A great source of knowledge to plan and conduct meetings is Liberating Structures — consisting of 33 different meeting types for Revealing, Analyzing, Spreading, Planning, Strategizing, and Helping. The site links to free mobile applications — Google Play & Apple App Store — that explain what each structure is good for, how to conduct the meeting, and the rationale behind it.
Liberating Structures can also help focus distributed work teams and groups. In addition, the restrictions created by the technology medium can provide more structure than many of the physical meetings we may have attended in the past. Moving these structures online might require a bit more planning, and likely more time, but can still get the job done. For example, online video conferencing platforms that offer breakout rooms are suitable for both large and small group discussions.
So if you want to articulate the paradoxical challenges that a group must confront to succeed, then Wicked Questions might be a good meeting structure. It requires groups of 4-6 and paper for note-taking. Just substitute chairs for a designated breakout room and use a whiteboard and recorded chat. Even the audio can be recorded. This exercise can be done as sessions over a period of time to promote more conversations and reflections. It does require good facilitation and curation skills by those conducting it.