kick off on may 1st

12:00PM – 1:30PM

Speakers: Katie Allan Zobel, Prosper and Bloom & Peter Taylor, Anchor Point Consulting

This workshop is designed for board members and CEOs who are looking for ways to identify, grow, and keep highly effective and deeply committed board at a time when many organizations are experiencing challenges with board recruitment and retention. We will review the lifecycle of a Board member and describe various systems and practices that support each stage of the lifecycle of recruitment, orientation, engagement, and maintaining a board leadership pipeline Whether you need to develop a system from scratch or strengthen one you already use, we will share ways to identify current and future needs, recruit and vet potential members to meet those needs, and processes to nominate, orient and continuously engage members using a lifecycle approach and the respective roles of the board’s governance committee and the CEO in this process. There will be time for participants to share practices that work well and to ask questions.

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: James McKim, PMP, ITIL, Organizational Ignition, LLC

Someone says something to you that is disrespectful of your heritage. You witness behavior that has sexist overtones. You observe a conversation where someone demeans a person because of their racial identity. Besides your legal and organizational policy obligations, you need to have a difficult conversation with the person who caused the affront. But how do you have that conversation in a kind and effective way that has a positive outcome? Combining recent research by cognitive neuroscientists such as Dr. Lara Boyd and Dr. Michael Gazzaniga; conversation experts such as Douglas Stone and Bruce Patton; and discriminatory behavior experts such as Resmaa Menachem, and Iris Bohnet this session will use videos and activities to give you insights into when and how to have these difficult conversations as well as tips on what to do when you see a discriminatory situation occurring.

Learning Objectives

By the end of this session, you will be able to:

• recognize when offensive situations arise
• feel the role trauma plays in contentious situations
• determine when to have difficult conversations  
• identify the three (3) conversations in every difficult conversation
• leverage the steps for having a difficult conversation

Intermediate/advanced content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: Carol Lavoie Schuster, Essex County Community Foundation

Are you considering joining a nonprofit board but unsure of what it takes to be an effective member? This interactive workshop will guide you through the fundamental responsibilities, expectations, and impact of board service.

Participants will learn:
· The core legal duties of board members
· How boards set strategic direction, secure necessary resources, and provide oversight
· The personal responsibilities of board members, including engagement, advocacy, and fundraising
· How to assess board culture, expectations, and fit before committing
· Key questions to ask before joining to ensure alignment with your values and strengths

Through real-world insights, discussion, and self-reflection, this session will empower you to approach board service with confidence and purpose. Whether you’re a first-time board member or looking to enhance your leadership skills, you’ll leave with a deeper understanding of how to contribute meaningfully to a nonprofit’s success.

Beginner content for Board Members and Aspiring Board Members

12:00PM – 1:30PM

Speaker: Steve Filosa, To the Good

Panel members: Kristina Black Wood, Founding Executive Director, It Kicks! Foundation; Jeff Black, Trustee, It Kicks! Foundation; Jeff Musman, Board Chair, It Kicks! Foundation

Ever wonder how family foundations come into existence, sustain themselves, and make governance and grant decisions? Designed for executive directors and nonprofit board members, this interactive workshop will provide valuable insights into how to cultivate strong relationships with funders, navigate grant application guidelines, and effectively steward foundation donors—all while making the process engaging and rewarding.
Facilitated by Steve Filosa (To The Good), this panel discussion will feature the founding executive director and trustees of It Kicks! Foundation (IKF), sharing their journey from inception to current funding decisions. Gain firsthand knowledge of what funders look for, how they approach grantmaking, and best practices for fostering long-term partnerships.
Come ready to share your own experiences, challenges, and aspirations in fundraising and foundation engagement. Walk away with actionable strategies to strengthen relationships with funders, enhance your nonprofit’s financial sustainability, and drive greater impact in your mission.

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: Whitney Slade, City by the Sea Consulting (CBSC)

Many young/start up nonprofits need guidance on how to begin the process of creating sustainability for their organization. Often these early decisions have a profound effect on the health and fiscal status and their impact on the future. In this workshop we will look at the areas fledgling nonprofits need to pay close attention to. Those topics are: organizational development-business and marketing plans; board development-profiling and Board recruitment; the basic structure of a high functioning board; doing a SWOT analysis; laying the ground work for a strategic/visioning plan; understanding the role of fundraising; Board make up that reflects the constituency served; and how to carve out time to be strategic.

Beginner/intermediate content for Board Members and Executive Directors of small to mid-sized nonprofits

9:00AM – 10:30AM

Speaker: Ryan Knight, Insource Services, Inc.

