leadership

September AMA: I’m a CISO Who’s Built Many Security Teams. I Want to Help You Level up Your Career. Ask Me Anything.

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CISO Series hosts a September AMA featuring experienced cybersecurity leaders who have built and led multiple security teams, offering advice on career growth, leadership, hiring, and team management within the security field. The panel includes CISOs and security directors from diverse organizations and covers topics such as AI security, cloud security, risk management, and security culture. Participants engage with the community over a week-long event on Reddit to answer questions and share insights relevant to advancing careers in cybersecurity.

https://cisoseries.com/september-ama-im-a-ciso-whos-built-many-security-teams-i-want-to-help-you-level-up-your-career-ask-me-anything/

EY Global Vice Chair: AI’s Biggest Paradox Comes Down to What AI Can’t Do

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EY Global Vice Chair Julie Teigland emphasizes that while AI excels at repetitive tasks and data processing, it cannot replace essential human judgment required to set goals, interpret context, and make decisions. She highlights that companies miss out on significant AI productivity gains due to gaps in talent development, particularly in cultivating AI fluency as a leadership skill that integrates technical operation with critical evaluation. Teigland advocates for collaborative approaches across organizations and ecosystems to efficiently scale AI technology without reinventing solutions, citing EY’s work with partners that improved operational performance and speed.

https://fortune.com/2026/09/27/ai-fluency-human-judgment-leadership/

The Accidental CIO Is Disappearing, and That Might Be a Problem

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The traditional “accidental CIO,” who gained broad leadership experience through varied, unstructured roles, is becoming rare as technology careers grow more specialized and structured. This shift creates a challenge because modern CIOs need not only deep technical expertise but also extensive business, financial, and leadership experience to effectively influence enterprise strategy and navigate complex transformations. To prepare future CIOs for these expanded responsibilities, organizations should deliberately engineer diverse experiential development—such as managing P&Ls, leading major transformations, and engaging with executive stakeholders—rather than relying solely on certifications or narrowly focused career paths.

https://www.cio.com/article/4225055/the-accidental-cio-is-disappearing-and-that-might-be-a-problem.html

‘Not My Cup of Tea’ Is the Most Expensive Sentence in Your Engineering Org

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As AI commoditizes much of traditional coding work, engineers must develop stronger communication and customer-facing skills to remain relevant and add value. The article argues that organizations should break down silos, promote cross-functional collaboration, and encourage engineers to engage directly with customers to improve judgment and product outcomes, while emphasizing coaching willing engineers in these capabilities rather than expecting all to do so. This shift reflects a market repricing of roles toward engineers who can understand the broader context, navigate trade-offs, and explain technical decisions beyond their specialization.

https://www.cio.com/article/4225109/not-my-cup-of-tea-is-the-most-expensive-sentence-in-your-engineering-org.html

Risk Management Isn’t an Insurance Decision, It’s a Leadership Decision

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Powell Brown, CEO of Brown & Brown, emphasizes that risk management is a leadership responsibility that requires continuous engagement rather than treating insurance as a transactional annual renewal. Effective risk management involves understanding exposures, preparing for diverse scenarios, and integrating risk considerations into business operations to protect organizational assets amid evolving threats like cyberattacks, AI governance challenges, and geopolitical uncertainty. Brown advocates for specialized, advisory-driven risk strategies tailored to each industry to help leaders make informed decisions and strengthen their organizations proactively.

https://www.chicagobusiness.com/crains-content-studio/publishing-partner/ccb-risk-management-insurance-leadership-brown/

7 Ways to Restructure IT for Maximum Productivity

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CIOs can boost IT productivity by restructuring around business value, consolidating key teams like security and engineering, and creating cross-functional groups with end-to-end ownership of business capabilities. Emphasizing workflow optimization, domain expertise with mentoring, disciplined tool management, and collaborative problem-solving reduces friction, breaks down silos, and aligns IT efforts with strategic outcomes. Integrating AI thoughtfully into platforms and operations further enhances agility and impact across technology functions.

https://www.cio.com/article/4224624/7-ways-to-restructure-it-for-maximum-productivity.html

Digital Transformation Fails Without This Culture Shift

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Akio Ueda argues that successful digital transformation hinges not on technology but on fostering a culture of psychological safety where employees feel secure to take risks and learn from failure. He emphasizes that building a learning organization with supportive relationships, ongoing challenge, and innovation enables continuous adaptation and growth in a rapidly changing AI-driven era. Strategic top-down and bottom-up efforts to embed this positive culture can transform DX into a sustainable competitive advantage.

https://www.cio.com/article/4222873/digital-transformation-fails-without-this-culture-shift.html

The Rise of the AI Operating Executive

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Marianne Johnson, EVP and chief product and technology officer at Cox Automotive, is pioneering a unified leadership model that integrates product, technology, data, AI, engineering, and cybersecurity to accelerate AI-driven business transformation. She emphasizes the need for multidisciplinary leadership capable of managing rapid change, promoting alignment, and reimagining roles to operationalize AI safely and at scale. Johnson advocates for leaders to develop AI fluency and adaptability to sustain competitive advantage amid evolving technologies and organizational structures.

https://www.cio.com/article/4217281/the-rise-of-the-ai-operating-executive.html

Strategies for Navigating Security Job Title Chaos

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Security employers increasingly prioritize candidates with exact job titles matching the roles they seek, using titles as shorthand for capability and seniority to reduce hiring risk. However, modern security leaders must combine executive presence with operational execution, managing both strategic leadership and hands-on tasks. To navigate inconsistent and overlapping security job titles, candidates should clarify their functional scope in resumes and interviews, pairing official titles with market-recognized equivalents and emphasizing their responsibilities and impact to better align with employer expectations.

https://www.securitymagazine.com/articles/102522-strategies-for-navigating-security-job-title-chaos

The Quiet Reason CIOs Are Slowing AI Down

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Despite widespread informal use of AI tools by employees, many CIOs slow enterprise AI adoption under the guise of governance due to concerns about risk and accountability, but often to preserve their traditional authority derived from technological scarcity. As AI democratizes capabilities once exclusive to specialists, CIOs face a shift where their domain expertise becomes less unique, and resisting change risks ceding influence as shadow adoption grows uncontrollable. To adapt, CIOs must embrace proportional governance, prioritize learning agility over tenure, engage hands-on with AI tools, and encourage evidence-based challenge within their teams to maintain strategic relevance amid rapid AI-driven transformation.

https://www.cio.com/article/4220792/the-quiet-reason-cios-are-slowing-ai-down.html

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