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Henderson coached the Southland Stags from 2005 through to 2013, before Rugby Southland opted to advertise the role.
Henderson reapplied but failed to get the job. During his tenure he helped mastermind two successful Ranfurly Shield-winning performances, in 2009 and 2011.
Both times Southland went into the games as underdogs against Canterbury in Christchurch but emerged as Ranfurly Shield holder.
Henderson said it took some heartbreak to eventually get it right.
He pointed to the 13-9 loss to Auckland in 2008 as a game which the Stags probably should have won to take the Ranfurly Shield, but came unstuck.
He said there had been a big focus on the Ranfurly Shield in the build-up to that game and as a result, the players ended up becoming too tense.
"If you go back to that Auckland game, the guys were a bit stiff and just got caught up in it all," Henderson said.
"At the captain’s run [in 2009] in Christchurch, before we played Canterbury, you could tell the boys were relaxed. I don’t think there was a ball dropped.
"Before that, there had been mistakes made with how we prepared."
"The one thing we found is it was best not to put too much focus on the Shield."
Southland’s next attempt for Ranfurly Shield glory will be against Waikato in Hamilton on Saturday. The Stags are at long odds to take home the log o’ wood.
Southland has lost all six games this season, extending its run to 17 straight Mitre 10 Cup losses.
But the Dave Hewett-coached Stags team has a starter’s chance, and that faint hope was what the faithful was hanging on to heading into Saturday’s challenge.
Henderson said it was about getting all the small details right to claim Ranfurly Shield glory.
"Wouldn’t it be lovely to get our hands back on it?"
"It’s about doing the five percenters in Shield games. Just getting up off the ground quicker than you normally would, those sorts of things."
"You can’t let your guard down either. You can’t have patches where you are off."
Southland’s last Ranfurly Shield challenge last year against Canterbury started off well before it got messy.
At halftime, Southland and Canterbury were locked at 17-17 before Canterbury piled on 61 second half points to win 78-20.
Meanwhile, Henderson confirmed there had been some early discussions about holding a 10-year reunion next year to celebrate the 2009 Ranfurly Shield victory.
It was a special time for Southland rugby, Henderson said.
- Logan Savory