The challenges of undertaking digital transformation within Small and Medium Enterprises (SMEs) are multiple. The constraints of limited resources and a lack of clear strategic purpose for the transformation are readily evident across many existing case studies. Underlying these evidenced challenges is the persistent issue of the digital maturity of an overall organisation and its people individually as key factors in the success or failure of these change projects. We examine the use of a digital maturity assessment tool within an established membership-based SME to understand these many challenges and the way they are revealed through tools of this kind. We utilise a reflective approach based on direct organisational observations to consider the veracity and value of these assessment tools in supporting the drive for positive organisational change. Our conclusions are loosely critical of the generalised nature of these tools but support their intended purpose through the benefits that they generate through a Hawthorne Effect.