Executive Workflow Optimization: Tim Ferriss X Sam Corcos
I watched the this 3-hour Tim Ferris Podcast episode. Here are 5 lessons from Sam Corcos on executive workflow optimisation that can help you become a more productive Executive Assistants.
If you’re an executive assistant like me looking to become a Chief of Staff (CoS), working with a highly systematic executive like Sam Corcos (Co-founder and CEO of Levels) will be life-changing.
From this podcast episode with Tim Ferris, you can almost see how systematised he is. You have to learn to think and work like him to earn his trust and become a Chief of Staff. This article is an opportunity to deepen my learning by sharing the top five takeaways from the conversation, which will help me improve my work.
From the show, I learned that the bar goes beyond merely being organised or on top of things. That’s the benefit of learning about how to be a great EA from an executive. You’re learning from a horse’s mouth. Sam says that it’s about creating and maintaining high-leverage systems that safeguard the executive’s focus, amplify their impact, and lessen reliance on personal heroics.
Wait a minute: It is important to understand the key difference between an EA and a Chief of Staff. I think:
An EA is usually responsible for imperative work: the executive tells you exactly what to do, and you do it (schedule this, book that, send this).
A CoS is responsible for declarative work: the executive tells you the outcome they want, and you figure out how to get there.
Lesson 1: Treat the calendar as the command centre (not a to-do List)
The most important tactical shift in Sam Corcos’s system is simple but radical: stop using a to-do list. Instead, treat the calendar as the definitive record of commitments.
Most people are overly optimistic about what they can get done. A long to-do list feels productive, but time is finite. The EA’s job is to apply time constraints to everything.
When you adopt this mindset, the calendar becomes the operational heart for your executive.
In practice:
Immediate triage and time estimation: When a task is created (typically via email, Slack, or a comment), the EA or executive immediately estimates how long it will take. No vague “I’ll get to this later.” Every task must have a rough time budget.
Calendar slotting: Once the time estimate is finalised, you block the time on the calendar. For larger items, the calendar event should include:
A link to the originating email, Loom, or doc
A short description of the intended outcome
This prevents the executive from re-reading threads and re-building context. When they open the block, everything they need is already there.
Mandatory slack time: Without it, the calendar is just a Tetris. One unexpected look at Slack and everything collapses. Sam recommends starting by targeting approximately 50% open time, then using data and practice to gradually reduce it to approximately 25% as your time estimation improves.
This slack is not “wasted time.” It is the shock absorber that:
Absorbs emergencies and overruns
Prevents cascading failures
Protects focus blocks and writing time
Why this matters for my CoS journey: When I run the calendar as a command centre, I’m actively shaping the executive’s priorities and attention. I go from reactive calendar manager to architect of how the executive spends their most precious resource: time.
Lesson 2: Use Loom to turn work into scalable raining
If you’re working remotely, the most powerful thing you can do is leverage one-off actions into reusable assets. This is where Loom (or any async video tool) comes in.
Sam Corcos calls Loom “the most important business-enablement tool of the last five years.”
Let that sink!
Why?
Because it lets people capture:
The screen (clicks, navigation)
The voice (tone, nuance)
The context (why, not just what)
Instead of writing step-by-step instructions from scratch, you record real work while it is happening.
How does this work:
Zero-effort training:
When delegating a task, the executive or the EA (in case you’re sharing with other EAs or handing over to another EA) turns on Loom and simply does the task while narrating:
What they are doing
Why are they doing it and
What good looks like
How this helps:
The video becomes:
A reusable training asset
A permanent reference for future hires
A concrete example of how the executive thinks
Record in “one-take”:
To avoid perfectionism, treat Loom like a conversation. No editing, no retakes unless absolutely necessary. If there are mistakes, pauses, or restarts, that is completely fine. The goal is speed and volume of captured knowledge—not production-quality media.
Never mind that some people hate voice notes but many teams even run “async weeks” where people are required to use video and voice notes to overcome discomfort, so recording Looms becomes second nature.
Use parallel tasking to build trust:
One of the most powerful patterns for delegation is parallel tasking:
The executive completes the task as usual (e.g., assembling a weekly investor update or an internal forum message) and records a Loom recording.
The EA simultaneously replicates the process and sends the output only to the executive, not to the complete distribution list.
Sam says that after a few cycles of correctness, the executive can hand off the task entirely. This is a much more effective learning method for me, as I think it will be for other EAs, because nothing tops seeing someone do exactly what they want you to do and explain as they work.
Lesson 3: Fight organisational entropy with living documentation
Sam Corcos says that documentation begins to expire the moment it is created. It is organisational entropy: the natural decay of processes and knowledge.
Both EAs and CoS are responsible for fighting this entropy. Our job is not just to “write docs once” but to keep them alive.
In practice:
Centralise the knowledge base
Use a tool like Notion (or its equivalent) for:
Processes and SOPs
Onboarding flows
Strategic memos
Checklists and recurring workflows
Scattered Google Docs and random files guarantee entropy. Centralisation is the first step toward control.
Link “proof of work” to documentation
Documentation is most valuable when it is connected to real examples. For every process, link:
The relevant Loom(s) showing the process executed
Recent artefacts (emails, decks, reports) produced using that process
When something breaks, or a task is done incorrectly, you can go back and “debug” the process:
Was the documentation unclear?
Was the Loom outdated?
Was the person following an old version?
Instead of just fixing the one mistake, you fix the system.
