When Playbooks Hurt More Than They Help: A Cautionary Tale from a CS Leader

Early in my Customer Success leadership journey, I believed playbooks were the answer to everything.

Renewal on the horizon? Playbook.

Customer going through M&A? Playbook.

Onboarding, low adoption, escalations? You guessed it—playbook.

If I could create a workflow for it, I did. I genuinely thought I was doing my team a favor by removing ambiguity and building in all the things I’d learned over the years. It felt like I was empowering them. Setting them up to succeed.

But then something unexpected happened.

My team—brilliant, capable, thoughtful people—started pushing back.

At first, I was shocked. Weren’t these resources meant to help? Weren’t they saving time, improving consistency, reducing risk?

What I quickly realized was that my good intentions had taken a wrong turn.

What I saw as structure, my team experienced as constraint.

What I thought was empowering, they experienced as disempowering.

The problem wasn’t the existence of playbooks—it was how we were using them.

The Promise (and Problem) of Playbooks

Let’s be clear: I still believe in playbooks. In the right context, they’re invaluable—especially in high-stakes or high-complexity situations like:

• Customer kickoffs

• Renewal conversations

• Onboarding

• Executive business reviews

• Commercial discussions

These are moments where guidance matters. Where a structured approach can elevate the experience, reduce missteps, and ensure consistency.

But somewhere along the way, we stopped guiding our teams—and started controlling them.

Where Playbook Strategies Go Wrong

Here’s what I see all too often:

🚫 A playbook for everything – Oversaturation leads to confusion and diluted focus

🚫 30+ steps per playbook – We unintentionally kill critical thinking

🚫 Administrative overload – Teams spend more time tracking than delivering

🚫 Tracking tasks, not outcomes – Mistaking activity for impact

🚫 Conflicting playbooks – Competing priorities cause chaos

Sound familiar?

If so, it’s time for a reset.

How to Make Playbooks Actually Work

Here’s how I approach it now:

✅ Audit playbooks every 3–6 months – Ruthlessly remove what’s no longer useful

✅ Involve your team – Get their feedback on what’s helping, hurting, or missing

✅ Shift the focus to outcomes – Milestones matter more than micromanaged tasks

✅ Use playbooks for coaching, not control – They’re a guide, not a script

You hire smart people. Let them be smart. Trust their judgment. Create systems that support—not suppress—their ability to think, decide, and act.

Ask Yourself Before Building Another Playbook:

Does your team need another checklist?

Or do they need clarity, coaching, and the confidence to do what’s right for the customer?

Playbooks should enable. Not inhibit.

They should support action. Not stifle autonomy.

They should elevate thinking. Not eliminate it.