What My First CEO Taught Me About Leadership That I Still Use Today

I giggled when I read Kelly Cate's first email.

Here was a CEO who'd been running a company for 22 years, sending me a stream-of-consciousness message that was refreshingly informal, telling me about his previous assistant who chose "the bar over money" at age 21. He ended with: "By the way, if you pick apart my email for spelling, etc., that is the first reason we need you."

This was April 2022. I'd been searching for an executive assistant position for eight months after leaving hospital management. I had the skills but not the bachelor's degree to become a director. More importantly, I couldn't protect my team from corporate decisions made by people three states away who had no clue what my staff faced daily.

I wanted out. I wanted to work directly with someone who made decisions, not implement policies I couldn't change.

Kelly's email felt like a green flag wrapped in a red flag wrapped in something I couldn't quite identify.

The Sports Bar Interview

Kelly asked me to meet him at a sports bar in Sarasota on a Friday night. Halfway between his office in Homosassa and my home. He also told me—not asked, told—to bring my husband.

"First of all, this is a different level," I remember thinking. "I've never done an interview over dinner. I've never talked money over dinner. I've never met with a CEO at a table."

When we walked in, Kelly stood up. He was tall, maybe six-foot-something, but felt like he was ten feet tall. He shook my husband's hand first.

He explained later that he wanted my husband there because he'd been married before. He understood this was a decision we'd make together. Not just my decision.

That respect for my family became a pattern. In my official contract, I got to pick which holidays I wanted off. If a holiday fell on Thursday, I could take Friday too. I had to give him my kids' birthdays, my husband's birthday, our anniversary—important dates that I'd get off without using vacation time.

I'd worked in corporate healthcare for five years. I'd never seen anything like this.

The Morning Voice Test

The first couple weeks were slow. I knocked out assignments quickly, got my home office set up with decor from Michael's, and waited for more work.

Then Kelly started calling me out on everything.

Forgot to attach a file? He'd email back: "You didn't attach this."

Fonts didn't match on a document? He noticed.

Woke up 20 minutes before his call? He knew. "Did you just wake up?"

I started doing jumping jacks when I saw his name on my phone. Literally trying to get the morning voice out before answering. It didn't work. I needed to be awake at least 45 minutes to an hour before Kelly's first call, or he'd know.

This irritated me deeply.

I'd been "so great as a manager" at the hospital. I'd managed 25 medical assistants, nurse practitioners, front office staff, and doctors. I'd been taught the corporate way: when you counsel an employee, you give two positives, then a negative.

Kelly's approach? "I'm going to tell you what you're doing wrong."

No sugar coating. No compliment sandwich. Just direct feedback on every single mistake.

I cried a lot that first year.

When Trust Looks Like Freedom

Here's what Kelly did while calling out every mistake:

He gave me passwords to everything. His iCloud. His Netflix. His email. Every single account.

He gave me a credit card with a $2,000 spending limit. No approval needed. Just an expense report at month's end.

He bought me an iPhone for work. Apple AirPods because he couldn't hear me on speakerphone. An Apple Watch. A gas allowance even though I worked from home.

When he asked me to plan the company's first team-building event, he didn't give me a budget. He trusted me not to go crazy. I booked hotels for the seven-person team spread across Florida. Organized a boat trip. Hired a photographer. Created branded towels and bags with the logo I'd designed.

For the Christmas party, I arranged hibachi cooked in front of everyone. Again, no budget constraints. Just trust.

Research shows that 93% of employees perform at their best under bosses who set clear expectations while creating autonomous space to operate. Kelly understood this instinctively.

But I didn't see it at the time.

The Zoom Call Where I Broke

One day on Zoom, I told Kelly he never said thank you.

His response: "Well, you already know what you did right."

That stung. But he was right.

He showed appreciation through freedom. Through not checking in constantly. Through letting me order whatever I needed off Amazon for my office. Through trusting me with his traffic ticket (which I got reduced to $49 with no points), his birth certificate, his driver's license renewal.

I was doing things for Kelly that I didn't even know how to do for myself. Personal tasks that felt like I was helping my husband—navigating bureaucracy, managing payroll, tracking accounts across a spreadsheet of passwords.

He was ex-military. Southern. A bit redneck-ish, honestly. He hunted in Missouri. Spent time on his boat. But when Kelly called, people answered.

Not because he demanded it. Because he'd earned it.

What I Didn't Learn Until I Left

I worked for Kelly for about a year. We lived three hours apart, and the distance eventually became too much. When I left GTW Marketing in 2023, I didn't realize I was taking a masterclass with me.

For the last three years, I've thought about Kelly almost daily.

