So much of the technology we use today reduces the requirement for face-to-face human interaction in the workplace. But Chris O’Reilly’s tech-based insights company is all about supporting managers to ask honest questions, listen to the answers and do better when leading others. 

It sometimes feels like a lifetime ago. A fresh-faced university graduate took a job as marketing director for the regional economic development arm of the then Hastings City Council. 

It was his first role, and like anyone in a similar position, he wanted to make an impact. “I remember this brochure I was tasked with developing,” begins Chris O’Reilly. “It was aimed at what we called ‘non location-dependent industries’. It was 1984, I was keen to make an impression and I had some big ideas on getting some large Auckland businesses to relocate, including inadvertently targeting Ports of Auckland to move down here. The irony is, of course, that some 35 years later, they might have actually considered that!’” 

And another irony, not lost on Chris, is that in 2022, Hastings has become so attractive that he’s moving his own organisation – AskYourTeam – in. Right now, the 40-strong head office crew are beginning to pack up their desks and shift them a few kilometres down the road, from Havelock North to the former Hastings Health Centre building on Queen Street. Chris and the business – which has gone from start-up to grown-up – have completely outgrown their premises. 

It’s quite something, for a business that is notoriously difficult to describe. At its heart, says Chris, AskYourTeam is finding ways to better involve people in running their organisations. It’s a business that straddles the human resources space, the customer experience space, and more recently, has entered new realms by, for instance, creating a framework to assess and enhance Māori cultural competency within organisations. Another AskYourTeam innovation, a tech tool called Ethical VOICE, helps identify instances of worker exploitation and modern slavery – a hot topic for the current government, which is hellbent on finding a solution to the worrying trend of abuse of, in particular, migrants. 

AskYourTeam started life, however, as a company called True North, the brainchild of Andrew Bayly. Marcus Smith and Jo Dowley were the other co-founders and initially, the idea was, says Chris, “delivering an MBA in a box. We quickly learned that that wasn’t going to work longer term, but that what leaders really wanted were the tools to get it right – so that they could run a better, safer work environment where people flourish.” 

His passion for leadership started when he was just 27 and was chosen as CEO for Christchurch’s Red Bus company, which was being deregulated and the operating model changed. “I don’t think anyone else wanted the job!” Chris quips, but says he made it his mission to “just talk to people, ask questions and involve them in the changes we needed to make.” 

It didn’t always go smoothly. “Actually, on the very first day, I went down to the cafeteria and got a pie thrown at me. I hadn’t realised that the company was so fragmented that the cafeteria was effectively only for drivers – managers never stepped foot inside it. So part of that initial culture change was to bring the team together – to get the drivers to work with the mechanics, to have the tourism staff talk to the passengers, and for everyone to tell me what the business needed so that I could find a way to make it happen.” 

While it was a big challenge for a mid-20s first time CEO to bring his whole company on the journey, sometimes Chris was able to see simple leadership solutions that his predecessors had perhaps not. Even if, he says, not all would be as viable in today’s health and safety environment. 

“We operated out of a three-storey building with a number of entrances and everyone had different ways of getting in. So I bought some chains and padlocks, and created just one route, which meant everyone had to see everyone else – the admin staff would chat with the drivers, the mechanics would see the cleaners.” 

It’s just one illustration of many examples Chris is able to offer from his time spent at major New Zealand and global businesses, such as Citibank and KFC, that demonstrate how enjoyable leadership can be when all voices in a business are heard and most importantly, acted upon. 

And that’s what AskYourTeam does – it creates software that helps organisations reach their full potential by asking the right questions, involving every level of the business and gathering answers anonymously so that people are able to speak their truth. 

Why is software required to achieve what seems like a pretty simple objective? “We hear organisations say, all the time, that people are their greatest asset,” explains Chris. “It’s become almost cliché! Yet what I see over and over again is leaders who are out of touch with what’s going on in their own business. And the main issue tends to be that they just aren’t involving their people and gaining their feedback. How many of us go to work and think ‘there’s a way we could do this better, but nobody ever asks me’? People doing the work invariably have the best ideas on how to improve things. As a leader, you’re an idiot if you think you have all the answers. But you do need to know how to get them.” 

He’s certainly not one to shy away from taking his own medicine. The 60 staff spread across AskYourTeam’s offices (there’s the HQ in Hawke’s Bay, a Wellington office and they’re in the midst of establishing an Australian team as demand grows over the ditch) all use the software every three months, feeding back to Chris and his leadership team valuable insights into how they’re tracking, what might need improving, and where opportunities lie. “Invariably,” Chris says with a smile, “I hear about my own need to improve in the areas of communication and leadership effectiveness, clarity on strategy, that sort of thing.” 

Ethical VOICE – the tool that helps flush out instances of bullying, harassment and intimidation at work – has already been warmly welcomed by several members of our Recognised Seasonal Employer (RSE) scheme, as well as global apparel manufacturers such as Kathmandu, who use it in their factories in China to ensure that every piece of their clothing is being produced as ethically as possible. The tool also recently attracted the attention of HRH Princess Eugenie and her Anti-Slavery Collective in the United Kingdom. “It’s pretty amazing for the AskYourTeam team, based here in little old Hawke’s Bay, to have created something that can actually have an impact on society. We see lives changing with the work that we do.” 

Certainly, Chris has a deeply-held commitment to doing the right thing by his fellow humans which comes, he thinks, from his upbringing. His father, Laurie O’Reilly, was the New Zealand Commissioner for Children, a law lecturer and the first-ever coach for the New Zealand women’s rugby team. Mum Kay was a national netball selector and coach, and together they operated an open-door policy at their Christchurch home. 

“I don’t think I realised at the time how hugely influential my upbringing would be,” muses Chris, who, as a sidenote, played two games “badly” for the Magpies as a 21-year-old. “We lived in an environment of social justice and social equality. My parents were both advocates for those that needed it, so our house was always full of street kids, unwed teenage mothers, and travellers from around the world. My sister and I can only remember about nine months of our lives when we didn’t have the spare bedrooms full!” 

“I think it all led to me asking, ‘how do we better value and respect people?’” 

So, what’s next for Chris and AskYourTeam? Well, there’s that move to consider – bigger premises to house a greater number of staff as they grow (and a rooftop terrace, if you please!). There are possibilities for further expansion into Europe, and partnerships to develop with external organisations, governments and charities. While seed funding for AskYourTeam came from private equity and small capital raises, Chris anticipates there will be a requirement for more capital in the coming year, particularly as the Ethical VOICE platform takes off. 

And he also sees plenty to be done in the diversity and inclusion space. “If you have a look around, there are far too many people like me leading companies,” he says. “We’ve still got a long way to go on diversity.” 

It wouldn’t make sense to end the interview without some of Chris’s own insights into what trends might be emerging in the workplace in a post Covid world. “People are looking for a lot more purpose in what they do,” says Chris. “And they’re demanding more balance – and maybe that’s a percentage of time based at home, and some time in the office. Leaders need to find ways to be more present and available to their teams, wherever those teams are based.” 

“Having said that,” he says, no doubt remembering that day he locked all the doors but one at the bus company, so his colleagues would actually talk to each other, “nothing builds trust like having a face to face relationship”. 

Fiona Fraser is the director of Contentment PR & Communications. Nominate a savvy entrepreneur to feature in an upcoming column by contacting 


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