Leading with purpose: Practical tips for purpose-driven work

Dale Waterman is a Solution Designer and regulatory expert at Diligent, with deep experience translating evolving mandates into practical governance requirements for organizations. In this episode, we look at how today’s shifting risk universe is reshaping the regulatory landscape for nonprofits and what boards need to do now to move from basic compliance to true resilience.

We explore why diverging global regulations on issues like AI, cybersecurity and operational resilience make life more complex for mission‑driven organizations operating across multiple jurisdictions, and how boards can adapt to a “tsunami” of change without losing sight of their purpose. Dale explains the shift from rules‑based to risk‑based regulation, what “appropriate and proportionate” controls really mean in practice, and why documenting risk decisions is now just as important as the policies themselves.

We discuss how boards can build a continuous‑learning mindset, ask better questions of management, and embed resilience into strategy rather than treating it as a standalone risk function. We explore operational resilience as a source of advantage, not just recovery: anticipating “grey rhino” risks, using scenario planning and stress tests, and turning crises into opportunities to better serve beneficiaries, donors and communities.

Stick around to the end for Dale’s key recommendation for how to strengthen resilience and future‑proof nonprofit governance for 2026 and beyond.

Further resources on regulations for nonprofit boards

You can find the guide mentioned on the podcast along with other useful resources at www.boardeffect.com/leadingwithpurpose.

Kristy Grant-Hart is Vice President for Compliance Services at Diligent, advising organizations on how to build effective, modern compliance programs in an era of rapid regulatory change. 
In this episode, Kristy shares a compliance expert’s view on AI, cyber risk and governance for public-facing boards — from school districts and education boards to municipalities and local councils. 

We explore the core responsibilities of public sector boards today: staying on top of current and upcoming regulation, keeping risk assessments up to date, and tailoring regulatory requirements to the size, structure and context of each organization. Kristy explains why “application” of a rule often matters more than the rule itself and how boards can balance rising expectations for transparency and accountability with the realities of politics, elections and competing community opinions. 

We also discuss what it takes to build a proactive compliance culture, including understanding skills gaps on the board, bringing in external experts on topics like cyber and AI, and making smart use of associations and umbrella bodies for guidance and training. 

And we also speak about operational and organizational resilience, looking at how reputation, school and community ratings, and regulatory scrutiny intersect — and why boards should be using tabletop exercises and crisis simulations to expose vulnerabilities before a privacy breach, ransomware attack or system outage hits. 

Stay tuned to the end as Kristy shares her advice for leaders on future‑proofing their organizations amid regulatory uncertainty.

Further resources on regulations for public facing boards

You can find the guide mentioned on the podcast along with other useful resources at www.diligent.com/leadingwithpurpose.

Kira Ciccarelli is Senior Research and Programs Manager at the Diligent Institute, where she leads research into how boards and governance professionals are navigating today’s rapidly evolving risk landscape.

In this episode, we explore what nonprofit boards can learn from emerging trends in the corporate world — and how they can apply those insights to strengthen compliance, oversight and stakeholder trust. We discuss why regulatory risk is climbing so sharply and which areas are set to demand even more attention in 2026, from policy and procedure updates to targeted ethics and compliance training and more robust internal monitoring.

Kira shares fresh data from the Diligent Institute’s GC Risk Index and explains what it signals for charities, foundations and other mission-driven organizations that are already stretched thin. We also talk through practical steps boards can take to put the right governance around AI, even as they experiment with new technology.

We also dig into the fundamentals of future‑ready governance for nonprofits: building and maintaining a clear board skills matrix, planning succession at both board and C‑suite level, leveraging board management platforms like BoardEffect as a single source of truth, and using scenario planning and tabletop exercises to prepare for regulatory shocks before they hit.

Throughout, Kira offers concrete advice on fostering a culture of proactive compliance and communicating clearly with donors, regulators and the public to protect and grow stakeholder trust.

Stay tuned to the end as Kira shares her best advice for board chairs and governance professionals on future‑proofing their organizations against regulatory uncertainty and staying one step ahead of emerging risks.

