Shed and Shine – Episode 65

Title: Delegation Mastery: How to Let Go & Lead Without Micromanaging
Hosts: Gino Wickman & Rob Dube
Release Date: June 4, 2025

Overview

In this episode, Gino and Rob dive deep into the art and psychology of delegation, exploring why entrepreneurs must master the skill, the mindset blocks that prevent effective delegation, and actionable frameworks to become a transformative leader—freeing yourself and unlocking your true potential. Drawing from decades of experience, both hosts share personal stories, proven strategies, and real-world examples for making delegation a cornerstone of entrepreneurial success.

Key Discussion Points & Insights

1. The Imperative of Delegation and Elevation

• Rob recounts learning to delegate from Gino years ago:

  "I thought I was delegating prior to meeting you, but I realized that I was doing a 50% job at best." (01:07)

• Why delegate?
  • Frees up time for unique abilities
  • Empowers and develops your team
  • Maximizes impact, income, and creates inner peace
  • Rob: “Time is your greatest asset. And delegating allows you to place greater focus on what aligns with your unique abilities.” (01:15)

2. Mindset: The Root Blocker

• Gino stresses the essential mindset shift:

  “If there were an objective for this episode, it’d be that we convince every listener…they must delegate everything in their life they shouldn’t be doing and elevate themselves to their true self.” (02:25)

• Addressing the “nobody can do it like me” mindset:
  • Gino challenges listeners to accept that others may do it 10% worse—but the freedom is worth it (04:58)
  • Often, others will do it even better or simply differently
  • The perfectionist’s trade-off is missing out on higher-value work
  • Example: “Do you choose the 10 [tasks] that are the highest gain... or cling to the rest for marginally better output?” (05:22)

3. The Control Freak Dilemma

• Everyone faces it:
  • Gino: “We’re all control freaks…that’s how we got here.” (07:13)
• Letting go isn’t a sudden act—it’s incremental
• Gino shares his biggest delegation: selling his company

  “To let go of control of the business you built for 15 years, that's really hard. But what was on the other side was far more important.” (08:18)

  • Result: The company thrived without him, growing 5X

4. Practical Routines for Letting Go

• Rob shares a client’s annual “biggest task” delegation practice (09:40)
• Gino’s 90-Day Delegation Discipline:

  “Every quarter I delegate something else. 30 years—120 delegations.” (10:57)

  • Suggests listeners adopt a one-delegation-per-quarter pace: “Take it one thing at a time.”
• Simple 3-Step Delegation Track:
  1. Find the right person
  2. Teach them how to do it
  3. Let go
  • “Where it goes wrong is one of those three things … don’t overcomplicate it.” (11:27)

5. Setting Clear Expectations

• Rob outlines an example for delegating client follow-up (12:43):
  1. Outline follow-up timelines (e.g., “within 24 hours of a client meeting”)
  2. Define the desired outcome (“update CRM with detailed notes and action items”)
  3. Establish checkpoints (e.g., “weekly review summaries”)
• Gino affirms this is part of the critical teaching step in delegation (13:33)

6. Resilience & Patience in Delegating Big Roles

• Rob tells the story of the Cliff Bar founder persisting after 6–7 hiring failures (13:49)
• Delegating key roles (CEO/visionary) is a long game
  • Gino: “My succession plan…was a three-year timeline. It takes time and there will be failures…but it’s worth bumping your head a few times.” (15:00)
  • For big transitions, think in years, not months

7. Real-world Current Example

• Rob is presently delegating his own visionary role in their company (14:53, 19:00)
  • Gino: “We put the stake in the ground…by December 31st our new visionary is going to be in place…It’s a complete commitment.” (14:57)

Actionable Frameworks & Guidance

Gino’s 3-Step Delegation Formula

1. Find the right person (inside or outside your org)
2. Teach them properly (clear expectations, boundaries, outcomes)
3. Let go (trust and allow for actual ownership of the role)

“Where it goes wrong is one of those three things…Please don’t overcomplicate it.” (11:27)

Routine for Delegation Mastery

• Delegate one major task per quarter
• For big roles, set multi-year plans and accept trial and error
• Regularly list all your responsibilities—keep those leveraging your unique abilities, delegate or eliminate the rest

Notable Quotes & Memorable Moments

• On time and value:

  "You can't control all 50 things...but you can put all your energy into the ones that take you and the company to the next level." – Gino (05:32)

• Facing the control barrier:

  "We're all control freaks...it's a matter of understanding why am I such a control freak? What do I really want?" – Gino (07:13)

• On the hardest kind of delegation:

  "I delegated an entire company. It was more valuable to be on the other side of that sale so that I could make a bigger impact on the world." – Gino (08:06)

• On failing forward in hiring:

  "I just knew I had to find the person. I didn’t mind failing." – Cliff Bar founder story, as told by Rob (14:16)

• The case for an executive assistant:

  "If you are a driven entrepreneur that's a visionary...if you don’t have an executive assistant, I don’t know how you’re functioning at full capacity." – Gino (16:57)

• Get ruthless about your core contributions:

  "There’s only three things that I do now: create content, teach content, and navigation...everything else I delegate." – Gino (18:49)

Timestamps for Important Segments

• 01:04 – Rob credits Gino with teaching him to delegate and elevate
• 02:25 – Gino explains the ultimate objective and value of delegation
• 04:58 – Addressing the “nobody can do it like me” objection
• 07:13 – Gino on how control issues hold entrepreneurs back
• 08:06 – Gino’s story about delegating and selling his company
• 09:40 – Rob’s client’s annual major delegation practice
• 10:57 – Gino’s “every quarter” delegation discipline
• 11:27 – Gino’s 3-step delegation process
• 12:43 – Rob outlines steps for setting delegation expectations
• 14:53 – Discussion of resilience in executive role delegation
• 16:57 – The executive assistant imperative
• 18:49 – Gino’s personal scope: create, teach, navigate

Final Takeaway

Delegation is not just an operational task—it's a mindset and leadership discipline. To let go is to grow: define your core impact areas, regularly shed tasks that don’t belong to you, and bring your True Self to the highest-value contributions. Start small, go slow if needed, but never stop delegating.

"If you spend all your time [on your unique abilities], you’re gonna be happier and everything’s gonna be better." – Gino (19:06)