The “Who Not How” Framework for ADHD Delegation: How Operators Escape the Weeds

The Shame of the “Fixer”

We need to talk about the shame of the unstarted project.

You know the one. It’s been on your to-do list for three weeks. It’s strategic. It’s important. You want to do it. But every day, you look at it, feel a spike of anxiety, and then scroll down to something easier—like putting out a minor fire, or in my case, opening a blank Google Sheet.

For years, my personal kryptonite was spreadsheets. I don’t mean basic Excel; I mean complex Google Sheets with sophisticated query functions and custom macros.

I wouldn’t just build a tool; I’d hyperfocus on building a masterpiece. I wanted it to be powerful and beautiful. I’d spend days adding bells and whistles, not because the business needed them, but just because I could or wanted to.

At the time, I didn’t know it was my ADHD brain seeking dopamine. I just knew I loved the puzzle. I’d get locked into a state of hyperfocus and stay up until 3:00 in the morning, telling myself it was the only time I could get quiet work done. In reality, it was a justification—my secret indulgence.

The result? A dashboard that should have taken an afternoon took a week. Critical product deliveries were put on the back burner. Strategic work sat on my desk collecting dust because it didn’t feed the dopamine rush.

As a COO, this feels like a moral failing. Why was I paralyzed by the big strategic work but obsessed with the weeds?

I told myself I was ensuring quality. But if I’m honest, it was fear. Early in the startup days, I did it because no one else could. But later, even after we had funding and a team, I kept doing it out of pride. I convinced myself, “No one else can do this as well as me.”

I was holding onto the work because letting go felt like losing control. My pride—and my need for that dopamine hit—had become the company’s biggest bottleneck.

Why Your Brain Freezes on “How” (The Science)

This isn’t a character flaw; it’s executive dysfunction.

Leading ADHD researchers like Dr. Russell Barkley, author of books like Taking Charge of Adult ADHD and Executive Functions: What They Are, How They Work, and Why They Evolved, explain that ADHD is fundamentally a disorder of executive functioning and self-regulation. The ADHD brain often knows what to do but struggles to organize the steps to do it over time.

Your brain struggles with sequencing. When you look at a large, complex goal and ask, “How do I do this?”, your brain doesn’t see a simple path. It sees a 50-step mountain climb. The cognitive load of organizing the “How” is so high that your brain pulls the emergency brake. You freeze.

For me, the biggest “How” freeze was always Finance. I am not an accountant and have no desire to learn more than what I needed to.

But, I learned the hard way you should absolutely not be the one creating these documents – you’re too close and there are too many things you could do wrong. The stakes of legal failure were paralyzing, and the relief I felt when I finally hired an accredited accountant was immense.

Another massive trap was coding. Tell me I can’t do something, and I’ll prove you wrong. I’ve wasted countless hours chasing a stray comma in a script, trying to force myself to be a developer. Even with AI tools, debugging and translating technical concepts takes up massive amounts of time, and AI isn’t perfect.

My brain would freeze on the infinite technical “Hows,” stopping me from focusing on the strategic “Whys.”

You have to remember the “Iron Triangle,” a foundational model in project management that illustrates the interdependent relationship between three core constraints: scope, time, and cost. Translated: You can have something done well (scope), quickly (time), or affordably (cost). Pick two.

• I want this project done Fast and Well. Be prepared to make a sizable investment.
• I want something made Well, but we don’t have a big budget. We can do that, but it will take time.
• I want this product launch to be Fast and Cheap. Well, then, be prepared for the quality to be minimal.

When you are bootstrapping, you often choose Good and Cheap, which means it will be Slow. That’s necessary in the beginning. It’s how you learn the skills that will allow you to be better at hiring later.

But the danger is staying in either place too long. When you try to do everything yourself as you scale, you become the constraint. As an entrepreneurial operator, your most valuable asset is time. Your goal is to identify your strengths, pour your energy there, and find a different way for everything else.

The Solution: The “Who Not How” Framework

This is why Dan Sullivan’s concept of “Who Not How” is a game-changing framework for the ADHD brain.

When you shift the question from “How do I do this?” to “Who can do this for me?”, you bypass the sequencing part of your brain entirely. You replace 50 decisions with one decision: Pick a person.

• The How: “Research, select, and implement a new CRM.” (Brain says: Error. Too many steps. Abort.)
• The Who: “Ask Sarah to research the top 3 CRMs and present a recommendation on Friday.” (Brain says: Done. Next.)

By shifting to “Who,” you move from the role of the Fixer (who has to draw every line) to the Architect/Client (who just has to approve the design).

The Tool: The Captain’s Wheel Assessment

How do you know what to delegate first? We’re going to use a tool I call The Captain’s Wheel.

Imagine the steering wheel of a ship. To steer effectively through a storm, you need leverage. That leverage comes from the spokes of the wheel. If a spoke is too short, you can’t grip it, and you lose control.

