Insights
Insights for Executives
This library is for original, practical material written for boards and senior leaders—not generic summaries of technology trends. Every article should leave the reader with a clearer executive question, a distinct point of view, and a practical next step.
Articles in development
Published essays will appear here. Until then, the content pillars below describe the questions Harold is writing toward.
Content pillars
AI as an Operating Capability
- Why AI pilots fail to become enterprise capabilities
- How to prioritize AI investments by business value
- What boards should ask about agentic AI
- The operating model required for responsible AI
Enterprise Transformation
- Why transformation programs lose momentum
- The difference between technology modernization and business transformation
- How to establish an executable future state
- Why operating-model decisions must precede major platform decisions
Architecture and Technology Investment
- Architecture as an executive decision system
- Reducing application and integration complexity
- Connecting business capabilities to investment priorities
- How to prevent architecture governance from becoming a bottleneck
The Future of Real Estate
- Why the MLS should be a data source—not the operating system
- Returning property data control to owners
- Why real estate needs a unified operating environment
- How AI can reduce transaction time without replacing licensed professionals
Speaking topics
- Building the Intelligent Enterprise
- From AI Experimentation to Enterprise Value
- Architecture as a Business Leadership Discipline
- What Real Estate Can Become When Its Systems Finally Connect
- Leading Transformation When the Existing Model Is No Longer Enough
If an insight raises a mandate question, begin the conversation
If your organization is preparing for a major transformation, evaluating its technology leadership, establishing an AI agenda, building a new platform, or seeking an experienced executive who can connect vision with execution, Harold welcomes a confidential conversation.