Contemporary language documentation workflow is a largely digital process. While this has had many benefits for how linguists undertake language documentation projects, it has also lead to a disparity between how the process is conceptualised by academic researchers, and how it is conceptualised by the speakers of endangered languages. In this paper I discuss the nature of this disparity, and illustrate this with my own experience of working with speakers of Tibeto-Burman languages in Nepal. In my own research I have incorporated ongoing discussion regarding digital methods into my working relationships with participants, but other researchers have made digital training a specific feature of their research methodology. I discuss two projects that provide positive models for this kind of digital gap bridging. The first is the Iltyem-iltyem sign website and the second is the Aikuma language documentation phone application. After discussion of these positive developments in digital outreach I discuss some of the challenges that we still face in ensuring that what we do is engaging and relevant for the communities we work with. This discussion is not only relevant for language documentation researchers, but for all who work in the digital humanities, as we need to be more aware of the different needs and levels of digital education of different communities.