Further resources on regulations for nonprofit boards

You can find the guide mentioned on the podcast along with other useful resources at www.boardeffect.com/leadingwithpurpose.

Dottie Schindlinger is Executive Director of the Diligent Institute and a founding member of BoardEffect and Nithya Das is General Manager of Diligent’s Governance Business Unit and Chief Legal Officer. Together, Dottie and Nithya bring deep expertise on how purpose-driven organizations can strategically harness technology and AI to transform their impact.

We discussed why the urgency to modernize governance is greater than ever for nonprofits, foundations, school boards and local governments. Dottie and Nithya share how economic pressures and shifting regulations make nimble, tech-enabled governance absolutely critical — and how AI is moving mission-driven boards toward more efficient, transparent and equitable practices.

We also talk about what practical impact looks like, discussing real examples from boards using tools like Diligent Community and BoardEffect to streamline meetings, track strategic goals, boost community engagement and improve decision-making with AI-powered features.

Listen in as we explore the ethical side of AI adoption, touching on data privacy, bias and the importance of thoughtful policies. Dottie and Nithya offer actionable advice for leaders starting their digital transformation journeys, including the value of pilot programs, upskilling and collaborative change.

Plus, they share bold predictions about the future of governance that you’ll want to hear. And do stick around to the end for their great advice to help boards future-proof their governance and embrace technology confidently.

Further resources on technology and AI for governance for public facing boards

You can find the guides mentioned on the podcast along with other useful resources at www.diligent.com/leadingwithpurpose.

James Page is Chief Information Officer at the New York State School Boards Association, and Jay Worona is a partner at Jasper Schlesinger & Narendra and former Deputy Executive Director and General Counsel for NYSSBA. Together, they bring a wealth of experience in school board governance, legal policy and technology strategy.

In this episode, James and Jay share their insights on how AI and digital tools are reshaping governance in school districts. From streamlining administrative tasks and enhancing board decision-making to improving transparency and equity. We explore the opportunities AI presents for strategic planning, risk management and community trust, while also addressing the ethical and practical challenges that come with rapid technological change.

We discuss the importance of human oversight, professional development and creating clear policies to guide responsible AI adoption. Jay and James offer thoughtful advice on how school boards can foster innovation while safeguarding student data, ensuring equitable access and maintaining accountability.

Listen now as we explore how school boards can move from reactive to proactive governance, what skills board members need to develop, and why curiosity, courage and critical thinking are essential in the age of AI. Stick around to the end for their top tips on future-proofing governance in K-12 education with technology.

Further resources on technology and AI for governance for public facing boards

You can find the guide mentioned on the podcast along with other useful resources at www.diligent.com/leadingwithpurpose.

Nonie Dalton is Vice President of Product Management and Phil Lim is Director of Product Management at Diligent. Together, they bring deep expertise in how mission-driven organizations like nonprofits, school boards and local governments can harness emerging technologies such as AI while keeping ethical governance at the core of their mission.

Nonie and Phil share their perspectives on how AI is transforming governance from a reactive function to a proactive, insights-driven practice. We explore the opportunities AI presents for efficiency, transparency and impact measurement, while also addressing the ethical challenges around accountability, bias and data security.

Listen in as we find out how Diligent is building cool AI tools with privacy and control in mind, and how features like Smart Prep, AI Search and risk management tools are helping boards make better decisions with less effort. From community engagement to multilingual access, they share exciting developments that are shaping the future of governance for mission-driven boards.

Stick around to the end to hear their excellent advice for how boards can future-proof their governance and why human judgment remains essential.

Further resources on technology and AI for governance

Our technology and AI guide for nonprofit boards mentioned on the podcast along with other useful resources can be found at www.boardeffect.com/leadingwithpurpose while the technology and AI guide for public facing boards can be found at www.diligent.com/leadingwithpurpose.

Darian Rodriguez Heyman, a speaker, consultant and best-selling author with deep expertise in fundraising, governance and AI. Darian has worked with mission-driven organizations around the world and recently released his latest book, “AI for Nonprofits”.

