Brian Rowlands pauses to take stock over coffee at his "local" in Llanishen, Cardiff, as he contemplates the advertisement for his replacement.
He is proud that the organisation he built from scratch has emerged as an effective vehicle whose voice is heard in the corridors of power. The Secondary Heads Association Cymru came into being in 1999 in response to the creation of the Welsh Assembly government.
Mr Rowlands, 67, the retiring SHACymru secretary, is also happy that he has managed to build a strong executive and branch secretary network, and to have extended the membership umbrella to include assistant and deputy heads and bursars.
The organisation is now 660-strong and 200 of Wales's 225-odd heads are members. His support for many post-devolution developments (including the abolition of national tests and league tables in Wales) is unequivocal. But the issue of funding remains an open wound.
He cites the enduring disparity of funding, not only between schools in England and Wales but between schools in Wales itself, as the one regret of his tenure.
"There is a huge gap between the best-funded areas, such as Ceredigion, and the worst-funded areas such as Denbigh or the Vale of Glamorgan," he says.
"The Assembly has failed to narrow this gap and it's an issue my successor will have to speak strongly upon.
"I would also like to see a transparent funding system in place. Currently education money goes through the local authorities, and we strongly believe that at times they divert funds destined for education to service other priorities."
Indeed, SHA Cymru is so convinced of the funding system's failings that it has commissioned a survey on the process. The results will be published shortly, and Mr Rowlands predicts that its contents could have powerful repercussions.
As his administration draws to a close, colleagues stress that Brian Rowlands will be a hard act to follow. Politically astute, forthright in voicing his opinions, he has forced those in authority to sit up and take notice of SHA.
Mal Davies, chair of the General Teaching Council for Wales, and head of Willows high school in Cardiff, commends him on "being his own man".
"Heads can get confused with the sheer volume of information sent to them by the government and local authorities," says Mr Davies. "Brian has the confidence to run with things that are of benefit and to push the rest to one side."
Brian Lightman, head of St Cyres school in Penarth, advances Mr Rowlands'
comprehensive contacts book as a key asset. "Brian knows everyone," he says.
Mr Rowlands says: "In Wales you have greater access to people in power because it's a small place. There's a sense of connection. I grew up with the system and I know all the players."
Having graduated in history and politics from Swansea university (politics remains a lifelong passion, hence his delight at occupying a front-row seat as devolution took place), he spent nine years teaching history in England.
He returned to Wales in 1970 - as the comprehensive system rolled in - to take up a deputy headship at Cathays high school, Cardiff. He took over as head of the city's Rumney high school in 1973. And under his helmsmanship in 1985, St Cyres in Penarth took on the controversial grant-maintained status.
As for the future, he and his wife Pamela, herself recently retired, share a passion for golf and play regularly at Llanishen golf club. The couple have two grown-up daughters, an active social life and a penchant for exotic travel.
But after a lifetime spent im-mersed in the education system, he is ambivalent about retirement. "It's time to let a fresh face take over, someone with a more recent experience of school life.
"But I don't want to just play golf. Perhaps I can continue to help out with SHA, just in a less time-consuming role," he says.