Protect Dissent

When planning or engaging in strategy work, we're subject to any number of cognitive biases that cloud or ability to objectively evaluate the odds of success. We're irrationally optimistic about the expected outcomes, but underestimate the cost of delivery. Groupthink makes us reluctant to voice a contrary opinion for fear of rocking the boat. In most organizations, dissenters are punished more than those who maintain the harmony of the group, even if the dissenters are right.

To overcome these and other biases, it's important to build a process around productive disagreement. This can be achieved through a variety of techniques.

One common technique is "red teaming," a military practice whereby a team is assigned to poke holes in a proposed strategy or plan. The job of the red team is to come up with ideas of how to defeat the proposed plan. This helps expose gaps and identify areas that may need to be supported or adjusted.

Another similar technique is the pre-mortem. In this technique, the team projects ahead a certain period of time and imagines that their initiative was a complete and utter failure. They then work backwards and discuss what must have gone wrong to produce this result. Again, this can expose weaknesses that might undermine success.