Career insights with Jason Wilk FAICD

Candid conversations with directors on the interests and insights that have shaped their careers.

Directorships

Executive director BoxxedIn Media, practice director – governance of risk Peakstone Global, managing director Wilk Advisory, senior facilitator/course author/reviewer AICD

Most-valued lesson?

Early in my career, I’d been appointed IT security manager for a big insurance company. I was trying to change opinions in the boardroom around cyber risk, but it wasn’t working well. An experienced director took me aside and told me there’s no amount of data or discussion that will help you change their subconscious risk appetite. What you have to do instead is say, “I see your perspective, so explain why you see it this way”. Then you draw a line in the sand and ask, “Our personal risk appetites are perfectly valid for us individually, but what’s right for our organisation as a whole?”

Career risk that unexpectedly paid off?

In 2010, someone from the AICD saw me speak about cyber governance and asked if I had considered teaching governance. To take a group of professional directors on a learning journey was not on my bingo card back then, but I’ve been with the AICD for 15 years now and it’s my happy place. I like to get away from discussing technology and move into that grey space of human interaction around governance and big decisions.

Top-of-mind governance issue?

There is a massive vacuum sucking investment dollars into AI. When it comes to technology, there’s generally a huge peak of expectation, a trough of disillusionment and then we reach a plateau. Yes, AI will transform lots of businesses, but many are just bolting AI onto everything. I’m concerned it’s redirecting capital out of other elements of innovation as a whole, which represents missed opportunities for society.

Prediction about the future of leadership?

The future of leadership has got to be human-centric. We also need to shift more towards objective-centric risk management, rather than approaching risk through fear and a “what’s the worst that could go wrong” attitude. We need a better discussion around the balancing acts of compliance and getting stuff done.

Favourite way to unwind?

About 23 years ago, we realised we didn’t want to live in a city — we wanted to bring our kids up in nature. We now live on an acre of land we’ve turned into a nature reserve. I love tinkering and pottering. There’s always something that needs fixing with my hands — or the occasional boot!

Favourite podcast?

I listen to Freakonomics. I love the insights about how economics drive societal decisions that don’t seem intuitive. I also like 99% Invisible, about hidden design elements that affect everything we do. Intelligent Machines is my go-to tech podcast.

Favourite travel spot?

In 2019, we went to Finland. It was fascinating to see how they chase happiness. We also went to Moscow, where the people were incredibly warm and open. We were in Red Square for Orthodox Christmas and it was a festival of lights, spontaneity and fun.

This article first appeared under the headline 'Favourites' in the October 2025 issue of Company Director magazine.