Special Ops – 5 Situations for Deploying a Red Team

By Kris Putnam-Walkerly

We all need friends and colleagues who have our backs. When we’re going out on a limb, we need support. But maybe we need something else, too. Maybe we need someone who can think like the enemy.

The CIA calls it the “Red Team.” The military, the Federal Aviation Administration, and major corporations like IBM also use the term to refer to a group designed to penetrate your defenses — with your enthusiastic approval. This idea isn’t often discussed in philanthropy circles, but I believe it holds tremendous value for us.

In information technology, a Red Team might be the hackers who try to break into a system; in the military, the Red Team plays the role of the enemy trying to overcome your defenses. In any organization, a Red Team is charged with finding out what can go wrong, where the holes are, and why what you’re trying to do won’t work. The point is to question your assumptions, plans, operations, concepts, and capabilities. The purpose, of course, is to increase the effectiveness of your organization or your project by uncovering why something won’t work so that you can either fix it or abandon it, before you become irreparably entangled. This goes beyond the typical due diligence often done by foundations.

Here are five situations in which a funder should have a Red Team:

1. There’s a lot of money on the line. Perhaps you’re making a very large grant, significantly higher than most that you make. Maybe it’s one of the largest grants in your foundation’s history. Are you sure you’ve considered all the holes that money could fall into, or do you need to bring another level head or two to the table before you hand out the cash?
2. The foundation’s reputation is at stake. Perhaps you are taking on a controversial issue, or maybe you’re taking the lead in your community to solve a particular problem. Have you thought through all the implications clearly? Do you need someone who can look at your actions through the eyes of, say, a local news reporter hunting for a juicy story?
3. A project will use a lot of your foundation’s internal resources. Perhaps it will draw a significant amount of your CEO’s time, or it will need involvement from multiple departments, diverting them from their other important work. Who has helped you think through what this will mean for staff morale and productivity?
4. You can’t walk away. Perhaps you’re thinking of committing to a five-year project to fund technology upgrades for schools in disadvantaged neighborhoods. You are going to need to stick with it, and not pull the plug mid-way (e.g., leaving schools with new technology but no training to use it). A Red Team could help you identify unforeseen obstacles that could sabotage the project in early stages, or conclude that this is not the best use of your philanthropic resources.
5. You’re responding to an emergency — or a perceived emergency. The community you serve has been hard hit by an unexpected storm or other disaster, and suddenly you’re tempted to rechannel your support. But you’re not an emergency-response unit; do you have advisors who can help you think through the results of a knee-jerk reaction, no matter how well intended?

A Red Team doesn’t have to be complicated. It does need to involve smart people who are given permission to kick the tires — and to do so quickly. What are you working on right now that could use a Red Team? Who are three individuals you could call tomorrow to be on your Red Team? And how might they help you avoid costly mistakes? A Red Team isn’t always necessary, but when you need one, its contribution is invaluable.

© 2014 Kris Putnam-Walkerly. All rights reserved. Permission granted to excerpt or reprint with attribution.