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The son of a postman, Wilshaw grew up in a Roman Catholic household in south London in the 1950s. He went to Clapham College, a south London grammar school, and then St Mary's teacher training college in Twickenham. He later took a part-time History degree at Birkbeck, University of London while teaching in various London schools. At the age of 39 he was appointed head teacher of St Bonaventure's Catholic Comprehensive School, also known informally as St. Bon's, in Forest Gate, London. Whilst there, he was knighted in the 2000 New Year Honours "for services to education".
In 2003, he was appointed executive principal of Mossbourne Community Academy in Hackney in London. The school is the best performing in Hackney, with 89% getting five good GCSEs as of 2013. The school has been described as the country's most feted, praised for getting excellent results in a deprived inner-city area. The school was rated as Outstanding by Ofsted in 2006 and 2010.
Speaking on BBC TV's The Andrew Marr Show in the wake of the GCSE English results controversy in August 2012, Wilshaw said the row was a "really good opportunity" to examine whether examinations were "rigorous enough", adding that "Two-thirds of our schools are good or better. We have got a third of schools, 6,000 schools, that are not good, that are satisfactory and below. We have to make sure that schools know they have got to get to good soon as possible. We have given them a prescribed period of time, up to four years, in which to get to good."
- The London Gazette: . 31 December 1999. Retrieved 21 June 2013.
- How the hero of Hackney aims to save our schools, from The Daily Telegraph, 2 November 2011, pg 29
- ‘WILSHAW, Sir Michael (Norman)’, Who's Who 2012, A & C Black, 2012; online edn, Oxford University Press, Dec 2011 ; online edn, Nov 2011 , accessed 31 May 2012
- bbc.co.uk 2 September 2012