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/

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/

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.

Navigating Uncertainty: Preparing for Success in 2026 with Johanna Rothman and Mark Kilby

In this episode of the Reluctant Agilist, host Dave Prior welcomes Mark Kilby and Johanna Rothman to discuss their reflections and plans for the new year. The conversation begins with a candid admission from Dave about feeling lost in setting goals for 2026, prompting Johanna to suggest a shift in focus from preparing for risks to preparing for success. The trio explores the importance of collaboration and the need to let go of what hinders progress, particularly in the context of AI and its implications for project management. They emphasize the necessity of resilience and adaptability in a rapidly changing world, advocating for a more positive outlook on success rather than a fear-based approach to risk management.

As the discussion unfolds, they delve into the challenges posed by generative AI, the importance of trust in technology, and the need for personal and organizational resilience. The episode culminates in a reflection on the significance of collaboration and the value of learning from one another, highlighting the importance of community in navigating the complexities of modern work environments. Ultimately, the conversation serves as a reminder to focus on personal growth, inclusivity, and the pursuit of meaningful connections in both professional and personal spheres.

The video version of this podcast is here

The audio version of this podcast is here

Building a Virtual Board of Directors with AI featuring Victor Njoroge

In this conversation, Dave Prior interviews Victor Njoroge about the intersection of AI and product management. Victor shares his background and role at Clarion, emphasizing the importance of optimizing workflows for sales development representatives. They discuss the concept of Sidebar, a platform for brainstorming and sharing ideas among professionals. Victor explains how he built a virtual board of directors using AI to gain diverse perspectives on product management challenges. The conversation highlights the significance of trust in AI tools, the need for continuous learning, and the enduring value of human skills in the age of AI.

Video: https://youtu.be/Z1oVjbl6V8Y

Audio: https://on.soundcloud.com/7SpXAA8EZRsxKiwP6o

Receiving the Gift of Feedback with Lonnie Weaver Johnson

In this engaging conversation, Dave Prior and Lonnie Weaver-Johnson delve into the complexities of giving and receiving feedback. They explore personal experiences, the emotional challenges associated with feedback, and practical strategies for improving feedback dynamics. Lonnie shares her insights on the importance of mindset, recognizing triggers, and the four Rs of feedback: recognize, receive, react, and respond. The discussion emphasizes the value of self-awareness and the need for constructive communication in both personal and professional settings.

You can find the video recording here.

You can find the audio version here.

Navigating AI - Making Sense of Agents and When To Use Them with Hugo Bowne-Anderson

In this conversation, Dave Prior and Hugo Bowne-Anderson discuss the evolving landscape of AI and data science, focusing on the role of AI agents in solving business problems. Hugo shares insights on how to effectively implement AI solutions, the importance of understanding the underlying data, and the need for continuous improvement in AI systems. They also touch on the skills necessary for navigating the AI landscape, the value of collaboration between technical and non-technical teams, and the importance of assessing the value of AI projects. Hugo concludes by offering a course on building AI applications, emphasizing the iterative nature of AI development.

You can find the interview here.

No One Is Coming to Save You - Johanna Rothman Takes Over DrunkenPM

Johanna Rothman offered to interview Stuart Young and me about our new book 'No One Is Coming to Save You'. This was only my second time handing over the podcast to someone and it was a gerat interview. 

If you are curious about the book, you can check the interview here.

Personal Kanban Questions with Alex Silva

Way back in the olden days before the pandemic,  Alex Silva took a class with me and we talked about Personal Kanban. It's been a few years since we spoke, he's been using it, and he reached out to ask if my use of it had changed.

That's kind of a huge question, so I invited him to take over the podcast and interview me about it. We ended up having a great conversation discussing how we've each adapted it, what makes it work and if you are into PK at all, there is some great stuff in here for you.

You can check out the podcast here.

