In a recent podcast episode, Lauren Hawker Zafer, the Head of Training and Education at Squirro Artificial Intelligence, joined the discussion on Education in Enterprise digital transformation. As more and more organizations embark on their digital transformation journeys, the importance of educating employees on the changes that come with it cannot be overstated. One of the key questions we discussed in the podcast is, "When should you educate an enterprise?" We discuss why educating employees at the beginning of the digital transformation process is important. This helps set the tone for the changes that will take place and helps employees understand why these changes are necessary. It is also essential to continuously educate employees throughout the transformation process to ensure that everyone is on the same page and that there are no knowledge gaps. Another important topic discussed was what education should cover when undergoing a digital transformation. We explore why education should cover the technical aspects of the transformation and the cultural changes that come with it. This includes communication, collaboration, and teamwork, which are all essential for a successful digital transformation. Finally, the podcast touches on what many CDOs have failed to educate on when carrying out a digital transformation. According to Lauren, many CDOs still need to educate employees on the potential impact the change could have on their roles and responsibilities. This can lead to resistance and confusion among employees and ultimately hinder the transformation's success.