Tools for Thinking Ahead

Hilary Pearson

One of the most difficult things for any organization is to think ahead, to imagine new scenarios, to picture different or more innovative strategies for your work. At the beginning of a year, there is both opportunity and temptation to draw back for a period and consider the present and the future. But how to do it well? 

Just in time, two knowledgeable authors have offered nonprofit leaders some ways to think in an open-ended but rigorous way about the future. Foundation staff and board members would certainly be able to take advantage.

Jacob Harold offers a new book The Toolbox: Strategies for Crafting Social Impact. Lucy Bernholz offers her Blueprint 2024 in an online format. Both writers are longstanding observers and analysts of philanthropy and civil society, particularly in the United States (both are American). But their advice is not culturally or contextually specific, except in the sense of the types and sizes of nonprofit organizations that they address.

Harold and Bernholz have different backgrounds although both are focused on social change. Harold explicitly calls himself a social changemaker and has led several nonprofits. Bernholz has consulting and academic experience and is based at Stanford University. Both are practical and experienced writers and neither one underestimates the challenges of thinking about the future in the context of social changemaking.

Bernholz is more of a futurist than Harold. She is acutely aware of the difficulties of making forecasts about directions for philanthropy and civil society. She notes that “our current efforts at understanding the present and future are failing – largely because we’re using out-of-date data, built on assumptions that no longer hold, and with models that can’t account for the kinds of dynamics we think are coming but have yet to experience.”

Why should foundations in particular try to better understand the present and the future, given these difficulties?  Because grantmaking foundations, as many (including me) have often argued, are uniquely able to take a long view and to act on it, taking greater risks and offering more patient funding. Social change is slow change, as Rebecca Solnit puts it in a recent essay.  Solnit makes the case that the most radical change can be the hardest to see because it takes time to accrue, to evolve and to build. Taking a long (multi-year) view, she says, “shows you movements shifting what’s considered possible, reasonable, and necessary, setting the stage and creating the pressure for these events, offering a truer analysis of power.”

So it’s worth taking time to identify and reflect on what can be seen, even if it’s small or incremental. “Somewhere in our future”, says Bernholz,” lies the moment when the old gets outnumbered by the new”. Knowing the difficulty of hearing the signal in the noise, Bernholz has helpfully included in her Blueprint a pull-out section of what she calls ‘sensemaking worksheets”. These worksheets can be used to start sensemaking conversations. She suggests collecting a series of today’s headlines and events and trying to make sense of them in the context of your work – looking for patterns, asking how the work of philanthropy may or may not contribute to the story, thinking about how social media play into story, brainstorming wild card events and then seeing how they might affect philanthropic work., asking how AI might change stories and assumptions, etc  There are many possibilities here for generative conversation.

Jacob Harold for his part has put together a book-length guide to tools that can be used for making sense of the present and the future. He suggests that these tools are “frameworks for thinking and acting”. More specifically, they are ways of understanding and shaping context, data, individual behaviour and institutional relationships. In his creatively designed book, complete with images, poetry, charts and texts, Harold describes a “toolbox”, or way of thinking about social change strategies, and nine “tools” for the box, that can be used as approaches to the work of crafting action for social change. Harold’s purpose is not purely sensemaking but helping social changemakers in their effort to create strategies for their work. But like Bernholz, many of Harold’s questions can be used for brainstorming and collective creativity. My review of Harold’s book in The Philanthropist Journal gives you a feel for the tools and the uses that can be made of them. Reading these resources reinforced my view that reflection and creative conversations can be enormously helpful to philanthropies and social sector organizations alike.  We may not know what the future will bring but we can prepare ourselves by collecting evidence and asking thoughtful questions about the directions we see around us.

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