The lack of 21st century skills within classrooms and schools globally is a critical challenge that we are facing across education today. The current job market demands these skills for employability, yet employers continue to vocalize their dismay about the difficulty in finding employable candidates, because of their lack of 21st century skills. How can we possibly prepare our students for the competitive demands of this rapidly growing job market, if we are unable to support educators and leaders in acquiring the skills needed to successfully create this infrastructure as a culture? How can we also expect students to successfully develop these skills confidently, if we’re not taking ownership to ensure that our educators and parents are also being granted equal opportunities to learn? Given that senior school leaders genuinely have the best interests of their communities at heart, then what’s holding them back in fostering a school culture that empowers all stakeholders to build 21st century skills? They have extremely high-risk priorities that govern their community’s ability to thrive equally across their plan. Is it therefore challenging to balance and/or include education technology into their digital strategy priorities? Or is it merely that senior school leaders do not have sufficient awareness of the importance, options, and/or planning involved in successful digital transformation implementation? Money carries its own burden for senior school leaders, so does budget play a large factor as well? Could it be that senior school leaders may be hesitant to consider and/or implement digital transformation solutions because of fear of change and/or the unknown? Whatever the reasons, it’s our responsibility to support senior school leaders to overcome these challenges, so that our students are successfully equipped with the 21st century skills needed to thrive in tomorrow’s competitive job markets.