All Right Yet All Wrong

Early in my customer success career, I faced more challenges than I could count. Like many of us, I fell into customer success without fully understanding the role or its complexities. My understanding boiled down to two objectives: delight customers and secure renewals. It was a high-stakes environment, our smallest customer was a $1M+ enterprise account.

What I lacked in skill and knowledge, I compensated for with confidence, paired with the patience and support of my leadership team. After two years of trial and error, I finally found my rhythm. But looking back, the journey was far more painful than it needed to be.

The Hard Truth About “Doing It All Right”

Reflecting on those years, one glaring mistake stands out: I was doing many of the right things but in the wrong order. Here’s a hard truth: you can do everything right, but if it’s done in the wrong order, you will still fail. Worse, you might make progress but never fully realize the potential of your efforts.

Years later, I’ve learned that there’s an order to everything. When you begin with the end in mind, as Stephen Covey famously recommends in The 7 Habits of Highly Effective People, the path forward becomes much clearer. What took me years to achieve could have been accomplished in a fraction of the time if I had understood the importance of sequencing.

Lessons From Experience and Expertise

No matter the organization, the fundamentals of customer success are strikingly similar. That’s why Wayne McCulloch’s The 7 Pillars of Customer Success is a permanent fixture on my desk. Whenever I face uncertainty, I turn to it for clarity and inspiration.

Stepping into a new organization isn’t a clean slate. I’m often inheriting a mix of scattered processes, good intentions, and misaligned strategies. My role is to evaluate the current state, prioritize immediate wins, and craft a plan to deliver value.

In many ways, this mirrors project management: the tools and processes are endless, but you don’t need them all. You need the ones that make sense for the outcomes you want to achieve.

Here’s what I typically encounter when stepping into a new organization:

1. CRM systems are in place but poorly optimized for CS.
2. Customers in crisis are waiting for attention.
3. Teams are disjointed or burned out from previous leadership.
4. Fragmented processes and tools exist but are abandoned or forgotten.
5. Cross-functional misalignment (Sales, Product, CS) is rampant.
6. Business goals lack clarity or are overly sales-focused.
7. Leadership buy-in varies: one leader might champion CS, while others remain skeptical or unsure of its value.

A Playbook for Building a Strong CS Program

Every organization is unique, and no single plan fits all. However, I’ve developed a general playbook to stabilize and grow CS programs in real-world conditions. Whether you’re new to a role or looking to recalibrate an existing program, this guide may save you time—and pain.

Phase 1: Assessment & Stabilization (Days 1–30)

Objective: Gain situational awareness and stabilize urgent issues.

1. Build rapport with the team and leadership.

• Conduct 1:1 meetings to understand alignment challenges.
• Identify organizational misalignments, especially between CS, Sales, and Product.
• Share early retention wins to establish trust.

1. Audit CRM and tools.

• Evaluate the tech stack’s scalability and data integrity.
• Prioritize quick, impactful improvements.

1. Triage at-risk customers.

• Identify high-risk accounts using available data.
• Stabilize X% of critical accounts within the first 30 days.

1. ?Map existing processes.

• Assess onboarding, escalations, and renewals for scalability and impact.
• Address immediate gaps with modular fixes.

1. Establish cross-functional communication.

• Start aligning teams with the customer journey.

Success Metrics:

• % of at-risk customers stabilized.
• Reduction in escalations.

Phase 2: Alignment & Early Wins (Days 31–60)

Objective: Build trust and momentum through clear wins.

1. Develop a customer health framework.

• Collaborate cross-functionally to define shared metrics.
• Start small with a Minimum Viable Health Score (MVHS).

1. Draft and share a vision for CS.

• Align CS’s mission with broader organizational goals.
• Use early wins to advocate for CS as a growth engine.

1. Address burnout and team dynamics.

• Re-engage the team with small development initiatives.
• Reassign critical accounts to build ownership.

1. Collaborate on the customer journey.

• Facilitate workshops to map the customer experience.
• Educate skeptical leaders on CS’s role and impact.

Success Metrics:

• Customer health visibility.
• Reduction in onboarding time.
• Increase in customer satisfaction.

Phase 3: Strategy & Roadmap Development (Days 61–90)

Objective: Position CS as a strategic function.

1. Create a data-driven CS roadmap.

• Tie insights to strategic priorities.
• Build scalable processes for engagement and expansion.

1. Align business goals with customer outcomes.

• Advocate for deeper CS investment using customer impact stories.

1. Establish rhythms for continuous improvement.

• Build reporting cadences to keep CS metrics top of mind.
• Showcase revenue impact to leadership.

1. Invest in team development.

• Build long-term growth plans and address hiring gaps.
• Highlight progress with leadership regularly.

Success Metrics:

• Net Revenue Retention (NRR) improvement.
• % of QBRs completed.
• Reduction in manual workload.
• Increase in cross-selling and upsell success rates.

Final Thoughts

Customer success isn’t a one-size-fits-all formula, but there are universal principles that guide success. By focusing on sequencing and prioritization, you can transform a chaotic environment into a well-oiled growth engine.?

The journey may not always be smooth, but with the right tools, frameworks, and mindset, it doesn’t have to be harder than it needs to be.