You never know quite how they will react. They are used to being in charge and don't always take kindly to a listening role. So far, however, I've managed to avoid turning them into a lynch mob - despite, on more than one occasion, having suggested that a suitable collective noun would be "a harangue of heidies". I usually manage to coax a smile out of them when I propose that, given the multiple realities they have to inhabit, "a hallucination" might be more appropriate.
Make no mistake: being a headteacher is not an easy job. It carries huge responsibilities and, when something goes wrong (as inevitably it does from time to time in any school), there is no escaping the spotlight. That is why recruiting people to take on the top job is sometimes problematic. Many capable people decide it's just not worth the hassle - or the heart attack.
Part of the problem is that there are so many constituencies to satisfy (pupils, parents, staff, the local authority, the inspectorate, the Scottish Executive), and each may be looking for different approaches to leadership.
From the perspective of staff, for example, headteachers exhibit good leadership qualities when they fight for resources, deal firmly with difficult pupils and parents, and provide worthwhile staff development opportunities. From the perspective of the local authority, however, the leadership qualities of headteachers are most in evidence when they follow approved policies, do well at inspections and gain good publicity within the community. The priorities and criteria of judgment are quite different.
This indicates that leadership is not a fixed quality that can be encapsulated in a checklist and reduced to a formula. To a significant extent it is dependent on the position of the observer - and, given the multitude of observers, headteachers have to reconcile themselves to the fact they will never manage to please everybody all of the time.
Often they have to take a considered judgment based on their best assessment of the issue, the context, the people and the constraints.
Sometimes they will get it wrong: taking risks and making mistakes goes with the territory. Playing safe all the time will not provide the stimulus to innovation and development.
For me, one of the most revealing aspects of leadership styles is the extent to which people are explicit about the values and principles they stand for and the extent to which they live up to them. In Scottish education, the easy option is often to "go with the flow" or settle for a soft consensus.
The hard option is to be prepared to express dissent and say that a proposed policy, however strongly endorsed by political or bureaucratic authority, is not consistent with one's professional principles and will not serve the interests of pupils.
This takes courage and a determination to resist the various forms of pressure that can be exerted. But it is precisely because education is such an important public service that it needs leaders who, when necessary, are willing to speak out on important matters of policy.
Headteachers have special insights to offer, drawn from their day to day experience of schooling at the sharp end. They should not be afraid to tell inspectors, directors of education and politicians that members of the educational establishment are capable of error. A "harangue of heidies" may not be such a bad collective noun after all.
Walter Humes is professor of education and head of educational studies at Strathclyde University.