Episode 12.5: The 10M Question

After recording The AI Speed Trap, Judy Dinn and Gary Teelucksingh stayed in their seats and turned the questions on each other. The result is a candid ten minutes that feels like pulling up a chair to the coffee conversation that happens after the cameras usually stop rolling.

Gary opens with what clients ask Electric Mind for, which is usually lower costs and faster delivery, and what we tell them in return. His advice is to go slow to go fast, starting with principles, governance and a clear view of what you’re trying to accomplish. Judy adds that too many organizations treat new technology as a checklist item, when the real work is right-sizing the technology to the problem.

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L to R: Gary Teelucksingh, Senior Partner, Electric Mind | Judy Dinn, Chief Information Officer, TMX Group

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When Gary asks how she would spend $10 million on the best thing for her organization, Judy puts about $1 million into AI tooling and the other $9 million into coaching people in finance, HR, legal and sales to build with it themselves. Gary then explains how he helps teams become more strategic, by anchoring every decision to the business imperative and weighing the timeframe and speed of the outcome they want.

Judy closes with advice for up-and-coming leaders, especially young women in technology. She encourages them to spend less time proving themselves and more time learning to tell the story behind their work, so they can sell an idea in the time it takes an elevator to reach the 54th floor. She also shares her yearly habit of adding one new skill to her LinkedIn profile over the holidays, and her reason for saying yes to opportunities she never planned for.

For anyone building a career in technology, this bonus episode is a generous reminder that curiosity, humility and a willingness to say yes can carry you further than any single skill.

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