In our rapidly evolving work environment, the gap between principal and staff expectations has never been wider. From practical to unrealistic, the needs and wants of our workforce have shifted dramatically in only a few short years. This keynote explores the shifting dynamics of the modern workplace, addressing how we can bridge this “expectation divide”. Learning outcomes include fostering better communication, understanding generational differences, and ways to address new expectations like remote work options, mental health prioritization, and feedback & value alignment.