Bolland worked for the Advertising Standards Authority and the Press Complaints Commission before serving as Deputy Private Secretary to Charles, Prince of Wales, from 1997 to 2002.
[4] Bolland and the prince's Private Secretary, Stephen Lamport, helped devise a media strategy that enhanced the public image of Charles and Camilla's relationship.
A June 2000 article in The Times by Andrew Pierce said that the media coverage of the meeting between the Queen and Camilla had marked 'the culmination of three years work by Bolland and Lamport' who since the divorce of Charles and Diana had 'worked tirelessly ever since on the public rehabilitation of Prince Charles and Parker Bowles...In the past week Parker Bowles has lost the loaded word mistress.
[10] The first report of the Highgrove meeting was published in The News of the World, then edited by Rebekah Brooks, a close friend of Bolland.
[13] A two-part television series on Bolland's work for Charles, Reinventing the Royals, was due to be broadcast on BBC Two in January 2014 but was postponed.
[15][16] Bolland has held numerous positions in the third sector, having joined the Journalists' Charity, which was known as The Newspaper Press Fund when it was first established, as its vice-president[17] in 2007, and serving as a trustee of the Open Futures Trust from 2010 to 2014 and the Middlesbrough and Teesside Philanthropic Foundation from 2012 to 2014.
[5] Bolland was portrayed by Ben Lloyd-Hughes in the fifth and sixth seasons of the historical drama television series The Crown.
[28] Bolland entered a civil partnership with his partner Guy Black in February 2006 at Islington Town Hall, in a ceremony witnessed by Murdoch MacLennan, the chief executive of the Telegraph Media Group, and Rebekah Brooks, then editor of The Sun.