When Your Old Ways Stop Working | FREEDOM DECODED Ep 54: A Podcast From Demir & Carey Bentley

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Time stamps:

01:49 - Flying the Plane While You’re Still Building It

04:58 - The Advantage of a Clean Slate (Building vs. Resetting)

05:52 - The Importance of Specific KPIs in Ambiguous Roles

06:59 - Creating a “Headline” for Your Year

07:18 - You Only Have One Priority: The New Job

07:48 - Transition as Opportunity, Not a Problem for the Old Team

08:39 - Don’t Make a "Mona Lisa" Out of the Transition

10:08 - Time-Boxing Support to Avoid Becoming the Permanent Middleman

11:00 - Expectations Management as a Leadership Tool

12:00 - The Risk of Overlong Transitions

13:00 - Stress-Testing the “Best Case” Plan

14:15 - Comfort Bias Toward the Old Role

15:30 - Delegation as a Development Opportunity for Others

16:45 - Redesigning the Transition Model

17:05 - Best Case vs. Worst Case Thinking in High-Stakes Moves

18:15 - The Perfectionism Trap in Leadership Transitions

21:00 - Shifting from Execution to Strategic Visibility

22:30 - Health as a Non-Negotiable Constraint

22:55 - Stress-Testing Assumptions vs. Being Negative

25:00 - Gradual Boundary Enforcement Over Abrupt Pushback

28:30 - Professional Liabilities: When Overthinking Stalls Progress

30:00 - Transition Clarity Prevents Emotional Damage

37:07 - Creating a "Breadcrumb Trail" of Accountability for Your Team

41:15 - Putting Order to Chaos: Leveraging Process Skills

43:47 - Clarity as the Definitive Attribute of Great Leaders

44:45 - Using AI as a Thought Partner for Leadership

46:05 - Translating Strategy into Living Documents and Processes

51:34 - Relieving Managerial Pressure Through Ownership

52:40 - AI as a Brain Accelerator, Not a Miracle

53:44 - Becoming the Leader Who Sees the "One Key Thing"

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