How often have you sat down with your team and have asked them to plan a project to intentionally fail? Often we plan for success, we strive to be optimists and in doing so we end up believing we have covered all eventualities as fewer and fewer issues arise.
A deliberate exercise
In a group, your only requirement is to make the project a failure. What would that look like and could you do anything to prevent it?
Asking people that know the business and systems to tell you where your blind spots are will return massive results. Suddenly you are looking at extremes of failures and now have to ask which one can seriously hurt your goal or the project.
Asking a team that represents the entire business is beneficial as you gain different view points.
Asking a team made up of developers or just testers can also lead to interesting outcomes, as this SHOULD BE a representative team effort you should ensure that a mixture of people and skills are there to play.
Yes play, have some fun. Treat this as a game because you would be surprised at how creative people can get attempting to destroy a project.
Jot down on post-its, index cards or even on a white board something that could cause the project to fail. From Dave being abducted by aliens to a process not being followed correctly.
Once you all have had fun doing trying to destroy the project, a member of the group should be nominated to read out the first failure, discuss it and vote on a scale of unlikely to likely to hurt the project, then rotate to the next person in the group to read out the next failure.
Once you have those notes in some order on that scale. Ask people to vote on the ones they would like to see rectified, then ask people to take ownership if they can.
Yes even the Line Manager can take ownership to prevent Dave's abduction.
Plan to meet again to discuss if progress has been made on any failures and what is blocking that progress, can somebody in that group help or should it be flagged to someone else?
Even a temporary chat channel is ideal at this point.
It sounds like a retrospective from a sprint and in some ways it is, adjusting this tool slightly for another use can help uncover areas outside or inside the project that you and your team can control. Ensuring the business is fully aware of all the risks facing another successful project.