There is a growing body of literature suggesting that cybersecurity competitions are an important tool for increasing the interest in cybersecurity in light of an urgent need for cybersecurity specialists. At the same time, students rely on their advisors and mentors to be well prepared for these extra-curricular activities. This paper assesses the extent to which educators' and students' views on cybersecurity competitions overlap and to which they differ. The data for the study was collected through three surveys: two, offered to students at Capture the Flag (CTF) events, organized by a higher education institution in Virginia, and one - to teachers/professors who participated in the Virginia Cybersecurity Education virtual conference. Based on the results, we make recommendations how benefits related to cybersecurity competitions can increase for both sides, as they continue to work together to close the cybersecurity skills gap.