In boardrooms from city halls to global retail chains, the artificial intelligence wave is surging. CEOs are bombarded with AI hype, but translating buzz into value is complex. The right questions can provide clarity, no matter whether you are starting your first pilot or marshaling AI at scale. This playbook outlines two pathways: for public sector leaders launching their AI exploration, and for retail executives aiming to tie investments to business outcomes.

AI 101 for City-Government CEOs: 7 Strategic Questions to Get Your First Project Right
For government agency CEOs, AI strategy begins with skepticism—can these tools truly serve citizens, given the realities of budgets, regulations, and public trust? These seven questions form the backbone for responsible, effective government AI adoption.
First, every conversation about artificial intelligence must start not with technology, but with citizens. What tangible outcomes will AI improve in people’s daily lives? Whether it’s speeding up permit processing or targeting building inspections more intelligently, framing every AI project around resident impact helps prioritize investments and justify them to elected officials.
Second, data is both the fuel and the brake for any AI strategy in government. Most agencies operate with siloed departments and incompatible databases. CEOs should ask: What core data assets do we have, and what will it take to make them usable across the enterprise? Conducting a data inventory is indispensable, not only for project feasibility but also for clarifying where data-sharing agreements or upgrades will be necessary.
Budgeting represents a unique challenge for government leaders. Unlike the private sector, public agencies are bound by annual appropriations cycles. Before launching any initiative, CEOs must ask how AI pilots can be funded within these constraints, and how to present them so that they won’t stall at the next budget hearing. Pilots should be sized for quick wins that align with both fiscal calendars and mission outcomes.
AI procurement in government is notoriously slow, often hampered by legacy processes. Leaders should reconsider procurement models to foster innovation. Is there room for agile contracting or partnerships with technology accelerators? Innovative procurement not only streamlines deployment, it signals to technology partners that the agency is ready to move proactively, rather than reactively.
No agency can build or buy every capability. To keep pace, CEOs should explore public-private partnerships and join consortia that enable resource-sharing. Asking how to create or join a partnership ecosystem is crucial for tapping into skills and ideas that may not exist internally.
Trust is a major variable—especially in social service and law enforcement domains. How will your team ensure algorithmic fairness? Mitigating bias involves auditing data, assessing model outcomes, and committing to transparency with community stakeholders. Set these standards early to preserve public confidence as projects unfold.
Finally, define what success looks like in language that resonates with both technologists and elected leaders. Are you measuring reduced call wait times, successful case closures, or public satisfaction? Clear, simple metrics bridge the gap between political accountability and technical achievement, ensuring AI doesn’t lose momentum after launch.

Scaling AI for Retail CEOs: 10 Board-Level Questions That Accelerate ROI
Retail CEOs often face a different challenge: moving beyond isolated AI pilots toward full-scale transformation. These board-level questions will help drive enterprise-wide value, ensuring AI strategy is tied directly to profit and growth.
The first frontier for scaling AI in retail lies in inventory. As pilots prove value at the SKU level or in limited geographies, CEOs must ask what it will take to deploy predictive inventory systems chain-wide. Are the right integrations and process changes in place to enable enterprise-level decision-making?
It’s essential to link AI KPIs to conventional metrics like margin-per-square-foot and e-commerce growth. If a chatbot boosts online conversion, how does that track to quarterly goals? Board discussions should insist on clear, quantifiable connections between AI investments and financial outcomes, shaping not just tactical initiatives but overarching strategy.
Infrastructure is the silent backbone behind every scaled AI project. Foundational investments in cloud and modern data-mesh architectures can determine how quickly pilots become business as usual. CEOs must prioritize architectural modernization, asking whether legacy platforms are holding the enterprise back.
Accelerating AI without governance invites risk. Board and executive teams should establish oversight structures that balance the need for speed with essential risk management. Who is accountable for outcomes? How are privacy and security being managed as AI is embedded throughout customer interactions?
Change management is often underestimated. Employees in distribution centers or store floors will need support as AI reshapes roles and workflows. Change management levers can include retraining programs, incentivizing adoption, and recognizing new skills. CEOs should ask how frontline teams are being engaged and motivated to embrace these technologies.
Funding the next phase of transformation also requires tough choices between OpEx and CapEx, with each offering different advantages for AI innovation. Boards need to clarify capital allocation—should AI investments be considered ongoing operational costs or capitalized assets? Flexible models may unlock faster scaling.
Brand trust is the final, crucial thread in the retailer’s AI journey. As customer-facing AI is deployed for everything from service bots to personalized offers, measuring and managing public perceptions becomes a board-level issue. Is your organization monitoring sentiment and adjusting strategies to preserve trust, especially when algorithms make errors or unexpected recommendations?
The journey from AI pilot to organizational scale is not linear. For both government and retail CEOs, asking the right questions at the right time is the most reliable compass. By focusing on impact, data, governance, and trust, leaders can convert AI’s promise into lasting strategic advantage—starting with their very next executive meeting.