Do Good To Lead Well with Craig Dowden

How do you lead well in a world transformed by AI? This week, Do Good to Lead Well tackles this question head-on, as I speak with Mike Sullivan, co-founder and Chief Growth Officer of OneDigital, and the co-author of the timely and insightful book, Workforce Intelligence. Throughout our conversation, Mike breaks through both the hype and the fear surrounding AI in today’s workforce. As a champion of people-centered AI, he offers an inspiring roadmap for activating, not replacing, the human workforce.

Listeners are invited into the story of “Ben,” a digital coworker, and how Mike and his team treat AI onboarding like hiring a real employee: with transparency, development, and high expectations. The result? A culture where humans and digital agents collaborate, learn, and continuously improve together. We also discuss how workforce intelligence is being redefined and how high-performing teams are built not on software alone, but on empathy, transparency, and courage.

For leaders and organizations seeking practical strategies, this episode brims with actionable advice, from measuring workforce intelligence to ensuring HR has a seat at the AI table. It’s a compelling argument for seeing the faces behind the headcount, and for cultivating trust as the cornerstone of 21st-century leadership.

What You’ll Learn
- Start with honesty, not hype when it comes to AI.
- Don’t treat AI as ‘software’: Treat it like a coworker.
- Transparent roles & faces build trust.
- What is your Workforce Intelligence (WI) score? The success metric.
- Activation moments matter.
- Top-down Is the only way forward.
- People Always Come First.
- It’s not either/or. It’s Human Intelligence (HI) + Artificial Intelligence (AI).

Podcast Timestamps
(00:00) – Personal Fear and the Human Side of AI
(06:02) – No Code? No Problem – Mike’s Personal AI Journey
(10:05) – The Human Side of AI Deployment
(12:29) – Hiring AI Coworkers: Internship to Full-Time
(16:33) – Managing a Blended Human-AI Workforce
(21:54) – HR’s Role and Navigating Workforce Change
(26:29) – Defining Workforce Intelligence and the WI Score
(30:58) – Overcoming Employee Fears and Building Trust
(37:43) – Leadership Activation and Empathy in the Age of AI
(53:00) – Final Reflections and The Humanity Test

KEYWORDS
Positive Leadership, AI, Artificial Intelligence, AI Transformation, Workplace Intelligence, People-First Leadership, Human-Centric Organizations, AI Adoption, Digital Coworkers, Organizational Change, Employment Disruption, Job Automation, Human Resources (HR), Talent Management, Growth Mindset, Trust in Leadership, Empathy in Business, AI Onboarding, Blended Workforce, WI score, Transparency in AI, Disruption, Future of Work, Human-AI Collaboration, Managing AI Anxiety, CEO Success

Over the past three episodes, I had a very special guest; Kevin Ford, the former CEO of Calian. Our previous conversations trace a powerful progression from self-leadership to connecting with others. In the final episode of this series, we explore how a profound sense of purpose united by a set of core values truly anchors an organization.

Our discussion moves beyond corporate clichés, as we dig into how purpose statements can resonate from the C-suite to every desk and production floor, and why stories, not slogans, are the secret to unlocking commitment and pride. Listeners will also find practical insights on transforming company values from static posters into lived behaviors, using transparency, feedback, and authentic leadership. This journey ultimately challenges every leader to reflect on the following question: Are your company’s values visible in the daily experience, or just in the posters on the wall?

Through the lens of firsthand leadership stories, our conversation examines the risks of focusing only on financial metrics and offers powerful reminders that true value is created when people are proud not just of their work, but of its impact. Tactics like regular storytelling, open surveys, and clear expectations set the stage for a culture where integrity, respect, and community involvement drive both performance, engagement and well-being.

For leaders and teams navigating the complexity of today’s business world, this episode serves as both an inspiration and a toolkit for embedding purpose and values that last.

What You’ll Learn
- The Power of Purpose-Driven Organizations.
- Developing and Communicating Core Values.
- Storytelling as a Leadership Tool.
- Metrics Matter: Move Beyond Just the Financials.
- Balancing Performance and Values.
- Navigating Personal and Organizational Values Misalignment.
- The Ongoing Practice of Authentic Leadership.

