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A thriving knowledge economy inherently relies on a highly skilled and adaptable workforce. And, as the [Coronavirus Disease 2019] COVID-19 pandemic has revealed, knowledge-intensive sectors are far more resilient in times of disruption than most other sectors. So what does it take to build the workforce that will help Canada transition to a knowledge economy? Despite a strong post-secondary system combined with robust labour market development programs, industry points to a lack of the right talent as a critical inhibitor for their growth. The enduring and frustrating irony to this challenge is that while Canadian [information and communications technology] ICT firms are struggling to hire business talent, significant numbers of workers in the Canadian labour market have the foundational skills to succeed in these roles. This paper sets out to explore this gap, beginning to answer these critical questions: How do we ensure that opportunities are maximized for Canadians in the transformation to a knowledge-intensive economy? What are the appropriate support mechanisms for mid- to late-career workers who are most in danger of being displaced during this transformation? How should Canada’s skilling and education systems evolve to prepare those entering the workforce in an environment where skills needs are constantly evolving? Most importantly, it asks the fundamental question: Is the problem really mismatched skills? To answer this, the authors go back to first principles and ask: What does it take to land a job in tech, especially if you have the skills but are coming out of a totally different sector?; To explore these and other questions the authors created Palette Inc., a national not-for-profit talent platform that strives to meet the needs of Canada’s most innovative companies by rapidly upskilling diverse and non-traditional workers. Palette provided a platform for testing real-world assumptions and gaining new perspectives, in part by seeing the skills debate through the eyes of companies and workers. Overall findings indicate that the talent challenge faced by ICT firms is less a problem of an underlying skills gap in the workforce and more a problem of skill underutilization. It is argued that ICT firms’ inherent biases are stalling the transition of large numbers of well-qualified workers into these firms. Such biases arise because the hiring processes ICT firms use are not capable of identifying skills picked up in more traditional sectors. This contributes to a chronic inefficiency and underutilization of talent within the labour market and bolsters the refrain that there is a skills gap and/or talent shortage. The challenge for policy-makers in thinking about how we support the burgeoning knowledge economy is to identify where the requisite skill set already is and how firms can tap those workers.