This qualitative case study was conducted to explore factors affecting educational leaders' ability to access program technology tools during initial software adoption. The problem was organizational leaders are often provided digital support tools when implementing a new digital program, but many factors may affect their ability to access and use those tools. The purpose of this qualitative case study was to explore factors influencing an educational leader's ability to access and use additional supporting materials and dashboards designed for supporting staff when adopting new digital programs. Theoretical frameworks were aligned with the self-efficacy theory proposed by Bandura and the contingency theory introduced by Fiedler. A gap in the literature indicated more information was needed on factors influencing educational leaders' ability to access support tools during software solution adoption. The research questions were designed to explore leaders' technology self-efficacy during educational software adoption and factors affecting their ability to use staff-facing support tools. Data collection came from a purposive and convenient non-probability sampling of 17 educational leaders through semi-structured and unstructured interview protocols. Creswell and Poth's Spiral analysis method was used to identify codes and the three major themes: (a) beliefs about technology, (b) technology self-efficacy, and (c) organization contingencies. Key results were: (a) organizational culture and structure during program adoption, (b) high motivation to access technology tools comes from a desire to support staff, and (c) background knowledge drives technology self-efficacy. Recommendations include researching how leaders create positive organizational cultures for software adoption and how educational leaders develop onsite staff to be technology leaders. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]