Agile and Project Management - DrunkenPM Radio

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
LinkedIn: https://www.linkedin.com/in/darbystrong/

Discover how AI can be seamlessly incorporated into Scrum teams to enhance productivity, storytelling, and problem-solving. Claudio Lassala shares real-world experiences of leveraging AI to fill skill gaps, automate tasks, and scale solutions, challenging traditional notions of team roles and developer identities.

Key Insights:
• The importance of teaching AI your principles for better, personalized outcomes
• AI's role in automating routine tasks allows developers to focus on high-value stakeholder engagement
• Emphasizing a solution-oriented mindset rather than coding as an identity
• Managing resistance by framing AI as a problem-solving partner, not a threat
• Continuous re-skilling and mindset shifts needed for teams to thrive with AI
• Leaders should focus on enabling their teams to leverage AI ethically and effectively

Timestamps:
00:00 - Introduction and Claudio's background in IT and agile coaching
02:21 - How AI is integrated into Scrum teams
03:45 - Using AI to write user stories and acceptance criteria
05:24 - The importance of conversations and stories in Agile
07:01 - Teaching AI to reflect team principles and critique solutions
08:15 - Addressing fears of losing roles with AI integration
09:42 - Resistance from team members and how to approach it
11:08 - Demonstrating productivity gains with AI-driven planning
12:13 - Balancing automation with the human touch in problem-solving
15:03 - Clarifying misconceptions about AI automating all tasks
16:38 - Managing detailed task decomposition with AI
18:04 - The evolution of developer roles and knowledge retention
20:17 - Using analogies like cars with carburetors to explain technological shifts
21:34 - Passion projects and opportunities AI unlocks
23:29 - How AI might change the identity of developers
26:38 - The need for continuous retraining and knowledge updating
29:43 - Supporting team members in adapting to AI tools
33:01 - Leadership strategies for leveraging AI ethically and effectively
36:16 - Personal storytelling: AI in content creation and blogging
37:04 - Claudio’s favorite guitar solo and closing thoughts

Contact Claudio
• LinkedIn https://www.linkedin.com/in/claudiolassala/
• Web / Blog https://lassala.net/
• Improving https://www.improving.com/profile/claudio-lassala/

Endava set out to reinvent how IT services get delivered in an AI-native world. Dava.X.AI is the group inside Endava driving that shift. Miro is the workspace they're building it on. Together they've shipped Davaflow — an AI engagement lifecycle that runs from signal to explore to govern to evolve, with humans and agents working alongside each other the whole way.
On the latest drunkenPM Radio, Matt Cloke (CTO, Endava), Joe Dunleavy (Global Head of Dava.X.AI), and Dave Ross (Evangelist at Miro) talk about how the three came together, what real partnership looks like when two roadmaps quietly merge into one journey, and what it took to actually make it work.
Full episode is live.

Takeaways
- Reframe from value capture to value creation — don't use AI to make existing processes 10–15% better, reimagine the work entirely from an AI-first perspective.
- IT services hit its "ChatGPT moment" two years ago when clients and analysts started asking Endava why they were needed if AI could just write the code.
- AI is becoming a method, not a tool — just as Agile organized humans to do work, this new method organizes agents and the people working alongside them.
- The technology question is largely settled; the change management question isn't — quality has hit the inflection point, and what remains is the human shift, much like Waterfall-to-Agile.
- DavaFlow runs in four phases — Signal, Explore, Govern, and Evolve — moving from identifying the right problem, through virtual personas and prototypes, to governing agent output, to evolving in production.
- Chat is the wrong interface for most of this work — humans are visual creatures, and tools like Miro give LLMs context that a chat box never could.
- AI-driven work can produce better traceability than humans ever did — every decision and prototype connects back through the chain of thought, what Joe called "traceability on steroids."
- Anyone can buy the tools — what separates enterprise work from vibe-coding chaos is policy-as-code, defined skills, and human-in-the-loop checkpoints.
- Adoption happens in baby steps, not the full vision — showing people the end of the journey overwhelms them, so start at signal and layer in each next step.
- The hardest part is the identity question — engineers liked writing code and designers liked crafting prototypes, and the shift is a growth-mindset problem, not a skills problem.

Links from the Podcast
Endava: https://www.endava.com/
Dava.X.AI https://www.endava.com/dava-x/dava-x-ai
Miro: https://miro.com/index/

Upcoming Miro Canvas Events
Main Canvas 2026 landing page: https://canvas.miro.com/
Register for the streaming event on May 19 where Joe will be speaking:  https://canvas.miro.com/sanfrancisco/virtual-keynote
Register for the in-person event on May 19th in San Francisco where Joe is speaking live:  https://canvas.miro.com/sanfrancisco
Register for the in-person event on June 2nd in London where Matt will be speaking live: https://canvas.miro.com/london
Register for the in-person event on June 16th in Sydney where Wesley Fagan the APAC SVP for Strategy and Chief Design Officer at Endava will be speaking live: https://canvas.miro.com/sydney

Contacting the Guests
Matt Cloke https://www.linkedin.com/in/mattcloke/
Joe Dunleavy https://www.linkedin.com/in/joedunleavy/
Dave Ross https://www.linkedin.com/in/davidmross/
Dave Prior https://linktr.ee/mrsungo

