Entrepreneurs love solving problems—it’s one of the reasons they become entrepreneurs in the first place. The downside is that many founders keep solving every problem long after they should have started delegating. The result isn’t a better business. It’s an exhausted business owner spending valuable hours on work someone else could easily handle.
After our conversation with John McKenna about virtual assistants, our Friday discussion shifted from theory to execution. Rather than debating whether AI or virtual assistants are better, the focus turned practical: how do you actually begin delegating?
The answer isn’t hiring someone tomorrow. It’s understanding what you’re already doing today. That’s where this delegation challenge begins.
Why This Challenge Matters
One theme kept surfacing throughout the interview with John McKenna: entrepreneurs often believe they’re overwhelmed because they have too much work. More often, they’re overwhelmed because they’re doing work that doesn’t require them—administrative tasks, scheduling, status updates, routine follow-ups, documentation. These activities are necessary, but they don’t necessarily require the founder’s expertise.
Whether you eventually delegate those responsibilities to a virtual assistant or automate them with AI, the first step is recognizing where your time is actually going. You can’t improve what you haven’t measured.
Before you delegate work, you need to understand how you’re currently spending your time.
AI and Virtual Assistants Both Require Good Delegation
During the Friday discussion, one interesting realization emerged: the same entrepreneurs who struggle to delegate work to people often struggle to use AI effectively. Why? Because both require clear communication.
Whether you’re writing instructions for ChatGPT or handing work to a virtual assistant, success depends on defining the outcome clearly. Poor instructions create poor results; good delegation creates consistent results. Technology hasn’t changed that principle—it’s just made it more obvious. The better you get at communicating expectations, the more productive every tool and every person becomes.
The Challenge: Imagine You Already Have Help
Here’s the exercise Rob challenged listeners to complete.
Imagine you’ve already hired a virtual assistant. Give yourself a realistic budget—maybe enough for a few hours each week, maybe a small monthly package. The exact number doesn’t matter. Now ask yourself one question: if someone started working for you next Monday, what would you have them do?
Don’t answer with general ideas. Actually write the assignment. Create the email, list the tasks, describe the desired outcomes, and explain what success looks like. Be as detailed as possible. If you can’t explain the work clearly, neither a person nor AI can consistently complete it.
Test Your Instructions Before You Delegate
Once you’ve written your assignment, don’t stop there. Test it.
Give those instructions to ChatGPT or another AI assistant and ask it to complete the work. Better yet, ask someone unfamiliar with your business to read the instructions. Do they immediately understand the task? Do they have questions? Are there missing steps?
Every question they ask reveals another assumption you’ve been carrying inside your own head—and that’s incredibly valuable. Many entrepreneurs discover they don’t actually have delegation problems. They have documentation problems.
If someone can’t understand your instructions, the issue probably isn’t the assistant. It’s the process.
Calculate the Real Value of Your Time
The next step is one many entrepreneurs never perform: estimate the value of your own time.
Rob suggested a simple calculation—take your annual income and divide it into an approximate hourly rate. Then estimate how many hours each week those delegated tasks would save. If you recover two hours a week, what’s that worth? More importantly, could someone else complete those tasks for less than the value of your time? If the answer is yes, doing those tasks yourself may actually be costing your business money.
This isn’t just about reducing workload. It’s about making better investments. Every hour spent on administrative work is an hour unavailable for sales, product development, customer relationships, or strategic planning.
Delegation isn’t an expense. It’s an investment in buying back your highest-value hours.
Don’t Waste the Time You Recover
The final part of the challenge is the one that’s easiest to overlook.
Suppose delegation saves you three hours next week. What will you do with them? Too many entrepreneurs immediately fill the empty space with more busy work, and that’s not the goal. The goal is to create capacity, then use those hours intentionally: schedule meetings with customers, improve your marketing, document another business process, develop a new product, learn a new skill, or simply spend more time with your family.
Delegation creates freedom. Intentional choices determine whether that freedom actually creates growth.
Before you delegate your first task, decide exactly how you’ll use the time you expect to recover. Protect that time just as carefully as you protect important customer meetings.
The Businesses That Scale Learn to Let Go
Whether your future includes AI, virtual assistants, employees, or all three, one truth stays constant: growing businesses depend on leaders who stop trying to do everything themselves.
Delegation isn’t about avoiding work. It’s about ensuring the right work reaches the right person. AI will keep improving, virtual assistants will keep evolving, and new tools will keep appearing—but none of it matters if entrepreneurs never learn one of the most important leadership skills they’ll ever develop: learning to let go.
Conclusion
This week’s delegation challenge isn’t really about hiring a virtual assistant, and it isn’t even about AI. It’s about changing how you think about your time.
Every successful entrepreneur eventually discovers that growth isn’t created by working longer hours. It’s created by protecting those hours and investing them where they generate the greatest return. Complete the challenge, write the assignment, test your process, calculate your time—then take the first step toward building a business that doesn’t depend on you doing everything yourself.
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