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Letting Go to Lead: Putting My Questioning Hat Back On

By Melissa Gibson, CEO, Len Reynolds Trust

July 2026

On Thursday, I attended an excellent session facilitated by Philanthropy New Zealand on the idea of letting go to lead. The workshop explored mana-enhancing practice: what it means, why it matters, and what might change if funders genuinely designed their systems and relationships around enhancing the mana of communities. We considered examples of mana-enhancing funding processes, the role of power and trust in philanthropy, and what a mana-enhancing relationship between funders and communities might look like in practice.

I left with more questions than answers, which was exactly what I needed.

There are times when attending a workshop gives you a handful of useful tools, a new framework, or a list of things to implement. This session caused me to revisit some of my assumptions, including practices I have previously felt confident defending. Since Thursday, I have had thoughts swirling around in my head, and I wanted to capture some of them while they are still fresh. What follows is my own reflection on the questions the session raised for me, without attributing comments to individual speakers or others in the room.

One thing I cannot stop thinking about is a comment from one of the speakers: if you do this job properly, working in philanthropy is one of the hardest jobs in the world. If you do not, it could be one of the easiest.

Working for a philanthropic funder can be incredibly easy if we allow it to be. We can create a strategy, establish criteria, open a funding round, receive applications, assess them, make decisions and distribute money. We can point to the number of grants made, the total funding distributed and the reports received. We can remain busy, compliant and administratively efficient while also remaining largely unchallenged.

Doing the job well asks us for much more. It requires us to consider who created the system, who benefits from it, who can navigate it successfully and who may never even approach us. It requires us to examine how our privilege shapes our view of what is reasonable, strategic, measurable or worthy of investment. It requires us to hear criticism without immediately becoming defensive and to recognise that our processes are never neutral. It also means being in the trenches with community: standing alongside people when the work is difficult, using our voice when it matters, and sharing some of the responsibility rather than remaining at a comfortable distance.

Every system benefits somebody. Every requirement creates an advantage for some and a barrier for others. Every decision about what information is required, how it must be presented and when it must be submitted reflects a choice about whose time and convenience matter most. Doing this work properly means continuing to examine those choices.

One of the most powerful things in the room on Thursday was watching people speak truth to power. There were many nodding heads, and I found myself nodding too, while also wondering whether agreement is enough.

It is relatively easy for those of us working in philanthropy to say that we welcome challenge. Remaining genuinely open becomes harder when that challenge is directed at a process we designed, a decision we made or a system we believe is already progressive. I want to mihi to those who enter rooms like that and challenge funders directly. There can be a real personal and organisational cost to speaking honestly to institutions that hold resources. It takes courage to name practices that diminish mana, reinforce inequity or serve institutions more than communities, especially when the people being challenged may have influence over future funding.

That should make us pause. When people challenge us, our first response should not be to explain why our process is different, why our intentions are good or why change is complicated. Those things may all be true, but defensiveness can prevent us from hearing the substance of what is being said.

I enjoy it when someone questions our processes. At least, I believe I do. That belief also needs to be tested. Do I enjoy being questioned only when I already have a good answer? Am I equally receptive when the challenge exposes something I have overlooked? Am I open when the answer is unclear, or when responding properly might require us to give something up?

There is little point attending a session about power and trust unless we arrive with an open mind and an open heart. We need to challenge ourselves and our practices. Our peers and community leaders are often the people best placed to do that, particularly those with deep experience, strong relationships and significant mana who are already showing the sector what more equitable practice can look like.

The session also made me reflect on the gatekeeping role of chief executives and senior leaders within funding institutions. I personally try to do a significant amount of co-funding. In some cases, we take a genuinely collaborative approach, working with other funders and community organisations to develop proposals together. This takes far more time than making an isolated funding decision, and it would certainly be easier not to do it.

I increasingly see part of my role as being a funding broker. The Len Reynolds Trust is a relatively small funder. We cannot afford to fund every worthwhile initiative to the level it needs or deserves. When we believe in the kaupapa, our responsibility should extend beyond the limit of what our own organisation can contribute. We may be able to connect people, open doors, advocate, introduce other funders or help bring a group of partners together around a shared opportunity.

That brokerage role carries power too. As leaders within institutions, we decide which ideas reach a board, which relationships receive attention, which proposals are developed, which conversations happen and whose work is introduced to others. Even where the final decision belongs to trustees, executives often shape the information, context and recommendations on which that decision is based.

That means we need to keep asking who we are opening doors for and who remains outside. Whose work do we instinctively understand and champion? Whose work are we asking to be translated into language that makes sense to us? How do people find us, particularly if we describe ourselves as proactive funders?

