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Effective upskilling isn't about random training. Leaders must first identify the new capabilities the business needs (e.g., AI-driven marketing). Only then should they assess which current team members have the desire and aptitude to learn and implement those new skills, creating a clear path for growth.

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Effective AI integration requires first upskilling existing marketing teams in "AI literacy" so they can understand workflows and evaluate tools. Only then should leaders augment the team with specialized external talent (consultants, vendors) to fill specific gaps, rather than hiring a single "AI expert" who lacks business context.

Digital transformation is a human challenge. Beyond tech adoption, companies must future-proof by intentionally evolving their talent—hiring for deep subject matter expertise and upskilling current teams for complex, high-empathy roles that AI can't replace.

Don't hire based on today's job description. Proactively run AI impact assessments to project how a role will evolve over the next 12-18 months. This allows you to hire for durable, human-centric skills and plan how to reallocate the 30%+ of their future capacity that will be freed up by AI agents.

Companies once hired siloed 'digital experts,' a role that became obsolete as digital skills became universal. To avoid repeating this with AI, integrate technologists into current teams and upskill existing members rather than creating an isolated AI function that will fail to scale.

Anticipating that AI will automate baseline work of junior analysts, Temasek’s strategy is to push these employees to develop skills and perform at a level two grades above their current role. This preemptively adapts their talent development model for an AI-enabled world, focusing on higher-order thinking from day one.

True AI adoption requires more than technical know-how. Salesforce's internal training mandates proficiency in Agent skills (AI literacy), Human skills (adaptability, EQ), and Business skills (problem-solving, storytelling), recognizing that technology is only one part of the transformation.

To ensure AI adoption is a core competency, formally integrate it into your team's operating system. Webflow is redoing its career ladder to make AI fluency a requirement for advancement, expecting team members not just to use tools but to lead, own, and push the boundaries of AI in their work.

Instead of immediately seeking outside consultants, leaders should identify and empower employees who are already using AI effectively. This validates their initiative, leverages existing knowledge, and provides them with a clear path for professional development and company-wide impact.

To bridge the AI skills gap where 55% of employees lack proficiency, Dropbox's VP of Engineering suggests a targeted training approach. Instead of generic programs, identify the company's existing high performers, who are likely already using AI effectively, and empower them to train their colleagues.

A study identifies a persona of highly effective AI users, “Augmented Strategists,” who achieve the highest net productivity gains. A key differentiator for this group is that they are two times more likely to have received substantial skills training, proving that targeted upskilling is essential for creating valuable AI adopters.

Upskill Your Team by Identifying Needed Capabilities Before Selecting Employees | RiffOn