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Ultimate Guide to Managing Executive Assistants and Delegating Like a Pro — Sam Corcos (4K)

Brought to you by: AG1 all-in-one nutritional supplement https://drinkag1.com/tim Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business https://shopify.com/tim Resources from this episode: https://tim.blog/2023/09/20/sam-corcos/ Sam Corcos is the CEO and Co-founder of Levels, an a16z-backed startup that shows you how food affects your health using continuous glucose monitors and other biosensors. Levels: http://levelshealth.com/ Levels on YouTube: https://www.youtube.com/c/LevelsHealth [00:00] Intro [00:17] Delegation implementation and common mistakes. [06:37] Recommended reading for delegators, delegatees, and all humans. [09:05] Building a company culture that treats people like adults. [10:54] Tools for performance and communication accountability. [16:35] Why Sam considers Loom the “most important” tool in the kit. [20:20] Friday Forum. [23:34] Acclimating the recording-averse to Loom. [27:05] Organizing Loom recordings for later search and use. [33:18] Common challenges of sourcing and properly utilizing EAs/chiefs of staff. [39:14] Novelty-seeking and board games. [40:19] Vetting, pairing, and onboarding EAs and chiefs of staff. [44:51] News and social media sobriety. [51:57] Why does new employee onboarding take a month at Levels? [57:52] What most delegators wish they’d known as newbs. [1:02:09] Loom security and privacy concerns. [1:05:32] From to-do list to calendar. [1:10:53] How Sam skips the to-do list entirely. [1:14:31] General schedule and repeating items. [1:16:12] Scheduling stress reduction. [1:20:12] Selecting books and hosting themed salon dinners. [1:36:04] Calendly and related social hurdles. [1:37:50] Using email proactively. [1:40:42] The underrated power of hotkeys and shortcuts. [1:44:08] Scheduling spontaneity. [1:48:00] Calendar course correction. [1:49:40] How Sam utilizes multiple EAs. [1:51:37] Improvement growth for intermediate delegators. [1:58:58] The Working with Sam user manual. [2:04:33] Memo culture over meeting culture. [2:12:32] Fighting organizational entropy. [2:14:53] Raised secularly, what does Sam get out of theology? [2:24:02] The perils of postmodernism. [2:27:32] Network theory and relationship management. [2:42:00] The investor-swaying juice cart moment. [2:43:35] Metabolic health and the Levels mission. [2:47:52] Who is Levels hiring right now? [2:49:00] Physical over philosophical minimalism. [2:54:11] Why Sam has a travel-sized copy of the US Constitution. [2:58:16] Parting thoughts. Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

Tim FerrisshostSam Corcosguest
Sep 20, 20233h 0mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Sam Corcos’s systems for delegation, Loom workflows, and adult culture

  1. Sam Corcos describes a long-term, systematic approach to delegation that began with hiring an EA before he had clear tasks and improved through deliberate experimentation and feedback loops.
  2. He explains how Levels reinforces a “treat people like adults” culture with explicit norms like closing the loop, equating communication with performance, and routinely recording (and often sharing) meetings to reduce gossip and preserve context.
  3. He argues Loom enables scalable, asynchronous training and coordination, especially through one-take workflow recordings that let others replicate work without heavy documentation.
  4. He outlines practical time management via converting tasks (and even emails) directly into calendar blocks with intentional slack, using the calendar as the true constraint on commitments.
  5. He gives concrete examples of how multiple EAs and Notion databases support recurring processes, call preparation, social inbox triage, time tracking, and semi-automated decision-making support.

IDEAS WORTH REMEMBERING

5 ideas

Start delegating before you feel “ready,” and treat it as a skill to build.

He described hiring his first EA right after reading Tim Ferriss’s book, even though he “had nothing for her to do,” and then proactively searched for tasks to hand off. He framed delegation as a learnable skill that improves with deliberate practice over years.

If delegation fails, consider rematching before you abandon the approach.

He said a single bad EA experience often reflects a mismatch rather than delegation being impossible, and gave an example where rematching an EA for a legal leader led to “night and day” improvement, doubled output, and reduced stress. He also said Levels rematches about 30% of EAs due to fit.

Record your real work (one take) to transfer context faster than writing process docs.

He emphasized “workflow recording” as a near-zero-effort way to train others: turn on Loom and do your normal work, then share it. He said people routinely overestimate how complex their tasks are, and that watching 2–3 recordings can let an EA replicate work with high accuracy.

Make communication a core part of performance and use recordings to reduce organizational friction.

He described Levels’ culture as downstream of “treat people like adults,” including norms like “closing the loop” and the principle that “a lack of communication is a lack of performance.” He also explained recording meetings (and often sharing recordings) as a forcing function to reduce gossip and improve access to first-person context.

Move tasks from lists into time-blocked calendar reality, with deliberate slack.

He said the calendar should be the to-do list because time is finite while to-do items are infinite, and recommended building in substantial slack (he suggested 50% when starting, later reducing as estimation improves). He also described scheduling email/communications blocks and retroactively calibrating estimates by comparing planned vs. actual time.

WORDS WORTH SAVING

5 quotes

A lack of communication is a lack of performance.

— Sam Corcos

Content scales, time does not.

— Sam Corcos

I’ve been fully news sober for almost 10 years.

— Sam Corcos

Your time is finite, and the number of digital items you can add to a to-do list is infinite.

— Sam Corcos

Writing is thought.

— Sam Corcos

Early delegation and learning curveEA fit, rematching, and proactivityLoom workflow recordings and async communicationNotion databases for processes and task historyTreat-people-like-adults culture and closing loopsMeeting recording and anti-gossip forcing functionsCalendar-as-to-do list and time slack planning

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