As managing director of the Virgin Group from 1984 to 1989 he was responsible for pounds 350m sales across its businesses. Now he is chief executive of the National Health Service in Scotland, responsible for a pounds 3.4bn budget and 150,000 staff. In some ways, he says, the jobs are not that different: both involve 'large numbers, objective setting and playing a visible role as chief executive. It's the context that's different.'
There's also the small matter of salary. As chief executive, his job is roughly equivalent to that of a grade 3 civil servant, which commands a salary of between pounds 50,000 and pounds 60,000. 'I get paid about a quarter of what I did in the private sector,' he says ruefully. He agrees he knew that before he took the job. 'But I still miss it.'
Mr Cruickshank's CV reads like a textbook career path. After gaining an MBA from Manchester Business School, he spent five years at McKinsey & Co, the firm that spawned the current and immediate past director general of the CBI. This was followed by three years at Times Newspapers - including his stint on the Sunday Times - before he moved to Pearson plc as managing director, where his responsibilities included the Financial Times and Penguin. In 1984 he joined the Virgin Group as managing director.
Now, he maintains, 'for me, public service is better than growing earnings per share'. One consequence of his private sector experience is that the burden of the job does not weigh heavily. 'A characteristic of people in key positions, public or private, is that, basically, you sleep well,' he says.
Mr Cruickshank arrived in his office in Edinburgh in October 1989, the first chief executive in the history of the Scottish health service. His appointment was part of the Government's plans to improve health service management.
It also made him the meat in the sandwich: positioned in the hierarchy between the 15 health boards and the Secretary of State for Scotland, he became responsible for issuing strategic guidance to the boards, setting their performance targets and reviewing their achievements. It was a potentially invidious position. The health boards had previously reported to ministers through the secretariat of the Scottish Office, and had not been accountable to one senior manager.
'Under the old system, it was fairly chummy,' says one observer. 'There was a loose planning and advisory structure. But now there's more of a management atmosphere, with much clearer responsibility for administering resources.'
Part of this is undoubtedly down to the Government's moves to reform the health service; part to Mr Cruickshank's methodical approach to the job. His first priority, he says, was to agree its aims and objectives.
His job description said he was accountable for the performance of the NHS in Scotland. 'I thought, I have some ideas about what that means, and ministers have - although they might not be the same - but I wonder what the health service thinks?' So he and his staff asked around 500 health service workers and patients, in an exercise that took over a year.
The result was the Framework for Action, a 26-page booklet. With quotes from patients and health service staff - from receptionists to consultants - it sets out how the NHS in Scotland will deliver the Patient's Charter. In it, the new chief executive states: 'I see it as our job to lead the NHS safely through this period of change and to a stronger, fitter and more cohesive public service, (one) that demonstrably works.'
The idea of leadership crops up often in the conversation: he maintains it is one of his key aims in the job. But the high profile this requires sits uneasily with his status as a civil servant. 'That is the major problem with this job. I am chief executive of a very large organisation, therefore all the things I learnt in my experience of the private sector - visibility, commitment and leadership - are required to do that job well. But I'm also a senior civil servant, and it's unusual for civil servants to be asked to operate in that style. I'm playing two roles. But I have reconciled them, I believe.'
The NHS post is not Mr Cruickshank's first experience of public service sensibilities. While managing director of Virgin he spent three and a half years as chairman of Wandsworth health authority in south London. He remembers being 'almost at two ends of the spectrum. I was working ten hours a day with Richard Branson and two hours a day with the public sector.' According to an acquaintance, he had 'quite a tough time at Wandsworth - they weren't just rubber-stamping things'. But the job gave him a taste for analytical debate away from the rigours of the balance sheet. When Mr Branson took Virgin private again in 1989, Mr Cruickshank decided 'It was not for me.' He looked at a number of jobs. 'When this one came up I thought, why not?'
As a senior civil servant he reports directly to ministers, a new experience after the private sector. But he maintains that the Yes Minister image of the Civil Service is undeserved. 'You get more 'Yes, chairman' in the private sector. The Civil Service is in a more privileged position against ministers than your average management team is against the chairman - particularly the chairman and chief executive, if the two roles are combined in a public company.'
He envisages more senior executives making the move into the public sector, particularly as people recognise that 'some of these public sector jobs are at the cutting edge of management'. But 'you've got to be prepared to fit into the system of accountability. You cannot be cavalier and try and act as if that didn't exist.'
This is from the heart. He describes 'the contrast between the annual general meeting of the Virgin Group and my appearance in front of the Public Accounts Committee. They are chalk and cheese.' An AGM is easier 'by a ratio of 100:1, in terms of tension, challenge, obligation to answer questions, inability to obfuscate or say, 'I'm not going to answer that' '.
Unsurprisingly, he is enthusiastic in his praise for the qualities of public service managers. 'If we in the private sector had had the level of commitment we get from public sector managers, UK organisations and the economy would not be in (such a) parlous state.'
He admits that NHS managers may lack 'certain technical skills' such as negotiating and marketing. 'But their capacity to tolerate ambiguity and to exercise leadership - all that's much better.' While recognising that public sector salaries often fail to attract staff, he looks to the new health service trusts for the solution. 'Younger managers coming through will be closer to the decision making. That, plus better management development, will attract more people into the health service.'
With two years of his five-year contract to run, Mr Cruickshank will not be drawn on his future plans. Despite having reconciled his two roles in the NHS, he admits he sometimes feels he is trying to push a round peg into a square hole. 'I don't expect by the time I've finished this job to have succeeded,' he says. 'I'll just hopefully pass on the round peg in better shape than I found it.'
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