This is the Sixteenth Lesson in “My 21 Lessons in 21 Years” Series

To celebrate 21 years in business, based on what I have learned from working with accountants, bookkeepers and tax advisors over 21 years I am sharing my journey and some of the lessons I learned along the way. I hope you join me on this journey and maybe learn something along the way too.

16/21: Go Big or Go Home -The C-Suite Dream – What Happens When You Confuse Delegation with Abdication

The Meeting

It was a Tuesday morning in mid 2021.

I was sitting on a Zoom call with a member of my newly assembled C-suite team. They’d been with us a few months.

“You don’t understand how proper businesses work,” he said, leaning into their camera with the confidence that comes from having done this before. “What you’ve been doing for 17 years—it’s not how real companies operate. You need to step back and let us fix this.”

I remember feeling something in my chest. Not anger. Not defiance.

Relief.

Because someone finally understood what I’d been thinking for months: I didn’t know how to run a “proper” business. I’d built this thing to over €2 million in revenue, but clearly I was winging it. Clearly I needed adults in the room.

So I said: “Okay. You’re the expert. What do you need from me?”

“Nothing. Just stay out of the way and let us do the work. You need to trust the process.”

And I did.

That’s the moment I went from entrepreneur to employee in my own company. That’s the moment I abdicated responsibility instead of delegating it. That’s the moment I ignored the loudest red flag I’d ever seen and convinced myself it was wisdom.

On the one hand I wanted to rise to the next level. I wanted to follow in the footsteps of real entrepreneurs who built the experienced C-suite around them to scale to the next level. But my gut and my heart was experiencing discomfort that I rationalised in my head.

This is the story of how hiring people smarter than me nearly destroyed everything I’d built. And how the lesson wasn’t in the hiring—it was in what I did after.

THE VISION: BUILDING THE DREAM TEAM

Let me take you back to late 2020.

I’d just come through hell. COVID had been brutal. My brother and I were in the final throes of our partnership dissolution—a 16-year relationship ending in pain and complexity.

The business model had been turned upside down. 150 in-person events cancelled overnight. Everything we’d built for 16 years suddenly obsolete.

But we’d survived. We’d pivoted. We’d grown through it.

And now I was sitting there thinking: this is the moment. This is when we scale properly. When we graduate from a teenage business that was sometimes chaotic to something mature, stable, and genuinely scalable.

I’d been reading about building C-suite teams. About surrounding yourself with people who’ve been where you want to go. About hiring people smarter than you who actually know how to build proper business infrastructure. Hiring people who had been there, done that and bought the T-shirt. People who had the experience to say no to me when I was being overly creative and too entrepreneurial.

It made perfect sense.

For 17 years, I’d been the bottleneck. The answer to every question. The decision maker on everything. I’d built OmniPro through sheer force of will and an inability to quit.

But will only gets you so far. At some point, you need systems. Processes. People who actually know what they’re doing.

Dan Sullivan’s “Who Not How” had taught me this. When you face a problem, don’t ask “How do I solve this?” Ask “Who can solve this for me?”

It’s brilliant. It’s collaborative. It takes the weight off your shoulders.

It’s also dangerous as hell if you don’t understand what comes next.

THE ASSEMBLY: JANUARY TO JUNE 2021

Over the course of a few months, I assembled what looked like a dream team.

People with impressive CVs. People who’d built businesses, scaled operations, managed significant growth. People who knew how to do the things I’d never learned properly—financial controls, sales infrastructure, technical systems, organizational structure.

I looked at this team and thought: “This is it. This is how you scale. This is how teenage businesses become mature ones.”

They were all good people. Well-intentioned. Genuinely experienced. They’d done impressive things in other businesses and in their past careers. They came with credentials and track records that made sense on paper.

And I was excited. Finally, I wouldn’t have to figure everything out myself. Finally, I’d have people who knew what they were doing. Finally, I could step back from being the answer to everything and let experts do what experts do. Finally I was going to have an executive team. I was going to have a Dream Team in the boardroom

What I didn’t realise—what I completely failed to see—was that I was about to cross a line I didn’t even know existed.

THE RED FLAGS I WAVED AWAY

Things started feeling wrong almost immediately.

Financial reporting became inconsistent. Explanations for delays became more elaborate. “We’re implementing new systems. We’re doing a complete overhaul. It’s going to be better, but it takes time.”

Performance issues emerged. Tensions developed between the new team and the people who’d been with us for years. Things that used to work smoothly suddenly required multiple meetings and approval processes.

But every time I raised a concern, I got the same response:

“This is how proper businesses work, Des. You’re used to a small operation. This is what scaling looks like. Stick with the process. Trust the system.”

