"If I can do it for me, I can do it for you," he says.
In 2004, when Ashby took over the Momentum business from the colleagues with whom he'd co-founded it eight years earlier, he immediately put in place a high-quality board.
He looked outside the business for advice and governance, enlisting a former national chairman of KPMG New Zealand, Michael Morris, who has since stepped down, and Shipley.
The support of four external board directors gave Ashby the confidence to introduce new brands under the Momentum banner and ride out the global financial crisis. "I just felt we were becoming a bit one-dimensional in our thinking and a little bit safe at a time when we needed a fifth person.
"In particular, because we had all these new brands and people on board, I wanted someone who knew a lot about leadership." While doing a research paper on leadership, Ashby got the chance to sit down and interview Henry, fresh from his World Cup success.
"When I was talking to him he impressed me so much about the way he had changed his leadership style that I just started thinking, 'Gee, it would be great if I could have more access to you'." Henry, who joined the board in 2012, not only provides a sounding board for Ashby, but is on tap for executive clients who want to chew over leadership dilemmas.
When Ashby took over Momentum 10 years ago he was concerned the firm had reached a plateau. He had been set to walk away from the company, but instead bought out the other shareholders.
What followed were several years of good growth, but a few false starts in getting a new strategy for the business in place.
Ashby says he needed to diversify the business and its revenue sources, but the new areas of specialisation didn't flourish under the Momentum banner.
Instead he created a "house of brands" approach in 2006, spinning out individual specialist recruiters into stand-alone businesses.
IT recruiter 920 was first out of the blocks, followed by business support staff finder Velocity.
It was work Momentum was already doing, but putting the businesses into separate brands boosted growth significantly, says Ashby.
Not everything was a resounding success. Venator, a subbrand that originally focused on hunting down senior executives, has specialised in property recruitment.
Ashby says he loved the original idea for Venator, but says part of creating a successful new brand was having people leading it who loved it as much he did, which didn't happen initially with Venator.
Having someone in the role now who has the vision, drive and determination to make it work has reinforced the idea that it is all about having the right people in charge, says Ashby.
"If they lie awake a little bit at night in the early stages because they're concerned, they're the sorts of things you want," he says.
"If they think like an employee and they're starting a new brand for you, you're buggered."
While he has doubled revenue since the takeover 10 years ago and created a revenue mix that has seen temp and contract placements grow to more closely reflect international trends, "it's taken a bloody long time because basically there was a thing called the GFC that absolutely got in the way".
Ashby says the strategy was right but the economy slumped, dragging down performance.
"If you believe the strategy is correct, and the landscape still supports the strategy, and the intel that you receive still supports the strategy, but the economic landscape is not supportive of it, then you find a way to keep the strategy going while managing the cost base." Only four people were cut over that period but a lot of fat was trimmed from costs in the firm's Auckland and Wellington offices.
"The biggest problem with cost management is you stop investing and the moment you stop investing is the moment you stay the same or go backwards."
Ashby says his aspiration is to at least double profit and improve turnover by 50 per cent.
"[Sir Graham Henry] always talks about the extra 10 per cent and that's the hardest piece.
"His way of doing it was devolvement of leadership to the team and that's where we're at right now, devolving leadership to the team and getting teams to run businesses rather than me run it."