[1] During the COVID-19 pandemic in the United Kingdom, he expanded Eton's online learning platform EtonX to state pupils and opened the school's accommodation to Key workers.

[1] He stated his interest in widening the school's intake to those of different backgrounds, saying "we want talented boys to be able to come to Eton whatever their financial circumstances".

[2] In response to a parent and alumni-led petition after the murder of George Floyd in May 2020, he pledged to focus more on teaching about systemic racism and "decolonising" aspects of the school.

He also stated he would increase efforts in diversifying the faculty after it was pointed out that there were only two black teachers at the school.

[3] Henderson's wife, Ali, worked as a civil servant at 10 Downing Street under Tony Blair and Gordon Brown.