The dialogue in the field of mentoring has changed over time. In the early days mentoring was a straightforward and pragmatic means to an end: developing others. The blooms of mentoring flowered everywhere. Then thorny issues started to be encountered, both in theory and in practice. Case studies are used here to illustrate the mixed fortunes experienced in contemporary times in three different organisations. A balance between mentoring blooms and mentoring thorns is evident in each case. Three major themes are then identified from these case studies that raise questions for the mentoring discourse. These are: different views of systems thinking, different value bases for evaluating mentoring, and different ideas about the kind of relationship mentoring ought to be. In conclusion, there is a need for a balance: between on the one hand understanding these different positions to promote dialogue and on the other hand developing rivalries to animate dialogue in the first place.