Many people and organisations have had space to reflect on some big issues over the course of the last two years. This might lead to a need to have some potentially difficult conversations. And for most of us, a sustained period of relentless change, restriction, uncertainty and potentially trauma has had an impact. So, what do we do with a context that includes big questions and burnout? Is this a bad time for difficult conversations? Is there such a thing as a good time for them? Below, I outline what considerations might be part of a healthy and effective approach to these tricky questions.