Voice of private sector departs
For almost 20 years he has acted as gatekeeper when bad news broke at one of the 1,280 schools that the Independent Schools Council represents.
His background in journalism - three years on the Cambridge Evening News and seven on the Sunday Telegraph - has enabled him to keep both camps happy.
By his own admission, though, the director of the ISC's information service has never made the full switch from poacher to gamekeeper.
Now, as a result of a major reorganisation of the ISC's information arm, the man who has shaped the independent sector's relationship with the press, public and politicians finds himself out of a job. It has been a controversial decision, leaving colleagues perplexed and angry.
But Mr Woodhead, 60, who also became the ISC's deputy general secretary five years ago, said: "I'm not bitter. Organisations change, they are restructured and that's that."
He arrived at the then Independent Schools Information Service in January 1985 from the hotbed of the Inner London Education Authority (ILEA) where he worked for 10 years, seven as chief press officer. When Ken Livingstone took over the Greater London Council in 1981, and with it the ILEA, Mr Woodhead found himself plunged into the policies of the "loony left".
"That change was even more dramatic than if we had gone from one party to another," he said. "It became a very faddish regime. But the ILEA did do a lot of good things. Its provision for special needs, adult education, music and the arts generally was second to none."
Once at ISIS, he set about turning it into a multi-faceted organisation: a slick press office kept private schools in the news and taught heads how to promote and defend themselves, a lobbying team championed their cause in Westminster, and an information service sold the idea to parents both here and abroad.
He also told independent school heads that they had to start speaking with one voice if they were to have any political clout.
"Achieving a much more favourable political climate for independent schools to exist in has been one of the things which has given me the most satisfaction," said Mr Woodhead.
"That was unimaginable 20 years ago when the Labour party was committed to putting VAT on school fees and ending charitable status with the aim of abolishing independent education altogether."
The turning point came during Jack Straw's tenure as shadow education spokesman in the early 1990s. "He recognised the futility of trying to abolish charitable status for independent schools. From that point on the climate began to change."
Greater autonomy for state schools has led to a "blurring of the edges" between the maintained and private sectors, he believes. Labour's policy of setting up partnership schemes between the two sectors has also helped.
"But in no country do you get genuinely wide access to private schools unless you get state help. In Australia, 30 per cent of pupils are in private schools, which are heavily subsidised by the government," said Mr Woodhead.
Even in communist China - where Mr Woodhead addressed a conference on private education - 11 million pupils are educated in 55,000 independent schools.
"Our private sector is still associated with academic selectivity," he said. "No other country has that degree of prestige attached to a certain type of school."
Mr Woodhead grew up in Wakefield, West Yorkshire, where he attended Queen Elizabeth grammar, then a direct grant school, before studying history and politics at Leicester university. He now lives in Leatherhead, Surrey, and he and his wife Carole have two grown-up sons.
So, as Mr Woodhead looks to the future as an educational consultant working for both private and state schools, surely it is time for him to tell tales out of school?
"Maybe in five years' time," he said. "There's been the occasional eccentric head. It's a pity there are not as many about now. I think on the whole schools are the poorer for that."