The Central Otago District Council has opened its "Cromwell Town Centre Action Plan" discussion document for public submissions after many mall retailers and the community called for a more accessible shopping area which would draw patrons into the centre.
Mr Gillespie says the mall, opened 23 years ago, has always posed design problems.
Just before Old Cromwell Town was flooded by Lake Dunstan in 1993, businesses were clumped together in a new location. Some exotic trees and a trickling stream were hidden away behind a frontage of shops that offered no incentive to see what was behind that facade.
So, about 10 years ago, the community board considered doing "something radical" about making changes, but nothing came of it.
"It was too early for the people of Cromwell at that time, and if it had been that important, there would have been drivers to make it happen," he said.
There had been major changes in recent years in Cromwell, including the rapid growth of the town's industrial area, so it was time to look at the options again.
Consultants had come up with a plan that would see roading changes and the creation of a town centre space, or piazza.
"We need to look at the town centre and see what's going on in the Mall and around it. If we decide to make changes, we have to do that carefully as, if we get it wrong now, it could be too late to fix it.
"If you make changes, bowl buildings and build new roads, then you have to ask who pays for that. We need to make sure the concept we are developing is the right one and then work out who is going to pay for it," he said.
Fellow CODC councillor Gordon Stewart, who is also a community board, member, has lived in the area all his life and has watched the changes with interest.
He said the Mall had worked well for the first 10 years for many reasons - not the least of which was the high wage packets of about $100,000 a year some families were earning while working on the construction of the Clyde Dam.
"We had a grocery shop at each end of the mall and a post office in the middle, which meant people were using the mall all the time.
"But when the dam was completed and families moved away, they were replaced by pensioners on limited incomes and living trends changed," Mr Stewart said.
The population dropped from about 4500 to 2500.
Just when the mall was at its most vulnerable, a new supermarket was opened in 1995 on the outskirts of the town centre and delivered a king hit to several retailers.
The post office and two banks closed, so the mall had a "really tough time" for about eight years, Mr Stewart said.
In 2006 the population of the town was 3585 and continues to increase, thanks in part to the booming Central Otago wine industry, which has boosted Cromwell's economic confidence, as well.
This in turn has led to a revival of the retail section resulting in the mall's once empty shops being filled.
"There are no empty shops and the only office space left for rent is at the top of the old post office, with a back entrance. We have had a 95% occupancy in the retail area for about the past five years," he said.
Seeking a piece of the highly lucrative tourist trade, Cromwell Mall's cafe's and bars have set up pavement tables near the car parks to make it more attractive to stop.
The Cromwell Visitor information Centre, which, according to the planning reports needs to be made more prominent, still draws about 45,000 visitors annually.