Growth Lives in the Gray: Why Waiting for "Perfect Health" Can Kill Opportunity

Early in my Customer Success career, I had a bad habit.

I blocked expansion conversations at the first sign of risk.

If a customer wasn’t in perfect health glowing usage, high satisfaction, zero friction I wouldn’t let Sales anywhere near them.

Even the smallest bump in the relationship?

I’d shut the door and throw away the key.

I genuinely thought I was doing the right thing.

I thought I was protecting the partnership, preserving trust, and “doing right by the customer.”

But I wasn’t.

I was avoiding the hard conversations.

I was making assumptions.

And I was costing the business potential growth.

The Gatekeeper Era

When I was managing a book of business, I saw myself as the protector.

The last line of defense.

The person who made sure no one messed up the fragile relationships I had worked so hard to build.

But that mindset made me a gatekeeper.

One who believed that expansion was only safe when everything was perfect.

Here’s the thing: perfection doesn’t exist.

No customer is ever 10/10 on every metric, every day.

Most of your accounts live in the gray area, some value delivered, some usage gaps, some unmet needs.

And that's where the opportunity actually lives.

The Moment That Changed Everything

I remember a customer who wasn’t using much of their product.

By my old logic, that was a red flag.

It would’ve been an account I kept off-limits.

But instead of pulling back, we leaned in.

We had a real conversation not a pitch, not a sales handoff, but a thoughtful dialogue about where they were struggling, what they needed, and what success actually looked like to them.

What we uncovered changed everything.

The product they originally purchased wasn’t the right fit.

The real pain they were trying to solve required a different solution within our suite.

So we restructured their entire contract.

We gave them what they needed.

They renewed. They expanded. And we rebuilt trust.

That conversation didn’t damage the relationship.

It saved it.

The Lesson

I had spent so much time trying to shield my customers from Sales, assuming commercial conversations would scare them off.

But I had it backwards.

When done right, those conversations are about solving problems not pushing products.

They're about aligning solutions to needs, not forcing growth for growth’s sake.

Waiting for “perfect health” was just an excuse to delay the uncomfortable.

And that delay could’ve cost us the entire account.

Stop Over-Filtering

Customer Success Managers: if you're filtering your book of business and only flagging “green” accounts for expansion, you’re missing out.

Real growth lives in the gray.

In the honest conversations.

In the moments where needs shift and new problems surface.

You don’t need a perfect score to start a meaningful dialogue.

You just need curiosity, courage, and a commitment to solving real business problems.

Don’t wait for perfection.

Create alignment.

Create value.

Create opportunity.