Make documentation maintenance a cultural norm.
At Levels, new employees are expected to update any onboarding docs they find to be wrong or outdated. The mindset is: every new document, process, or page is an ongoing obligation to maintain.
As an EA or emerging CoS, you can:
Add a “Last reviewed” field to key pages
Create recurring review tasks on the calendar
Ask, “Where should this live?” any time a new artefact is created
Analogy: the librarian of the organisation
Think of the organisation’s knowledge as a library. Without a librarian:
New books get dropped anywhere
The catalogue quickly becomes wrong
People stop trusting the system and start asking the same questions over and over
As the EA/CoS, you are the librarian adding energy to the system. You:
Make sure each “book” (process) has a place
Keep the catalogue (Notion) accurate
Ensure people can actually find and use what already exists
Lesson 4: A lack of communication is a lack of performance
Sam also says:
It is not enough to quietly do great work; the loop must be closed.
Executives carry heavy cognitive loads. Every open loop—every “I wonder if that got done?”—burns mental energy and undermines trust. It’s our job as EAs to remove that burden.
How does this work?
Always close the loop.
Any time you complete a task, send a short, clear update:
“Done – here’s the link.”
“Completed X. Waiting on Y from Z, will update by [date].”
What it does:
Reassures the executive
Eliminates mental reminders
Demonstrates reliability
If you don’t close the loop, even once, it can cause the executive to second-guess future delegation. Trust is built slowly and broken very quickly.
Use “playback” to confirm understanding.
When you receive a new task—especially a complex or ambiguous one—reply with a concise playback:“Here’s what I heard: You want [outcome] by [date]. My plan is to [approach]. I’ll send you [artifact] to review.”
This simple habit:
Surfaces misunderstandings early
Shows that you’re thinking about the how, not just the what
Moves you toward the declarative side of the spectrum (owning outcomes)
Manage the executive’s information inputs
Part of radical accountability is protecting the executive from noise. This can include:
Inbox triage: filter newsletters, low-value threads, and FYIs into separate folders. Flag only what needs a decision, reply, or deep read.
Semi-automation of social channels: you monitor LinkedIn, X, DMs, and prepare suggested responses. The executive’s job becomes simple: approve, tweak, or ignore.
Over time, as you learn their voice and preferences, you can draft near-final responses and handle entire classes of messages on their behalf.
Create and maintain a “Working With X” manual
A “Working with [Executive’s Name]” document clarifies:
Communication preferences (async vs sync, emergencies vs non-emergencies)
Meeting norms (when interruptions are okay and when they are not)
Decision-making style (data-heavy, principle-first, memo-driven, etc.)
What “good” looks like in updates and escalations
You can also create your own “Working with Me as Your EA/CoS” manual. This sets expectations and shows you’re thinking about the relationship as a system. It will also help the company avoid failing to onboard new hires effectively.
Lesson 5: Build a memo-first culture
Lastly, Sam Corcos says:
If you cannot write out your ideas, you do not have coherent thoughts.
For Sam, serious decisions demand serious writing.
Memos replace hand-wavy conversations with durable, clear thinking.
In practice:
Memos over meetings
For major decisions, strategy shifts, or new initiatives, long-form memos (typically 10–40 pages) are preferred to meetings. A memo forces:
Calm, structured thinking
Tradeoffs and risks to be written down
A record that can be revisited months or years later
Meetings can still happen, but they become memo reviews rather than brainstorming sessions without a foundation.
Writing as a way to earn confidence
Sam often says that leaders “earn trust” not through charisma but through clear written strategies. The same is true for an aspiring CoS like me:
Write out how you would design a new process.
Summarise a complex conversation into a one-page decision memo.
Draft the first version of strategic docs for the executive to refine.
When your writing consistently makes the executive’s thinking easier and sharper, you signal that you are ready to operate at a higher level.
Protect “maker time” on the calendar.
High-quality writing requires uninterrupted focus. As the EA:
Block out large, recurring writing blocks for the executive.
Protect that time as fiercely as you would an investor meeting or a board call.
Add context to each calendar block, indicating which memo or topic it covers.
You can also recommend “Think Weeks” or deep-work days where meetings are minimised or cancelled, and the agenda is mostly reading and writing.
Turn raw thoughts into structured drafts.
Many executives find it easier to talk than to write. Here is where you can add enormous leverage:
Ask the executive to record a Loom or voice note where they “brain dump” ideas.
Transcribe and organise the content into an outline, then a rough memo.
Highlight open questions and assumptions so they can respond.
Instead of facing a blank page, they now react to something that already has structure. You have effectively moved from “assistant” to “thought partner.”
Putting it all together
These five lessons—calendar-as-command-centre, Loom-powered training, rigorous documentation, radical communication accountability, and memo-centric strategy— represent a mindset shift.
You are:
Designing and enforcing systems
Turning work into reusable assets
Shaping strategic thinking through writing
Fighting entropy so the organisation can scale
Owning communication and trust with the executive
Start with one pillar.
Make the calendar truly accurate.
Or commit to capturing three Looms per week. Or pick one messy process and document it properly, linking a Loom and real artefacts.
As you stack these systems, you will find that your relationship with your executive changes. They will start asking not just “Can you do this?” but “How do you think we should handle this?”
Executive assistants who function using these methods are invaluable. It’s why Sam Corcos said he had four at the time of this interview, and it’s why they have a solid pool of EAs at Levels.
P.S. If you want to watch me write this live, here.