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Many digitally successful companies have established a dedicated digital transformation strategy. An SME perspective on this topic remains unclear. I fill this research gap with a qualitative research approach. Main findings include a set of 14 strategic questions along four summarizing categories – use of technologies, changes in value creation, operational changes, and financial aspects. Three out of these four categories hold true in SME environments as they are valid in large corporation settings. I recommend establishing the term “organizational changes” instead of “structural changes” in order to increase fit to the mindset of SME owners. Answer options enrich these strategic questions, based on the experience of successful examples from the field. I identify differences between SME and large corporations in the areas of value creation, organizational changes and financial aspects. This paper elaborates theory on digital transformation strategy, contributing to understand management behavior and decision levels in an economic environment, where the adaptation of digital technologies has become an imperative.