Using AI as a Thought Partner – Webinar Replay

Originally presented as: “AI in Action: Best Practices for Using LLMs in Mission-Driven Work.” 

This piece is written by Remy Reya, Director of AI and Thought Leadership at Compass Pro Bono. Compass Pro Bono is a nonprofit that helps other nonprofits strengthen their impact through strategic support. In this piece, Remy Reya shares practical ways organizations can approach AI as a thought partner. 

Many nonprofits have begun exploring how AI tools can amplify their work and free up staff time to focus on the warm-touch, relational activities that power our missions. 

It can be exciting and empowering to figure out how AI can support our work. It can also feel exhausting trying to keep up with all the new platforms, features, and techniques emerging seemingly every day—especially for a bandwidth-stretched nonprofit leader. 

Luckily, you don’t actually need to keep up with everything; most of us in the nonprofit sector can get outsized value by focusing on just a few core tools and techniques. In the webinar below, Compass Pro Bono shares some tried-and-true best practices for using large language models (LLMs) in mission driven work: prompt engineering, deep research, reasoning, customization, connectors/integrations, and more. 

Watch the Replay:


As you begin to implement these techniques and integrate AI more deeply into your work, you will also have to contend with where it should fit in, and how to engage these tools in ways that keep your critical thinking and creativity at the center.

One technique we recommend is to bake this philosophy into the tools you use. For example, most large language models (LLMs) allow users to set custom instructions that shape every conversation (sometimes called “personalization features”). Instructions on how to configure these in Claude here, ChatGPT here.

Personalization Language: 

We’ve designed these custom instructions to help you stay in control when using LLMs. We hope you’ll read them over, customize as needed, and paste into your LLM of choice: 

  • I like to use [preferred LLM] as a thought partner. That means my voice, ideas, and critical thinking must stay front-and-center throughout all of our collaborations. Your job is to augment my cognition and creativity. 
  • When I ask you to help with a complex task, start by asking me clarifying questions to surface what I’ve already thought through on my own. Push back if it seems like I’m outsourcing thinking I should be doing on my own. 
  • After completing a task, if appropriate, share something I might not know about the topic we’ve been discussing (an interesting concept, an unexpected connection, a robust counterargument, etc.) along with a link to an article, podcast, or resource where I can go deeper. 
  • Default to helping me think, not thinking for me. Offer frameworks, questions, starting points, and syntheses rather than finished products (unless I explicitly ask for a finished product). 
  • Finally, do not proactively offer to complete a new task after completing a request I make. Wait for me to decide what I need next, even if that’s just asking you what should come next; I want to stay in the driver’s seat.

Explore additional resources in the accompanying slide deck here.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

Real-World AI Strategies for Nonprofits – Webinar Replay

Artificial Intelligence (AI) is reshaping how nonprofits operate, communicate, and serve their communities. In this discussion, experts from The Do Good Institute at the University of Maryland and Compass Pro Bono joined TIFF Investment Management to share how organizations can approach AI adoption strategically, drawing from Compass Pro Bono’s own implementation journey — what worked, what didn’t, and what others can learn.

Watch the Replay:

Key Takeaways:

  • AI can significantly increase nonprofit efficiency when adopted thoughtfully. AI is already embedded in many common tools, and when used intentionally, it can augment human work and free staff to focus more time on mission-driven activities.
  • Building a responsible, intentional AI strategy is essential for success. Compass Pro Bono’s experience shows that clear policies, targeted use cases, staff training, and a culture of experimentation create the foundation for safe and effective integration.
  • AI can meaningfully redirect staff capacity toward high-value work. Teams can reclaim several hours per week—sometimes 10–12—by automating routine tasks and enhancing critical thinking tasks, allowing more time for strategy, storytelling, and stakeholder engagement.

Explore additional resources in the slide deck here↗.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

TIFF Impact Day: Learning, Leadership, and Mission in Action

TIFF held Impact Day on Tuesday, November 4, 2026, bringing our team together for a series of inspiring conversations with leaders across sectors — from technology and education to philanthropy and conservation. The day underscored TIFF’s commitment to learning from organizations driving meaningful change, deepening our understanding of the impact they aim to achieve, and exploring how we can translate those insights into our own work and communities. Here are some of the highlights from each of the day’s speakers.

Matt Gillin, Relay Network
Matt discussed his journey as an entrepreneur, from his family’s influence to founding two successful companies. He emphasized the importance of believing in your mission, staying agile, and harnessing artificial intelligence (AI) to amplify — not replace — human potential. Matt described AI as a platform shift unlike any we’ve seen before and reminded us that while the greatest risk may be not deploying AI fast enough, it’s ultimately human creativity and curiosity that move organizations forward.