Getting Your Resume Past ATS with Wahresume Featuring Johnu Marattil

If you are searching for a new gig right now, you know all to well how unbelievably frustrating it can be to send your resume out. You can spend hours on tailoring it and still not get a response.  WahResume is one of the tools that can help you prep your materials so that they have a better chance of making it through the ATS gauntlet. 

Click here to check out my interview with Johnu Marattil.

David Marquet - Distancing - How Great Leaders Make Better Decisions

David Marquet is back! He's the author of 'Turn The Ship Around', 'Leadership is Language', and the co-author of 'Distancing - How Great Leaders Reframe to Make Better Decisions'.  David is always great in an interview, and this is no exception. He was even kind enough to share my favorite story from Leadership is Language.  

Check out the interview and then pick up the book!

You can find the interview here.

You can pick up the book here.

Distancing - How Great Leaders Reframe to Make Better Decisions with Dr. Michael Gillespie

In this conversation, Dave Prior interviews Dr. Michael Gillespie about his book 'Distancing - How Great Leaders Reframe to Make Better Decisions', which explores psychological distancing as a tool for better decision-making. They discuss the importance of stepping outside one's own perspective to gain clarity, the different types of distancing (self, time, and space), and practical applications of these techniques. The conversation also touches on the role of journaling, the significance of construal level theory, and how mindfulness can complement these strategies. Ultimately, the discussion emphasizes the need for individuals to pause and reflect in order to make more informed decisions.

You can find the podcast here: https://www.projectmanagement.com/blog-post/78726/distancing---how-great-leaders-reframe-to-make-better-decisions-with-dr--michael-gillespie

And you can pick up the book here:
Distancing - How Great Leaders Reframe to Make Better Decisions by L. David Marquet and Michael A. Gillespie https://tinyurl.com/wtadnumb

From Theater to Flow: A Conversation with Ross Beurmann

Join Dave Prior as he sits down with Ross Beurmann, author of "From Theater to Flow: Rebuilding the System Behind Agility." In this episode, they delve into the challenges of agile transformations, the concept of "Agile Theater," and the importance of focusing on the middle management to drive meaningful change. Ross shares insights from his book and discusses the need for organizations to rethink their approach to agility.

Key Topics:

• The pitfalls of "Agile Theater" and how to avoid them 
• The role of middle management in successful transformations 
• Ross's unique approach to integrating governance and agility 
• Real-world examples and lessons learned from Ross's consulting experience

You can find the podcast here.

Building Resiliance with Agile2025 Keynote Speaker Tricia Broderick

Dave Prior interviews Tricia Broderick for the Agile 2025 pre-conference, focusing on her keynote on building resilience. Tricia discusses the challenges of the current job market, including high unemployment and overworked employees. She emphasizes the importance of resilience and community support. Tricia also highlights the upcoming AI Readiness for Professionals course, starting August 6, which aims to help professionals stay competitive in an AI-driven world. The conversation touches on the emotional toll of supporting others and the need for empathy and practical support. Tricia looks forward to the Agile 2025 conference, particularly the opportunity to honor past community members.

You can find the podcast here.

Getting Ready for Agile 2025 with Reese Schmit

In this conversation, Dave Prior and Reece Schmidt discuss the upcoming Agile 2025 conference, focusing on its structure, keynotes, and unique features like the Hackathon for Good. They emphasize the importance of preparation for attendees, including tips for maximizing the conference experience, networking, and engaging with speakers. The conversation also addresses resources for introverts and those who may feel overwhelmed, ensuring a supportive environment for all participants.

You can find the interview here.

Agile 2025 Preview with Chris Murman

An interview with Agile Alliance Conference Chair Chris Murman on what’s happening at Agile 2025 and why you want to be there. During the conversation, we discuss ways this year's event is different from the previous ones, focusing on the importance of addressing real problems within the Agile community, the challenges faced by professionals in the field, and the evolving role of AI in Agile practices. We talk about the need for collaboration, innovation, and a proactive approach to shaping the future of Agile methodologies.

Bottom line - come to Agile 2025 to create, not just consume

You can find the podcast here