He was Her Majesty's Chief Inspector of Schools in England from 1994 to 2000, and was one of the most controversial figures in debates on the direction of English education policy.

[6] Woodhead was appointed head of the Office for Standards in Education (OFSTED), the schools inspection service, in 1994.

[6] By this time, Woodhead advocated "traditional teaching methods" and took a scornful view of "progressive educational theories" introduced into English schools from the 1960s onwards.

Critics argued that he was generating poor morale, rarely identified successes in schools, and that the "progressive teaching" he attacked was a straw man, with little resemblance to actual classroom practices.

[6] When the Labour government came to power in 1997 there was much political pressure to replace Woodhead, either immediately or when his initial term expired in 1998, but instead he was retained and his appointment renewed by Education Secretary David Blunkett.

In February 2005, The Guardian obtained information[9] using the Freedom of Information Act, which confirmed that in 1997 Woodhead had over-ruled a unanimous decision by his own inspectors, and a subsequent inspection visit by HMI inspectors, to declare that Islington Green School was failing and required special measures.

[2] He continued to speak out in public on many issues relating to education at both school and university level, often provoking great controversy.

[17] They insisted that their relationship had begun after they had left the school[6][18] but his former wife disputed this version of events and stated that she had been asked to consider a ménage à trois with Johnson when the latter was just 17,[19] a claim in which she was supported by a number of Woodhead's colleagues at Gordano[6] and Tony Robinson, who knew the Woodheads in Bristol.

[27] Woodhead enjoyed running and rock climbing until he was diagnosed with the neurodegenerative condition motor neurone disease in 2006.

In an interview with The Sunday Times published on 3 May 2009,[28] he stated publicly that he would prefer to end his own life than suffer the indignities of the final stages of the disease; in an interview he stated, "The truth is that I would be more likely to drive myself in a wheel-chair off a cliff in Cornwall than go to Dignitas and speak to a bearded social worker about my future.