Kerry Woodward, Philadelphia Financial Scholars
Kerry spoke about expanding access to personal finance education for Philadelphia students by equipping educators and bringing practical, classroom-ready resources to schools. She also highlighted the PFS Summer Experienceship, which provides students with real-world exposure, skill-building, and mentorship across local organizations, helping them grow financial confidence and envision pathways into future careers.

Keith Palmer, Travis Manion Foundation
Keith shared powerful lessons on leadership and teamwork drawn from his service in the Marine Corps and his work supporting veterans and families of the fallen and mentoring young people. He reminded us that effective leadership starts with “mission first, people always” — an understanding that you can’t accomplish the mission without investing in your people. Anchored in the Foundation’s guiding principle, “If Not Me, Then Who…,” Keith spoke about the importance of mentorship, community engagement, and collaboration as the true drivers of meaningful leadership and impact.

Oliver Bass, Natural Lands Trust
Oliver shared reflections from his 28-year career at Natural Lands Trust, highlighting how the organization’s endowment provides the financial stability needed to pursue mission-critical work — from protecting open spaces and managing development pressures to restoring wildlife habitats. He spoke about how the nature of conservation challenges has evolved, even as the organization’s purpose remains constant, and emphasized that strong financial partnerships make it possible to achieve long-term environmental impact.

A Commitment to Promoting Exchange

Impact Day is born out of one of TIFF’s most fundamental beliefs: that continual learning and open exchange strengthen how we serve our clients. By embracing broad perspectives, we challenge ourselves to think more creatively and to deepen our impact on the communities and missions we support. We’re grateful to each of the speakers for their insightful stories and contributions.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

Capital Connect: Building Community, Education, and Partnership

In September 2025, TIFF Investment Management hosted our inaugural Capital Connections event at the Boston Harbor Hotel—an invitation-only gathering designed exclusively for independent sponsors, managers, leading E&F investors, and TIFF Board Members. TIFF has been making direct investments alongside Independent Sponsors since 2014 and remains an active participant in this growing area of the Lower Middle Market. We were thrilled to host this event as a way to spark candid conversations, share ideas, and strengthen long-term partnerships.

The program began with a two-hour closed-door educational session led by InRider Partners, where independent sponsors engaged in interactive discussions on go-to-market and fundraising strategy. Key takeaways included:

  • Market your investments effectively: Clearly articulate Why You, Why Your Fund, and Why Now. With investors, first impressions matter—and your materials must speak for you even when you’re not in the room.
  • Position with clarity and differentiation: In a crowded marketplace, memorable points of differentiation and a concise strategy statement ensure your edge stands out—because every word counts.
  • Plan for a strong fundraise: Success depends on preparation. Strong closings balance timing and amount, and the best GPs plan early, knowing scrutiny only intensifies with each subsequent investment and fund.

Building on these insights, the evening also highlighted broader themes shaping today’s investment landscape:

  • Lower Middle Market Opportunity: TIFF’s conviction in the lower middle market remains stronger than ever, with compelling opportunities for high real returns.
  • Fundraising Fundamentals: Success with institutional LPs requires thoughtful preparation, positioning, and relationship-building—not just a strong strategy.
  • The Power of Partnership: Enduring relationships across the TIFF community—sponsors, managers, clients, board, and friends—remain central to our mission of generating returns and creating lasting impact.

We extend our gratitude to all who contributed their expertise, creativity, and partnership to make this evening possible. We look forward to hosting Capital Connections as an annual event, and invite you to reach out to learn how you can be part of the next event.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.

TIFF Webinar Replay – Underweighting Equities is Usually a Bad Idea

On June 12, 2025, TIFF hosted an insightful webinar exploring key points from our latest white paper, “Underweighting Equities is Usually a Bad Idea,” led by Trevor Graham and Brad Calder.

In this session Trevor and Brad highlighted key takeaways:

  • Market Timing Pitfalls: Market timing is often counterproductive
  • Impact on Investment Strategy: Underweighting equities creates unattractive opportunity costs
  • Investment Discipline: Long-term, equity exposure critical to achieving investment objectives

Read the white paper here.
Watch the webinar recording here.

The materials are being provided for informational purposes only and constitute neither an offer to sell nor a solicitation of an offer to buy securities. These materials also do not constitute an offer or advertisement of TIFF’s investment advisory services or investment, legal or tax advice. Opinions expressed herein are those of TIFF and are not a recommendation to buy or sell any securities.

These materials may contain forward-looking statements relating to future events. In some cases, you can identify forward-looking statements by terminology such as “may,” “will,” “should,” “expect,” “plan,” “intend,” “anticipate,” “believe,” “estimate,” “predict,” “potential,” or “continue,” the negative of such terms or other comparable terminology. Although TIFF believes the expectations reflected in the forward-looking statements are reasonable, future results cannot be guaranteed.