Podcast Timestamps
(00:00) - Introduction to Part 3: The Road We Travelled with an Introduction to Purpose and Values
(03:04) - Defining Purpose in Organizations
(05:25) - Developing and Living a Purpose Statement
(09:28) - The Tangible Benefits of Purpose-Driven Organizations
(13:45) - Strategies for Building a Purpose-Driven Culture
(18:36) - Defining and Living Core Values
(23:06) - Ensuring Alignment Between Stated and Lived Values
(27:05) - Balancing Performance Pressures with Values
(35:06) - Navigating Personal vs. Organizational Value Misalignment
(41:00) - Final Reflections on the Foundations of Positive Leadership

KEYWORDS
Positive Leadership, Purpose-Driven Organization, Core Values, Empathy, Transparency, Respect, Candor, Organizational Culture, Community Involvement, Storytelling, Company Mission, Organizational Alignment, Values Drift, Employee Motivation, Behavioral Anchors, Values-Based Leadership, Organizational Trust, Accountability, Purpose and Values Integration, Lived Values, CEO Success

In this episode of our 3-part series exploring the foundations of positive leadership, I speak with Kevin Ford, the award-winning, past CEO of Calian Group, about how to effectively connect with others.

In a world grappling with AI, remote work, and breakneck change, we examine explore what meaningful connection looks like in practice. Starting with candor and transparency, our discussion explores why authentic openness isn’t just a nice-to-have, but a business essential. Kevin shares some real-life examples from leading a global, publicly traded company to amplify the conversation from theory to tangible action.

Our journey continues with a deep dive into respect, which is not a formality rooted in title, but rather the lived foundation of innovative, resilient culture. Empathy emerges as our final, essential ingredient, with stories illustrating how courageous listening and presence lead organizations through uncertainty and drive sustainable results.

Key moments include revealing the inner workings of boardroom transparency, the contagious effects of a leader’s sincerity, and the simple yet radical act of asking, “How are you really doing?” Insights on how accountability and compassion coexist provide leaders with a nuanced blueprint for addressing hard truths without losing humanity.

Listeners will come away with a wealth of practical strategies, from how to tune into team energy, to acting on feedback with genuine care. For anyone looking to elevate their leadership and transform team dynamics, this episode delivers both the why and the how.

What You’ll Learn
- The Importance of Candor and Transparency in Leadership.
- How Transparency Builds Trust and Followership.
- Cultivating a Culture of Respect.
- Navigating Difficult Conversations With Respect.
- Demonstrating and Developing Empathy: A Leadership Superpower.
- Positive energy matters, especially in tough times.
- Balancing Empathy, Accountability, and Performance.

Podcast Timestamps
(00:00) - Introduction to Part 2: Connecting with Others
(01:59) - The Challenge of Connection in a Tech-Driven World
(02:36) - Candor and Transparency in Leadership
(07:36) - Transparency Across Stakeholders
(13:09) - The Foundation of Respect
(19:59) - (25:03) - Respect in Difficult Conversations and Layoffs
(29:01) - Empathy as a Leadership Imperative
(36:29) - Empathy in Action and Leading Through Crisis
(47:03) - The Courage to Embrace Raw Emotions
(55:07) - Reflecting on the Leadership Journey

KEYWORDS
Positive Leadership, Candor, Transparency, Authenticity, Self-Leadership, Respect, Empathy, Leadership Culture, Company Values, Accountability, Performance Management, Giving Feedback, Employee Engagement, Emotional Intelligence, Human-Centered Leadership, Difficult Conversations, Building Trust, Stakeholder Communication, Navigating Change, Remote Work, CEO Success

What makes great executives stand out? I’m thrilled to share Part 1 of a 3-part series that will explore the foundations of positive leadership. Throughout this special set of episodes, I will be sharing the stage with Kevin Ford, the award-winning CEO of Calian who recently stepped down.

In this episode, Kevin and I start the conversation by taking an honest look at why leading yourself matters most. We unpack the critical role of self-awareness, sharing a powerful personal journey that moved Kevin from early-career overconfidence to the life-changing benefits of welcoming tough feedback.

We also discuss insightful research, amplified with real-life examples that makes the case that self-awareness isn’t soft. Our discussion touches on structured approaches (like 360 reviews) and everyday, observational cues that help leaders read the room and adjust in real time. We reframe humility as a leadership strength, curiosity as the operational side of great leadership, and positivity as the superpower needed to weather today’s challenges.

If you’re searching for ways to advance your leadership, build resilience, and foster authentic relationships, this episode provides an actionable roadmap to transform self-awareness from a buzzword into your most valuable asset.

What You’ll Learn
- Self-Awareness is foundational
- Feedback is a gift: Receive it well
- Embracing (tough) feedback, can be transformative.
- Make time for self-reflection.
- Curiosity is operationalized humility.
- Positive energy matters, especially in tough times.
- Legacy is about the journey.

