It is widely recognised that having applicable digital skills is crucial to a lot of professions and is highly relevant to economic growth and digital transformation. Additionally, a lot of digital training does not consider, the specific needs of the individual. As such, this paper presents an adaption for means of digital skills assessment and training readiness, and practical skills appraisals, which allows training to be modified to individual needs. This paper focuses on a skills' assessments (appraisals) for working professionals that are not in traditionally IT specialist roles such as physio therapists and food technicians, specifically in how working professionals can be assessed and better prepared for digital upskilling. An adapted framework is motivated by using concepts of digital skills' assessment by Van Laar et al. (2018), which includes adapting their established set of measures for 21st century Digital skills. The results and findings, to date, are based upon twelve skills appraisals and six short training sessions, across six participants. Resulting in qualitative data in the form of researcher observations and participant narrations over skill-based activities with non-IT based professionals. Participants were recruited primarily from a regional skills support scheme focused upon digital skills' development, for people in employment. The aims of this paper are to report the findings of active research and to provide initial insights regarding strategies for digital trainers. The suggested approaches are intended to highlight areas of interest and focus for trainees. These approaches should benefit skills development and delivery for a large population of non-IT based professionals.