Shipley chafed at the government's slow pace, and in December 1997 convinced her National colleagues to support her as leader.

The coalition was dissolved in August 1998, but Shipley was able to remain in power with the aid of Mauri Pacific, an NZ First splinter group.

Shipley involved herself with business and charitable interests since leaving politics, and is a member of the Council of Women World Leaders.

[7] When Bolger led the National Party to victory in the 1990 general election, Shipley was reelected in Rakaia, essentially a reconfigured Ashburton.

[8] In her role as Minister of Social Welfare, Shipley presided over sharp cutbacks to state benefits.

[9] Shipley grew increasingly frustrated and disillusioned with the cautious pace of the National-led government under Jim Bolger, and with what she saw as the disproportionate influence of New Zealand First.

Later that year, while Bolger attended the Commonwealth Heads of Government Meeting, Shipley convinced a majority of her National Party colleagues to back her bid for the leadership.

While Bolger had been able to maintain good relations with New Zealand First and with its leader, Deputy Prime Minister Winston Peters, the alliance became strained after Shipley rose to power.

[15] Shipley's ascension to the leadership marked a shift to the right politically with subtle returns to the neo-liberal policies of the first term of the Bolger government.

[26] In the 2003 New Year Honours, Shipley was appointed a Distinguished Companion of the New Zealand Order of Merit, for services as a Member of Parliament.

In 2007, she joined the financial services firm Source Sentinel, and from 2009 to 2018 was chair of the Genesis Energy Limited board.

In December 2012, Shipley resigned from the board of directors of Mainzeal Property & Construction (MPCL), which went into receivership on 6 February 2013.

[39] Within a week of the Court delivering its verdict, Shipley resigned from her Chair of the China Construction Bank New Zealand.

An appeal against this judgment was filed along with a counter claim brought by the original plaintiffs for a vastly higher award against the Directors.

[41] In August 2023 New Zealand's Supreme Court upheld the long-contested judgements, determining "“Mainzeal was balance sheet insolvent from 2005, albeit this was not apparent from its financial statements” and ordered the four directors, of whom Shipley was one, to pay $39.8m together with interest, although the liability of Shipley is limited to $6.6m plus interest.

Shipley accepted redesignation as a Dame Companion of the New Zealand Order of Merit on 14 August 2009, following the reintroduction of titular honours by the Fifth National Government.