There comes a point in almost every entrepreneurial business where the founder starts saying some version of the same thing: I need help.
Usually, this realization arrives long after help was actually needed. The inbox is overflowing. Projects are backing up. Sales opportunities are getting less attention than they deserve. Administrative work has somehow colonized entire afternoons. You know you shouldn’t be doing all of it anymore, but every attempt to hand something off creates a new problem. Someone asks a question. You answer it. They ask another. Eventually you decide it would have been faster to do the damn thing yourself.
For a long time, I assumed this was mostly a hiring problem. Find better people. Hire someone more experienced. Get somebody who can “take ownership.” After spending the better part of 20 years running businesses with myself somewhere near the center of the machinery, I’m increasingly convinced that explanation is incomplete. Sometimes the employee isn’t the problem. Sometimes the founder has simply built a company that nobody else knows how to operate.
That distinction matters. There’s a huge difference between knowing how to perform a task and knowing how to explain the system behind it. Entrepreneurs become unusually good at the former because repetition creates instinct. We know which client needs a phone call instead of an email. We know which number in the report actually matters. We know how far we can push a vendor, what a good lead looks like, where a project usually goes sideways, and which exception to make because we’ve seen this movie before. Eventually all of that judgment gets compressed into something that feels obvious. To us.
Then we hire someone and discover that “obvious” is a terrible operating procedure.
I’ve run headfirst into this in my own work. As I’ve tried to move myself farther from the center of the businesses I’m building, I’ve had to confront how many processes I understand perfectly but have never actually documented. I can tell someone I want them to take something over, but when they start asking reasonable questions—What does good look like? When should I escalate this? Which part matters most?—I sometimes realize the complete answer has existed only in my head. That isn’t delegation. It’s handing someone a destination without giving them a map.
And this is where founders can be a little unfair. We complain that people don’t “get it.” We redo their work. We decide nobody cares as much as we do. Occasionally that’s true. Plenty of bad hires exist. But if five smart people have struggled with the same responsibility, it may be time to stop blaming the sixth person you haven’t hired yet. The problem might be the role, the process, the expectations—or the founder who hasn’t made any of those things clear enough to survive without constant intervention.
Effective delegation is more about transforming your knowledge into something others can take ownership of, rather than simply relinquishing control. It involves clarifying desired results instead of assigning tasks haphazardly. It requires discerning what needs your judgment and what can follow a process. Perhaps most challenging, it means accepting that others might achieve the outcomes differently than you would. If your business relies on every decision passing through you, you’ve created dependence instead of leverage.
That tension came up repeatedly in my recent conversation on Eggs! The Podcast with Chris McShanag, founder and CEO of Virtual Teammate. Chris has spent years helping healthcare practices and other businesses rethink how work gets distributed across teams. His argument is simple, but it lands differently when you’ve lived the problem: before you worry about finding the right person, you need to get much clearer about what that person is actually supposed to own—and whether you’ve created a business they can succeed inside.
Building a Business Beyond the Founder
Chris McShanag has spent much of his career thinking about how companies grow—and what gets in the way when they try. Originally from Australia, he began his career with IBM before moving into a company that eventually went through an IPO and acquisition. Entrepreneurship was already familiar territory; his father owned a metal recycling company, and Chris credits both his father and grandfather with shaping his belief in controlling his own destiny and surrounding himself with capable people.
That path eventually led him into healthcare consulting, where he worked with health systems, hospitals, and medical practices on technology and process improvement. But a pattern kept surfacing. Better software and better processes could only go so far when doctors, dentists, and practice leaders were still struggling to find good people—and spending too much of their own time on work that pulled them away from patients and higher-value responsibilities.
Chris ultimately sold his consulting business and founded Virtual Teammate, a global remote staffing company focused primarily on healthcare. Today, the company helps medical, dental, and veterinary practices build teams around clearly defined outcomes, pairing remote professionals with the administrative and operational work that doesn’t require the founder—or the physician—to remain at the center of everything.
Where Delegation Actually Begins
Delegation gets easier once the work is clear. Chris kept returning to the same idea throughout our conversation: before another person can take ownership, the founder has to define what success actually looks like.
“I think the biggest mistake we see is they try and improve or accelerate a process that isn’t quite working.”
