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.

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

 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/

Integrating AI into Scrum Teams: Insights with Claudio Lassala

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

 

drunkenpmradio · How AI is Transforming Scrum Teams - Practical Strategies from Claudio Lassala

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/

The AI Engagement Lifecycle with Endava, Dava.X.AI, and Miro

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.

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

Surfing Chaos - Storytelling and the AI Ready Project Manager - EP 6

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

 

Mastering AI in Business - RAG vs CAG with Braden Cundiff

Braden Cundiff joins Dave to explore some of the emerging ways  AI tools can be used to support project management, including RAG and CAG approaches. During the interview they cover what they are, how they are different, and how they can transform organizational processes. The discussion covers practical applications, ethical considerations, and strategies for learning AI effectively.

Key Topics

• Differences between RAG and CAG in AI
• Practical applications of AI in project management
• Ethical considerations in AI deployment
• Strategies for learning and adopting AI technologies

Chapters

00:00 Introduction to AI in Project Management

00:55 Meet the Expert: Brayden Cundiff and BloomFilter

01:56 BloomFilter's Role in AI and SDLC Integration

03:52 AI as a Scrum Master: Enhancing Agile Processes

05:09 Limitations of ChatGPT for Project Contexts

05:37 Understanding RAG and CAG Approaches

18:27 Differences Between RAG and CAG Explained

23:05 Implementing CAG for Consistent AI Responses

29:01 Security, Bias, and Ethical Considerations in AI

34:06 Learning AI: Resources and Strategies

42:46 Closing Remarks and Next Steps

LInks

• AI Ready for PMs - One Day Accelerator https://www.beforeaiready.com/
• BloomFilter AI - https://bloomfilter.ai

Contacting Braden

• Braden’s Book - Flip: Projects to Products: A Problem Playbook https://tinyurl.com/599y6fpf
• LinkedIn: https://www.linkedin.com/in/braden-cundiff-52479121/

Sway 2.0 with Marina Alex - How Agile Coaches Can Thrive in a Changing Market

In this insightful interview, Marina Alex shares her journey from a successful sales executive to an agile coach, discussing the challenges faced during the pandemic, the importance of adapting to market changes, and strategies for agile professionals to find new opportunities in a shifting landscape. She emphasizes the need for the agile community to broaden its reach beyond IT, focus on measurable results, and leverage local relationships to build a sustainable coaching and consulting business.

Key Topics

• Market shifts and the decline of traditional agile coaching
• Strategies for finding clients outside of IT and enterprise
• The importance of measurable results and ROI in agile consulting
• Building relationships with local businesses and community engagement
• The role of AI in transforming small and medium businesses

Watch the video version here
Listen to the audio version here

Chapters

01:52 Introduction to Agile Coaching and Personal Journey

06:59 The Shift in the Agile Market

11:49 Reframing the Agile Value Proposition

19:44 Building Self-Organizing Teams in Non-IT Businesses

26:54 Implementing Agile Practices in Diverse Environments

28:49 Implementing Change in Traditional Environments

30:02 Setting Measurable Business Goals

31:51 The Role of a Coach in Business Transformation

34:19 Starting as a Local Coach

34:37 Optimizing Your LinkedIn Presence

37:26 The Importance of Practical AI Knowledge

40:33 Simplifying AI for Local Businesses

45:35 Finding Clients in Your Community

Links

Sway 2.0 AI Modern Consulting Blueprint

Class begins April 6, 2026

Sign up here: https://www.swaysystem.com/sway-2026-Programs

The promo code DAVE takes $250 off!

Contacting Marina

• Marina Alex's Guide to Finding Your First Client in SMB - https://example.com/marina-alex-guide
• LinkedIn Profile of Marina Alex - https://linkedin.com/in/marinaalex
• Sway System by Marina Alex - https://example.com/sway-system

Contacting Dave

• Linktree: https://linktr.ee/mrsungo

Dave’s upcoming classes

• Certified Scrum Master https://tinyurl.com/mu74rwuc
• Certified Scrum Product Owner https://tinyurl.com/mpw6p622
• PMI Project Management Professional (PMP)® Boot Camp and Exam Prep https://tinyurl.com/3znzpt7j
• PMI Agile Certified Practitioner (PMI-ACP)® Boot Camp https://tinyurl.com/bdebrrrb

Mastering Troubled Projects: Strategies from Richard Broo

In this insightful interview, Richard Broo shares his expertise on managing troubled projects, the importance of scope and risk management, and how traditional and agile methodologies can be effectively integrated. Learn practical strategies to improve project success and navigate the complexities of modern project management.

Click here to watch the video version

Click here to listen to the audio version

Adapt to Win! with Evan Campbell

Dave sits down with Evan Campbell to discuss his new book, Adapt to Win: A Framework to Overcome Strategy Decay Using OKRs and Lean Portfolio Management, published by Wiley. Evan shares why most organizations fail to execute on beautifully crafted strategies — and what to do about it.

Watch the video version here.

Listen to the audio version here.

Navigating AI in Business Strategy with John Tanner

In this conversation, John Tanner discusses the evolving role of AI in business strategy, emphasizing the need for leaders to understand AI's impact on their organizations. He highlights the challenges of integrating AI, the importance of data management, and the necessity for project managers to adapt their skills in the face of new technologies. Tanner also introduces his course on AI readiness, which aims to equip professionals with the knowledge and skills needed to navigate the AI landscape effectively.

Watch the video version here.

Listen to the audio version here.

The Art of Giving Feedback with Lonnie Weaver-Johnson

In this episode of the Reluctant Agilist, Dave Prior and Lonnie Weaver-Johnson delve into the intricacies of giving and receiving feedback. They explore personal experiences, the importance of empathy, and various models for effective feedback. The conversation emphasizes the need for clarity, intent, and kindness in feedback delivery, while also addressing the challenges of navigating feedback in professional settings. Lonnie shares her insights from years of experience in performance reviews and coaching, highlighting the significance of understanding individual differences in feedback reception.

Watch the video version here.

Listen to the audio version here.