“Being Strategic” Is Vague - and How to Make It Real

Why the advice CSMs hear most is also the least actionable

At some point in their career, every Customer Success Manager hears the same feedback:

“You need to be more strategic.”

It’s often well-intended.
And almost never explained.

CSMs are left to interpret it on their own, which usually results in:

• More slides
• More meetings
• More data
• More anxiety

None of which reliably leads to being seen as “strategic.”

Why “Be More Strategic” Falls Flat

The problem with “be strategic” isn’t that it’s wrong.

It’s that it’s directionless.

Without shared meaning, it becomes shorthand for:

• “Think bigger”
• “Act more senior”
• “Figure it out”

And when expectations aren’t defined, performance becomes subjective.

CSMs don’t struggle with strategy because they lack intelligence.
They struggle because the bar is invisible.

What Strategy Actually Looks Like in Customer Success

In Customer Success, being strategic isn’t about vision decks or long-term plans.

It’s about judgment.

Strategic CSMs consistently:

• Prioritize the right problems
• Focus on outcomes over activity
• Understand tradeoffs and constraints
• Make fewer, better recommendations
• Know what not to spend time on

Strategy shows up in decisions, not posture.

The Shift: From Activity to Intent

A non-strategic approach asks:

“What can I do for this customer?”

A strategic approach asks:

“What actually matters right now; and why?”

That shift changes everything.

It affects:

• How you prepare for meetings
• What you escalate (and what you don’t)
• How you frame progress
• How you use time - yours and theirs

Being strategic is less about doing more, and more about doing with intention.

What Strategic CSMs Do Differently

They don’t react to every signal equally.
They don’t treat all customers the same.
They don’t chase every metric.

Instead, they:

• Anchor on defined outcomes
• Sense when priorities have shifted
• Adjust engagement before risk is visible
• Speak in business terms, not product language

They don’t need permission to lead; they already are.

Why This Is Hard (And Why It’s Not Your Fault)

Most CSMs are promoted into “strategic” expectations without:

• Training on business context
• Guidance on judgment
• Permission to deprioritize
• Shared definitions of success

So they overcompensate.

They work harder instead of sharper.
They add instead of refine.
They stay busy instead of effective.

That’s not a capability gap - it’s a clarity gap.

Making “Strategic” Actionable

If “be strategic” were translated into something usable, it would sound more like:

• “What is the most important outcome right now?”
• “What is the risk of not addressing this?”
• “What tradeoff are we making by focusing here?”
• “What does success look like in this customer’s context?”

Strategy lives in the questions you ask, and the choices you make based on them.

Closing Thought

Being strategic isn’t a personality trait.
It’s not a job title.
And it’s not something you either are or aren’t.

It’s a practiced way of thinking.

When Customer Success teams are taught how to apply judgment, not just execute motions, strategy stops being vague.

And the work finally becomes clearer.

👉 Want more clarity on how to think - not just what to do?

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