How I Delegated Email (and Reclaimed Six Weeks a Year)
“What you don’t do determines what you can do.”
— Tim Ferriss
The Inbox Illusion
A few years ago, I realized I was spending nearly an hour a day in my inbox. That is six full weeks a year. And for what?
At the time, it felt like leadership. I was responsive. Informed. On top of things. But the truth was, I was not leading. I was reacting.
My inbox had become a scoreboard for busyness, not effectiveness. Every message was a tiny dopamine hit, a problem solved, a question answered, proof I was needed. But when you zoom out, you see the cost: six weeks spent inside other people’s priorities instead of advancing my own.
In The Delegation Dilemma, I wrote that most leaders struggle to let go because control feels safe. For me, the biggest test of that came in my inbox.
Delegating email was not about saving time. It was about reclaiming my focus, energy, and impact: coaching leadership teams, building this platform, and showing up fully for the people who matter most.
Trust Over Control
For years, I understood the logic of delegating email. I had worked with assistants before, mostly to manage the basics: cleaning spam, flagging urgent requests, organizing messages into folders. It helped, but I was still the bottleneck. Worse, I was still chasing inbox zero, a more streamlined version of the same problem. My time was still being driven by the requests of others.
Around that time, I was seeking ways to maximize my energy and impact. I had known Gino Wickman, creator of EOS and author of Traction, since 2017. I reached out for tips, and he sent me a draft of what would become The 10 Disciplines for Managing and Maximizing Your Energy, material he had used in a speech earlier that year and would later be included in The EOS Life. I devoured it. The ideas reshaped how I thought about focus, leverage, and where to deploy my time.
One principle stopped me cold: "Don't do $25 work."
This was never about literal wages or devaluing anyone's work. The phrase is about relative value and leverage. Depending on your role, your “$25 work” might actually be $50, $100, or $500 an hour. The principle is the same: certain work creates exponential impact and certain work does not.
Every minute I spent cleaning my inbox was a minute I was not coaching leaders, building this platform, or creating something that multiplied value for others.
When I asked Gino how he managed his time, he told me something that changed everything: he had fully delegated his email.
Then, in true Gino fashion, he delegated the explanation to Karen, the person who actually runs his system. She walked me through how they worked together, the trust they built, and the structure that made it possible.
That conversation became the blueprint. What follows is the system I built from it.
The System That Changed Everything
Once I understood the principles behind delegating email, the next step was building a system that worked for me and my team. The goal was simple: protect my focus, keep me informed, and ensure that every client or partner received timely communication.
Ciella, my Practice Manager, monitors my inbox throughout the day. Every message falls into one of three categories:
1. Junk
She deletes these automatically. Simple, obvious, and one less distraction I never have to see.
2. Emails She Can Handle
Most messages are administrative: scheduling, rescheduling, requesting documents, answering simple questions, or clarifying logistics. She replies immediately.
If it is administrative, she responds as herself.
If it requires my tone or personal continuity, she responds as me.
Some leaders worry this is misleading. It is not. She is an extension of my judgment, trained in my voice, and every response reflects alignment, not fiction.
3. Emails That Require My Input
When something needs my perspective, she flags it and brings it to me through our communication cadence.
How I Stay In the Loop
One of the biggest misconceptions about delegating email is that you will be out of touch. The opposite is true.
To keep me informed without interrupting my focus, we follow a simple cadence:
Twice a day, I receive a text or voice memo from Ciella that includes:
Important updates
New inquiries
Calendar changes
Anything else I should be aware of
It takes less than a minute to read or listen, and I am completely up to speed. If she needs my input, I respond with a quick voice memo. She uses that guidance to reply on my behalf.
When something requires nuance, when a client needs deeper insight or a live conversation would be faster than typing, I simply say:
“Have them call me.”
“I will call them this afternoon.”
She sets it up, and I handle it directly. Complex conversations stay where they belong: outside the inbox.
Training the System (and the Person)
When we first started, we met twice a day to process emails together. If Ciella was unsure how to respond, I coached her. She typed the reply, learned the thinking behind it, and within a week or two she was off to the races.
Over time, her confidence grew and my involvement decreased. The more clarity and trust we built, the fewer decisions needed my time.
Of course, none of this works without the right person in the role. Trust is the foundation. I am fortunate that Ciella and I have a deep level of trust and respect. If you do not have the right person, start there. The system works because the trust does.
