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Welcome executives and professionals. CEOs need a fuller appreciation of AI-related risks.

Since the previous edition, we have reviewed hundreds of the latest insights in agentic and generative AI, spanning best practices, case studies, market dynamics, and innovations.

This briefing outlines what is driving material value — and why it’s important.

In today’s briefing:

• The CEO’s AI appreciation deficit.

• The talent architecture imperative.

• Human skills for AI adoption.

• Entry-level hiring in the AI era.

• Transformation and technology in the news.

• Insights for Executive+ members.

• Career opportunities & events.

Read time: 4 minutes.

MARKET & BEST PRACTICE INSIGHT

The CEO’s AI appreciation deficit

Brief: HCLTech published a 38-page AI adoption report based on insights from 467 senior executives, including CAIOs, CIOs, CTOs, and CDOs, examining how they view CEO and board-level understanding of AI.

Breakdown:

• 87% said CEOs and boards underestimate the investment risk tied to AI and that not every initiative will bear fruit.

• 85% said CEOs and boards underappreciate that leading in AI may require medium-term margin pressure due to capital outlays.

• 83% said CEOs and boards do not adequately understand that the risk of underinvesting in AI may be existential for the organization.

• The report also explores broader enterprise AI adoption challenges and what leading organizations do differently.

Why it’s important: While AI adoption is accelerating, the ability to translate investments into value remains uneven. AI challenges extend to the very top of the org chart. In fact, in some ways, HCLTech’s data shows the CEO and board may be the source of organizations’ biggest AI pain point.

IN PARTNERSHIP WITH TELEPORT

Unsecured MCP is a data governance emergency

Brief: MCP unlocks new ways for LLMs to interact with data sources. But without proper controls, enterprises risk exposing data to unauthorized users. Teleport secures and governs MCP access alongside SSH, databases, Kubernetes, and more.

With Teleport, you get:

• Short-lived privileges issued per request that automatically expire

• Governed developer and LLM access to MCP servers

• Zero trust access to self-hosted inference endpoints

• Every query logged in a unified, tamper-resistant audit trail

Start your 14-day free trial of Teleport.

BEST PRACTICE INSIGHT

The talent architecture imperative

Brief: Cognizant’s Chief People Officer Kathy Diaz outlined how enterprises can redesign careers, roles and skills from the inside out, and how the firm is applying those changes internally first through its Client Zero approach.

Breakdown:

• Mapping how tasks within professions are changing reveals three patterns: old roles, new tasks; old work, new ways; and entirely new roles.

• Rebuild careers around trajectories instead of rigid job structures. Cognizant consolidated ~90 legacy groups into ~20 job families.

• The most valuable roles in AI-native firms are, in many cases, held by individuals rather than managers. Invest in individual contributor tracks.

• Cognizant's skills approach builds a more comb-shaped professional: someone with deep skills across multiple areas (image above).

Why it’s important: AI is creating one of the most defining moments for talent strategies in decades, prompting organizations to rethink how work is structured, how skills are developed and how careers evolve. Leaders who move with clarity and intent will be better positioned to unlock long-term value.

MARKET & BEST PRACTICE INSIGHT

Human skills for AI adoption

Brief: IDC research, sponsored by Microsoft, shows a widening gap between investment in AI tools and readiness for AI-driven work, with many leaders citing insufficient human skills to support new AI ways of working.

Breakdown:

• Although 58% of firms invest in AI-enabled learning tools, just 44% offer training in critical human capabilities (e.g. leadership, collaboration).

• Without those capabilities, organizations will struggle to translate AI investment into sustained performance, innovation, and trust.

• IDC outlines a six-month human skills roadmap: Months 1–2 orient and de-risk, 1–4 practice and embed, 3–6+ prove and scale (image above).

• The research highlights training examples like AI judgment simulations and avatar-based management training, plus how to measure success.

Why it’s important: As AI deployment accelerates, enterprises discover that technical training alone is insufficient. The human capability gap threatens competitive advantage. Organizations investing in AI learning tools must balance technical training with human skills development.

