Henderson says based on population and geographic spread, during his reign the regime realised it was better off in terms of securing funds from New Zealand Cricket.
"I think it was extremely coincidental that Wellington suddenly wanted to change their geography after their funding model had been adopted."
He doesn't suspect NZ Cricket will redefine boundaries because Wairarapa and Horowhenua want to be part of CD, amid media reports those regions are disgruntled with the lack of men's domestic games staged at their venues.
"They recognise their cricketers have a better opportunity that way and ultimately that's the way it'll stay."
Henderson feels the state of CD cricket is great from the perspective of cricketing talent the district produces.
"That's a credit to them [as well as] the ongoing programmes and the desire to be part of a bigger entity being CD."
The difficult aspect, he says, is harnessing and co-ordinating it all because of the geographic challenges the region poses.
"All of that makes it really a hard thing to try to pull together in the right direction at the same time."
Financially the district is a yo-yo and "some of it suffers and that's totally beyond your control".
Weather, for example, governs the outcome of a game.
"In my final year we lost about four of the home five T20 games to rain so that impacts your bottom line by about $80,000."
If a gaming grant is declined during that spell it becomes even more stifling.
"You look at that and it's almost like you're farming because you're always reliant on weather so it's a tough place to be," says Henderson, bracketing it as CD's biggest challenge.
Juxtaposing the district's expenditure with the Wellington association, he says their neighbours' development officer simply needs to drive to Upper Hutt.
"We have to send a guy in a plane or a ferry across to Nelson and Marlborough."
He often discussed such matters with Furlong only to find it was never easy and something his predecessor had to comprehend annually.
CD's future is "pretty rosy" from a playing perspective, with the likes of Ben Wheeler, George Worker and Will Young catching the eye of Black Caps selectors to break into the premier team in the country on the success of Adam Milne.
"It shows that you can do it from here. William Young, Ben Smith and a good range of players are coming through in the 23, 24 age group - that's when you start to come through at first-class level and that's quite heartening to see."
However, the endless challenge for Lander and the board will be how to make the association fiscally stable.
Henderson says he gave himself a four-year spell in the CEO role but in the last two years hip problems constantly plagued him.
"Which I don't think helped me mentally and physically because I clearly felt drained."
The position was a hard and time-consuming one.
"I just weighed it up all at the end and thought if I'm going to work that hard I might as well work for myself."
When an opportunity arose to buy into his own business he grabbed it.
"At the end the decision was easy at the time."
Henderson runs a Bay-based marketing consultancy, Volom, set up in Auckland several years ago and which "outsources" expertise to help businesses grow. Fourteen of them are based around the country with myriad clients.
"It's very broad to be involved in sporting events like the Melbourne Storm game right through to developing direct mail campaigns for smaller clients and businesses," says the former New Zealand Rugby Union senior manager.
Having to move his family to Napier, Henderson didn't want to relocate to another centre.
"We were really, really happy here and that hasn't changed so that was quite important."
