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You Say Delegation Doesn’t Work. I Say the Problem Might Be You.
Here’s the one sentence I gave a new hire instead of training, and everything it taught me about what delegation actually requires.
Back in the early days of Hawaiian Vacations, when the whole operation ran out of one cramped office in Anchorage, and every new hire felt like an act of desperation, I brought on a new reservations agent. Flights to book, condos to track, phones ringing nonstop, and I needed help fast. So I sat her down, pointed at the desk, and gave her exactly one instruction: “There’s the phone. Answer it.” That was the whole training.
I still cringe thinking about it. But it taught me something I now tell every business owner I coach: if you haven’t documented the job, you haven’t actually delegated it. You’ve just hoped for the best.
When a handoff falls apart, the instinct is to blame the person you handed it to. She didn’t get it. He dropped the ball. Nobody on my team can just figure things out. I used to think that too, and every time I traced a failed handoff back to where it actually broke, it wasn’t a skill problem. It was a clarity problem. I never defined “answer the phone.” I didn’t give her any tools, any parameters, any resources for information.
That’s the trap. An instruction isn’t a system, and “handle it” isn’t a process. If you can’t write down the steps, you don’t have a job to delegate. You have a job you’re still doing in your head while someone else takes the blame for not reading your mind. I wrote a whole post on this one, called Clarity Is Power, because confusion, not laziness, is the real bottleneck in most businesses, and it almost always starts at the top.
You can’t delegate a job you never actually defined.
When was the last time you wrote down the actual steps of a task before you handed it off, or did you just say the words and walk away?
Robert Kiyosaki taught me the fruit bowl theory of business years ago, and it’s still the fastest way I know to explain good delegation. You’ve got a bowl made of wood, china, or metal, and the sides are fixed. Inside that bowl, the fruit can be whatever you want, arranged however you want, as long as it stays inside the shape. That’s leverage, principle three of my six. When it comes to delegating, owners often get it backward. They think delegating means giving up control. It doesn’t. You just need to shift your focus from doing the task yourself or making sure someone else does it exactly as you would to defining the bowl’s shape.
Years later, I thought about that reservations agent and realized I never built her a bowl. No boundaries, no shape, nothing to work inside. So she had to make one up on the fly. I actually wrote about the fix for the delegation dilemma in a post called I Used to Delegate, and It Still Felt Like I Did Everything Until I Changed This One Thing.
The shape stays fixed. What’s inside it can move however it wants.
Have you actually built your team a bowl, or have you just handed them fruit and hoped they’d figure out where it belongs?
My husband John has a phrase I stole and never gave back: your ego is not your amigo. A lot of owners hear “trust but verify” and flinch, like checking in means they don’t really trust their team. Ronald Reagan didn’t mean it that way, and neither do I. Effective delegation only works when paired with a follow-up loop. One built-in check-in point can ensure that the fruit stays inside the bowl. John likes to refer to it as a snow fence: it’s not there to stop the snow; it’s there to keep you on the road. Your team needs the same thing. Guardrails, not a cage.
If you’re not sure whether the real bottleneck in your business is your team or you, my free Owner Diagnostic takes about three minutes and tells you exactly where you are on the operator-to-owner journey.
Trust but verify isn’t a lack of faith. It’s the fence, not the cage.
Where’s your one built-in check-in point, or are you still waiting to find out if something went wrong?
It took us years, not weeks, years, to go from that reservations desk with one badly trained agent to a team that ran Hawaiian Vacations while we were an ocean away. We didn’t get there by working harder. We got there by finally documenting what we knew, defining the boundaries, and remembering to do the follow-up loop. That’s duplicating yourself in practice, and it’s the whole reason the business could scale past what two people could carry on their backs. I still remember the moment it actually sank in, the one I wrote about in The Moment I Knew Our Team Could Run the Business Without Us.
Duplicate yourself. That’s what gives you the freedom.
If you disappeared for two weeks tomorrow, would your business run, or would it just wait for you to come back?
This Week’s Exercise
- Pick one task that keeps boomeranging back to you no matter who you hand it to.
- Write down the actual instructions you gave, word for word if you can remember them. Were they a system, or just a sentence?
- Rebuild it using detailed step-by-step instructions and a well-defined outcome.
- Set one check-in point before the deadline, your trust-but-verify moment.
Expert Spotlight: Kelly Resendez
Transformational Business Strategist | Entrepreneur | Author
Meet Kelly Resendez, a transformational business strategist passionate about empowering professionals to shatter limitations, embrace abundant living, and create success that extends beyond the balance sheet.
As the owner of GoBundance, Kelly has dedicated herself to building a community where visionary entrepreneurs and leaders come together to accelerate their growth, expand their impact, and live more intentionally. GoBundance is more than an organization—it’s a movement connecting high-performing individuals with mindset strategies, mastermind experiences, and authentic relationships designed to unlock exponential possibilities.
Kelly also serves as President of Menrva, a women’s telehealth and technology company, and previously held an executive role at GoodLeap, a multi-billion-dollar innovator in the fintech industry. Across these ventures, she has seen firsthand that lasting transformation happens when strategic thinking is aligned with personal growth.
She is also the author of Big Voices, where she helps individuals and organizations break through barriers and design intentional paths toward success.
The Problem She Helps Solve
High-achieving women have built remarkable success—often while juggling businesses, careers, families, health, and countless other responsibilities. Yet many have learned to do it all alone.
They’ve been conditioned to be strong, self-reliant, and independent. Asking for help can feel like failure, while admitting they’re struggling can feel like weakness. As a result, they continue carrying the weight of business decisions, family obligations, personal goals, and dreams deferred—all while making it look effortless.
Kelly helps successful women recognize that they don’t have to choose between professional excellence and personal fulfillment. Through strategic guidance, community, mentorship, and meaningful relationships, she helps them move beyond isolation and step into a more abundant version of success.
Who Kelly Helps
Kelly works with entrepreneurs, investors, and business leaders who have achieved significant external success and are ready to optimize their lives as a whole.
Her community is designed for individuals with a minimum $1M+ net worth or $200K+ annual income who are ready to move beyond simply achieving more and instead create greater alignment, fulfillment, connection, and impact.
Connect With Kelly
Learn more about Kelly and the GoBundance Women community at:
You can also connect directly with Kelly on LinkedIn: https://www.linkedin.com/in/kellyresendez/
Final Thoughts
I think about that reservations agent every time an owner tells me delegation doesn’t work for them. It worked exactly as badly as I set it up to work: one sentence, no system, no boundaries, no follow-up. The problem was never her. It was the shape of the bowl I never built.
Delegation doesn’t fail because your team can’t handle it. It fails because most of us hand off tasks the same way I handed off that phone: fast, vague, and hoping for the best. This week, pick the one thing you keep saying “I just can’t delegate that” about, and write down, really write down, what you’d need to say for someone else to do it exactly the way you would. That’s not busywork. That’s the job you’ve been skipping.
To your freedom,
Ral West
Livin’ the Dream
