers like you, but that doesn't guarantee renewals.
3. The Waiter 🍽️
Taking orders from customers without pushback. "You want that feature? How would you like it prepared? Would you like fries with that?"
4. The Fixer 🔧
Solving every problem customers bring you, becoming their go-to person for issues rather than business outcomes.
While these roles feel helpful in the moment, they position you as a service provider, not a strategic partner.
What Does "Strategic" Actually Mean?
I referenced Richard Rumelt's definition from "Good Strategy Bad Strategy": Strategy is a set of actions that is credible, coherent, and focused on overcoming the biggest hurdles in achieving particular objectives.
For CSMs, this translates to three key areas:
1. Identifying the Biggest Hurdles
Stop treating symptoms and dig deeper to find root causes. Like a tree with dying branches - you might spray the leaves, but if the roots are the problem, surface-level fixes won't work.
2. Focusing on Business Outcomes
Move beyond vanity metrics like email open rates to outcomes that actually matter to your customer's business success.
3. Creating Concrete Action Plans
Great conversations mean nothing without execution. Strategic CSMs don't just talk - they create actionable plans with clear next steps.
The Three Shifts Every CSM Must Make
From Product Expert → Customer Business Expert
Instead of knowing every feature inside and out, understand your customer's industry, challenges, and business model.
From Adoption Focus → Outcome Focus
Stop measuring success by feature usage and start measuring by business impact.
From Customer-Centric → Customer AND Company-Centric
Yes, advocate for your customers. But also understand that bashing other departments won't get you promoted.
Practical Frameworks You Can Use Today
The Three C's (Pre-Call Preparation)
Before every customer meeting, research:
Company: What do they do? What products do they sell? How much do they cost?
Customer: Who are their end users? What terminology do they use?
Challenges: What business challenges are they facing beyond your product?
Pro tip: Use AI tools like Perplexity to quickly gather this information in just a few minutes.
The OARS Framework (for Strategic Conversations)
Borrowed from psychotherapy, this framework helps you have more strategic customer conversations:
Open Questions: Ask "how" and "what" questions that uncover deeper insights
Affirmations: Give genuine recognition for achievements and progress
Reflections: Demonstrate active listening by interpreting what customers tell you
Summaries: Tie everything together at the end of conversations
The magic happens in reflections - when you interpret what customers say, you show you're listening AND can guide the conversation strategically.
Business Outcomes Framework
Break down business outcomes into three parts:
High-level business outcome (save money, make money, generate leads)
Success criteria (specific metric + change + timeframe)
Goals (concrete actions to achieve the outcome)
The Hard Truth About Cross-Functional Alignment
Here's my most controversial advice: Stop blaming other departments.
Yes, it's fun to create memes about sales or product teams. But if you want to advance your career, you need to become known as someone who helps the organization, not someone who complains about it.
Try this radical approach: Go to other departments and ask, "How can I help you?"
Sales reps will be shocked. But they have expertise you can leverage, and you need their support for renewals and expansions.
Your Action Plan
Assess your current role: Which of the four stuck roles do you find yourself in most often?
Implement the Three C's: Start researching customers beyond your product usage before every important meeting.
Practice OARS: Focus especially on reflections - interpret what customers tell you instead of just moving to the next question.
Define business outcomes: Work with your top 3 customers to clearly define what success looks like beyond product metrics.
Build internal relationships: Identify one person from sales, product, or marketing to build a stronger relationship with this month.
The Bottom Line
Customer Success isn't easy - if it were, we wouldn't need strategic frameworks and mindset shifts. But the CSMs who break through from tactical to strategic don't just survive; they become indispensable partners who drive real business impact.
You're not stuck because you're not good enough. You're stuck because you haven't yet learned to be strategic.
The question is: Are you ready to make the shift?
Want to dive deeper into these concepts? My soon-to-be-released book "The Strategic Customer Success Manager" provides detailed frameworks and real-world examples for making this transition. You can join my launch team at strategiccusuccess.com for early access and additional resources. The book is going through formatting right now.