June 18, 2025
The biggest leadership mistake I see — whether at a Fortune 150 company or a $2M small business — is this:
Leaders think they’re hiring for roles.
But the best leaders know they’re hiring for a future.
When you sit down to interview someone, you're not filling a seat. You're shaping culture. You’re reinforcing standards. You’re investing in your ability to rest one day —because you built something others could carry forward.
But that kind of discernment doesn't happen when you're distracted. You can't fake clarity. You can’t evaluate character in between Slack pings.
I’ve interviewed hundreds of people — across the corporate boardroom and kitchen tables in rural towns. And if I’ve learned anything, it’s this:
The quality of your questions reflects the quality of your leadership.
And often, so does the quality of your presence.
That’s why I created the UnbreakableOS Interview Tool.
This is a practical, ready-to-use framework to help you slow down and actually see the person across from you. Not their resume. Not the hype. Their mindset, their wiring, and whether they can handle the weight your business is carrying.
These questions are built on real experience — and the 7 Laws of UnbreakableOS, the operating system I’ve spent the last decade using to start, scale, lead, and rebuild companies.
This tool alone will sharpen your instincts. But sometimes what leaders need isn’t just better tools— it’s a trusted advisor in the room with them.
That’s where coaching comes in.
Not “rah-rah” accountability or someone sending you book summaries. Not performance hacks or motivational fluff. I’m talking about real coaching — with someone who’s in the trenches of leadership, too.
I’m still the CEO of Sherman Portfolios, where have over $1B in assets under management and serve 600+ financial advisors all over the country. I’ve led teams from ten to nearly a thousand. I’ve launched, scaled, turned around, and rebuilt. And now, I coach a small handful of business leaders — not because I need to, but because I believe deeply in the impact of a single decision, made clearly and executed well.
Here’s what coaching looks like with me:
· We talk about your team, your systems, your decisions, your calendar, your margins.
· We make space for truth — the kind that reorders your priorities.
· We solve problems together, from someone who’s been there.
· We get eternal — reminding you that this business isn’t your kingdom.
And sometimes, that starts with how you hire. Because the wrong hire is a 12-month delay in momentum. And the right one? They become a culture-carrier, a multiplier.
If you're building something that needs strong hands and faithful character — download the interview questions below.
If you're ready to build yourself as the kind of leader God can entrust with more — then maybe it's time to talk about coaching.
Download the Interview Tool
→ Get the questions for you next interview. Try it. See how it changes your process and helps you uncover more during one of the most important elements of growing your business.
Inquire about 1:1 Coaching
→ Schedule a 15 or 30-minute call with me here so we can see if coaching is the right fit for you. I have limited openings as I only take on a small number of one-on-one coaching clients.