The New Manager's Dilemma: Why You Can't Review Every Email | Lazy Leverage #76

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Oct 23, 2025

Priscilla Montenegro de Nicaragua, a first-time manager at Sagan, delves into the challenges of transitioning from contributor to manager while seeking coaching from Jon. They discuss the danger of micromanagement and the importance of selective oversight, introducing the Marine Corps concept of 'directed telescopes.' The duo distinguishes between acceptable 'aggressive mistakes' and unacceptable 'sloppy mistakes.' Jon emphasizes training her team to anticipate her standards rather than reviewing every email, aiming for a strong collective accountability.

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INSIGHT

Accountability Without Doing It All

Managers are accountable for everything without doing everything themselves.
That accountability creates pressure to control, which undermines scalable leadership.

ADVICE

Sample Work, Don’t Monitor Everything

Use a "directed telescope": sample specific projects or people periodically instead of monitoring everything.
Check calendars, review select emails, and ask targeted questions in one-on-ones to build fingertip feel.

ADVICE

Adjust Sampling Frequency Intentionally

Dive deeper into newer people or changed processes more frequently and reduce sampling for trusted people.
Use selective sampling frequency based on experience and process changes.

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Jon coaches Priscilla, a first-time manager at Sagan, through one of management's fundamental challenges: being accountable for everything while not doing everything yourself. Priscilla manages six recruiters and struggles with the classic new manager trap: when something goes wrong, she pulls control back and starts reviewing every email.

Jon introduces the Marine Corps concept of "directed telescopes," where managers selectively sample their team's work rather than monitoring everything. Instead of being CC'd on every email, he advises Priscilla to periodically dive deep into specific projects, checking calendars, reviewing select emails, and asking targeted questions during one-on-ones. This creates "fingertip feel", or knowing what's happening without being in every meeting.

The conversation reveals a critical distinction between mistake types. Jon embraces "aggressive mistakes" (errors made while pushing boundaries or exercising judgment) and has zero tolerance for "sloppy mistakes" stemming from laziness or lack of attention. When a team member pushes back too hard on a client, Jon backs them up. When someone leaves AI prompts visible in an email, that's unacceptable.

Priscilla can't work her way out of this problem by staying later and reviewing more emails. She must think her way out by developing her team. The goal is getting her voice into their heads, so they anticipate her standards without needing constant oversight. Drawing from his own experience with mentors, Jon describes how effective leaders create space for growth while maintaining clear expectations and documentation through proper feedback frameworks.

KEY TOPICS
(01:40) Why Leaders Need to Foster Accountability Without Being a Control Freak
(04:55) "Directed Telescopes": The Marine Corps Sampling Method
(06:51) Creating "Fingertip Feel" Without Micromanaging
(09:31) Mistakes of Aggression vs Mistakes of Sloppiness
(12:51) The Four Steps of Giving Feedback Framework
(20:11) Getting Your Voice Into Your Team's Heads
(24:12) Rose-Colored Glasses: Priscilla's Leadership Strength and Weakness