In 2007, he settled into the big chair at Yellow Pages, a company that had been flogged to Unitas Capital and Canada's Teachers' Private Capital for $2.24 billion.
While some on what was then the Telecom board had wanted to keep publishing a big, fat cash cow of commercial phone listings forever, others saw Yellow Pages as a dinosaur wandering into a Google-infested swamp.
Looking back, the deal looks bananas.
"The sale price was 14 times earnings, debt was 11 times," says Cotterill, still shaking his head more than a decade later. By the time he got there, no fewer than 41 banks were holding $1.8b in debt.
In the torrid negotiations required to recapitalise the company, Cotterill says those banks "never came alone".
"Every time I had a meeting with bankers, there were 82 people in the room, plus me and the CFO".
As he'd done before, he mopped up and moved on.
"I'd love to write a book about it," he says. "I've done my share of tough businesses, underperforming relative to bankers' expectations and all that, but oh boy, the behaviour of the banks on Yellow Pages ..." He trails off. There will be no book on that anytime soon.
Instead, Cotterill has decided he's successfully led enough companies that he can add to the already-groaning pile of management advice books by former chief executives.
But, as this small business owner discovered, The Best Leaders Don't Shout immediately proved to be a disarmingly useful tome.
Flicking through it on returning from holiday to an unsettled team after a senior departure, a highlighted quote caught my eye: "this question should haunt every manager", it said: "'can you please tell me what we do?'" Having been asked exactly that question an hour earlier, it rang frighteningly true.
Employees' uncertainty about their purpose is far more common than most business owners would like to think, says Cotterill.
If it's true that 85 per cent of businesses don't have a plan, he says it's hardly surprising if most employees don't have a clue about what you really want from them.
This is at the core of Cotterill's approach and it's really no more complicated than assuming that "no one knows what the boss actually does" and that you should "always assume the message doesn't get through".
Talk, talk, talk. Rather than assume that it's everyone else's fault, a successful leader takes those assumptions on the chin and commits to the "big three Cs of management: clarity, consistency, and communication", Cotterill says.
"Be clear about what you want to achieve. Get that message through to your people. And then act in a manner that's consistent with that. That last point is critical."
Too often he sees leaders who make heavy demands on their people and then disappear, either to the golf course or behind their office door.
He relates the story of a large Australian company that asked for his help.
"Talking to the CEO, I discovered that he caught the goods lift to his office each day to avoid meeting his people", whereas the Cotterill Doctrine advocates communicating until it hurts.
"A lot of people won't read an email but they'll get a lot out of bumping into you in reception. A lot of people prefer a formal management meeting sit-down, some prefer to sit down with coffee and talk over morning tea. Some need to have it drawn on a whiteboard."
He's a big fan of morning teas and of carving out time every week to do some "management by walking around".
Failure to endlessly explain has consequences. Within weeks of leaving Yellow Pages, he found himself fielding a call a week from former staff wanting references as they bailed from a company that had just been set back on its feet.
When yet another "terrific young guy" rang to tell Cotterill he was bailing, they met for a beer.
"I said: 'what's going on in there? Why are so many people, good people, leaving?' And he said: 'you remember when you were there we always had those big Monday morning meetings that you ran and everyone knew what was going on? Well, we haven't seen anybody from upstairs since you walked out the door'."
Sometimes, he says, managers are scared of what people will ask for, but his experience is that they usually just want reasonable answers to reasonable questions.
He claims the most expensive thing to come out of a staff meeting was a $1500 spotlight to make a carpark safe for Woman's Day staff leaving late on the day of the weekly deadline.
It's also important to deal with people whose behaviour is blocking the lines of communication. Especially difficult is the office bully.
"I can give you four or five examples of organisations that I've gone into fresh where I've had a high performer, a high-profile person who, culturally, has been a disaster.
"You agonise over whether to keep them or let them go," he says.
"And ultimately, you let them go and you worry like hell. And yet what happens when the cultural disaster leaves? As soon as you get rid of that person, the team can flourish."
Imposing a "no dickheads" approach to management is important to improving the culture.
"As a 50-something, it's a lot more obvious to me now than it was as a 30-something."
However, focusing on culture rather than performance is a trap, he suggests.
"I always smile when I hear people say: 'oh, we've gotta change the culture'. You heard it at the Warriors, you're hearing it with Fletcher Building. Well, you can't just turn up and say: 'I'm the guy who's going to change the culture'.
"What you can do is go in and say: 'I'm the guy who's here to help us become a better employer, or help us get our product out on time, or help us generate happier customers, or manage our financial performance better'.
"If you do all that, the culture change will follow."
As a baby boomer in his late 50s, Cotterill also has firm views about the different generations of workers.
"My father's generation probably saw that things were wrong in a business but they would never contemplate telling the boss.
"My generation would have talked in the pub afterwards about 'these stupid buggers'."
Millennials will tell you to your face what's wrong.
"There's a generation of managers and leaders who aren't very comfortable with it, but we'd better be, because these kids are fantastic. They've got a better education than us, they're more capable than we were, they're digitally unbelievable." And they've been brought up in a world where they expect answers and will find their own if the boss won't tell them. If there's a chink in their armour, it's that "they're desperate to be appreciated more than to succeed".
The Best Leaders Don't Shout: How to Engage Your People, Manage Millennials and Get Things Done, by Bruce Cotterill, published by Book Club Media, RRP, $39.99.