Your business has 8 Critical Spokes:

1. Vision & Strategy
2. Finance & Accounting
3. Marketing
4. Sales
5. Operations & Systems
6. Product/Service Delivery
7. People & HR
8. Customer Success

Some ships (business) may have more, others less. You can get as granular as you want here, but I would recommend staying broad – no need for unneeded complexity. It’s part of the reason for this article.

The Exercise: Rate Your Reach

Rate your personal proficiency and enjoyment in each area on a scale of 1 to 10.

When I was a Tech CEO, my strongest spokes were Vision and Sales. I managed investments and negotiated our acquisition. But my Product/Technical spoke was a 2. If I had tried to learn to code, we never would have launched. We hired talented developers as our “Whos” immediately. Their technical grip allowed me to steer the company to a successful exit.

Conversely, as a Startup COO, my Operations spoke was a 9, but my Finance spoke was a 3. My “Who” was my co-founder/CEO, whose strategic role in fundraising required a deep knowledge of the numbers. It was the perfect strategic extension.

And as a Martial Arts Operations Manager, running a 300-student school, my “Whos” were a team of volunteer instructors. They extended the Product Delivery spoke, allowing me to grip the Sales, Marketing, and Systems spokes required to keep the school running.

The Lessons

Your goal is not to be a 10 in everything. Your goal is to ensure every spoke extends to a 10, whether that reach comes from your hand, your co-founder’s, a paid employee’s, or a volunteer’s.

Looking back, Operations was one of the few spokes that were consistent across all aspects of my career; others had to be utilized and extended over time depending on the role.

The Warning: The Trap of the “Impulsive Who”

Before you rush out and hire a virtual assistant, we need to pause.

For the ADHD brain, “Who Not How” comes with a dangerous side effect: Impulsivity. We get excited about an idea, realize we don’t want to do the work, and immediately hire someone to “handle it” without knowing what “it” actually is.

I’ve fallen into this trap. As the CEO of a tech startup, we hired the most skilled coder on paper, ignoring the fact that his attitude was a drain on our culture. It was a disaster. We later hired someone with fewer skills, but an incredible problem-solving attitude, and he became invaluable. You can teach skills; you cannot teach attitude.

Later, in a financial literacy company, we succumbed to the “cheap VA” trend. We paid less in money but twice as much in management time because we hadn’t defined the work clearly.

An Additional Warning

Just because you are good at something doesn’t mean that you should do that role. It might not be what excites you, and you need excitement to keep going when your energy levels are low. For me, that is Vision work. I can do it, but it drains me more than it fulfills me.

Also, as you get further from the day-to-day problem-solving of a startup COO, your time is better spent doing only the things you can do, and you need the time to plan. It’s okay to find people whom you can train and delegate to, giving you back your time.

The System on How to Delegate Without Losing Control

So, how do we balance the need for “Who” with the danger of impulsivity? We use a system that prioritizes clarity over volume.

I learned this lesson as a freelance designer. Clients often couldn’t define what they wanted, yet were unhappy with the result. The lesson stuck: If you cannot explain what success looks like, you cannot expect someone to deliver it.

Conclusion: From Hero to Captain – A Summary of Your Shift

The journey from being a reactive Operator stuck in the weeds to a strategic Leader is not about learning a few new productivity hacks. It’s a fundamental identity shift that requires work, discipline, and a heap of courage.

You are moving from being the Hero—the addicted “Fixer” who saves the day by rowing harder and diving into every fire—to being the Captain. The Captain doesn’t row; they ensure the ship stays on course by leveraging every spoke on the wheel and trusting their crew to do their jobs.

Let’s recap the key frameworks for making this transition:

• Understand Your Brain: Acknowledge that your executive dysfunction freezes on the complex sequencing of “How.” Delegation isn’t a luxury; it’s a neurological necessity for scaling.
• Diagnose with the Captain’s Wheel: Use the wheel assessment to be ruthlessly honest about where your personal reach ends. Those gaps between your grip and a full spoke are your roadmap for future delegation.
• Avoid the “Impulsive Who”: Don’t just hire a body to make the pain go away. Remember, you cannot outsource a process that doesn’t exist. Define the “What”—the clear outcome—before you find the “Who.”
• Delegate with a System, Not Hope: Use tools like a clear Definition of Done, ADHD-friendly “chunking,” and the Monday/Friday meeting rhythm to maintain control without slipping back into micromanagement or ghosting.

Make no mistake, this transformation is uncomfortable. It requires letting go of the pride of being the one who knows everything, releasing the control you’ve held onto out of fear, and finding new, healthier sources of dopamine beyond immediate problem-solving. It requires giving yourself permission to stop doing the work you were never meant to do forever.

But the reward for stepping back from the helm is massive. It’s the difference between building a grueling job for yourself that leads to burnout and building a scalable company that can run without you.

It’s the one thing you think you can’t have: Freedom.