Tim FerrissUltimate Guide to Managing Executive Assistants and Delegating Like a Pro — Sam Corcos (4K)
CHAPTERS
- 0:15 – 0:48
Delegation origin story: hiring an EA before having work for them
Tim Ferriss sets the goal of creating a comprehensive tactical guide to delegation. Sam Corcos explains he started taking delegation seriously after reading Tim’s book, posting a Craigslist ad for an executive assistant, and then figuring out what to hand off once she started.
- •Sam hired Lori as an EA about 10 years ago after reading Tim’s book
- •He initially had “nothing for her to do” and had to proactively find tasks to delegate
- •Example of leverage: capturing gift ideas throughout the year so holiday gifting is handled end-to-end
- •Delegation is treated as a skill to develop, not something you wait to need
- 0:48 – 6:39
Why delegation fails: bad matches, imposter syndrome, and avoiding busywork
Sam and Tim unpack common reasons people don’t delegate or give up after trying. Sam highlights mismatch as a major factor, along with psychological barriers like imposter syndrome and the temptation to create low-value busywork just to fill an assistant’s time.
- •A single bad experience often reflects inexperience or poor fit, not that delegation “doesn’t work”
- •Sam describes rematching EAs at Levels and gives an example where a second match doubled output and reduced stress
- •Imposter syndrome can block delegation; Sam suggests reframing delegation as trust and growth opportunity
- •If work is light, don’t invent busywork—explicitly give lower workload weeks, reading, or time off
- 6:39 – 9:02
Reading that supports culture and communication (and process-minded delegation)
Tim asks for recommended books for employees and assistants. Sam shares the company’s strongly recommended reading list and discusses why some communication frameworks matter broadly, plus a process-oriented book that can help assistants.
- •Levels runs a monthly team book club and cycles books over time
- •Sam cites titles the team revisits, including books on culture, leadership, and communication
- •Sam argues one of the communication books should be “required reading for all humans,” despite an off-putting title
- •For EAs specifically, Sam suggests process-oriented reading such as a checklist-focused book
- 9:02 – 16:44
Treating people like adults: transparency, closing loops, and recordings to reduce gossip
Sam explains Levels’ unusually transparent operating style and what “treat people like adults” means in practice. The conversation digs into communication as performance, the value of recording meetings, and how sharing recordings can act as an anti-gossip mechanism.
- •Levels publishes investor updates and weekly all-hands recordings publicly, emphasizing transparency
- •Sam defines culture as the assumptions you can make about coworkers without having met them
- •“Closing the loop” reduces exhausting open loops; sending explicit completion messages is part of the norm
- •Sam says “a lack of communication is a lack of performance,” making communication integral to accountability
- •Recording and sharing meetings (including one-on-ones by default) is framed as first-person context sharing and a forcing function against gossip
- 16:44 – 23:35
Loom as an async leverage engine, plus the Friday Forum all-hands format
Tim and Sam focus on Loom and why Sam considers it uniquely high-leverage for remote work. Sam ties Loom to the idea that content scales while time doesn’t, and then describes Levels’ weekly all-hands (Friday Forum) and its intent.
- •Sam calls Loom a top business enablement tool due to low-friction screen + video async communication
- •Sam contrasts “content scales, time does not,” and compares early Loom usage to early radio copying theater
- •Async recordings enable replay, speed-up viewing, pausing, rewinding, and reuse as durable content
- •Friday Forum is the weekly all-hands with an explicit intent: celebrate wins and highlight progress
- •Friday Forum structure includes weekly highlights, a customer/member guest, team updates, and personal highlights
- 23:35 – 33:13
Getting people comfortable on camera: one-take rule, async week, and workflow recordings
Sam addresses the discomfort many people feel recording Looms and how Levels trains the habit. He describes an onboarding “async week” where employees must communicate via audio/video only, and explains workflow recording as a core delegation accelerator.
- •Sam pushes a “one take only” norm to prevent perfectionism and over-recording
- •Levels uses an onboarding week where employees can’t type—only audio/video communication is allowed
- •Sam argues medium should match message: writing for long memos, Loom/audio for other contexts
- •Workflow recording: turn on Loom and do normal work to reveal delegable patterns
- •Example: recording editing workflows helped show tasks were more replicable than assumed
- 33:13 – 44:49
Sourcing EAs and structuring support: agencies, pools, and EA vs. chief of staff
Tim asks about sourcing EA talent and how Levels organizes assistants across the company. Sam compares agency sourcing versus direct sourcing, explains an EA pool model, and clarifies the difference between EAs and chiefs of staff using a declarative vs. imperative spectrum.
- •Sam prefers sourcing through an agency and names the agency Levels uses
- •He contrasts agency cost versus sourcing directly (including platforms and lower-cost approaches)
- •Levels uses an EA pool for shared capacity, with increasing dedication as context needs grow
- •Time zones can be a challenge, and Sam notes how some assistants align with US hours
- •EA work is framed as more imperative/routine and well-defined; chief of staff work is more declarative/problem-solving and project-oriented
- 44:49 – 51:58
Delegation boundaries and attention hygiene: Slack as a “slot machine” and news sobriety
The conversation pivots to attention management and why certain tools create compulsive checking. Sam describes avoiding Slack-style dopamine loops and then outlines his long-term “news sobriety,” including how it changed his reading habits and anxiety levels.
- •Sam criticizes Slack as creating a compulsive dopamine loop similar to social media
- •He references a study about frequent checking of communication tools and its impact on focus
- •Sam describes a month-long experiment of consuming no current events and replacing it with books
- •He reports reading eight books in that month and feeling less anxious physically and mentally
- •Sam argues the news industry persuades people that constant news consumption equals responsible citizenship
- 51:58 – 1:05:31
Onboarding done deliberately: templates, cultural assimilation, and fighting organizational entropy
Tim returns to onboarding quality and how Levels structures it as a month-long process. Sam details checklists, weekly guidance videos, required updates to onboarding materials, and the concept of “organizational entropy” that makes maintenance a permanent obligation.