AI-NATIVE PROFESSIONAL

How to process vendors with Claude Cowork

Brief: In this guide, you'll learn how to process vendors with Claude Cowork. Claude reads vendor files, adds each to your tracker, generates their contracts, and completes intake forms in your browser.

Step-by-step:

1. Describe the end state "I need to onboard several vendors...". Claude plans the workflow, and runs independent steps in parallel.

2. Claude works through the workflow, moving between your local files and browser to complete the full onboarding.

3. Using the Claude in Chrome connector, Claude opens your procurement portal in a new browser tab and fills out intake forms.

4. Claude also reads vendor details and generates contracts leveraging the templates in your folder.

Best practice: Cowork displays which files Claude is reading and the actions it performs at each step. Guide the workflow in real time when needed.

For the full guide, including prompts, upgrade to Executive+ or The Boardroom.

MARKET INSIGHT

Entry-level hiring in the AI era

Brief: Strada Institute for the Future of Work surveyed nearly 1,500 executives and senior talent leaders across the US to better understand how entry-level hiring is evolving during the early stages of enterprise AI adoption.

Breakdown:

• Nearly three times (2.7 times) as many senior talent leaders expect AI use to increase entry-level hiring in 2026 as to decrease it.

• Among employers reporting increased entry-level hiring, 27% said growing AI adoption across the organization was the leading driver.

• 40%+ of employers said AI increased analytical responsibilities assigned to entry-level employees while routine administrative tasks fell.

• Critical thinking, communication and collaboration skills remain more highly valued in entry-level hires than AI literacy.

Why it’s important: Entry-level jobs have long represented the first step on the career ladder. As AI reshapes tasks once handled by junior employees, organizations are reassessing how these roles evolve. The findings suggest AI will change the nature of entry-level work more than it will eliminate it.

McKinsey examined how AI is changing the nature of entry-level work, plus how the US can capture the AI advantage in defense.

BCG examined how AI always-on retention is rewiring insurance growth, and how AI is reshaping the M&A tech and digital playbook.

Bain explored redesigning tech company operating models for an AI-accelerated world, and how AI will reshape software organizations.

Deloitte detailed how the agentic AI productivity wave is impacting wealth management, and four strategies for scaling agentic AI architecture.

Forrester says SAP is attempting to become the gatekeeper of enterprise AI and CIOs should push back.

BCG outlined seven principles from behavioral science that explain the difference between AI change efforts that succeed and those that do not.

Gartner published its Magic Quadrant for enterprise AI coding agents, naming OpenAI, Cursor, Anthropic and GitHub as leaders.

OpenAI launched Guaranteed Capacity, an enterprise compute reservation program with 1–3 year commitments and tiered discounts.

Anthropic is reportedly in talks to use Microsoft Maia AI chips after similar deals with Google for its TPUs and Amazon for its Trainium chips.

OpenAI released another wave of Codex upgrades, including the ability to attach app windows, goal mode, locked computer use, and more.

Trump called off plans to sign a new AI executive order hours before White House ceremony, citing concerns it could weaken US AI competitiveness.

SpaceX's IPO prospectus revealed that Anthropic is paying $1.25B monthly through 2029 for compute across Colossus and Colossus II.

CAREER OPPORTUNITIES

Citi - Head of AI Strategy

Lloyds Banking Group - Agentic AI Strategy Lead

MetLife - AI Innovation Vice President

EVENTS

Salesforce Connections - June 3-4, 2026

AI Con USA - June 7-12, 2026

Microsoft AI Skills Fest - June 8-12, 2026

Reach enterprise AI decision-makers:

• 66% of readers are C-level executives or VP and Director-level leaders.

• 63.2% of the audience is based in the U.S., EU, UK, ANZ, and Singapore.

• Read by leaders at Microsoft, Deloitte, the Fortune 500, and more.

Guaranteed impression and custom sponsorship packages available, with post-send performance reporting.

Conceived as a practical communication for executives Lewis Walker has worked with, this briefing has become a trusted resource for thousands of senior decision-makers shaping the future of enterprise AI.

We welcome your feedback.