Proactive funding may reduce the burden of open applications, but it creates its own risks. If we primarily fund through existing relationships and networks, we can easily continue finding organisations that look familiar to us. We may inadvertently privilege groups with visibility, connections, professional networks or proximity to decision-makers. Proactive funding does not automatically shift power. Sometimes it simply moves the gate.

Another thought buzzing around my head is whether our funding partners would come into a room like that and present our practices as an example of good funding.

The real test goes well beyond whether our systems are more flexible or relational than traditional funding models. Most organisations receiving funding will understandably express appreciation for that support. I am more interested in whether they would independently describe the relationship as mana-enhancing. Would they say they felt trusted? Could they be honest when things went wrong? Were our reporting expectations useful and proportionate? Could they challenge us without worrying about the financial consequences? Did our processes respect their expertise, time, tikanga and relationships with community?

The power imbalance complicates any feedback we receive. When we ask funding partners what they think, how confident can we be that they feel safe enough to tell us the truth? Those of us who hold the money also influence the conditions in which feedback is offered. A polite response may tell us very little about the health of the relationship.

Another comparison from one of the speakers challenged me: do I have to prove to my board every month that I am worthy of receiving my salary?

Of course I am accountable in that I report to the board, and I believe my performance matters. The Trust has responsibilities, and I have obligations within my role. But I am not required to reapply for my job every month. I am not asked to repeatedly prove that I am still worthy of being paid while also delivering all the work I was employed to undertake.

Yet that is close to what the funding system can ask of community organisations. We ask people to continually explain the problem, establish their credibility, demonstrate demand, describe their activities, forecast their outcomes, calculate their budgets, evidence their reach, report on their progress and then begin the process again. Often, they are doing this for multiple funders through different systems, using different language and working to different timelines.

Meanwhile, the people completing these applications are often also responsible for delivering the mahi, supporting whānau, managing staff, responding to crises, maintaining relationships and keeping their organisations financially viable.

We need accountability while also recognising the difference between meaningful accountability and repeatedly asking organisations to prove their worth. We should ask whether our requirements produce information that genuinely improves our decisions or relationships. Some requirements may provide little more than institutional reassurance. Others may ask organisations to repeatedly perform competence and legitimacy because that is what funding systems have traditionally expected.

There is also a tension between openness and clarity. A broad strategy can feel more generous and community-led because it leaves room for communities to define their own solutions. Even then, decisions are still being made behind the scenes.

There are boundaries, preferences and judgments about alignment, readiness, scale, leadership, geography, risk and impact. When those judgments remain unclear, organisations are left to navigate rules they cannot see.

To be clear is to be kind. If we know that certain work is unlikely to be funded, we should say so. If our available funding is already heavily committed, we should be transparent. If we are looking for a particular kind of relationship, leadership or contribution, organisations should not have to discover that through an unsuccessful process.

There is also a deeper question beneath the strategy: who has the right to decide it? Funders are often encouraged to be strategic, but strategy is itself an exercise of power. We determine which issues are priorities, what outcomes matter, which communities are named and what kind of change we regard as legitimate.

At the Len Reynolds Trust, our strategy asks us to acknowledge our privilege, act with humility, uphold Te Tiriti o Waitangi, support Māori-led solutions, challenge power dynamics, practise empathy in partnerships and be a proactive ally in advocacy and leadership. It also commits us to challenging sector norms and pursuing disruptive change. Those commitments matter most when they are visible in our behaviour, particularly when acting on them carries risk.

Funding community organisations is only part of what it means to stand alongside them. The harder question is whether we support them publicly when advocacy becomes uncomfortable.

Funders often describe themselves as partners and allies. That relationship is tested when communities advocate for policy change, challenge injustice or confront systems that are causing harm. In those moments, are we willing to use our relationships, reputation, networks and institutional voice? Are we prepared to say something politically inconvenient? Will we stand alongside a funding partner when there is no grant announcement or positive story to share?

Money is only one form of power held by philanthropy. Access, legitimacy, convening power and influence also matter. Choosing not to use them is still a choice.

Perhaps the biggest question I took away from the session was how much of our funding system has been designed around what is administratively convenient for funders. This question keeps going around in my head because the answer is probably more than we would like to admit.

Funding rounds are one obvious example across the sector. Although we do not use funding rounds at the Len Reynolds Trust, they illustrate the wider issue clearly. Funders open them when it suits us, close them when it suits us and set assessment periods around our own meeting schedules. Community organisations are then expected to organise their plans and needs around institutional calendars that may bear little relationship to the realities they face.

Why do funding rounds need to be the default at all? If applications are part of a funder’s process, could they remain open throughout the year and be reviewed in regular batches? Could proposals be considered monthly or at more natural decision points? Could we reduce the pressure created by a single closing date?

