WB-40

(329) AI Leadership


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On this week’s show Julia and Matt interview Matt Cockbill, an executive search consultant specializing in hiring tech leaders for over 20 years,

A fundamental challenge for organisations is finding experienced leaders to navigate the new wave of AI and generative technologies. While the possibilities are vast, Matt emphasises the crucial need for leaders to focus on the value case – defining what will actually be useful and deliver tangible business outcomes.

Finding leaders with proven experience specifically in generative AI is challenging due to its relative novelty, sometimes requiring organisations to be bold and partner with academia or research institutions. Leaders claiming extensive generative AI experience warrant careful scrutiny.


The discussion highlighted the evolution of tech leadership, with CIOs and CTOs increasingly focused on shaping strategy and enabling value for the business, a trend accelerated by events like Covid-19.

The rapid arrival and hype of AI necessitate leaders who can assess organisational appetite and marshal resources towards valuable activities.

Ultimately, succeeding with AI means balancing a compelling vision with a clear understanding of where the return on investment lies. This requires tech leaders to leverage essential skills like storytelling to build confidence and clearly articulate how technology, including AI, can deliver on strategic objectives.

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WB-40By Matt Ballantine & Chris Weston

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