Taylor stepped down as captain in 2012 after being asked to hand over the one-day and Twenty20 reins to Brendon McCullum. The decision was announced after he had led New Zealand to their first test victory in Sri Lanka in 14 years.
Taylor declined an offer of splitting the role with McCullum before taking a break from the international game by opting out of the tour to South Africa.
In an interview to be aired on Sky Sport's The Pod tomorrow night, Hesson said he still thinks back on the situation.
"It was one of the toughest times in my coaching career, without doubt," Hesson, who coached the Black Caps for six years, said.
"There are a few times were I've gone 'am I doing the right thing here' and I guess I kept going back to the reasons why I coach. Many times I'd ask myself at night 'am I making the decision for the right reasons?' and that was the question I asked myself throughout my whole coaching career.
"If I make a decision whether it be selection, captaincy, assistant coach or whatever, am I doing it because I think it's going to make the team better."
"It was one of the toughest times in my coaching career, without doubt," Hesson, who coached the Black Caps for six years, said.
"There are a few times were I've gone 'am I doing the right thing here' and I guess I kept going back to the reasons why I coach. Many times I'd ask myself at night 'am I making the decision for the right reasons?' and that was the question I asked myself throughout my whole coaching career.
"If I make a decision whether it be selection, captaincy, assistant coach or whatever, am I doing it because I think it's going to make the team better."
While Hesson said he doesn't regret the decision, he wasn't happy with how things unravelled.
"I have a lot of empathy for what Ross went through and it was a really difficult time for the whole team, to be honest," he said. "We also had people within the environment who were being a little bit snaky around it as well in terms of trying to play both sides. It was just a really untidy time.
"I don't regret the decision, I certainly regret the fall out from it and the way people felt throughout it. But even looking back, it was the right decision."
Hesson stepped down as coach in June 2018 with a year to run on his contract, citing family reasons, as Gary Stead took the coaching reins into the 2019 Cricket World Cup.
