The Unsexy Onboarding Playbook That Actually Works.

Hey hey! Happy Monday!

The past week in NYC was EPIC. For everyone who flew out, attended our events, or referred a friend - seriously thank you for making 72 hours in the city so damn fun. So many cool memories packed into three days. Last week was all about loving life, but my inbox hates me today!

I’m trying to crank through 320+ unread emails on this Monday morning before I head off to Bonnaroo with my best friends this week. I’m committed to getting to inbox zero today and have spent the past 30 minutes creating SO MANY filters to auto apply all the standard emails I get to automatically be marked as read and hit the archives.

As much as I love Miami, I’m missing the city. Love or hate NYC, the energy is simply unmatched. Lynds and I waited 20 minutes in line for that now-viral TikTok matcha spot, 12 Matcha (verdict: solid 9).

Worth the wait? I guess so.

Somehow survived the most sketchy massage of my life. $48 for a 30 minute foot massage and 30 minute back massage. It was incredible, but I’m still not sure if I have both my kidneys. I guess we’ll find out later this week….

Never letting Lyndsey book us a massage again.

Our first NYC Founders Club dinner of the summer was a massive win. Big energy. Smart founders. The kind of night that reminds you why we built this thing. We even had some people fly in from Kentucky and Canada just to break bread for a few hours.

Always grateful for the way that TFC has grown and continues to.

Also top secret news but we are throwing a MASSIVE 250+ person event on September 19th in New York City in Gramercy. This will be our take on a traditional conference, stacked with powerhouse speakers, incredible founders, and best of all not feel like one of those shitty events where people are shoving business cards in your hands. Real connections, real insights, walking out of the room 1% smarter. Pre-sale for tickets and all will be on sale shortly, if you want to get involved as a sponsor or speaker please shoot me a note back.

This one is gonna be crazy.

Oh, and if all goes to plan, you might be seeing a BODY location pop up in NYC soon.

More to come.

So lets get into this week’s newsletter!

As I work on bringing on two new team members this week, I want to spend time talking about a topic that I don’t see people talking about enough. Maybe because its not sexy or it gets overlooked. But damn is it important.

Onboarding.

Not the exciting part of hiring. Not the announcement post. Not the dopamine hit from bringing someone new into the fold.

I’m talking about the slow, methodical, often overlooked part where you actually make sure the person you just hired knows how to win.

Because here’s the hard truth: Great hires don’t fail because they’re underqualified. They fail because you under-onboarded them.

And I’ve been guilty of this.

I’ve hired the “perfect” candidate. Great track record. All the right buzzwords. Strong referrals.

And within 90 days? They’re underperforming. I’m frustrated. They’re confused. The team’s whispering. And I’m wondering how I missed the red flags.

What I’ve learned? It wasn’t them. It was me.

Let’s break down what most founders get wrong, and how to actually build a ramp that ensures success.

The Mistake Every Founder Makes

You hire because you need help. Fast. You’re overloaded. Bottlenecked. Burnt out. Drowning in ops or marketing or sales. So you bring someone in with the mindset of:

“I just need them to take this off my plate.”

And in that moment, you stop leading, and start hoping.

You hope they:

“Figure it out,”
“Run with it,” and
“Fill in the blanks.”

But that’s not delegation. That’s abdication. And you’ll pay for it with time, morale, and eventually, momentum.

What Onboarding ACTUALLY Is

Real onboarding isn’t about sharing a Notion doc and a Slack login. It’s about transfer of context.

What have you tried before?
What failed, and why?
Who owns what?
What’s the unspoken rhythm of your team?
What’s success in this role: quantified, time-boxed, and de-risked?

Most hires don’t need 10X skills. They need 10X clarity.

And when you don’t give it to them? They default to their last playbook. Their assumptions. Their habits. Which means you’ve accidentally brought someone into your company who’s operating off someone else’s blueprint.

No wonder it’s not working.

The Playbook We Use Now

Inside TFC, we talk a lot about building “process gravity.” A rhythm of ops that makes success easier to repeat and harder to break. So here’s the onboarding system we’ve seen work time and time again, whether you’re hiring a VA or a VP:

The Immersion

Walk them through your product, mission, history, and goals
Set the tone: how decisions get made, how feedback gets shared, how wins get celebrated
Share your 90-day vision for their role, what “done” looks like
Make sure they leave the week understanding the “why,” not just the “what”

The Rep Cycle

Assign small, clear tasks with feedback loops built in
Review their process, not just the outcome
Encourage them to document what’s confusing or missing

Have them shadow key calls or client interactions
Build in time to audit: where are they defaulting to old habits?

Ownership Ramp

Shift from “helping” to “handing off”
Give them one core outcome to own
Schedule a midpoint review: are they tracking? Are expectations clear?
Ask them to pitch what success looks like going forward

Proof of Alignment

Are they proactive or reactive?
Are they asking the right questions?
Have they earned trust cross-functionally?
Do they bring energy to the role, or need to be dragged?

If by week 8 you’re still wondering if they’re the right fit, they’re not. And if you’re still giving them tasks instead of outcomes, you didn’t onboard, you babysat.

Why Most Founders Avoid This (and Why You Can’t)

Founders don’t skip onboarding because they’re lazy, they skip it because they’re moving fast. They think speed will solve the problem, or that someone “experienced” won’t need guidance.

They might even think that hiring someone smart means they’ll just get it. But here’s what I’ve learned after scaling CROSSNET and building TFC: Speed without clarity creates churn. Clarity creates compounding. 

Every hire is an investment, and onboarding is the multiplier.

Stop Hoping. Start Leading.

You don’t need perfect hires, you need aligned ones. And alignment doesn’t come from intuition. It comes from intention. So before you wonder if your new hire “just isn’t getting it,” ask yourself:

Did I equip them to win?
Or did I set them up to guess?

Slow down, set the tone, transfer the context.

Because the fastest way to scale is having fewer people doing better work, and the only way that happens is if you onboard like it matters, because it does.

Keep building,
Chris