Herbert ended up in India through connections made during a Phoenix pre-season trip in 2012 and team owners got in contact in April to offer the North East role.
"We are probably one of the smallest franchises and I don't think there were big expectations," says Herbert. "I was brought in to get things going, get it operational - a bit like the Phoenix - but we have done quite well and surprised a few people."
Spanish World Cup winner Joan Capdevila was hooked as the marquee player but their biggest 'name' is owner John Abraham. An ex-model, Abraham is a Bollywood megastar with an estimated net worth of more than US$50 million ($63.73 million) and over 40 films to his credit.
North East spent most of their pre-season based in Shillong, more than 1500m above sea level, before the matches kicked off in October. Since then, it has been frenetic. Because the league is compressed into 10 weeks, traditional schedules go out the window.
"We played our first three home games in six days and, after that, we were on the road for a while," says Herbert. "It was play, fly, recovery and then play the next day."
The distances can be massive and even commuting within some of India's cities is not straight forward.
"In Mumbai, it took us more than two hours to get from our hotel to the stadium," Herbert says. "In other cities, it can be a 90-minute trip to the training ground."
North East upset league leaders Chennaiyin (co-owned by Dhoni) 3-0 last Friday to move to fifth, one spot out of the playoff zone. The Highlanders have struggled to score but Herbert is otherwise satisfied with his work.
Aside from 14 local players (at least five Indians have to be on the field at any one time), North East have 17 imports, including players from the Czech Republic, Brazil, Colombia, Brazil, New Zealand (former Phoenix midfielder Leo Bertos) and South Korea. Some are journeymen, others more useful, like 2012 Africa Cup of Nations winner and Zambian international Isaac Chansa, Trinidad and Tobago striker Cornell Glen and Portuguese defender Miguel Garcia, who has played in two Europa League finals.
"Miguel is a class player and he has been very important for us," Herbert says. "There's no doubt he could do a job in other leagues. We have plenty of other talent and, together with the young Indian players, they have come together well."
Herbert has also enjoyed off-field experiences such as meeting Tendulkar, watching elephants and cows roam busy city streets or taking in the bustling markets India is famous for.
Critics see the ISL as a retirement home for fading stars. In some instances, that's true - 41-year-old Robert Pires is well past his Arsenal prime and another former Gunner, Freddie Ljungberg (37), has managed only one appearance due to hamstring problems. But others such as Nicolas Anelka, Alessandro Del Piero, David Trezeguet and Luis Garcia are still quality players and have lifted the profile of the sport in India.
"The football is not bad, to be fair," says Herbert. "It's comparable to other leagues around Asia."
What's not comparable is the interest, which has been massive.
During North East's match on Friday, the cumulative league attendance ticked over the one million mark and average crowds of more than 25,000 are the highest in Asia and compare favourably with many European leagues.
Smart marketing and plenty of hype have helped, with ingredients stolen from the IPL. It might not be a long-term venture - most predict the I-League and ISL will merge in the future - but it has helped to put some fizz into football in the cricket-mad country. The national team is far from being a contender but there's a feeling momentum is building.
"There's a landscape of opportunity here to do something big in football," Herbert says. "It's a privilege to be part of - there have been challenges - but it's been a great experience."
Herbert is in illustrious and infamous coaching company - others include Zico, Peter Reid and 2006 World Cup final headbutt recipient Marco Materazzi - and has thrived in his first job outside New Zealand.
"I was massively loyal to the national team - maybe too loyal at times - and thought it was time for something completely different," he says. "Maybe these opportunities don't come your way too often. It's been a great four-month window to get back into it."
The positive experience has left Herbert wondering if he should have sought an offshore job earlier.
"It does cross my mind sometimes. Off the back of the 2010 World Cup, should I have gone somewhere? Should I have stayed? I don't really know. I'm really pleased I have done this. I don't want to look back."
Herbert will return to New Zealand at the conclusion of this ISL season, which could be either mid or late December depending if his team make the playoffs.
He's unsure of his next move but has clearly rediscovered his passion for coaching.
"It's been great working here, especially with the young players. I'm sure something will come up in the future."
But it may not involve elephants at zebra crossings.
