The Human Side of Change:
Lessons from the
Frontlines of Customer Success

There’s something no one tells you about digital transformation — it’s not the technology that’s the hard part. It’s the people part.

I know because I live it every day, both with the customers I support and inside our own team. Even at SmartCert — a company built to help manufacturers modernize their certification processes — we’re still human. And humans? We love what’s familiar, even if it’s not efficient.

Our Head of Technology, who’s at the forefront of our platform innovation, still prints his boarding pass. Every time. If that’s not the perfect metaphor for how hard change is, I don’t know what is.

The F*ing First Time Factor

Brene Brown calls this the “F*ing First Time” — that moment when you’re doing something new, and it feels clunky, awkward, and downright painful. Whether it’s your first time trying to build a digital cert package, review a digital cert, or even just your first time using SmartCert — it’s uncomfortable. That’s normal.

Brene’s advice?

👉 Name it (This is new and new is always hard.)
👉 Normalize it (Everyone struggles the first time.)
👉 Reality check your expectations (You’re not supposed to be good at this yet.)

Why Change Management Matters More Than Technology

We see this every day in Customer Success. Rolling out a new tool is easy compared to changing the way people work. That’s where most transformations fail — not because the tech didn’t work, but because the team didn’t have the right mindset, support, or space to stumble through their F*ing First Time.

Tips From the Trenches

Here’s what we’ve learned — and what we coach our customers through all the time:

1. Admit that the first time will be awkward.

Own the clunkiness upfront. If you pretend it’s going to be seamless, you lose credibility the moment things get weird. (And they will.)

2. Find the “Boarding Pass Printers.”

Every team has them — the ones who still love paper and manual processes. Don’t shame them. Invite them into the process early so they feel heard (and maybe even win them over as champions).

3. Celebrate progress, not perfection.

We all want perfect data and spotless processes, but transformation is about progress — one less missing cert, one faster approval, one supplier saying “hey, this was easier than last time.”

4. Make room for humor.

Change is awkward. People will click the wrong buttons, send the wrong files, and curse their computers. It’s okay. Laugh about it. We do.

At SmartCert, we’re not just here to sell you a solution — we’re here to guide you through your F*ing First Time with digital cert management. It’s messy, but we’ve got you.

Want to hear more real talk? Join me on LinkedIn for a new series: “The Human Side of Change.”