In thinking about how to facilitate strategic discussions in a not face-to-face environment, it is easy to treat the exercise as simply translating in-person activities into an online environment. I believe that is a trap. The reality is that even in person we don’t often conduct good meetings, and we rarely leverage the full diversity of the people at the table. For complex and messy we substitute simple and easy. In discussing strategically important questions online, that is a potential recipe for disaster.
We’ve all been challenged by that one person in the meeting who opposes everything, simply for the sake of opposing. Or because they’re afraid. Or because they just like to argue. The role of the devil’s advocate is challenged. It’s also challenging. But under the right circumstances, it can be hugely helpful.