And I did.

Because these were people with experience I didn’t have. They’d built things I hadn’t built. They knew things I didn’t know.

When they told me I didn’t understand how C-suites work, I believed them.

When they told me I needed to step back and let the process unfold, I did.

When they told me the discomfort I was feeling was just the growing pains of scaling, I accepted it.

I confused their experience in other businesses with understanding my business.

I confused stepping back with giving up responsibility.

I confused trust with abdication.

THE DIFFERENCE BETWEEN DELEGATION AND ABDICATION

Here’s what Dan Sullivan teaches about “Who Not How” that I completely missed:

When you “Who” something, you’re not giving away responsibility. You’re bringing in capability.

You’re still the ultimate decision maker. You’re still accountable. You’re still the one who owns the vision and ensures it’s being executed.

What I did wasn’t delegation. It was abdication.

As I said to Dan Sulivan in a 10x Strategic Coach meeting in 2023 as I looked back on the debacle that I unfolded “Dan I Whoed the sh1t out of it but I lost sight of my fundamental responsibilities as the entrepreneur and leader”

I handed over critical business functions to people who immediately changed how they worked—and I accepted explanations that I needed things “fixed” rather than questioning whether they actually needed fixing.

I brought in expertise and then let that expertise override my own judgment about my own business.

I allowed people who’d known my business for weeks to tell me that 17 years of building it meant I didn’t understand how businesses work.

That’s not “Who Not How.” That’s “Who Takes Over While I Step Back.”

And here’s the brutal truth I had to face later:

These were well-intentioned people. They genuinely had impressive experience. They’d done impressive things in their previous roles.

But they had no idea how to run MY business.

Because my business was my business. My vision was my vision. My relationships with clients were built over 17 years, not downloaded from a playbook about “how proper businesses operate.”

When they told me I didn’t know how to run a business, what they really meant was: “We don’t know how to run YOUR business, so we’re going to try to turn it into the kind of business WE know how to run.”

What worked in their previous companies didn’t automatically translate to this one. But I was so convinced they knew better that I couldn’t see what was actually happening.

THE OUTCOME: GROWTH WITH CRACKING FOUNDATIONS

Here’s the part that makes this lesson complex:

During this period, we grew.

Revenue grew. Team expanded. Things looked like they were working from the outside.

It looked like success. Like the C-suite strategy was paying off exactly as promised.

But underneath, the foundations were cracking.

Financial visibility disappeared. Team morale fractured. Performance issues multiplied. And me? I was increasingly disconnected from my own vision.

Standing back. Trusting the process. Convincing myself that discomfort was just part of growth.

I was signing off on decisions based on partial information because the full information was always “coming next week.” I was accepting explanations for why things weren’t working yet because “these things take time.”

And deep down—in my heart and soul—I knew something wasn’t right.

But I’d handed over my authority to people with impressive credentials, and I couldn’t figure out how to take it back without admitting I’d made a mistake.

THE CRISIS: TEACHING WHAT I’D LOST CONTROL OF

By 2022, I was in an impossible position.

I was teaching accountants how to run profitable, sustainable, scalable, exit ready firms while I’d lost control of mine.

The public humiliation would have killed me. The incongruence of standing on stages teaching advisors to entrepreneurs how to grow their businesses while my own business was in disarray behind the scenes—that took every bit of resilience I had.

To be in the situation I was in, dealing with the mess I created, facing what I was facing, all in the public eye, while trying to serve thousands of loyal clients and protect loyal and valued team members.

Honestly at times, just getting out of bed each morning was a feat.
I don’t really know where I found the energy, will and resilience to keep presenting the outer persona I was while the inner persona struggled.

But I did. I had faced challenges before. This was a tough one. But I managed to run a marathon at 285lbs with no training. The footpath was never more than 2 or 3 feet away. I could have quit that race at any time and there would have been no shame.

Yes on some level this was about fear of failure, but it never felt like failure. Failure was not an option this was just the most expensive and valuable lesson of my life.

So I kept getting up every morning and I kept facing the challenges with gratitude and grace and every day I would say to myself –  “Des just keep putting one foot in front of the other and do your best every day. Keep lifting your head to see where you are. Keep working the 6 Step Success Path. Mindset – Belief – Action.”

But here’s what I learned that I’ll never forget:

The flaw wasn’t in hiring experienced people. The flaw wasn’t in “Who Not How.” The flaw wasn’t even in the specific people I hired.

The flaw was in what I did after hiring them.

