StarZero All shows Try the podcast clipper →

Apr 27, 2023 · 15m · founders-journal

I Suck at Delegating. My 2 Ways to Get Better at it.

Alex Lieberman · 13m spoken Jesse Pujji · 2s spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Morning Brew co-founder Alex Lieberman examines his personal shortcomings in task delegation, diagnosing the psychological habits behind them and sharing two actionable frameworks—the Eisenhower Matrix and Ari Meisel's Six Levels of Delegation—to help entrepreneurs build business leverage.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 99.8% of the talking time here. How this is scored →

Alex as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Alex pushing back 0.0
05100:0010:001:55–6:25 · Alex as informed peer 0/10 The Realization: How Travel Exposed Flaws in Project Delegation This is a solo monologue segment where Alex Lieberman reflects on how recent travel revealed his personal struggles with delegating tasks for his startup. Because it is an uninterrupted solo journal entry, all host-guest interaction metrics are scored at 0.6:25–9:54 · Alex as informed peer 0/10 Tool 1: Applying the Eisenhower Matrix to Task Management Alex explains how he applies the Eisenhower 2x2 matrix to categorize tasks and decide what to do, delay, delegate, or delete. Being a solo educational monologue, host and guest interaction scores are strictly 0.9:54–14:24 · Alex as informed peer 0/10 Tool 2: Ari Meisel's Six Levels of Delegation Alex details Ari Meisel's six levels of delegation, walking through trust levels from order-taking to full autonomy. As a solo presentation without a guest present, all interaction scores are 0.14:25–15:10 · Alex as informed peer 0/10 Episode Summary and Community Feedback Invitation Alex wraps up the solo episode, summarizes the key takeaways, and asks listeners to submit their own pain points. No guest interaction occurs, so all scores remain 0.1:55–6:25 · Guest teaching 0/10 The Realization: How Travel Exposed Flaws in Project Delegation This is a solo monologue segment where Alex Lieberman reflects on how recent travel revealed his personal struggles with delegating tasks for his startup. Because it is an uninterrupted solo journal entry, all host-guest interaction metrics are scored at 0.6:25–9:54 · Guest teaching 0/10 Tool 1: Applying the Eisenhower Matrix to Task Management Alex explains how he applies the Eisenhower 2x2 matrix to categorize tasks and decide what to do, delay, delegate, or delete. Being a solo educational monologue, host and guest interaction scores are strictly 0.9:54–14:24 · Guest teaching 0/10 Tool 2: Ari Meisel's Six Levels of Delegation Alex details Ari Meisel's six levels of delegation, walking through trust levels from order-taking to full autonomy. As a solo presentation without a guest present, all interaction scores are 0.14:25–15:10 · Guest teaching 0/10 Episode Summary and Community Feedback Invitation Alex wraps up the solo episode, summarizes the key takeaways, and asks listeners to submit their own pain points. No guest interaction occurs, so all scores remain 0.1:55–6:25 · Guest disagreement 0/10 The Realization: How Travel Exposed Flaws in Project Delegation This is a solo monologue segment where Alex Lieberman reflects on how recent travel revealed his personal struggles with delegating tasks for his startup. Because it is an uninterrupted solo journal entry, all host-guest interaction metrics are scored at 0.6:25–9:54 · Guest disagreement 0/10 Tool 1: Applying the Eisenhower Matrix to Task Management Alex explains how he applies the Eisenhower 2x2 matrix to categorize tasks and decide what to do, delay, delegate, or delete. Being a solo educational monologue, host and guest interaction scores are strictly 0.9:54–14:24 · Guest disagreement 0/10 Tool 2: Ari Meisel's Six Levels of Delegation Alex details Ari Meisel's six levels of delegation, walking through trust levels from order-taking to full autonomy. As a solo presentation without a guest present, all interaction scores are 0.14:25–15:10 · Guest disagreement 0/10 Episode Summary and Community Feedback Invitation Alex wraps up the solo episode, summarizes the key takeaways, and asks listeners to submit their own pain points. No guest interaction occurs, so all scores remain 0.1:55–6:25 · Alex pushing back 0/10 The Realization: How Travel Exposed Flaws in Project Delegation This is a solo monologue segment where Alex Lieberman reflects on how recent travel revealed his personal struggles with delegating tasks for his startup. Because it is an uninterrupted solo journal entry, all host-guest interaction metrics are scored at 0.6:25–9:54 · Alex pushing back 0/10 Tool 1: Applying the Eisenhower Matrix to Task Management Alex explains how he applies the Eisenhower 2x2 matrix to categorize tasks and decide what to do, delay, delegate, or delete. Being a solo educational monologue, host and guest interaction scores are strictly 0.9:54–14:24 · Alex pushing back 0/10 Tool 2: Ari Meisel's Six Levels of Delegation Alex details Ari Meisel's six levels of delegation, walking through trust levels from order-taking to full autonomy. As a solo presentation without a guest present, all interaction scores are 0.14:25–15:10 · Alex pushing back 0/10 Episode Summary and Community Feedback Invitation Alex wraps up the solo episode, summarizes the key takeaways, and asks listeners to submit their own pain points. No guest interaction occurs, so all scores remain 0.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 99% · guest 1%0:00 · Alex 99% · guest 1%3:00 · Alex 100% · guest 0%3:00 · Alex 100% · guest 0%6:00 · Alex 100% · guest 0%6:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%15:00 · Alex 100% · guest 0%15:00 · Alex 100% · guest 0%
Sharpest disagreement ▶ 1:46 Jesse Pujji's Brief Intro

