Thursday, May 21, 2026

The Journey from Project Manager to Chief of Staff with Darby Strong


In this conversation, Dave Prior and Darby Strong explore the transition from project management to the role of chief of staff, emphasizing the importance of interpersonal skills, empathy, and systems thinking. They discuss how experiences in the restaurant industry can shape effective project managers and the significance of creating a supportive work environment. The dialogue highlights the need for leaders to be aware of their impact on team dynamics and the importance of fostering a culture of collaboration and trust. In this conversation, Darby and Dave explore the nuances of leadership roles, particularly the differences between project managers and chiefs of staff. They discuss the importance of trust, courage, and the ability to absorb ambiguity in leadership. Darby shares her personal journey and insights on transitioning from project management to a chief of staff role, emphasizing the need for cooperation and systems thinking. The conversation also touches on the significance of taking action and the value of interdisciplinary approaches in effective leadership.



 Takeaways


  • The restaurant experience provides valuable skills for project management.
  • Effective project managers are often generalists with a systems thinking approach.
  • Communication and empathy are crucial in leadership roles.
  • Creating a supportive environment helps teams thrive.
  • The role of chief of staff involves strategic partnership with leadership.
  • Project managers can influence organizational culture positively.
  • Understanding team dynamics is essential for effective leadership.
  • Compassion for leaders can enhance team performance.
  • Interdependence is key in collaborative work environments.
  • Project managers should focus on nurturing both teams and leadership.
  • Chiefs of staff need to absorb ambiguity for clarity.
  • Building trust takes time and consistent effort.
  • Courage to be candid is crucial in leadership roles.
  • Project managers can transition to chief of staff roles with the right mindset.
  • Creating systems for cooperation is essential in leadership.
  • Influence is a key skill for project managers and scrum masters.
  • Taking action can help overcome inertia and open new opportunities.
  • Interdisciplinary approaches can enhance leadership effectiveness.
  • Understanding natural systems is vital for effective project management.


Chapters


00:00 Introduction and Background

02:58 The Restaurant Experience and Project Management

06:03 The Importance of People in Project Management

08:56 Transitioning from Project Management to Chief of Staff

12:04 The Role of a Chief of Staff

14:53 Navigating Leadership and Team Dynamics

18:02 Empathy and Perspective in Leadership

25:26 Interdependence Day: A Unique Celebration

26:10 Traits of a Chief of Staff vs. Project Manager

30:12 Building Trust and Courage in Leadership

32:23 Absorbing Ambiguity: The Role of a Chief of Staff

33:20 Transitioning from Project Management to Chief of Staff

35:15 Creating Systems for Cooperation

37:12 The Influence of Project Managers and Scrum Masters

41:56 Taking Action: Overcoming Inertia

43:42 Interdisciplinary Approaches in Leadership


Contacting Darby

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