The First Week Was Uncomfortable
The first few days felt strange. I would open my laptop in the morning and instinctively reach for my inbox, only to remember it was no longer mine to manage.
By day three, I caught myself checking just to make sure nothing was falling through the cracks. Nothing was. Ciella had it covered.
That is when it clicked. The discomfort was not about the system. It was about letting go of the identity that came with being the person who was always on top of everything.
Once I named that, the tension dissolved. My focus sharpened. And I stopped checking.
Why This System Works
1. I Stay Out of My Inbox
This is the biggest win. I avoid the trap of reacting to other people’s priorities or getting pulled into distractions like the weekend J.Crew sale email sitting in my inbox. We have all been there.
2. Communication Is Faster for Everyone
If a prospective client reaches out while I am in an all-day session, I might not reply until evening. They respond the next morning while I am coaching another team. Two days gone over a simple scheduling request.
With Ciella managing everything, I often have an intro call booked for my drive home the same day the inquiry comes in.
Clients move forward faster and momentum stays alive.
3. I Deploy My Energy Where It Has the Most Impact
Every minute I am not in my inbox is a minute I can invest in coaching leaders, writing Simple Leadership, or being fully present with my family.
4. Issues Get Solved at the Right Altitude
Simple things no longer consume my time. Complex things no longer drag on through email. A scheduling question gets resolved in minutes. A strategic conversation happens live, not in a twelve-email thread. Everything gets handled at the level it deserves.
5. Trust Compounds
The more we worked this system, the more capable Ciella became and the more leverage I gained. What started as delegation grew into true partnership.
Today, I do not author more than a few emails a year, usually when Ciella is taking time off.
What Happened When One Leader Let Go
One founder I work with recently told me he is now so far out of the day-to-day that he is wrestling with a new question: “What is the best use of my time?”
He started by delegating his inbox. Then he let go of operations. Then he shed the work that kept him reactive instead of strategic.
Today he has answered that question. He spends his time as the visionary, building the relationships that create opportunity and driving growth for the firm.
That is not a problem. That is progress.
When leaders let go of the work that does not need them, they create space for the work that does. The inbox was only the beginning.
The Role of AI (and Why I Am Not Using It Yet)
People often ask, “Why not use AI to manage your inbox?”
It is a fair question. AI is already impressive at triaging messages, summarizing threads, and drafting responses. For some leaders, that may be enough.
But here is what AI cannot do yet: understand context, read tone, manage relationships, and make judgment calls in real time.
Email is not just information. It is nuance, history, timing, and judgment. It is knowing who is asking, why they are asking, what they really mean, and how a response will land.
Until AI can consistently deliver that level of understanding, I am sticking with something far more reliable: Ciella Intelligence.
One day, AI will manage a significant portion of what she handles today. When that happens, it will not replace her. It will free her to focus on even higher-value work: improving the client experience, refining our systems, and helping scale Simple Leadership.
AI is not the end of human leverage. It is the next chapter of it.
The Bottom Line
Delegating email taught me something I wish I had learned years earlier: freedom is not found in doing more. It is found in doing less, better.
The moment I stepped out of my inbox, my ability to lead expanded.
My impact expanded.
My energy expanded.
If you want to lead at a higher level, the question is not:
“How can I manage my inbox more effectively?”
It is:
“What am I holding onto that someone else could own better?”
Let go of the work that drains you.
Double down on the work that moves you forward.
The next version of your leadership lives on the other side of that choice.
Sources & Footnotes
1. Wickman, Gino. Traction: Get a Grip on Your Business. BenBella Books, 2007.
Referenced as the foundational EOS text and part of Josh’s long-standing relationship with Wickman's teachings.
2. Wickman, Gino. The EOS Life: How to Live Your Ideal Entrepreneurial Life. BenBella Books, 2021.
Referenced for containing the first published version of The 10 Disciplines for Managing and Maximizing Your Energy.
3. Wickman, Gino. The 10 Disciplines for Managing and Maximizing Your Energy.
Originally delivered as keynote content at various EOS and entrepreneurial events beginning in 2019, later published within The EOS Life. Referenced as the source of the “Don’t do $25 work” principle.
4. Ferriss, Tim. The 4-Hour Workweek. Crown Publishing, 2007.
The quote “What you don’t do determines what you can do” is attributed to Ferriss, widely cited in productivity and leadership literature.