I confused trust with abdication. I confused their experience with understanding my business. I confused stepping back with giving up responsibility. I abdicated my leadership.

And I ignored every single warning sign because I was so committed to the narrative that this was “how proper businesses scale” that I couldn’t see the reality in front of me.

THE UNCOMFORTABLE TRUTH

You can hire people smarter than you. You should hire people smarter than you.

But you cannot hire someone smarter than you about your own business.

They can be smarter about finance, marketing, operations, technology. They can have skills you’ll never have. They can bring experience you’ll never accumulate.

But they cannot know your vision better than you do. They cannot understand your clients better than you do. They cannot feel the pulse of your business better than you do.

When someone tells you that you don’t understand your own business after 17 years of building it—that’s not wisdom. That’s a red flag so bright it should blind you.

When your gut tells you something’s wrong but your ego wants to believe these experienced people know better—trust your gut. Your gut has 17 years of pattern recognition. Their credentials are impressive, but they’re not telepathic about your specific business.

THE LESSON FOR YOU

This connects to Strategy (knowing your vision), Your People (hiring, delegation, and accountability), and Leverage & Scale (building sustainably) in the ProfitPro 6-Step Success Pathway.

“Who Not How” is brilliant. It’s transformative. It’s essential for growth.

But it comes with a responsibility you cannot abdicate:

You are still the ultimate decision maker. You are still accountable for outcomes. You are still the keeper of the vision.

Delegation means: “I’m bringing in your expertise to execute my vision better than I could alone.”

Abdication means: “You know better than me, so I’m going to get out of the way and let you run things.”

One builds a business. The other dismantles it while you watch.

Here’s what I should have done:

When reporting stopped being consistent, I should have said: “That’s unacceptable. I need monthly reporting. That’s non-negotiable. Make it happen or make it happen.”

When performance issues emerged, I should have addressed them in weeks, not months. “This isn’t working. Let’s figure out why and fix it fast, or let’s part ways professionally.”

When someone told me I didn’t understand how proper businesses work after I’d built one to €2 million, I should have said: “I don’t need someone to fix what I’ve built. I need someone to help me scale what’s working. If you can’t see what’s working, you’re not the right person for this role.”

But I didn’t do any of that.

Because I was so desperate to believe that hiring these people would solve everything that I gave away my own authority. I let credentials override my judgment. I let their experience in other businesses trump my experience in THIS business.

That’s not “Who Not How.” That’s “Who Instead of Me.”

THE RECOVERY AND THE LESSON

Eventually, I had to face what was happening and take back control of my own business.

It wasn’t pleasant. It wasn’t clean. It cost me more than I want to specify here.

But here’s what came from it:

Despite everything—despite the crisis, despite the pain, despite the consequences—this was one of the most valuable lessons I’ve learned in 21 years.

The business grew during this period. It became the staging ground for what came next. The lesson that came from it is priceless.

And it’s a lesson I’ll never forget:

Hire people smarter than you. Absolutely. Build your team with people who have capabilities you don’t have.

But never let anyone—no matter how impressive their credentials—convince you that you don’t understand your own business.

You can delegate execution. You can bring in expertise. You can build a team of people who know things you don’t know.

But you cannot delegate ultimate responsibility. You cannot outsource your vision. You cannot hand over your gut instinct to people who don’t have your years of pattern recognition in your specific business.

The moment you stop being the ultimate decision maker in your own business, you’ve stopped being an entrepreneur and become an employee—in the company you built.

YOUR TURN

Be honest with yourself: Have you abdicated instead of delegated?

Where have you hired expertise and then let that person override your own judgment about your own business?

Where are you ignoring warning signs because you want to believe the narrative that “this is how scaling works”?

Are you really the owner of your business or are you tiptoeing in your own house?

And here’s the question that matters most: Are you still in charge of your vision, or has that been blurred or lost to people who don’t actually understand what you’re building?

Because you can delegate execution. You can bring in people with skills you don’t have. You can build a team of experts.

But you cannot delegate ultimate responsibility. You cannot outsource your vision. You cannot let credentials  or other peoples thinking about your business trump your judgment about the business you’ve spent years building.

I’m curious: Have you ever hired someone with impressive credentials only to realise they didn’t actually understand your business? Or that their way was just not as goo as your way? Or have you caught yourself abdicating responsibility because someone had a better CV than you? What happened?

Let me know what you think. You can connect with me on social or directly via my linktree – https://linktr.ee/desoneill

Tomorrow: Lesson 17 “Tomorrow: Lesson 17 – “The Reality Distortion Field – Everything Takes Longer Than You Think” – When Vision Outpaces Reality