Recently, I had a conversation with one of my partners who gave her team a seemingly simple task: capture real estate footage to help promote a few properties online. The assignment was clear: take pictures and videos that accurately reflected the condition of the homes: full-room shots, kitchen, basement, backyard, roof, and street views.
But when she reviewed the final content? Let’s just say it missed the mark by a mile.
Her frustration was valid. After all, what she asked for wasn’t complicated. But that moment reminded me of a powerful truth every entrepreneur encounters when growing from a team of me to a team of we:
Just because something is obvious to you doesn’t mean it’s obvious to everyone else.
The Gap Between Expectation and Execution
As a real estate investor, wholesaler, and someone who sources properties for other investors, I’ve spent years in the trenches. I know what “good” looks like. My partner does, too. But the people she delegated to didn’t have that same context or experience.
This is where so many entrepreneurs go wrong.
They assume people should just know how to deliver the result. If they say the “what,” the team will figure out the “how.” But here’s the hard truth:
If you don’t show people what excellence looks like, you can’t expect them to deliver it.
Telling Isn’t Training
I’ve seen this play out countless times, especially when onboarding new sales partners or marketing team members. Even if someone has a strong background in sales, when they step into an unfamiliar environment, like selling business and legal services, they face a learning curve.
It’s not just about charisma or hustle. It's about how to speak to different audiences. How to present the value proposition. How to dress depending on the industry or setting. These are nuances you only pick up through intentional exposure and mentorship.
That’s why I follow a simple system borrowed from one of my business mentors, John Hoffman:
Tell me. Show me. Let me. Grow me. Then rinse and repeat.
We do joint prospecting calls. Roleplay. Walk neighborhoods together. Share real audio and video footage of conversations and presentations. We give new team members articles, scripts, and playbooks. We record ourselves doing the work and make that training content repeatable.
The Real Work of Leadership
It’s not enough to say you want better results—you have to build a system for achieving them. That means:
Clearly communicating what “good” looks like
Demonstrating the process step by step
Documenting and recording that process
Giving people increasingly complex assignments
Reviewing their work with them consistently
Yes, it takes time. Yes, it takes patience. But if you’re serious about scaling, you can’t just delegate. You must develop.
Because here’s the truth: people don’t rise to your expectations, but instead fall to the level of your training.
A Final Word for the Builders
If you’re frustrated with your team’s performance, don’t just tighten the reins or complain about not finding “good people.” Re-evaluate your onboarding process. Revisit your systems. Ask yourself:
“Have I really shown them what good looks like?”
The shift from solopreneur to team builder is one of the most challenging in business. But if you embrace the mindset of mentorship—of growing people, not just managing tasks—you’ll build an organization that scales and sustains.
So here’s your assignment: don’t just lead from the front. Walk with your people. Let them see you win, or how you handle failings. Let them fail forward. Then rinse and repeat.
And if this landed with you, share it. Someone in your circle needs this reminder. Because when we show up as better leaders, we create more leaders. And that’s what changes everything.
I celebrate success in advance.
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The world around us wasn’t built by the exceptional. It was built by everyday people who were willing to do exceptional things. Let’s build taller buildings together.
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