Learn how AI can have a practical impact on your work through real-world examples of how nonprofits are leveraging AI’s ability to bring structure to unstructured information, enabling new automation, streamlining workflows, and ultimately saving precious time and resources. Insource will guide you through:

• Case studies showcasing successful AI implementations
• Understanding the fundamentals of where AI can / can’t help
• The “Do’s and Don’ts” of rolling out AI as a change process

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: Kimberly Zimmerman Rand, Dragonfly Financial Solutions LLC

According to the Center for Effective Philanthropy, burnout is a primary challenge facing nonprofit professionals in today’s workplace. Untenable workloads make it hard for nonprofits to retain the staff that they have worked hard to hire. While some staff may leave, many are mission-driven professionals committed to the work and their clients, making it more likely that they will stay in their positions, though they may struggle to maintain their performance. One way to improve staff retention is through promotions and raises, but that alone may not lead to a healthy productive leader. Staff members who are the first in their families to reach this level of professional attainment may continue to manage their increased income with the same mindset that they used when they were living paycheck to paycheck, thereby eroding the financial gains that they have made in the workforce. To support first-time managers, one local nonprofit is providing their newly promoted managers with personal finance coaching along with their salary adjustment. Professional coaching provides twofold benefits: first, it equips nonprofit managers with the knowledge and skills to manage their money in a clear and confident manner, and second, it gives managers exposure to professional coaching techniques that they can utilize with their teams and clients. Feedback on this approach is overwhelmingly positive – managers report higher satisfaction not only with their personal finances but also in other areas of their life, and their work performance improves as the result of having less financial stress and acquiring coaching skills.

Intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: Jenora Ledbetter, The Self Care Network LLC

As diversity, equity, inclusion, and belonging efforts face mounting political scrutiny, legal challenges, and cultural resistance, organizations must confront the elephant in the room – how to sustain and protect equity initiatives in an increasingly polarized environment.

This workshop equips leaders with practical strategies to navigate opposition, counter misinformation, and reinforce diversity, equity, inclusion, and belonging as essential drivers of organizational success. Participants will gain insights into the current political and legal landscape, learning how to proactively address challenges rather than avoid them. We will explore how to reframe equity work as a business imperative, mitigate risks, and ensure long-term organizational commitment.

Attendees will leave with a Resilience Toolkit, featuring risk considerations, messaging frameworks, and advocacy templates to help organizations embed equity into their culture—ensuring that inclusion and belonging remain priorities, even in turbulent times.

Intermediate/advanced content for Board Members and Executive Directors of nonprofits of all sizes 

9:00AM – 10:30AM

Speaker: Rachel Keir, CCS Fundraising

Nonprofits today face unprecedented challenges and opportunities in a rapidly evolving philanthropic landscape. This session is designed to equip nonprofit board members and leaders with the latest strategies to champion development and secure sustainable growth. We’ll dive into emerging trends and essential data that illuminate how philanthropy remains robust despite economic uncertainties. Attendees will gain insights into the powerful role of individual giving and the increasing impact of foundation support, especially through Donor Advised Funds and megagifts. This interactive session will offer practical, board-level approaches to prioritize and amplify fundraising efforts. We’ll discuss how boards can empower fundraising teams and ensure development is front and center in board agendas. Participants will leave with clear, actionable steps and frameworks to guide their organizations through change, ensuring long-term growth and mission success. Join us to strengthen your board’s influence in building a resilient, impactful nonprofit.

Intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speakers: Marissa Lewis, PENN Creative Strategy & Molly Penn, PENN Creative Strategy

Succession planning helps ensure your mission and programs remain stable in the face of leadership changes, it creates business continuity, and it creates a motivating and encouraging environment. It creates a mechanism to manage the ongoing development and movement of staff within the organization. We will cover how to effectively and efficiently navigate board succession planning strategically, and leave you with ideas (and tools!) to help you think about building your best board.

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speakers: Andrea Shapiro, Andrea Shapiro Consulting & Jackie Cefola, Jackie Cefola Consulting

Organizational financial management can be empowering and engaging – seriously! It can be really hard to talk about money. Nonprofit leaders, board, and staff may not agree about organizational priorities or funding strategies. Personal feelings and past experiences with money can also lead to a scarcity mindset or distorted thinking about how to budget effectively. Participatory organizational budgeting and authentic discussions about financial management – processes that engage the board and staff in talking openly about the money – can build trust, buy-in, leadership, and personal agency. When teams collaborate on budgeting and financial management, organizations can thrive while preparing the next generation of leaders. This workshop will NOT focus on spreadsheets or accounting categories. Rather, we seek to have real and engaging conversations about how the budget reflects organizational priorities and community needs. The budget also engages staff in creating a shared understanding of how organizations translate hopes and dreams to revenues and expenses.

