Rather than ask "what could go wrong?" the standard technique of premortems[1] is to imagine an specific thing went wrong and then brainstorm root causes. Our brains are much more creative when working backwards this way.
I've done premortems for the launches of new features where we imagine some symptom ("user apparently saves data, but it doesn't commit") and then have the team try to hypothesize causes for it. You can generate the symptoms either by thinking of common failure modes or having people on the team privately come up with their own cause-symptom pairs.
Another important thing to do is use the exercise to discuss what tools/dashboards/techniques you would use to diagnose and repair these issues. his can help you find gaps in your monitoring, logging, and diagnostic capabilities.
I've done premortems for the launches of new features where we imagine some symptom ("user apparently saves data, but it doesn't commit") and then have the team try to hypothesize causes for it. You can generate the symptoms either by thinking of common failure modes or having people on the team privately come up with their own cause-symptom pairs.
Another important thing to do is use the exercise to discuss what tools/dashboards/techniques you would use to diagnose and repair these issues. his can help you find gaps in your monitoring, logging, and diagnostic capabilities.
[1] https://hbr.org/2007/09/performing-a-project-premortem