On Culture: One Hard Question to Start the Year

Myste Wylde
1 day ago
5 min read

Dear Culturati Insider,

Happy New Year. Let’s start with a hard question.

If Q1 underperforms, what would you wish you had confronted earlier? Consider it a premortem.

One of the major leadership risks heading into 2026 is reliance on outdated operating models. As AI changes how work moves through organizations and how decisions are made, those built for slower cycles are creating significant exposure. CEOs are preparing for tighter capital, higher scrutiny, and less margin for error.

The financial threat of AI-driven cyberattacks is here. Energy demands are forcing difficult infrastructure choices, and boards are pressing for clarity on exposure, readiness, and decision quality. And in our polycrisis reality, leaders continue to be tested personally. Research shows that many high performing execs remain strong on productivity while running short on calm, the least developed capability despite being critical to sustaining judgment, energy, and steady presence with others.

Meanwhile, the pipeline beneath leadership is shifting. As AI absorbs routine work, early career roles no longer function as apprecticeships. Development requires greater intentionality, with future leaders entering closer to the decision layer. HR sits at the center of this transition, balancing uneven automation, skills-based hiring that is outpacing reskilling, rising legal and governance issues, and cultures showing strain after years of disruption. Across all of it, AI efforts continue to stall when layered on top of old labor-based operating models. We've no doubt that this year will test how we're designing work, including what changes we've made (or failed to make) to meet the future.

Together in 2026,

Myste Wylde, COO

12 CEOs Share Bold Predictions for 2026

Fast Company

By Stephanie Mehta

Summary: CEOs across security, infrastructure, manufacturing, and finance see 2026 as a year of correction and necessary clarity. Rick Caccia of WitnessAI expects the first AI-driven cyberattack with real financial damage, pushing AI security from compliance to business-critical and accelerating buying cycles. Ted Bailey (Dataminr) and Balaji Yelamanchili (ThreatConnect) say threat intelligence must translate cyber, physical, and geopolitical risk into direct organizational impact to be useful, while Filip Kaliszan of Verkada predicts a new era of standardized executive protection. On infrastructure, KR Sridhar of Bloom Energy sees AI overwhelming energy grids and driving onsite power, while Sami Issa (Global AI) expects sovereign AI capacity to be treated like national energy infrastructure. In growth markets, Bam Azizi of Mesh points to B2B agentic commerce and micropayments, while Micha Breakstone of Somite AI sees AI turning biology into a predictive engineering platform. Financial leaders Graham Weaver (Alpine Investors) and Sam Miller (Kasheesh) warn of overheated credit markets and uneven AI gains. The bottom line we're seeing: 2026 will separate companies that prepared early for security, infrastructure, and financial risk from those forced to react under pressure.

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Calm: The Underrated Capability Every Leader Needs Now

MIT Sloan Management Review

By Lynda Gratton

Summary: Research from Lynda Gratton, professor of management practice at London Business School and founder of HSM Advisory, shows that many high-performing executives are running out of capacity, not capability. Her eight-thread framework for sustainable working lives spans four productivity threads: mastery, focus, autonomy, and growth motivation, and four nurture threads: health, relationships, purpose, and calm. When executives assess themselves, productivity threads consistently score highest, particularly mastery, while calm ranks lowest. Only about 10% of leaders rate calm as a strength, despite carrying the same pace and accountability as peers. Gratton finds the difference is not workload but how people manage attention, energy, and response. The calm minority prioritize pacing, deliberately limit reactivity, and protect time for reflection and recovery. Calm, in this context, doesn't always equate slowing down, but rather choosing when speed adds value and when it undermines judgment.

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If Entry-Level Jobs Disappear, Who Becomes a CEO?

Fortune

By Ruth Umoh

Summary: AI is eliminating much of the routine work that defined entry-level roles, from data entry and basic analysis to support triage and junior coding, shrinking the traditional path for learning how organizations actually work. As they disappear, leadership development must become more deliberate. Recruiters report companies identifying potential earlier and moving away from tenure-based progression toward accelerated paths that emphasize judgment, ethics, and managing human and machine systems together. Future leaders will start closer to the decision layer, overseeing automated work and making trade-offs earlier in their careers, often through structured rotations and simulations rather than gradual exposure. At the same time, the CEO pool is widening to include founders, technical specialists, veterans, and career switchers.

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5 Trends That Will Shape HR in 2026

HR Dive

By Ryan Golden

Summary: This year, HR leaders are navigating a set of converging trends rather than a single, uniform reality. Many organizations have begun automating routine HR tasks, but adoption remains staggered, and the next challenge is integrating AI into management decisions without undermining judgment, fairness, or trust. Experts warn that informal AI use is steadily surfacing in hiring and performance reviews, making clear guardrails necessary. Talent markets remain volatile, with October 2025 job cuts up 175% year over year, yet skills have emerged as the most consistent priority. Skills-based hiring shows the strongest momentum among emerging HR practices, and while 54% of organizations expect AI upskilling to have high impact, only 1% have implemented it. Legal risk is also rising as courts allow more majority-group discrimination claims, increasing scrutiny of how DEI programs are designed and governed. Gartner points to growing culture atrophy, pushing HR to refocus on manager capability, human connection, and frequent, high-quality feedback.

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You Can’t Advise Reinvention While Selling The Past

Forbes

By John Winsor

Summary: Many executives say they want an AI strategy, but what they often seek is reassurance that AI can be bolted onto existing operating models. That mismatch is why so many initiatives stall. Organizations try to integrate AI into labor-based models instead of shifting to systems-based ones where value scales with workflow leverage and outcomes. AI-native firms are built this way by default. Agentic platforms and orchestration look like progress, but ultimately fail to deliver when they sit on top of utilization-driven economics. Trust still matters (perhaps more than ever), but it is increasingly earned through method. Leaders are asking practical questions: what work is automated, how much execution is system-driven, how decisions and actions are governed, and whether each cycle improves the next. In an AI economy, credibility comes from how work gets done. If the operating model has not changed, outcomes will not either.

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