- •Levels uses a month-long onboarding and does not expect new hires to produce for a month
- •Onboarding is driven by a Notion checklist template copied for each new hire
- •Sam records weekly Looms warning new hires not to skip onboarding despite impatience to start working
- •New hires must update onboarding documentation at the end, reinforcing that processes are editable
- •Sam frames artifacts as immediately “rotting,” requiring reinforcement mechanisms to counter entropy
- 1:05:31 – 1:37:48
Time management without a to-do list: putting tasks directly on the calendar
Sam explains his core time-management shift: using the calendar as the to-do list. He describes why to-do lists hide the real constraint (finite time), why slack time is necessary, and how recurring blocks and meeting batching make scheduling feasible.
- •Sam describes converting tasks to calendar blocks to reveal that the week can’t hold the whole to-do list
- •He recommends leaving significant “slack” time (initially around 50%) to prevent cascading schedule failures
- •Sam says he skips the to-do list entirely by placing new tasks straight onto the calendar
- •He batches meetings heavily on Mondays, keeping Tue–Thu mostly open for deep work
- •He suggests retroactively updating calendar estimates to improve time prediction accuracy over time
- 1:37:48 – 1:44:09
Calendly, inbox zero, and speed via hotkeys and snippets
Tim and Sam cover scheduling automation, social friction around calendar links, and reducing stress from email overload. Sam outlines an inbox-zero approach supported by assistants, and explains why hotkeys and reusable snippets are among the easiest productivity wins.
- •Sam describes Calendly syncing with Google Calendar and blocking availability based on scheduled work
- •He views sharing a scheduling link as giving others access to his time, though he notes some find it offensive
- •Sam aims for inbox zero weekly and uses assistants to move low-priority mail into a ‘not important’ bucket
- •He uses Loom feedback to train assistants’ filtering accuracy over time
- •Sam emphasizes hotkeys/shortcuts and snippets as “free productivity,” and gives examples from reviewing a co-founder’s email workflow
- 1:44:09 – 1:51:36
What four EAs actually do: call prep, social inbox triage, semi-automation, and time tracking
Tim presses for concrete examples of how Sam uses multiple assistants without creating unnecessary overhead. Sam describes repeatable behind-the-scenes systems for call preparation, message triage, and tracking how his time is spent so priorities can be audited and adjusted.
- •Sam maintains call notes and context pages assembled by assistants ahead of meetings
- •Assistants manage and triage LinkedIn messages and Twitter DMs, escalating only what matches criteria
- •Sam describes “semi-automation”: assistants propose actions via screenshots and drafts, and he approves most
- •He tracks time in categorized 15-minute blocks, with assistants maintaining the record and summaries
- •Sam argues the calendar is the empirical record of priorities, often revealing mismatches with stated values
- 1:51:36 – 1:58:57
Leveling up as an intermediate delegator: feedback loops, visibility, and parallel tasking
Sam shares patterns he sees when people have some delegation experience but aren’t getting full leverage. He stresses creating feedback loops and visibility into what assistants do, and explains “parallel tasking” as a way to reduce perceived risk while increasing trust and capability.
- •Sam describes a teammate who underestimated EA value until reviewing a database of ongoing tasks
- •He argues artifacts and celebrating wins help prevent people from forgetting behind-the-scenes leverage
- •Parallel tasking: have an EA or chief of staff draft alongside you, without putting them on the critical path initially
- •Concrete example: creating a slide deck in parallel to avoid last-minute quality surprises
- •Concrete example: an engineer wrote a retro while an EA drafted one from daily async updates, revealing how much could be offloaded
- 1:58:57 – 2:14:52
Working-with-me manuals and memo culture: how writing enables trust and decisions
Tim and Sam discuss creating “user manuals” for working effectively with individuals, then shift to Levels’ preference for memos over meetings. Sam argues writing clarifies thinking, preserves decision context, and is used as a test of competence and trust—sometimes requiring very long documents for high-stakes decisions.
- •Sam says Levels uses “user guide” docs and requires new hires to write one by the end of onboarding
- •He shares personal preferences included in his guide, such as minimizing interruptions and protecting deep work
- •Sam reframes his discipline as externally scaffolded structure rather than innate willpower
- •Memo culture is justified by the claim that writing is thought; meeting transcripts yield surprisingly little usable output
- •Long-form strategy memos are used to evaluate functional leaders and to justify high-impact decisions
- 2:14:52 – 3:00:19
Exploration year, truth debates, network theory, Levels origin story, and minimalist living
Sam describes taking time off to study theology and network/graph theory, and how those studies reshaped his respect for religion and his thinking about truth and postmodernism. The conversation then touches the early investor “juice cart” demo that helped validate Levels, before closing with Sam’s pragmatic minimalism, focus goggles, and why he carries a pocket Constitution.
- •Sam explains his theology study came from noticing highly intelligent friends who were also religious and wanting to understand what he was missing
- •He describes separating religion into community/ritual versus spiritual belief, and how epistemology led him to question objective truth and worry about postmodern outcomes
- •Sam defines network theory vs graph theory and describes focusing on weak ties and eigenvector centrality to expand access to new dense networks
- •He tells the “Health Drink” juice-cart demo story where a glucose spike helped investors viscerally understand the product’s feedback loop
- •Sam describes extreme practical minimalism (very few possessions), his custom “focus goggles,” and carrying the U.S. Constitution as a reminder and an organizational design artifact
