"The first is do I want to do it? I've put a lot of effort into my present school," he says, "and I'm not sure I want the hassle of starting from scratch again." Not only has he weathered the pressure of multiple education reforms since 1988 but his own school had difficulties when he arrived.
The fact that it is now popular, has a happy and hard-working staff and students who, by and large, seem as committed to the place as he is, causes him a great deal of satisfaction. "What should I do?" he asks. "Find somewhere else that needs uplifting and go through it all over again or take on a successful school with all the risks that involves?" It's a dilemma which faces many people. He knows the alternative is to stay another five or six years in his present job and then go for early retirement. "I'm not sure I want that either," he says. "I feel as though I could be treading water."
But second headship may not be an easy option. As well as the difficulty Roy highlights, there's also the question of whether the successful head should try for a school similar in size and type, or go for something different. In some cases, personal circumstances, including an unwillingess to uproot family, will dictate that only schools in the same or adjacent authority can be considered and this will limit choice.
But where this is not an issue then the moving head has to consider carefully. As someone who moved from headship of a large school in a deprived urban area to a small one in the country I can vouch for some of the difficulties.
Friends who knew I was moving said: "You lucky so and so. It'll be dead easy." And in some ways it's true. While rural deprivation exists more than people think, the impact on school is less marked than I was used to. Most children are well supported by parents and have fewer of the pressures which make school an irrelevance for some children on the kind of estate where I used to work.
But there are other pressures for a head. The smallness for one. In a large school, there's more flexibility. It's possible to delegate more and take the kind of strategic view that most management books tell you headship is about. In a small school we all fill multiple roles and I get much more involved in day-to-day issues.
Choice of school, though, is not the only problem. It's more than seven years since Roy last completed an application form and, although he has appointed lots of staff and written many references, he's never seen an application for headship. Should he rely on his record or make the kind of change-the-world statements that thrusting deputies can rattle off at will.
Then there's references. His own chairman is obviously the best, along with the CEO. "But he's comfortable with me," says Roy. "He may not take kindly to the idea of my going." If the process of leaving is drawn out, then the feeling of temporariness may get in the way of effective working.
There is also the emotional wrench. To leave one place to which you have committed energy and passion in July and start somewhere else in September demands great strength. Whatever his decision, Roy's experience of second headship will be quite different from his first. As a first-time head you are attempting to put into place all the bright ideas you ever had about how schools should be and were never allowed to carry out. In the second, there is a danger of doing precisely the opposite - attempting to re-create the old school in a new venue.
But different circumstances demand different strategies, even for superficially similar situations. What the second-time head has, however, is the confidence of knowing that having coped with the challenges once, he can probably do it again.
Mike Fielding is principal of The Community College, Chulmleigh, North Devon.