His desire to develop good governance among the region's organisations resulted in an appointment to the board of the local arm of Age Concern, which provides advocacy and support services for over-65s.
With his mother in the target market, Ashcroft says the charity's work was close to his heart.
He says Age Concern's challenges centre on how it can sustain funding in a difficult environment and still deliver on its vision.
A passion for the charity's mission combines with the ability to add value through his governance knowledge and financial oversight experience, says Ashcroft.
"It makes sense to do the training, cut your teeth in the volunteer sector, make sure that you know what you're doing and that you generally can add value, and then get into the commercial realm."
Ashcroft has also been elected to the board of trustees at the primary school attended by his three children.
He says the challenges facing a school board are not too dissimilar to the non-profit sector, with constrained funding meaning that effort has to be devoted to making the most of the available money.
"In all of that the biggest challenge is how do you not get distracted on those issues, that you can continue to still deliver the real outcomes, which is great little kids, kids that will grow up to be the community of the future." Ashcroft has sampled the life of a director in Tasmania, where he had a role on the board establishing a new primary school to serve the Port Sorell community, plus a directorship with Food Innovation Australia.
But it was seeing the dynamics of a commercial board at work at the Cawthron Institute that originally piqued Ashcroft's interest in training as a director. The institute is an independent science organisation, with a focus on the environment and primary industries.
During an earlier stretch with the institute, between 2004 and 2010, he witnessed the charitable trust that oversees the organisation introduce a commercial board stacked with experienced directors.
"They wanted to introduce a corporate style of directors just to bring some extra strategic and financial management oversight into what was effectively a growing business." Ashcroft says he was fascinated to see first-hand a transition from a legacy framework to a board of directors model with a new focus on governance.
These days the Cawthron Institute's board of directors focuses on managing strategy, holding the executive team to account and managing risk, leaving the board of trustees to oversee the distribution of dividends to benefit community initiatives in the Nelson region.
"The cold hard reality for the business here is that it is a charity but it needs to make at least some form of commercial return simply to reinvest in its public-good science." Ashcroft's ambition to further his board experience is being boosted by an aspiring director award from the Institute of Directors' Nelson-Marlborough branch.
He will benefit from further training, time with a mentor and the opportunity to gain access to a local board as an observer.
"It's the ability, again, to convert what I've learned from a textbook into a real life environment with people that are doing it for jobs."
If he was given the choice of any director to sit alongside and observe, Ashcroft says he'd pick Sam Morgan, someone "who didn't mean to start out as a director and has now become a hugely valuable director to any board he sits on".
"He's a forward-thinking, business savvy type of guy. Everything that makes New Zealand great - that innovative and collaborative spirit."
He says Morgan's Trade Me is also a good example of how an emerging technology decimated an established industry, in its case the classified advertising business.
Keeping on top of new technology and managing the business risk surrounding potentially disruptive high-tech newcomers is an emerging trend for directors, says Ashcroft.
He sees it already with his role at Age Concern, which is considering how technology will affect the way it provides services, such as home visits to the elderly.
"Boards will have their work cut out for them to be able to manage those sorts of things."
