🚨 New episode drop: We Fucked Up So You Don’t Have To (#WFUSYDHT)

With me 🤝 Melanie

This one came from a conversation we’ve both had way too many times.

You know that feeling when onboarding is “going well”? The calls are happening, the deck looks clean, timelines are being followed, everyone is nodding along… and yet something feels off.

I remember one customer specifically. We were ticking every box. Great kickoff, clear roadmap, solid follow ups. On paper, it was a perfect onboarding. But halfway through, I asked a simple question: “What’s been most useful so far?” And the answer was… vague. Polite. Safe.

That’s when it hit me.

We weren’t onboarding them. We were onboarding our process.

And Melanie had the exact same realization in her own way. Different customer, same pattern. Everything looked structured, controlled, “best practice”… but the customer wasn’t actually getting to value fast enough. They were just being guided through something that made sense to us.

That’s the trap.

We think onboarding success is about delivering a flawless journey. But customers don’t care about your journey. They care about their outcome. And if they can’t feel that progress early, the whole thing starts to fall apart quietly.

No complaints. No escalation. Just disengagement.

In this episode, we unpack the five shifts that completely changed how we approach onboarding. Not in a theoretical way, but in a “we learned this the hard way” kind of way.

We talk about why leading with your process is killing momentum, how personalization isn’t something you add later but something you start with, and why the best onboarding calls often feel less like a presentation and more like a conversation you didn’t over prepare for.

We also get into quick wins. Because nothing builds trust faster than showing value early, even if it’s small. And we challenge the obsession with metrics. Because a customer completing onboarding doesn’t mean they actually experienced success.

The biggest takeaway?

If your onboarding feels smooth for you but unclear for the customer, you’re optimizing the wrong thing.

This episode is basically us being honest about where we got it wrong, what we changed, and what actually started working once we stopped trying to be perfect and started trying to be useful.

If you’re in CS, onboarding, or honestly anywhere close to customers, this one will probably feel very familiar.

Curious to hear if you’ve had a similar moment where you realized things weren’t as “good” as they looked 👇