There may be sound reasons for some of our processes. Capacity is real. Governance calendars matter. Staff workloads matter. Limited funding means choices must be made. Even so, “there is a reason” should only begin the conversation. We should still ask whether the benefit to the funder justifies the burden placed on community.

Administrative convenience matters because funders need workable systems. The problem arises when our convenience carries more weight than the experience of those seeking support. Applications can be difficult for applicants, and removing them entirely creates other challenges.

Open applications provide a pathway for organisations outside a funder’s existing networks. They allow communities to bring forward ideas we may never discover ourselves and reduce the chance that funders alone decide who is worthy of attention. At the same time, applications can consume enormous amounts of time and emotional energy. They can reward professional writing rather than community impact, encourage organisations to reshape their mahi around funder priorities and create competition between groups that might otherwise collaborate.

Proactive funding reduces some of that burden by allowing funders to do more research, develop relationships over time and approach organisations whose work aligns with the strategy. It can also reinforce closed networks, making access dependent on visibility, reputation or who already knows whom. New organisations may have no clear way of getting onto a funder’s radar.

Every funding approach carries benefits and risks, and every system advantages someone. Our responsibility is to be honest about those trade-offs, listen to those experiencing the process and keep adjusting.

I was also grateful to be reminded about pōwhiri and the way relationships and koha can be understood through that process. A pōwhiri involves preparation, invitation, encounter, listening, acknowledgement, relationship, responsibility and reciprocity. Koha carries and expresses that relationship.

What might philanthropy look like if we approached funding in that way? What would change if our first question was, “What relationship are we entering into, and what responsibilities come with it?” What would it mean to recognise the knowledge, labour, trust and vulnerability that community organisations bring as part of the koha? How might we behave differently if we understood funding as one contribution within a much larger relationship?

Good stewardship and careful decisions remain essential. Holding charitable funds carries real responsibilities. Boards must think critically, limited resources mean choices have to be made, and some proposals will be declined. Mana-enhancing practice should shape how those decisions are reached, communicated and experienced.

We can make difficult decisions while treating people with dignity. We can decline funding transparently. We can ask questions without assuming that we hold all the expertise. We can undertake due diligence without continually requiring organisations to prove their legitimacy.

The reality is that while we hold the money, we hold power. We can share some of that power, be transparent about it, use it in service of community aspirations and design practices that reduce its harmful effects. The relationship will still carry an imbalance, and naming that imbalance is an important starting point.

Letting go to lead asks us to release the assumption that holding the resources means holding the answers. It may involve giving up control over how outcomes are defined, reducing unnecessary reporting, stepping out of the centre of the story, becoming more flexible about timelines and recognising that risk sits differently for funders and communities.

Community organisations already carry enormous risk. They carry the risk of services closing, staff burning out, whānau being unsupported and urgent needs going unmet. They carry reputational, cultural and relational risks within the communities they serve. Funders generally carry the risk that a grant may not achieve what was expected. Those risks are profoundly different.

Next month marks my seventh anniversary as chief executive of the Len Reynolds Trust. When I first started, I was very much in questioning mode. I asked why we did things a certain way, who each process benefited, why we needed particular information and whether we could make things easier.

Over the years, we have made significant changes. We have moved away from contestable funding rounds, placed greater emphasis on relationships, become more proactive, undertaken more of our own due diligence and tried to reduce the burden on the organisations we support. Those changes matter, and they also need to remain open to scrutiny.

Change can be followed by comfort. Practices that once felt innovative can become normal, and processes designed to solve one problem can create another. As time passes, it is easy to move from questioning a system to maintaining it. Perhaps the greatest risk is becoming too comfortable with practices that once felt bold?

Seven years feels like the right time to put my questioning hat back on. I want to look closely at the administrative traps we may have fallen into. I want to ask what we do because it is genuinely necessary and what we do because it is easier for us. I want to examine what we ask for because it improves our decisions and what we ask for because it provides reassurance.

I also want to consider where our proactive practices have opened access and where they may have closed it. How easily can someone who does not already know us find us? How do we hear from groups outside our existing relationships? Are we as open to challenge as we believe ourselves to be? Would our partners describe our relationships as mana-enhancing? Are we standing with community when it counts? Are our values visible in the moments when acting on them requires us to surrender control, take a risk or use our voice?

We need fresh thinking in philanthropy and the courage to keep examining systems that have become normal. Small adjustments should not be mistaken for a genuine shift in power. When communities tell us that our processes are not working, we need to listen carefully, including when those processes were created with good intentions.

Trust is experienced through our actions. Mana-enhancing practice lives in the quality of our relationships and requires humility, transparency, care, consistency, reciprocity and a willingness to change. The money may sit within our institutions, while the knowledge, leadership and solutions already sit within communities.

Perhaps letting go to lead begins with asking better questions, listening carefully and allowing the answers to challenge us.