Beginner/intermediate content for Board Members and Executive Directors of small to mid-sized nonprofits

12:00PM – 1:30PM

Speaker: Lyn Freundlich, Change for Good Coaching and Consulting

We talk a lot about ensuring that our organizations are equitable. But what does that actually look like in practice? Join us for a conversation about the organizational systems and structures we can put in place to ensure that all of our staff, regardless of identity, feel a true sense of belonging in our workplaces. We will talk about the full employee life-cycle, from hiring, to compensation and benefits, to performance management and professional development. In this highly interactive session, you will have a chance to think about the ways your organizational culture ensures all staff belong as well as concrete steps you can take to increase that sense of belonging. You will come away not just with good ideas, but with a host of resources to support you and your organization on this critical but also continuous journey.

Intermediate/advanced content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:00PM

Speaker: Erica Olmstead, Compass North Consulting

This foundational session equips participants with the tools and insights to create a living, breathing strategic plan that is bold yet realistic, clear, collectively owned, and adaptable. Through adaptive management models emphasizing learning, iteration, and flexibility, participants will explore how to gather essential information to assess their organization’s current position, engage stakeholders, and set actionable strategies for sustainable growth. You’ll learn how to define measurable goals, cultivate a culture of continuous learning, and establish feedback loops that provide valuable insights, allowing your organization to anticipate and respond to change. This workshop empowers leaders to achieve long-term goals by fostering a resilient strategic approach that maximizes impact and adapts in a dynamic world.

Beginner/intermediate content for Board Members and Executive Directors of small to mid-sized nonprofits

9:00AM – 10:30AM

Speakers: Cara McCarthy Hutchins, Communications, Ink, Cazzy Smith, Communications, Ink, Kimberley Ballard, The Cabot

At Communications, Ink, our team has helped non-profits and educational organizations raise over $200 million with our multi-channel, strategic approach. This workshop will use real-life examples and show you how to frame your campaign, craft effective messages, build a master plan and create materials that engage with your donor audience.

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speakers: Jenn Mayo, Essex County Community Foundation & Kelly Stimson, Greater Worcester Community Foundation

Join us to learn how partnering with your local community foundation to establish a Nonprofit Fund can help your organization plan for and invest in a sustainable future. Do you want access to a professionally managed investment portfolio for a low cost? Do you want to start building an endowment but need a partner who can offer structure and add to the investment knowledge on your board? Whether your goal is to establish a rainy-day fund or to eliminate the administrative aspects associated with your current endowment, a Nonprofit Fund offers your organization access to professionally managed investment pools curated specifically for charitable funds. And by partnering with a community foundation, you’re joining a local nonprofit organization with deep roots in your region, a wealth of financial expertise and a commitment to building a more equitable community for all of us.

Beginner/intermediate content for Board Members and Executive Directors of nonprofits of all sizes

12:00PM – 1:30PM

Speaker: Larry Raff, Copley Raff Inc.

• Personal and organizational mission alignment.
• What it means to be a leader of an organization.
• The processes, opportunities, and challenges of fundraising.
• Personal biases about money.
• What it means to interact with and be a philanthropist.
• Holding effective virtual donor meetings and asks.
• Cognitive dissonance and fundraising.
• Building confidence to participate in fundraising activities.

12:00PM – 1:30PM

Speakers: Kristin Noon, Hurwit & Associates & Valerie Sussman, Hurwit & Associates

An active and engaged board of directors can mean the difference in an organization’s ability to shift from survival mode to thriving. Sometimes, it can be hard to motivate volunteer leaders to engage—from fulfilling their most basic duties, like attending meetings, to truly supporting an organization in meaningful and impactful ways. In this session, we will explore steps organizations can take as soon as their next board meeting to better engage and activate your board members in supporting your organization.

The workshop will cover:

• Embeding board member responsibilities into corporate documentation, such as bylaws, governance policies, and orientation guides and handbooks;
• Bringing your board members closer to your organization’s work;
• Building relationships to foster engagement;
• Integrating conversations about the board’s responsibilities into the routine operation of the board;
• Holding candid conversations, if needed, with suggested scripts for challenging moments such as resignations and removals; and,
• A review of the duties and responsibilities of a board of directors and best practices in board recruitment, which can surface board candidates best aligned with your mission and needs.

The workshop will conclude with a brief question and answer session.

Intermediate content for Board Members and Executive Directors of nonprofits of all sizes