Not because I'm trying to copy his style. I don't call people out on every mistake like he did. I'm a "words person"—I tell people when I appreciate them, and that works for me. Kelly showed appreciation differently, through trust and freedom, and that worked for him.

But here's what stuck:

Kelly taught me how to take criticism.

When someone points out a mistake now, I don't spiral. I problem-solve. My skin is way thicker than it was back then. Today, a guest sent me a list of things wrong with my rental condo. My response? "Thank you, sir. I'll get those corrected."

No hurt feelings. Just appreciation for direct feedback instead of a bad review.

Kelly taught me that discipline shows up in details.

I'm obsessive about documents now. How do fonts look? Is everything attached? Would this make someone take me seriously? I still make mistakes, but I examine my work through Kelly's lens: "Would Kelly approve?"

Kelly taught me that networking is contact management.

He'd send me photos of business cards, signage, people he met during his long hauls across Florida. I'd upload everything to his contacts. He never had to ask for someone's number. If he was calling you, he already had your information.

That system stuck with me. Having information at your fingertips isn't just organized—it's respectful of other people's time.

Kelly taught me what trust actually looks like.

Not words. Not praise. Trust looks like giving someone freedom and watching what they do with it. Studies confirm that 96% of employees see feedback as valuable, with 69% becoming more productive after receiving constructive criticism.

Kelly called out every mistake because he trusted me to fix it. A boss who lets you keep making mistakes isn't helping you grow.

The CEO I Still Call

Three years after leaving, I still text Kelly.

When I started my own company in April 2025—exactly three years after getting that first email from him—I asked Kelly about investment returns. What would make something worth his money?

When my daughter competed in a pageant, Kelly sponsored her. Not just in his name, but in multiple names. He sent money for branded sweatsuits with the logo I'd designed years ago. He made it possible for her to go to States.

He's the only CEO I've ever worked for that I trust completely.

Not because he was easy to work for. Not because he made me feel good about myself in the moment. But because I always knew exactly where I stood with him.

I didn't have to hear from other people what Kelly thought of me. Kelly told me directly. If fonts didn't match, he said so. If I forgot an attachment, he pointed it out. If I did something well, he showed it by giving me more freedom, more responsibility, more trust.

Research on military leadership shows that flat communication—no buffer between leaders and team members—is critical for mission success. Kelly's directness wasn't just personality. It was trained behavior from his military background.

And it worked.

The Difference Between Hurt Feelings and Being Wronged

I cried a lot working for Kelly. But he never did me wrong.

There's a difference between a boss who hurts your feelings because they're direct about your work, and a boss who actually wrongs you. The line is respect.

Kelly respected my family. He invited my husband to that first interview. He gave me my kids' birthdays off. He asked if my husband was okay with me traveling for work. He never crossed professional boundaries. He never made me feel unsafe or disrespected as a person.

He just refused to let me stay comfortable with mediocre work.

The crying? That was because I had a corporate bubble around me. I wanted the two positives before the negative. I wanted validation for every small task.

Kelly taught me that sometimes the most respectful thing someone can do is tell you the truth without wrapping it in compliments first.

I look back now and think: "I was such a crybaby. How did he put up with me?"

But I also know I did good work in that role. And I know Kelly saw it, even when he didn't say it out loud.

What I'm Taking Forward

I don't know yet how I'll lead when my company grows. I'm at the very beginning—Kelly is way above where I am now. I can't say definitively what I'll do differently because what I thought three years ago, I don't think today.

But I know this:

I won't sugarcoat problems. I'll be direct when something needs fixing.

I'll pay attention to details that other people miss. Fonts. Attachments. How documents look when someone opens them.

I'll show appreciation through both words and actions—through freedom and trust, but also by telling people directly when they've done well.

I'll respect people's families and personal lives as much as their professional contributions.

And I'll remember that the boss who challenges you the most might be the one who believes in you the most.

Kelly didn't teach me by lecturing. He taught me by allowing me to learn. By giving me freedom to plan events, manage payroll, handle personal tasks, make mistakes, and fix them. By trusting me with passwords and credit cards and his professional reputation.

He taught me that leadership isn't about making people feel good in the moment. It's about making them better over time.

Three years later, I'm still learning from a CEO I only worked for directly for one year. That's the lasting impact of a first boss who gets it right not perfect, but right where it counts.

When I think about the kind of leader I want to become, I don't think about copying Kelly's style. I think about earning the same kind of loyalty he earned from me: the kind where someone still calls you three years later, not because they have to, but because they want to.

Because you never did them wrong. You just made them better.

Stay Inspired,

Jasmine Duwe