The Delegation Dilemma
How Doing Less Creates More
“Do what you do best, and outsource the rest.” — Peter Drucker
In 2018, I started working with VenturaX*, a team of 7 people doing $1M in revenue. Six years later: 350 employees, nearly $150M in revenue, and founders who could step away for months without missing a beat. They eventually sold for nine figures.
Their success didn’t come from grinding harder. It came from mastering one discipline.
Delegation.
I’ve also seen the opposite: leaders who seem tireless. They are in every meeting, cc’d on every email, touching every decision. From the outside, it looks heroic. Inside, they’re exhausted, their team is frustrated, and the company is capped at one person’s ceiling.
That’s the trap of doing it all yourself. The best leaders know a different truth: your greatest impact comes not from doing everything, but from doing only what only you can do.
Dan Sullivan tells a story about Frank Sinatra. He prepared to sing. And he sang. He didn’t move pianos, tune instruments, or manage logistics. He focused on the one thing he loved and did best, and delegated everything else.
That’s the essence of scaling: multiply your impact by letting go.
If everything depends on you, nothing can scale beyond you.
Why Delegation Creates More
Delegation is the ultimate multiplier. With five direct reports, your 40-hour week becomes 240 hours of output. Add another layer of leadership, and your influence scales into thousands of hours, without you working a minute more.
That’s why the most effective leaders don’t ask, “How much can I do?” They ask, “How far can my time multiply?”
Howard Schultz didn’t build Starbucks by managing every store. Sara Blakely didn’t grow Spanx by writing every ad. Reed Hastings didn’t scale Netflix by answering customer calls. They scaled their vision through leaders who multiplied their time.
In my work coaching leadership teams, I’ve found the ones who succeed all commit to four disciplines:
Protect Your Work Container
Know Your Best & Highest Use
Become Fanatical About Letting Go
Be Courageous
Step 1: Protect Your Work Container
Your energy is a container. Once it’s drained, you’re done.
Gino Wickman calls this your work container: the maximum number of hours you can give to work each week without burning out. Push past it too long, and the results are predictable:
Burnout that bleeds into every part of your life
Commitments you can’t keep
Work that slips from excellent to average
So here’s the real question: what’s your number? 40 hours? 55? 65? Whatever it is, that’s your 100%.
But clarity alone isn’t enough. Your container has to align with reality. If your true capacity is 40 hours but your role demands 60, that tension won’t fix itself. You either reset expectations, or change the role.
And remember: life isn’t just about work. You need space for what recharges you — family, health, passions, community. As Gino says, “We are all just balls of energy. Some of us burn brighter than others.”
What’s your work container? Does it truly align with your role and your life?
Step 2: Know Your Best & Highest Use
Frank Sinatra’s highest use was simple: to sing. He didn’t move pianos or tune instruments. He prepared to sing and he sang. That’s what made him great.
For me, it’s helping leaders turn vision into reality. That’s why I’ve delegated almost everything else — marketing, bookkeeping, scheduling, even email.
Dan Sullivan calls this your Unique Ability: the intersection of what you do best and what you love. This is the work that gives you energy and creates the most impact. When you operate in that zone, your performance and fulfillment skyrocket.
If you’re unsure, two tools can help:
EOS Delegate & Elevate™ — clarifies what to keep, delegate, or drop.
Strategic Coach’s Unique Ability® — reveals your sweet spot of energy and impact.
Here’s the litmus test:
Work in your Unique Ability → you end energized, wanting more.
Work outside it → you end drained and frustrated.
The leaders who scale protect their highest use relentlessly and design everything else around it.
Step 3: Become Fanatical About Letting Go
Once you know your best and highest use, the next discipline is clear: let go of everything else.
This is where most leaders stall. They know what drains them but they keep holding on, out of habit, fear, or control. To break through, every activity outside your Unique Ability needs to go down one of three paths:
Stop. Some activities simply don’t matter anymore. We keep doing them out of habit. Like the family who kept cutting the ends off the pot roast until they realized it was just to fit grandma’s small pan. If it doesn’t add value, stop.
