Courageous Delegation: Scaling with Trust and Intention

This summer, I had the honor of teaching my Courageous Delegation workshop at the Scaling New Heights conference. In that room, I watched accountants, bookkeepers, and service-based owners lean in as we unpacked one of the biggest barriers to sustainable growth: our relationship with control.

Delegation isn’t just a business tactic; it’s a personal evolution. It requires you to trust others with the work that represents your name, your reputation, and in many cases, your livelihood. It’s uncomfortable, yes, but it’s also the bridge between exhaustion and expansion. 

The conversations at Scaling New Heights were too valuable to stay within those four walls. So, I'm sharing the essence of that workshop here. It’s a roadmap for any leader ready to let go with intention and build a business that can grow beyond them. 

Why delegation feels so hard 

Fifteen years ago, I launched my firm wearing every hat: bookkeeper, salesperson, marketer, and even IT. Like many founders, I believed no one could do it quite like me. Sound familiar? 

That mindset almost broke me. Six months in, I was diagnosed with multiple sclerosis, and stress became my enemy. I had to make a hard choice: cling to control or choose freedom. I chose freedom and I built it through courageous delegation. 

Delegation is rarely about logistics; it’s about trust and systems. It’s about believing that someone else can not only handle the work but also carry your vision forward. That’s scary, especially when you’ve built something from scratch with your own two hands. 

Many of us have been burned before: hiring the wrong person, watching tasks boomerang back because they weren’t done “our way,” or feeling like it would’ve been faster to just do it ourselves. We tell ourselves we'll delegate when we have more time, more money, or the right person. But that day doesn’t come until we make a different kind of decision. 

Here’s the truth: “our way” isn’t the only way. When we loosen our grip, we make space for our team's genus to shine. That’s where growth begins, not just for our business, but for us as leaders. 

The frameworks that changed everything 

What allowed me to finally step out of the day-to-day wasn’t just hiring, it was systems. I had to rewire how I thought about delegation and build a structure that empowered others to succeed. Two frameworks changed everything for me and my clients: 

1. 1. The 4D Framework (from Clockwork)

Every task in your business falls into one of four “D’s”: 

• Doing – you’re executing tasks yourself.   

• Deciding – you’re assigning tasks but still making all the decisions.   

• Delegating – you’ve passed on both ownership and accountability.  

• Designing – you’re focused on strategy, innovation, and leadership.  

At first, I lived in the “doing” and “deciding” stages—constantly working, constantly answering questions, constantly tired. The breakthrough came when I learned to operate from the designing level, where my focus shifted from daily operations to the bigger picture of where the firm was going.

Your goal isn’t to eliminate doing, it’s to create enough space for designing. That’s where you move from managing chaos to leading with clarity. 

2. 2. The IPO Method (Information, Permission, Outcome)

The next shift was learning how to delegate with clarity instead of control. The IPO method became my go-to tool: 

• Information – Give your team everything they need to succeed.   

• Permission – Empower them to act and make decisions.   

• Outcome – Define what success looks like.  

This framework helps you communicate like a mentor instead of a micromanager. When your team knows the “why” behind a task and what “done” looks like, they can take ownership. You stop being the bottleneck, and they start becoming the solution.  

The sandwich test 

One of my favorite exercises from the workshop was deceptively simple: delegate how to make a peanut butter sandwich. 

Most people start with “spread peanut butter on bread.” But wait, what kind of bread? How much peanut butter? Is it crunchy or smooth? Do we use a knife or a spoon? Is the sandwich cut in half, or triangles? 

Even the simplest task reveals how many assumptions we make. Clarity is everything in delegation. When we don’t define what success looks like, we set our team up to fail. 

That same exercise applies directly to firm operations. Whether you’re delegating payroll, client onboarding, or content creation, detail matters. Clear expectations create confidence—for both you and your team. 

Building a team you can trust 

Delegation isn’t a one-time event, it’s a skill that gets stronger with use. The key is to start small and build momentum. 

Here’s how: 

1. 1. Track your time. For one week, write down everything you do. Identify tasks you dread, tasks that are teachable, and tasks only you can do.   

1. 2. Record yourself doing a task. Walk through your process out loud. You’ll be amazed at how many small steps you’ve internalized that others need to know.  

1. 3. Use AI tools to help. Let technology transcribe your walkthroughs, summarize the steps, and turn them into standard operating procedures (SOPs).   

1. 4. Hand it off with context and trust. When you give both information and autonomy, you create accountability and empowerment at the same time. 

When you start delegating this way, your team not only completes tasks; they grow into ownership. And that’s when you move from having helpers to having leaders.

Make it so

Courageous delegation changed my business and my life. It gave me the freedom to speak, to scale, to rest, and to serve in the ways only I can. 

It didn’t happen overnight. It started with one small, intentional decision—to stop being the bottleneck and start being the designer of my firm. Over time, my firm grew stronger because my team grew stronger. 

When I look back at that Scaling New Heights workshop, the energy in the room wasn’t just about delegation, it was about liberation. Every nod, every “aha” moment was a leader realizing they didn’t have to do it all to have it all. 

So, I’ll leave you with the same question I ended that session with: 

What are you ready to let go of and what could that make possible?