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The son of a postman, Wilshaw grew up in a Catholic household in south London in the 1950s. He went to 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 2000 for services to education.
In 2003, he was appointed executive principal of Mossbourne academy in Hackney in London. Some 82% of pupils achieve at least five good GCSE equivalent qualifications, including English and maths, above the national average of 53%. However, Wilshaw's style has been controversial, and his methods hit the headlines in 2007 when he banned pupils from hugging each other. He said at the time that it was to ensure accusations of people touching each other inappropriately could not be made.
Speaking on BBC TV's 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". Sir Michael added: "Two-thirds of our schools are good or better. We have got a third of schools, 6,000schools 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.".
Wilshaw is known for his outspoken manner and hard-line style. In December 2011, before starting the Ofsted post, he said "If anyone says to you that ‘staff morale is at an all-time low’ you will know you are doing something right."  In his first major speech as Chief Inspector in February 2012 he said "We have tolerated mediocrity for too long."  At an education conference at Brighton College in May 2012 he proclaimed that teachers are not stressed, adding that head teachers needed reminding what stress really was.
Wilshaw brought in a number of changes at Ofsted with the effect of providing an unforgiving climate for inspections, intended to drive up standards. The "satisfactory" judgment was discontinued in September 2012 and replaced by "requires improvement". The notice period for an inspection was also reduced, initially with proposals for zero-notice. However, following an outcry from teachers about the practicalities of such an arrangement, it was changed so that notice was given the day before, with Education Secretary Michael Gove acknowledging that teachers felt their profession was not trusted. Nansi Ellis, head of education policy at the ATL teachers' union, said "Ofsted is discredited in the eyes of many teachers and needs to even work harder to regain their trust." 
This background led to alienation of the profession, and teachers’ associations accuse him of bullying. At the National Association of Head Teachers (NAHT) conference on 6 May 2012, four months after Wilshaw took up the post, headteacher Mike Curtis proposed the motion "We are saddened and dismayed by his approach." He introduced the motion: "Can we really put our trust in Her Majesty's Chief Inspector? I suggest not. Successful careers are damaged or destroyed on a daily basis as more schools are put into categories. Fear reigns and confidence wanes as Ofsted waves its stick. We must stand up to the bully-boy tactics of Michael Wilshaw. We deplore his negative rhetoric which is demoralising our members and is creating a climate of fear in schools." The motion was passed by 98.9%.
On 22 September 2012 Wilshaw claimed that teachers would have to work harder to gain pay increases and that teachers should be denied promotion if they were "out the gate at 3pm". Teaching leaders criticised Wilshaw for not understanding teaching commitments - for example, research has shown that most teachers work in excess of 56 hours per week, and significant work is also carried out during holidays - and for being a "mouthpiece" for the Secretary of State for Education. As a result of his comments Ofsted, the organisation he leads, clarified that their role was based on the "quality of teaching and learning".