Grantbook’s Strategy & Design Delivery Lead, Leyla Razeghi-Hutchison, attended the WINGS Conference in Montreal, joining more than 500 participants from 50 countries to explore the ideas, challenges, and opportunities shaping philanthropy around the world.

A recurring theme throughout the conference was the value of learning across borders and contexts. Understanding what works and what doesn’t can help funders and philanthropic organizations challenge established assumptions and rethink how they support social change in their own communities.

From reimagining risk to exploring AI, several conversations stood out for their relevance to how philanthropy can become more responsive, collaborative, and effective.

1. Rethinking risk and how we move money

One of the conference’s central questions was how funding can reach organizations working in complex environments without allowing risk management to become a barrier to meaningful impact.

During the “Moving Money Well” session, participants worked through real-world case studies to examine the systems, assumptions, and decisions that influence how money moves. The discussions encouraged funders to look beyond individual transactions and consider the broader funding ecosystem, including the challenges faced by the organizations receiving support.

A related discussion explored how Global Affairs Canada considers both its risk appetite and its impact appetite. The distinction is important: while managing risk is necessary, funders must also consider the risks of not acting, including missed opportunities to support organizations addressing urgent and complex challenges.

For philanthropy, this raises an important question: Are funding decisions balancing the potential risks of an investment against the potential impact of withholding it?

Reframing risk in this way can help funders make more informed decisions while creating space for innovation and supporting organizations that may be best positioned to address challenges on the ground.

2. Listening to communities and reimagining impact

Another recurring theme was the importance of listening to the communities that philanthropy seeks to serve.

In one group discussion, participants explored what is working well across the sector. The conversation highlighted the value of creating space for innovation, centring community voices, and giving organizations the flexibility to respond to changing needs.

These ideas challenge traditional approaches in which funders largely define success, establish priorities, and determine how impact should be measured. A more responsive approach recognizes that communities and grantees bring essential knowledge about the challenges they face and the solutions most likely to work.

This also means allowing grantees to reimagine what impact looks like in their own contexts, rather than expecting every organization to fit within a predetermined framework.

Indigenous knowledge systems and approaches to social change offer important perspectives in these conversations, reminding the sector that there are many ways to understand progress, build relationships, and create lasting change.

Ultimately, listening to communities requires more than consultation. It means building funding relationships in which community knowledge informs decisions and organizations have the flexibility to adapt as circumstances evolve.

3. Moving beyond the one-year grant

Flexibility also emerged in conversations about grant structures and funding timelines.

During a discussion on the future of philanthropy, Noorain Khan of the Ford Foundation suggested moving away from the traditional one-year grant in favour of greater flexibility.

The idea speaks to a broader challenge in the sector: organizations are often expected to deliver meaningful, sustainable outcomes within funding periods that may not reflect the time required to achieve them.

Short grant cycles can create administrative burdens, make long-term planning difficult, and limit organizations’ ability to invest in the people, relationships, and infrastructure needed to sustain their work.

Longer-term and more flexible funding can give grantees greater room to respond to emerging needs, experiment with new approaches, and focus on their missions rather than continually preparing for the next funding cycle.

Of course, no single grant structure will suit every organization or circumstance. But the discussion reinforced the importance of questioning whether established funding practices are serving the needs of grantees — or simply reflecting how funders have traditionally operated.

4. Building philanthropy policy with global and local perspectives

The conference also explored how public policy can help shape the philanthropic sector.

Participants learned about Ireland’s National Philanthropy Policy, which was co-created with stakeholders engaged from the outset. The approach offered a useful example of how involving different perspectives early in the process can help ensure that policy reflects the needs and experiences of those it affects.

WINGS is also working on a global philanthropy policy, prompting discussions about how a shared framework can account for the different cultural, social, and institutional contexts in which philanthropy operates.

A global perspective can help build connections and encourage collaboration across regions. However, a common approach should not come at the expense of local realities. Practices that work well in one context may not translate directly to another, particularly where communities have different histories, traditions, and relationships with institutions.

The challenge is to identify shared principles while leaving room for local knowledge and approaches to guide implementation.

This balance between global collaboration and local relevance was one of the conference’s broader lessons: meaningful progress often comes from sharing knowledge across contexts without assuming that one model will work everywhere.

5. Approaching AI in philanthropy with curiosity and caution

Artificial intelligence was another important topic, with discussions exploring both its potential to address complex challenges and the risks it presents to organizations and communities.

The AI and Philanthropy panel, featuring Alex Tveit, offered a balanced perspective on the opportunities and potential negative impacts of AI. Rather than treating the technology as either a universal solution or something to avoid altogether, the conversation emphasized the importance of informed, critical engagement.

One particularly practical takeaway was that foundations do not need to be technology funders to begin understanding AI.

AI is already influencing many of the issues philanthropy supports, from how organizations deliver services and make decisions to how communities access information and navigate digital systems. Funders can therefore benefit from understanding how the technology is changing the environments in which their grantees work, even if AI is not directly part of their funding strategy.

For foundations looking to begin that learning journey, the discussions pointed to a few useful starting points:

• Understand the implications for the issues you fund. Consider how AI may affect the communities, organizations, and systems connected to your grantmaking priorities.
• Make space for learning. Encourage informed conversations about where AI may offer opportunities, where it introduces risks, and what questions remain unanswered.
• Consider the people affected. Assess potential consequences for grantees and communities, including unintended harms and unequal impacts.
• Stay open to both opportunity and uncertainty. Engaging thoughtfully with AI does not require having all the answers; it requires a willingness to learn and adapt.

For philanthropy, the goal is not necessarily to adopt AI as quickly as possible. It is to understand the technology well enough to make informed decisions about its implications for the work and communities funders support.

6. Recognizing that support extends beyond the cheque

One of Leyla’s final table discussions returned to a fundamental question: What does it take to help organizations do their best work?

Funding is essential, but financial support is only one part of the relationship between funders and grantees.

Participants emphasized the value of normalizing support for training, professional development, and connections that help organizations strengthen their capabilities and expand their networks. They also discussed the importance of giving grantees the flexibility to define and revisit their own understanding of impact.

This broader view of support recognizes that organizations need more than resources to deliver on their missions. They may also need opportunities to learn from peers, develop new skills, build partnerships, and respond to changing circumstances.

When funders recognize these needs as legitimate parts of organizational development, they can help create conditions for more sustainable work.

The concept of “support beyond the cheque” also invites funders to reflect on the nature of their relationships with grantees. Rather than viewing funding as a one-way transaction, philanthropy can approach these relationships as opportunities for collaboration, learning, and mutual accountability.

A more generous approach to philanthropy

Across the WINGS Conference, a number of interconnected ideas emerged: rethink risk, listen to communities, allow greater flexibility, learn across borders, approach new technologies thoughtfully, and recognize that meaningful support takes many forms.

Together, these conversations point toward a philanthropy that is willing to question established practices and adapt to the realities of the organizations and communities it seeks to support.

They also reinforce the importance of building systems that enable collaboration and learning, rather than relying solely on familiar processes or predefined measures of success.

One question from the conference has stayed with Leyla:

What kind of generosity does the world need from us now?

It is a question that extends beyond how much money philanthropy distributes. It invites the sector to consider how it shares power, responds to uncertainty, builds trust, and creates the conditions for communities to shape their own futures.

Thank you to WINGS and everyone who contributed to these conversations for creating space to learn, challenge assumptions, and connect across contexts. The ideas shared in Montreal offer plenty to reflect on — and an important reminder that strengthening philanthropy begins with a willingness to keep learning.