I think Naja had it right, you start with a plan of how you want to play in future and recruit a manager that meets that criteria, over the years I've supported the club we've had an image of playing adventurous style of football and should be looking for managers who buy into that, it's difficult to find such people as modern football is full of pragmatic system based candidates.
Can't imagine it is possible to find a more adventurous manager than one who will push the team completely into oppenent half when playing with 9 men.... and that didn;t go so well.... did it?