Taking Risks and Learning From Mistakes

About this collection: This NCFP Content Collection provides context for how generous families can assess philanthropic risk, tame and mitigate risk, and even expand their comfort zone to embrace uncertainty and learn from their mistakes.

Philanthropy is often described as society’s “risk capital.” This NCFP Content Collection provides context for how generous families can assess philanthropic risk, tame and mitigate risk, and even expand their comfort zone to embrace uncertainty and learn from their mistakes. Know of other good resources on this topic? Please suggest a resource.

NCFP Passages Issue Brief and blog posts

Expanding Your Comfort Zone: A Window Into Risk in Family Philanthropy

Passages Issue Briefs
Philanthropy is often described as society’s “risk capital.” Our generosity can support causes and ideas that business and government agencies cannot or will not. We can use our resources to inspire new ideas, challenge existing thinking, or continue supporting an organization when others won’t.

3 Ways Foundations Squash Risk-Taking

Article
There was a time not too long ago when you rarely heard the word “foundation” and “risk” in the same sentence…or paragraph…or entire document. Risk simply hasn’t been something formally and broadly associated with philanthropy over the past few decades.

Expanding Your Comfort Zone: Managing Risk

Article
As I sit here writing about risk, the date at the bottom of my laptop screen – September 11 – is a jarring reminder that risk analysis is both futile and indispensable. It’s futile if we use risk analysis to predict the future. Or come to believe that the act of reflection …

To Make a Difference, Family Philanthropy Must Take More Risks

Article
Many of us in family philanthropy are driven by a grand vision of a better world. We are motivated by bold ideas, and finding ways to use our philanthropy to make a difference and leave a lasting impact. And, at the same time, we are too often hamstrung by a …

Learning from mistakes

The Best Mistake We Ever Made: Jessie Smith Noyes Foundation

Article
A sure-fire indicator that we all make mistakes was the capacity crowd at the National Forum on Family Philanthropy workshop in Seattle entitled, “The Best Mistakes We Ever Made.” Using a rapid-fire format, each of ten speakers took three minutes to share a mistake they made in their family philanthropy …

Failure Reports: A how to guide

Tool
This document, developed by Fail Forward, is intended to support organizations who are interested in documenting and learning from their failures, and using the process as a launch point for organizational change. It is largely based on the process developed by Engineers Without Borders Canada (EWB), an organization which has …

Samples, checklists, and templates

A guide to risk taking at NYSHealth

Sample
In April 2011, a group of staff from the NYSHealth Foundation met and considered the topic of risk taking in their grantmaking. This checklist was developed for staff to more systematically assess the potential level of risk when evaluating a proposal or project. To learn more about tht thinking behind this …

Case Foundation: Be Fearless framework and foundation profiles

Be Fearless: The 5 Core Principles

Tool
Those charged with finding or funding solutions to social challenges — philanthropists, government, nonprofits — seem to be moving too slowly and often operating with the same set of tools, concepts and caution of the generations before us. To tackle today's big and ever-changing social challenges, we have to Be Fearless.

Be Fearless: A framework for action

Tool
A step-by-step guide from the Case Foundation for leaders and organizations that want to be fearless and create transformative change. Inside, you'll find assessment tools, ideas and discussion prompts specially designed for social sector changemakers like you who want to make a greater impact.

Surdna Foundation: Be Fearless Spotlight Story

Impact Story
On the eve of its 100th anniversary, the Surdna Foundation is stronger, more nimble and more effective as a philanthropic organization than it has ever been. The secret to its success? Stakeholders who encourage failing forward, experimenting with new ideas and collaborating with others

Open Road Alliance: Be Fearless spotlight story

Impact Story
Whatever the catastrophe, Open Road Alliance (ORA) stands ready to help, able to offer grants of up to $100,000—with decisions made within two to six weeks of applying. Their average grant is $76,000 and, since 2012, it has awarded $3.5 million to groups including the Global Press Institute and the Grameen Foundation. Read …

Jacobs Family Foundation: Be Fearless Case Study

Impact Story
An abandoned lot, an experimental initial public offering (IPO) and a culture that believes that failure leads to learning inspired the Jacobs Family Foundation to transform its business model from traditional grantmaker to place-based funder to maximize impact without sacrificing its core values and mission. A Be Fearless case study, …

Additional resources from NCFP colleagues

Philanthropy Lessons: Risk and Mistakes

Video
Effective philanthropy is a learning process that develops through experimentation. To be successful, we must take risks, support new ideas, acknowledge our mistakes, share experiences, and learn from one another.

Understanding Rsk Tolerance in Grantmaking

Article
Understanding decision-making patterns is the first step toward improving them. We know that despite best efforts to act rationally, human tendencies to avoid risk and loss while seeking certainty and gain can impact sensible decision-making. Research has demonstrated this phenomenon across many facets of our society—including finance, consumer products, …

How shortcuts cut us short: Cognitive traps in philanthropic decision making

Report
Cognitive traps can hinder any decision a foundation makes about its strategies. This includes how to construct a theory of change to address it, and which grantees are best suited to do the work. It also includes decisions made during implementation, such as whether strategy adjustments are needed or whether …

Due Diligence Tool For Pre-Grant Assessment

Tool
The Due Diligence Tool is the product of a collaborative effort and the contributions and thinking of grantmakers from a diverse set of foundations. The Due Diligence Tool represents a blending of best practices from a variety of foundations from around the country. Our process pulled together the practices and …

Risk in Philanthropy: A Framework for Evaluation

Tool
To help both grantmakers and NGOs better identify, assess, mitigate, and plan for risk in their portfolios, Open Road Alliance offers this framework for evaluating risk. This brief framework is designed to provide grantmakers and NGOs with tools to conceptualize and describe risk and its implications within the scope of …

Scenario and Contingency Planning in Philanthropy

Tool
Scenario and contingency planning help nonprofit leaders plan for and react to opportunities and challenges that may arise over a given time frame. They enable nonprofits to ask and answer the question, "What would we do if…?" for a variety of circumstances, taking time to consider strategic implications, identify and …