Pre-Planning: Ensure you are dedicating enough time to pre-planning with your ART teams. Remember, this is not a regular In-Person event where you would have everyone engaging equally. Work closely with your Product Owner and teams to ensure everyone is aware of the new PI priorities, any rollovers from previous PIs and the Acceptance criteria is getting massaged.
Tooling: In a virtual setting, tooling is on center stage. Ensure you have tools for:
Test bandwidth concerns. Work with your IT department to understand the nuances (video/no-video due to bandwidth concerns, any vpn related issues etc).
If your organization allows for it, consider backups or alternatives to your tool of choice. A lot of orgs use some combination of a standard enterprise solution and a more targeted cluster solution like Web-ex and MS teams, Skype, Jabber, Zoom etc. Weigh the pros and cons.
Remember that you would need to replicate breakout rooms/channels for the teams during the actual event. Choose tools which would allow you to do that or alternatives on creating separate invites.
Program Boards: This physical board is an output of the PI Planning meeting and clearly should be replicated in a virtual setting so that it allows for collaboration. Confluence (Gliffy), Miro, google docs, Mural might be good candidates to house your board for the purposes of the PI Planning. Ensure there is a way you can take this data back into your SoR (Jira/Rally/Version1 etc). Remember- multiple people should be able to access the board.
Icebreakers/Energizers: Kahoot, polleverywhere etc. offer great ways for fun icebreaker quizzes and exercises. Liberating structures and funretrospectives.com offers great facilitation techniques and games for RTEs and Scrum Masters to facilitate great meetings and ensure participation from all attendees.
Execution. The traditional two-day format should be revisited, and it is highly suggested you stretch the agenda out over 3 or more days. Remember, you are working with people who are now not only your team members but caregivers, parents, pet parents who will not be able to give you extended focus times. Therefore, it is important you show empathy and build in the slack time.
Consider getting some extra help: Be generous to yourself and recruit extra facilitators. You would need someone to monitor the time during team breakouts, help with scribing and need an extra hand incase you have to step away. Each Scrum Master should consider having a partner and the same applies to the role of the RTE.
Appoint proxies for ART level roles: With multiple virtual breakouts happening, it is possible that a single Product Manager might not be able to answer all questions, or a single Architect will not be able to float through multiple meetings happening simultaneously. If being held at the same time, these roles should be duplicated to allow for easier access by teams and faster communication channels.
Have a central location for all artifacts and links to documents/invites: It is important that you have a single page in either confluence or your enterprise wiki which houses links to all the ART artifacts, program board, meeting invites, breakout rooms etc. to allow for easier access for everyone
Create Remote Working Agreements: Remember to have more frequent breaks, account for children in the background and how everyone is expected to communicate during the planning event.
Plan around time zones/Geographic locations: If you are dealing with multiple time zones and geographic locations, consider going beyond 3 days and splitting the event up into 3-4 hr. chunks on a given day to allow for everyone to uniformly participate.
Wrap-up/Post PI Planning Activities
Retrospectives: Websites such as FunRetro, Trello etc. offer ways to capture real-time anonymous feedback and retro items. Use them in a combination with other online idea gathering tools like dotstorming.com, Miro (for fishbone diagram) etc. to ensure you deliver a power packed retrospective
Ensure to provide yourself as Scrum Masters and RTEs enough time to reconcile data back into your SoR (System of Record)
Communicate your PI Planning activities and plan out to the stakeholders (internal and external) and be clear of when the plan is expected to be shared. Consider uploading it to a shared repository where it is easily accessible.