If the following scene rings a bell, this blog post may be for you.
The meeting is drawing to a close, and your director, colleagues and board representatives are nodding along after hearing the new place-based strategy. It is a good one, and it aligns with the organisation’s vision. Stakeholders have been consulted; the difficulty of the context has been acknowledged. The language is of ambition, collaboration and systems change.
You look around the room and think: this is not going to work.
You feel the urge to ask: but what if?
What if someone whose support we need wants something different? What if an apparently supportive partner has another definition of success? What if a group we have underestimated can delay, redirect or stop what we are trying to do? What if this intervention creates losers as well as winners?
And then comes the second thought: I do not want to be the person who ruins the party. Again.
This piece is for those people inside foundations who find themselves asking those questions. Not the pessimists, but those who keep looking at the terrain while others keep their eyes on the destination.
These reflections grew out of a session at the London Funders Festival of Learning that I co-ran with Renaisi. The first part drew on Renaisi’s inquiry into sustaining place-based systems change. In the second, my Curiosity Society colleague Anna Crooks and I introduced a set of tools for a related problem: how do we remain capable of acting when alignment frays, interests diverge and a strategy encounters opposition?
Anyone who has tried to do place-based work already knows that places are political. Decisions create trade-offs and expectations. Some people and groups benefit more, some benefit less, and some have perfectly legitimate reasons to resist a particular design. Yet we are often more comfortable talking about participation, relationships and voice than about who can actually make, block or redirect a decision. Place-based strategy inevitably involves power, whether we use the word or not.
This does not mean abandoning optimism or assuming that every place is hostile. Quite the opposite. A strong vision matters, and believing that what you are trying to achieve is worthwhile matters too. It motivates teams, boards, donors and partners. But vision alone rarely sustains the work, and someone also has to ask what the strategy may be missing.
At the Festival, we tried to make this practical. We gave participants a fictional place-based scenario built around a group of funders considering how to regenerate a disused civic building. Each small group chose one of three tools to strategise around the situation: a power map to ask who could actually make or break the initiative; a pre-mortem to work backwards from failure; or red teaming, to stress test the strategy against plausible competing interests and sources of contestation.
Groups were free to pick one and focus on it. Interestingly, most chose red teaming, which was also the most demanding exercise: participants had to role-play, challenge and defend the strategy, adjudicate the arguments being made, and then come back together to identify what the strategy might need to change.
One moment from that exercise has stayed with me. A participant working with the red teaming tool made a powerful observation: before asking why the project might fail in the future, she asked what had made previous attempts fail.
It sounds obvious once someone has said it. Yet that is precisely the point. Obvious questions do not necessarily appear in the processes through which strategies are developed and approved.
Exploring that one question properly could take hours of work. Every vision of the future enters a place that already has a history, a politics, an economy, a geography, and countless previous failures. And of course each of those elements affects expectations, trust, and the energy people are prepared to invest in the next attempt. What might look like resistance to a new intervention may sometimes be an entirely rational response to what came before. And history is only one part of the terrain. Places contain multiple actors moving at the same time, with different sources of authority, different incentives and different ideas of what success looks like.
At times, place-based work resembles a dance. Partners adjust to one another, find a rhythm, share information and make something possible together. At other times, it is closer to a fight in the mud, with interests pulling in different directions, decisions stalling, and relationships being tested again and again.
A serious strategy needs to be prepared for both. That kind of lateral, critical thinking is what the three tools and the exercises were intended to encourage. To be clear, the goal wasn't to turn every foundation into machines for producing doubt, but rather to stress test early enough, to improve judgement without draining it of ambition.
Beyond the exercises themselves, I see three practical moves for the critical thinkers inside funding organisations.
- Inside the organisation, make the role explicit. Build permission to ask these questions into existing processes, from theories of change to investment committees and portfolio reviews, and use tools such as power mapping, pre-mortems and red teaming when they can sharpen the decision.
- Share what you have learned. If your work has produced a useful power map, identified recurring blockers or changed your understanding of how a place works, find ways to share those findings with other funders working on the same territory or issue. We should not have to rediscover the same dynamics organisation by organisation.
- Do not throw away what you did not use. The scenarios rejected, assumptions tested, alternative explanations and branches that never made it into the final strategy may still contain valuable knowledge. Where appropriate, anonymise and preserve that material so that others, including smaller local organisations with fewer resources for this kind of analysis, can build on it rather than start again.
Sustaining place-based systems change is not simply about eliminating conflicts – it is about acting under uncertainty and building the capability to remain flexible when circumstances change and interests pull in different directions.
Funders already contribute money, relationships and organisational capacity. But they can also play a role in developing better ways of reading power, remembering what came before and sharing what we learn. Done well, that knowledge becomes part of a place’s civic infrastructure, rather than disappearing with the project that produced it.