Automate. If it does add value, ask if technology can handle it — templates, formulas, AI, automation. And if you don’t know how, don’t learn. Find the right person who does.
Delegate. What’s left should go to someone else: a team member, a partner, or a new hire who creates capacity for the whole team.
This was the playbook at a fast-growing SaaS client I coached. Every quarter, the founders asked: What are we still holding onto that someone else could own? And then they let it go. That shift turned two founders doing it all into a true leadership team and unlocked their next stage of growth.
Delegation isn’t losing control. It’s multiplying it.
I’ve become fanatical about this discipline myself. Every quarter, I review my own activities and let go of anything outside my Unique Ability. And without exception, the leaders I coach who commit to the same mindset are the ones who grow the fastest.
But knowing what to let go of is only half the battle. The real challenge is having the courage to actually do it.
What are you still holding onto that someone else could own?
Step 4: Be Courageous
Even with a clear work container and a defined Unique Ability, many leaders still struggle to let go. Why? Because delegation is simple, but not easy.
Early in my career, when direct reports dropped the ball, I picked it up. I told myself I was being helpful. In truth, I was avoiding tough conversations. I was doing my work and theirs. That cycle doesn’t scale.
Courage is what breaks it. It takes courage to hand off responsibility and let someone else truly own it. It takes courage to delegate, watch it fail, and try again. Sometimes it won’t go well. Maybe it wasn’t the right person. Maybe expectations weren’t clear. That doesn’t mean delegation doesn’t work. It means you’re learning. The more you practice, the better you get, and the more trust you build in your team.
VenturaX’s founders leaned into this. They didn’t just delegate tasks, they had the courage to hire strong leaders, trust them fully, and make hard changes when needed. They delegated authority. That’s what turned a two-person startup into a $150M company.
The opposite is just as real. Leaders who cling too tightly — rewriting their team’s work at night, inserting themselves into every decision, quietly undoing what others try to own — end up exhausted, with a frustrated team and a business that can’t grow beyond its bottleneck.
Often, the barrier isn’t your team at all. It’s your own fear of losing control or being seen as less valuable. Those fears stall leaders as much as any external obstacle.
The truth is this: believing certain activities “can’t be delegated” guarantees you’ll stall. As Henry Ford said, “Whether you think you can, or you think you can’t — you’re right.”
Delegation is the multiplier. Courage is what unlocks it.
The Leader’s True Job
Recently, I had lunch with a founder who had just sold his company after scaling it to around $250M in revenue. I asked him what shifted most as the business grew. His answer was simple and profound:
“I finally stopped trying to do everyone else’s job.”
That’s the essence of leadership. Not doing more, but multiplying more.
Peter Drucker was right: “Do what you do best, and outsource the rest.” Sinatra showed it on stage. And countless leaders have proved it in the real world.
The highest job of a leader isn’t to carry everything. It’s to create the conditions that let your time, your people, and your vision scale far beyond what you could ever carry alone. That’s what separates leaders who stay stuck from those who build enduring companies.
The choice is always the same: cling to more, or multiply through others.
So here’s the challenge: Where will you multiply this quarter?
Footnotes & Sources
*Note: “VenturaX” is a pseudonym for a real client example, shared with permission.
Peter Drucker, Management Challenges for the 21st Century (HarperBusiness, 1999).
Catherine Nomura, Julia Waller, and Shannon Waller, Unique Ability® 2.0: Discovery (The Strategic Coach Inc., 2015).
Gino Wickman, “Official Website,” available at: https://ginowickman.com.
EOS Worldwide, “Delegate & Elevate™ Tool,” available at: https://www.eosworldwide.com.
Strategic Coach, “Unique Ability® Resources,” available at: https://www.strategiccoach.com.
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