Coffee roaster and merchant Mark Hillis said his company had 21st century ideas but was "using technology from the Middle Ages".
"We've been working really hard trying to integrate everything ... but our system's not quite up to standard," he said. "It would be far better to have a central system."
Chandelier restoration and repair company Chelsea Lighting said its office typewriter was sometimes more dependable than its computer.
"With a nine-year-old computer and an unreliable printer I have occasionally resorted to using my old trusty typewriter to do the deeds," said Patricia Clarke.
Tool shop owner Steven Hayes wants to print flyers but his existing set-up took all day to print just 500 copies.
The Herald will announce the winner on Monday, October 17.
Six finalists
* Atlas Power Coffee
* Mt Wellington-Panmure RSA
* Chelsea Lighting
* Tranzcarr Heavy Haulage
* Homevision Blinds
* a2z engineering hardware and tool supplies.