What if the biggest obstacle to AI success isn't the technology at all, but the way your business actually works?

In this episode of AI at Work, I sit down with Justin Watt, CEO and Co-founder of Switchboard, to discuss why so many AI initiatives disappoint and what organizations should focus on before adding another AI tool to the mix. Justin has spent his career helping growing businesses replace disconnected spreadsheets, manual handoffs, and fragmented workflows with systems that are designed to support the way people really work.

During our conversation, Justin explains why many organizations are trying to build an AI-first business on top of processes that were never designed for automation. Rather than chasing the latest technology, he argues that leaders should first understand how work actually moves across their organization, identify unnecessary complexity, and remove friction before introducing AI.

One of my favourite moments in our discussion is Justin's comparison between "single player AI" and "multiplayer AI." While many employees are already seeing personal productivity gains from tools such as ChatGPT and Copilot, the real opportunity comes when AI works across departments, connecting sales, operations, finance, legal, and customer teams instead of remaining isolated in individual chat windows.

We also discuss why spreadsheets continue to dominate business operations decades after their introduction, how companies can move beyond them without disrupting the business, and why operational workflows should be treated like products that are continuously improved rather than collections of disconnected fixes.

Justin also shares practical lessons from working with organizations that believed they had an AI problem, only to discover the real issue was broken processes. From legal teams overwhelmed by poor sales handoffs to businesses relying on undocumented workflows held together by spreadsheets and institutional knowledge, he offers a grounded perspective on where AI genuinely creates value and where better operational design delivers faster results.

If you're leading digital transformation, responsible for operations, or trying to move AI from experimentation into everyday business value, this conversation offers practical advice that can be applied immediately.

How well does your organization really understand its own workflows before asking AI to improve them? I'd love to hear your thoughts after listening.