Podcast Timestamps
(00:00) - Introduction to the 3-Part Series
(00:42) - Guest Introduction: Kevin Ford's Leadership Journey
(03:26) - The Importance of Leading Yourself
(04:11) – The Role of Self-Awareness in Executive Success
(06:08) - Transformative Feedback: The Value of Tough Conversations
(09:46) - Processing Feedback and Humility in Leadership
(12:12) - Creating Upward Feedback Culture
(14:24) - Reading the Room: Observational Self-Awareness
(16:43) - Internal and External Self-Awareness
(17:56) - Addressing Time Constraints and Feedback Reluctance
(22:18) - Curiosity as a Driver of Self-Awareness
(24:21) - Humility, Curiosity, and Leadership Legacy
(29:04) - Self-Awareness and Decisive Leadership
(32:59) - Positive Energy and Well-being in Leadership
(37:48) - Practical Steps for Sustaining Positive Energy
(41:45) - Final Reflections on Self-Awareness

KEYWORDS
Positive Leadership, Self-Awareness, Leadership Development, Executive Feedback, 360 Assessments, Upward Feedback, Humility in Leadership, Curiosity, Culture, Authenticity, Positive Energy, Well-Being, Mental Health, Physical Health, Energy Management, Legacy, Organizational Culture, Coaching, Empathy, Constructive Criticism, Personal Growth, Employee Engagement, Resilience, Performance Review, Self-Reflection, Emotional Intelligence, CEO Success

What happens when you leave your routine behind to embrace uncertainty? DJ DiDonna, Harvard Business School senior lecturer and founder of the Sabbatical Project, joins Craig Dowden to unpack the real benefits of sabbatical leave, drawn from years of research into hundreds of sabbatical-takers. DiDonna explains why extended leave delivers measurable physical healing, from resolving stress conditions like eczema and ulcers to reducing what he calls functional workaholism. The conversation also covers the confidence and creativity gains people report, the three sabbatical archetypes, and why the benefits of sabbatical leave extend to employers as well as employees.

DiDonna draws on interviews with hundreds of sabbatical-takers to show that the benefits of sabbatical leave aren't reserved for the wealthy or the lucky. He argues most people can plan toward a sabbatical five years out by setting aside a percentage of income and identifying a trusted example who has already taken one. The episode also explores why founders and CEOs, despite having more flexibility, often feel trapped by the businesses they built, and how stepping away can reduce key-person risk while creating growth opportunities for junior staff.

Throughout, DiDonna distinguishes the benefits of sabbatical leave from those of a simple vacation: vacations swap work tasks for leisure tasks, while sabbaticals create open space for identity change, healing, and experimentation. He closes with micro-moment strategies, like disconnecting for a long weekend, that let listeners borrow some benefits of sabbatical leave without leaving their jobs.

Key Takeaways
The benefits of sabbatical leave include physical healing, with sabbatical-takers reporting resolved eczema, ulcers, and trigger fingers.
Sabbatical-takers frequently describe the experience as a peak life event, comparable to a wedding or the birth of a child.
Three archetypes shape how people access the benefits of sabbatical leave: the achiever, the explorer, and the seeker.
Confidence and creativity gains often outlast the sabbatical itself and carry into everyday work life.
Employers benefit too: sabbaticals reveal key-person risk and reduce dependence on any single employee.
Emotional recovery from work identity typically takes six to eight weeks before people feel like themselves again.
Micro-moments, such as fully disconnected long weekends, offer some benefits of sabbatical leave without quitting a job.
Planning a sabbatical five years in advance makes accessing these benefits feel achievable rather than disruptive.

Chapters
00:57 Introduction and DJ DiDonna's background
05:31 Defining what a sabbatical actually is
07:55 Why extended time off matters
14:32 Reframing sabbaticals as realistic for everyone
22:20 Time vs. space: the real difference from a vacation
25:19 The emotional journey of a sabbatical
28:55 The three archetypes: achiever, explorer, seeker
34:02 Financial and logistical planning
38:45 Sabbaticals for founders and leaders
42:26 Micro-moments: everyday sabbatical practices
47:06 Closing thoughts and final advice

Guest Contact
Website: https://thesabbaticalproject.org
Book page: https://djdidonna.com/big-time-off/
LinkedIn: https://www.linkedin.com/in/djdidonna

FAQ

Q. What are the main benefits of sabbatical leave?
A. DiDonna's research points to physical healing, increased confidence, renewed creativity, and stronger organizational resilience.

Q. How long until the mental health benefits of sabbatical leave kick in?
A. Most people need six to eight weeks before feeling like themselves again, separate from their work identity.

Q. Do the benefits of sabbatical leave extend to employers?
A. Yes. DiDonna argues sabbaticals reduce key-person risk and reveal overly dependent business processes.