Not bad for a bloke who mixed teaching and coaching for a long time, left New Zealand in 1998 to coach Wales and returned to live out his All Black aspirations.
"It began as a part-time passion devising gameplans and tactical ideas more than individual tuition," he says. "That is where I come from because that is how I have grown up as a coach.
"Now, in a general broadbrush term, I am probably the big-picture person. I let the others [Steve Hansen, Wayne Smith and Mike Cron] coach the detail while I'm looking at the gameplan in the sense of outplaying the opposition."
Henry stepped into coaching not long after the Lions toured New Zealand in 1971. That visit, and the work of their coach Carwyn James, made a huge impression on the young teacher.
The 1984 Wallaby side were also a big influence, as was the Auckland team of the late 80s.
Since his arrival as a coach, Henry has been leaving his imprint in the amateur and professional worlds of rugby coaching.
The 65-year-old admits he is a dog with a bone at work. That's his nature. But he says to be a top coach you need the right people around you.
"If you are going to have a successful business, whether it is the All Blacks, Fletcher Challenge or Kelston Boys High School, you have got to get the best people involved to ensure that business is successful," he says.
Henry has high demands on those who work with him.
"I like to get the best out of myself and all the people round me and I have got some very talented people there. The other two coaches are better coaches than me and the whole staff are excellent."
That may be so, but there is a rich vein of rugby information contained in Henry's frontal lobe and in that red exercise book. The All Black detail for this World Cup is contained in those two compartments.
It has been an incredible voyage which began in earnest 13 years ago when Henry left New Zealand for a stint coaching Wales.
"It's a real privilege and in saying that I have done the hard yards and put the time in as well. It is special and I am very proud of it," he said. "It is a rollercoaster and I have been very lucky that the rollercoaster hasn't been too bad. I've only gone through that terrible pain of defeat 15 times out of a hundred.
"But those times are significant and particularly 2007. That does smash you around."
Everyone in the All Black group has high expectations, he says, and the ability to achieve those targets and cope with the disappointments makes for a weighty workload.
Henry did not put "rugby coach" as his occupation on his tax return until 1997 when he shed his teaching career.
He missed running Kelston Boys High and believes teaching is a far more important job than running a rugby team.
"I had 25 years in education which was a reasonably long stint in one career. I enjoyed the responsibility of being a headmaster and what all that meant because it involved influencing 1200 kids' lives.
"Circumstances meant my passion became my career, and that doesn't happen very often."
Henry would rather avoid the limelight, but knows it is entwined with his present job description.
The challenges of coping with pressure and meeting targets fuels his persona.
But coaching the All Blacks at this World Cup is his ultimate challenge, this tournament will define much of his legacy.
"It is career-defining I'm afraid," he said. "Even though there are a lot of things I am very proud of, this is whether we put the icing on the cake."
After the 2007 quarter-final exit, Henry says the players urged him to stand once more.
"They wanted me. I have answered this many times before and people seem to forget the answer.
"In this job, I put huge demands on them to front and do the business and that is part of the requirement.
"I had a situation where I either could front or run away and I could not do that [disappear] because I expected them to front every week in test matches. That's why I stood. I didn't think I would get the job.
"When I reapplied in 2007, I thought they would appoint Robbie [Deans], and even in the interview I thought Robbie would get appointed.
"It was not about me, it was about me living by the principles we had set in the All Black team."
Halfway through this World Cup marathon, Henry believes the experiences from 2007 have him, his staff and players better equipped to deal with this tournament.
And, of course, playing the tournament in New Zealand has special advantages - like spending time chasing blue cod.
