He was the Permanent Secretary to the Department of Health from 1997 to 2000, while Frank Dobson and later Alan Milburn were the Secretary of State.
In the run-up to the 2005 general election, Diamond worked as a special adviser to the election co-ordinator, Alan Milburn MP, leading the management of the Labour Party’s manifesto and preparation of the government’s third-term policy programme.
He was a member of the Joint Task Force on Partnership in Medicine Taking, established by Alan Milburn, the Secretary of State for Health, in 2001.
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He was a member of the Trade and Industry Committee from 1992 to 1997 and again from 2003; in between he was Parliamentary Private Secretary to Alan Milburn following the 1997 general election, but he resigned over Harriet Harman's decision to cut lone parent benefits in December of that year.