In this episode, Darian shares practical insights on how AI is transforming nonprofit governance, from streamlining board recruitment and engagement to enhancing meeting efficiency and impact measurement. He emphasizes the importance of intentional adoption, data security and creating clear policies to guide responsible use of AI.

We explore how leaders can overcome skepticism, build trust and use AI as a thought partner to unlock efficiencies and improve effectiveness. Darian also offers actionable best practices for board development, orientation, and strategic oversight, all while keeping the human element front and center.

Listen now as we discuss how to future-proof governance structures, the role of co-intelligence and why mission-driven leaders must embrace AI with thoughtfulness and purpose.

Stick around to the end for Darian’s one piece of advice every nonprofit board should hear when it comes to using technology and AI for governance. 

Further resources on technology and AI for governance for nonprofit boards

You can find the guide mentioned on the podcast along with other useful resources at www.boardeffect.com/leadingwithpurpose.

Scott Bridgen is the General Manager of the Audit and Risk Division at Diligent. Scott brings a wealth of experience and unique insights into the critical role of financial and risk oversight in the public sector.

In this episode, we talked about how public sector boards can manage their financial resources responsibly and effectively identify, mitigate and monitor risks. Scott highlights the need for a risk-aware culture that focuses on objectives and potential obstacles, rather than just the term 'risk.'

He also advocates for transparency and clear communication with your community to build trust, and the importance of speaking to that audience in a way that they're going to understand. Scott and I also explored leveraging technology for oversight, such as the Diligent One platform, how to manage and present risk information efficiently, and ensure a single source of truth for operational effectiveness.

Stick around to the end of the conversation to find out what advice he gives for boards that realize they don’t have a good handle on risks. 

Further resources on financial oversight and risk management for public facing boards

You can find the financial oversight guide mentioned on the podcast along with other useful resources at www.diligent.com/leadingwithpurpose.

Heather Rich is Executive Director of the American Board of Genetic Counseling, the national certifying body that sets and upholds professional standards for genetic counselors across the United States.

Heather shares her insights on the critical role of the board in ensuring financial transparency, proactive management and strategic oversight. She also emphasizes the importance of a robust onboarding process for new board members, which should include financial training to cover the basics as well as the organization's financial philosophy.

We also discuss the importance of a strong, supportive relationship between the board and the CEO, where the board has ultimate responsibility for financial and risk oversight, while the CEO and staff handle day-to-day operations and provide necessary information and training.

Heather shares real-life anecdotes, including how the American Board of Genetic Counseling manages its financial review process. We also discuss effective financial and risk oversight, and how board members can make informed decisions based on past data and trends for good oversight.

Stick around to the end to find out what advice Heather gives for maintaining financial integrity and oversight, including scenario planning to assess risks and opportunities.

Further resources on financial oversight and risk management for volunteer boards

You can find the financial oversight guide mentioned on the podcast along with other useful resources at www.boardeffect.com/leadingwithpurpose.

Dr. Chad Bledsoe is President of Montgomery Community College in North Carolina. The College offers a wide range of educational opportunities including associate degrees, technical diplomas, certificates and continuing education programs.

In this episode, we explore why financial and risk oversight is essential for effective governance and decision-making in community colleges. Dr. Bledsoe emphasizes the importance of aligning financial strategies with the institution's mission and goals, and ensuring that resources are used effectively to support student success and community engagement.

He shares his perspective on how boards can function efficiently by fostering a culture of transparency and accountability. We also discuss the importance of ongoing education for the board in areas such as financial management and risk assessment. And how the integration of technology to enhance board operations can help boards function more efficiently and enhance their oversight.

Stick around to the end to find out what advice Dr. Bledsoe gives for public leaders and board members for managing risk and financials. 

Further resources on financial oversight and risk management for public facing boards

You can find the financial oversight guide mentioned on the podcast along with other useful resources at www.diligent.com/leadingwithpurpose.