Maybe the problem is that the HoF is a technophobe whose fear of ICT is getting in the way of what you are all supposed to be doing. Her line manager should be checking that the documents produced do reflect what actually happens rather than exist as token responses. Have you asked for the use of ICT to be a standing item on a faculty agenda? Are there TLR holders in the faculty who feel the same way you do and who can be relied upon for support? The DH sounds a good idea, but you need the support of your other colleagues as your HoF may see it as something else. The DH has plenty of tactful ways of bringing this to your HoF's attention without involving you, e.g. in link meetings or more openly at the HoF's group. Those who, for understandable reasons, seek to protect themselves can do more long-term damage than they realise. It is your place to raise this. After all, your own teaching experience, your professional development and the subject are affected and not in a way you'd like. Good luck.