Jesse Pujji is not present during the monologue portion of the episode, only saying hello in the intro with no combative remarks.

 Hardest push from Alex ▶ 7:15 Pushback on Busywork

In his monologue, Alex pushes back against the common entrepreneurial habit of delegating tasks that should simply be deleted altogether.

 Biggest teaching moment ▶ 1:55 Alex Schooled by Reality

Alex describes being humbled by the realization that his travel halted company progress due to his own delegation failures rather than team performance.

 Alex holds their own ▶ 13:15 Synthesizing Frameworks

Alex demonstrates subject mastery by connecting the Eisenhower Matrix directly with Ari Meisel's delegation spectrum to formulate a coherent operational workflow.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
The Realization: How Travel Exposed Flaws in Project Delegation 0000 This is a solo monologue segment where Alex Lieberman reflects on how recent travel revealed his personal struggles with delegating tasks for his startup. Because it is an uninterrupted solo journal entry, all host-guest interaction metrics are scored at 0.
Tool 1: Applying the Eisenhower Matrix to Task Management 0000 Alex explains how he applies the Eisenhower 2x2 matrix to categorize tasks and decide what to do, delay, delegate, or delete. Being a solo educational monologue, host and guest interaction scores are strictly 0.
Tool 2: Ari Meisel's Six Levels of Delegation 0000 Alex details Ari Meisel's six levels of delegation, walking through trust levels from order-taking to full autonomy. As a solo presentation without a guest present, all interaction scores are 0.
Episode Summary and Community Feedback Invitation 0000 Alex wraps up the solo episode, summarizes the key takeaways, and asks listeners to submit their own pain points. No guest interaction occurs, so all scores remain 0.

Statements from this episode (5)

Disclosure
Lieberman Realized He Was Bad at Delegation After Starting New Businesses
“I always thought I was good at delegation. I assumed that I had to be, given Morning Brew's growth over the last eight years. But as I've re-immersed myself in new businesses outside of the brew, I have realized that this assumption was completely wrong.”
Alex Lieberman Apr 27, 2023 ▶ 1:55
Assertion Not checkable as stated
Morning Brew Still Hasn't Finished Its 2015 One-Year Pitch Deck Plan
“If you were to look at our original pitch deck that we shared with investors in 2015, we had shared in that deck a slide that was all about our one year strategy. And while that strategy in that one slide was actually spot on with how the business has grown ov…”
Alex Lieberman Apr 27, 2023 ▶ 3:42
Disclosure
Lieberman Aims to Complete Only One Important Task Per Day
“I can only get one very important thing done in a day. That's the assumption I have to have, which means that I need to be ruthless about picking what is the one thing that I want to do in my day, and I need to assume that everything else needs to be delegated…”
Alex Lieberman Apr 27, 2023 ▶ 4:14
Insight
Channel Busyness Into One or Two Enjoyable Tasks Instead of Quitting
“Rather than trying to eliminate busyness altogether, because I generally think when you try to go cold turkey, it isn't necessarily sustainable, I would argue the more moderated or sustainable thing to do Is to focus your busyness on one to two tasks that you …”
Alex Lieberman Apr 27, 2023 ▶ 5:52
Insight
Founders Often Delegate Tasks That Should Simply Be Deleted Entirely
“I would say the biggest issue that I have that many entrepreneurs have is they are really bad at deleting tasks. They, even if they're good at delegating, sometimes they'll delegate tasks that actually shouldn't be delegated because the fastest way to do a tas…”
Alex Lieberman Apr 27, 2023 ▶ 9:15
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more