Chapters

00:00 Introduction to Endava and AI Transformation
08:54 Navigating the AI Landscape: Challenges and Opportunities
17:52 The Evolution of Miro and AI Integration
24:00 Dava Flow: The AI Engagement Lifecycle
25:49 The Power of Visual Context in AI
27:03 Enhancing Contextual Understanding with AI
29:12 Temporal Dimensions in Decision Making
31:27 Navigating Change in Organizational Mindsets
35:40 Demonstrating Value to the C-Suite
38:13 Embracing the Future of Work
41:09 Amplifying Human Creativity with AI

In this engaging conversation, Dave interviews Nic Sementa about his new book, 'Breathing Ego,' which serves as a guided workbook for leaders under pressure. Nic shares his journey from a young salesman to a successful entrepreneur, emphasizing the importance of managing egos in leadership. He discusses the balance between servant leadership and command-and-control styles, the impact of AI on leadership dynamics, and the transition from being an entrepreneur to an employer. Nic also reflects on his failures and the lessons learned, advocating for radical self-responsibility in leadership. In this conversation, the speakers delve into the complexities of leadership, responsibility, and self-perception. They discuss the importance of taking ownership of one's role as a leader, the challenges of navigating ego, and the necessity of creating safe spaces for teams. The dialogue emphasizes the value of empowering employees through trust and the significance of self-kindness in leadership. The speakers also reflect on the entrepreneurial journey, highlighting the lessons learned from failure and the importance of resilience.

Key Takeaways

- Ego management is crucial for effective leadership.
- A healthy ego is necessary for personal and professional growth.
- The book 'Breathing Ego' is designed for leaders managing others.
- AI can serve as a double-edged sword in leadership dynamics.
- Transitioning from entrepreneur to employer changes risk tolerance.
- Failures in management can lead to valuable lessons.
- Radical self-responsibility is key for leaders.
- The journey of leadership is about playing the game, not just winning.
- Legacy involves creating a strong family and business to support each other.
- Leadership involves taking responsibility for the team's challenges.
- Self-perception can be influenced by the ego and external validation.
- Creating safe spaces requires a proactive approach from leaders.
- Empowering teams means trusting them to perform without micromanagement.
- Failure is a crucial part of the learning process for entrepreneurs.
- The journey of entrepreneurship often involves overcoming significant obstacles.
- Self-kindness is essential for effective leadership and team dynamics.
- Understanding one's limitations can enhance hiring practices.
- Conflict resolution skills are vital for maintaining team harmony.
- The narrative of self-worth should not be tied to external validation.

Chapters

00:00 Introduction to Nic Sementa and His Book
02:19 Nic's Background and Journey
04:42 The Concept of Ego in Leadership
08:04 Managing Egos: Balancing Leadership Styles
12:57 The Role of AI in Leadership
15:43 The Journey from Entrepreneur to Employer
20:50 Learning from Failures in Management
23:58 Radical Self-Responsibility in Leadership
24:55 The Role of Leadership in Responsibility
25:44 Navigating Ego and Self-Perception
28:02 Creating Safe Spaces as a Leader
30:00 Empowering Teams Through Trust
32:04 Embracing Failure as a Learning Tool
34:19 The Journey of an Entrepreneur
36:24 The Importance of Self-Kindness in Leadership

Nic’s Book
Breathing Ego https://tinyurl.com/2c4mhvmp

Contacting Nic
LinkedIn: https://www.linkedin.com/in/nic-sementa-2753242b/

Contacting Dave
https://linktr.ee/mrsungo

Links from the Intro
Systems of Imperfection - Discovering Your Superpowers
https://www.gsgvan26.com/agenda/session/1821410

Ai Readiness for Project Managers
https://beforeaiready.com

Recording of Gain Confidence as an AI Ready Project Manager
https://maven.com/p/4ac5d0/gain-confidence-as-an-ai-ready-project-manager

In this episode, Stu and Dave discuss the power of storytelling, the impact of AI on project management, time management strategies, upcoming training sessions, and their activities at the Vancouver Scrum Gathering.

Global Scrum Gathering Vancouver 2026 - May 3-6
https://www.scrumalliance.org/events/global

Dave's Sessions

Gain Confidence as an AI Ready Project Manager - April 28 11 AM Eastern https://maven.com/p/4ac5d0/gain-confidence-as-an-ai-ready-project-manager

AI Ready Project Manager One Day Accelerator - May 23
https://maven.com/c4g-academy/ai-ready-project-manager

Dave's Scrum Certification Classes:
https://www.eventbrite.com/cc/dave-prior-classes-4758623

Stuart's Sessions
Visual Thinking for Effective Collaboration - April 27
https://www.tickettailor.com/events/stuartyoungtrainingltd/2090279

All Stu's upcoming classes
https://www.tickettailor.com/events/stuartyoungtrainingltd

Find Stuart https://linktr.ee/stuartliveart

Find Dave https://linktr.ee/mrsungo

No One Is Coming to Save You: The Power-Ups you need to surf the chaos

Amazon: https://tinyurl.com/yv7chp54
Leanpub: https://leanpub.com/surfthechaos