After a few years designing and supporting reverse mentoring programmes, many of the same issues keep coming back. Reverse mentoring is often a great strategy to support the digital transformation of an organisation since it connects senior decision makers with junior digital natives. The idea is simple, by encouraging cross-generational discussions and experience sharing the organisation gains in agility in the digital era. However, in reality, many issues cloud this simple logic and we are going to explore why that happens and how to get over it.