In this episode of Talking Product, Collin and I discuss a tension we increasingly see inside organisations: digital capability is becoming an enterprise survival issue rather than a technology optimisation issue.

Unlike some of our previous episodes, this is less a discussion about a single topic and more a conversation between two practitioners trying to reconcile lived experience with organisational inertia. We believe this tension is surfacing more visibly now because of the disruption caused by generative AI.

Collin highlights an article I published on Substack at the end of last year. In it, I argued that the tolerance for organisational inefficiency and limited digital capability is likely to compress dramatically in the years ahead. Organisations that have invested time and energy into improving product delivery practices, architectures, infrastructure, data quality, and operating models are materially better positioned than those that have largely treated such initiatives as secondary concerns.

This led me to a broader question: if executives and boards are not asking deeper questions about AI, data, software capability, and operating models, who is? My conclusion is that institutional investors need to engage far more directly with digital capability risk because many portfolios are likely carrying significantly more exposure than is currently recognised.

We do not pretend to have definitive answers to many of these questions. In fact, part of the episode is an acknowledgement of just how difficult these topics are to navigate. But we once again argue for the importance of having these conversations inside organisations — because avoiding them does not reduce the risk. It simply delays the moment when those risks become visible.

Lastly, we once again argue that getting Chip Huyen’s book AI Engineering and starting conversations inside your organisation about the subjects she raises will be very good value for money — and may save you a great deal of money and grief further down the road.

Takeaways:

• An exploration of why digital capability is an enterprise-level risk rather than a delegated IT concern.

• A discussion about how generative AI accelerates the consequences of technical debt and organisational underinvestment.

• Questions around whether executives, boards, and institutional investors are asking sufficiently deep questions about AI, data, and operating models.

The Digital Laggard Thesis: https://johnyoung.substack.com/p/towards-an-investment-thesis-on-digital