Yesterday I holed up with 14 colleagues in a non-descript conference room here at the foundation to conduct what ended up being a very messy but nonetheless illuminating autopsy. We performed it on our initiative to support the health of democracy in the U.S. Now I know what you may be thinking: “Wait, you guys were just getting started with that line of grantmaking, and you’ve killed it off already?”

Well, not exactly. The autopsy we performed was a prospective one, a philanthropic “premortem,” if you will, that had us looking back to assess what happened with our work from a vantage point in the future; in this case, March of 2017. That is when we are scheduled to go back to our Board with an assessment of how our initial plans have unfolded.

The point of a premortem is to break through the bias of unwarranted optimism. The psychologist Daniel Kahneman has observed that, “most of us view the world as more benign than it really is, our own attributes as more favorable than they truly are, and the goals we adopt as more achievable than they are likely to be. We also tend to exaggerate our ability to forecast the future, which fosters overconfidence.”

If the “optimistic bias” is true for most people, it is especially the case for those of us working in philanthropy. Our grand strategies may have us walking around naked, but nobody is inclined to tell us we are not wearing any clothes.

As described by decision scientist Gary Klein, a premortem is “done at the beginning of a project rather than the end, so that the project can be improved rather than autopsied. Unlike a typical critiquing session, in which project team members are asked what might go wrong, the premortem operates on the assumption that the ‘patient’ has died, and so asks what did go wrong. The team members’ task is to generate plausible reasons for the project’s failure.”

By stipulating that something has already failed, you free people up to express doubts and critiques they have been harboring but did not feel at liberty to express. You unleash the devil’s advocates.

We did our pre-mortem with a bit of a positive twist, as recommended by Bob Sutton and Huggy Rao in their new book Scaling up Excellence. Half of our group was charged with telling our board in three years that “this Initiative is proving to be a disappointing failure, and we should wind it down.” They had to develop a concrete and plausible scenario for what went wrong—and why—between now and then.

At the same time, in order to stimulate debate, and to identify where failure or success might hinge on the same considerations, we charged the other half of the group with fleshing out the details of an alternative scenario, one that had them telling the board that “we have made exciting progress with this Initiative, and we should extend and expand our investment.”

By the end of the day, these two teams had wallpapered the conference room with their post-it notes and summaries on sheets of butcher paper. We are now in the process of reviewing and digesting these artifacts and our notes from the ensuing discussion. I’ll come back in next week’s post with the key findings of the premortem and the implications for our plans.