Actionable insight: More people won’t fix a broken system. Before you hire, outsource, or automate anything, make sure the underlying process is worth scaling in the first place.
“I’m a big proponent of focusing on outcomes, not necessarily job descriptions.”
Actionable insight: A list of responsibilities tells someone what to do. A clear outcome tells them what they’re responsible for accomplishing. That difference creates far more room for real ownership.
“You can’t do everything by yourself. You can’t be the driver, the pit stop, and everything.”
Actionable insight: Founders often confuse involvement with control. A business becomes more durable when critical work belongs to capable people rather than depending on one person to keep every part moving.
“If it’s urgent and important, that’s the best thing for the founder. If it’s urgent and maybe not important, that’s the best thing to be delegating.”
Actionable insight: Delegation shouldn’t begin with whatever you dislike doing. Start by identifying the work that consumes your time without requiring your judgment, relationships, or unique expertise.
“How many of your hundred-dollar resources are doing ten-dollar tasks?”
Actionable insight: The real cost of low-value work isn’t the hourly rate attached to it. It’s what your best people aren’t doing while their time is being spent somewhere else.
“If you don’t replicate yourself or really bring people along, then you can only go so far.”
Actionable insight: Scale begins when knowledge stops belonging exclusively to the founder. Processes, judgment, expectations, and standards have to become transferable if the company is ever going to grow beyond one person’s capacity.
“Don’t feel like you’ve got to do it all yourself.”
Actionable insight: There’s a point where self-reliance stops being an entrepreneurial strength and starts becoming a constraint. The next stage of growth usually requires letting other capable people carry meaningful parts of the load.
You Don’t Scale by Staying Essential
There’s a strange contradiction at the heart of entrepreneurship. In the beginning, being indispensable is often exactly what makes the business work. You know the customer best. You make the calls. You solve the problems. You hold the thing together. But if that remains true forever, the strength that helped build the company eventually becomes what limits it.
The goal isn’t to disappear from the business. It’s to become more selective about where your presence actually matters. Some decisions need your judgment. Some relationships need your attention. Some work genuinely belongs with you. The rest needs to become clear enough, documented enough, and trusted enough to live somewhere else.
That shift is uncomfortable because it asks founders to give up a little control in exchange for something more valuable: capacity. And if you can create that capacity without losing the standards, judgment, or culture that made the business work in the first place, that’s when the company finally starts becoming bigger than the person who built it.
Thanks for reading.
—Ryan
If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide
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Reading list
If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:
Buy Back Your Time — Dan Martell
Chris specifically referenced Martell’s framework during our conversation, and it fits this week’s theme almost perfectly. The premise is straightforward: founders shouldn’t spend their limited time doing work that someone else can own. Martell gets practical about delegation, hiring, and creating enough space for leaders to concentrate on the work that actually requires them.The E-Myth Revisited — Michael E. Gerber
A classic for a reason. Gerber examines the trap of building a company that depends entirely on the person who started it and makes the case for creating systems that allow the business to operate consistently without the founder personally touching everything. It’s remarkably close to the problem at the center of this week’s essay.Who Not How — Dan Sullivan and Benjamin Hardy
When entrepreneurs encounter something they don’t know how to do, the instinct is often to learn how to do it themselves. Sullivan and Hardy argue for a different question: who already knows how? It’s a useful shift for anyone discovering that personal capability and organizational scalability are two very different things.Clockwork — Mike Michalowicz
If the business stops when you stop, you still have work to do. Clockwork gets into the practical side of designing roles, transferring responsibilities, and creating an organization that doesn’t need the owner constantly intervening to keep things moving. For founders who recognize themselves in this week’s essay, this one is particularly relevant.
More to explore
Learn more about our featured guest — start here:
Virtual Teammate — Learn more about Chris’s remote staffing company and its work with healthcare, dental, and other organizations.
Visit Virtual Teammate
Chris McShanag on LinkedIn — Follow Chris for his writing and insights on leadership, delegation, remote staffing, healthcare operations, and building stronger teams.
Connect with Chris on LinkedIn
Virtual Teammate on LinkedIn — Follow the company for practical content on remote teams, healthcare staffing, delegation, and operational capacity.
Follow Virtual Teammate on LinkedIn
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RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
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Ryan Roghaar - Artist/Creative Director/Author
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Eggs! The Podcast - https://www.eggscast.com
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