The Critical Path: Best Practices for Managing Enterprise AI Projects

The Critical Path: Best Practices for Managing Enterprise AI Projects

Cross-functional team collaborating on AI project management

In my years leading AI implementations across healthcare, energy, and resources sectors, I’ve discovered that the difference between AI projects that transform businesses and those that fade into obscurity often comes down to project management execution. The technical components are critical, but without strategic leadership and methodical oversight, even the most promising AI initiatives can falter.

The AI Project Management Challenge

Managing AI projects presents unique challenges compared to traditional software development. The experimental nature of AI, the data dependencies, and the cross-functional collaboration requirements create a perfect storm of complexity. According to Gartner, through 2022, only 20% of analytic insights delivered business outcomes. This sobering statistic highlights why specialized AI project management approaches are essential.

Five Critical Success Factors for AI Project Management

Based on my experience leading multi-million dollar AI implementations, I’ve identified five critical success factors that consistently differentiate successful AI projects:

1. Problem-First, Technology-Second Approach

Best Practice: Begin with business problems and objectives, not AI capabilities.

When leading a $5M automation initiative at a major healthcare insurer, I insisted we start by documenting specific operational pain points. This approach led us to implement RPA solutions that reduced manual data entry by 50% rather than pursuing more complex natural language processing that wouldn’t have addressed immediate needs.

“The most successful AI projects start by asking ‘What business problem needs solving?’ not ‘How can we use AI?’”

Implementation Steps: – Facilitate problem definition workshops with business stakeholders – Quantify current pain points with metrics before proposing AI solutions – Create problem statements that focus on business impact, not technology – Prioritize based on value and implementation feasibility

2. Cross-Functional Team Alignment

Best Practice: Create a shared language and objectives between business and technical teams.

During the $110M Connected Worker Program I managed in the energy sector, I established “translation sessions” where data scientists, field operators, and executives aligned on terminology and goals. These sessions prevented disconnects between what business stakeholders expected and what technical teams delivered.

Implementation Steps: – Establish a cross-functional steering committee with regular touchpoints – Create a glossary of terms that bridges technical and business language – Use visualization techniques to make AI concepts accessible to non-technical stakeholders – Implement “day in the life” shadowing where technical team members observe business operations

3. Iterative Value Delivery

Best Practice: Structure AI projects for incremental value delivery rather than big-bang releases.

When implementing process mining solutions for a resources company, we delivered insights in two-week sprints, allowing operations teams to implement efficiency improvements immediately rather than waiting for the full-scale deployment. This approach delivered a 20% improvement in process turnaround times within the first two months.

Implementation Steps: – Break AI initiatives into clearly defined minimum viable products (MVPs) – Establish measurable success metrics for each iteration – Create feedback loops with business users after each release – Document and celebrate incremental wins to maintain momentum

4. Data Strategy Integration

Best Practice: Align AI project management with data governance and management.

For an AI-powered claims processing system, I established a data readiness assessment phase that identified critical data quality issues before model development began. This prevented months of rework and established data quality improvements as a parallel workstream to the AI development.

Implementation Steps: – Include data profiling and quality assessment in project initiation phases – Establish data governance protocols specific to AI training and validation – Create data improvement roadmaps aligned with AI development milestones – Allocate specific resources to data preparation and management

5. Change Management Integration

Best Practice: Integrate change management from day one, not as an afterthought.

When deploying AI-powered chatbots for customer service, I embedded change specialists within the project team who created personalized adoption strategies for each user group. This approach resulted in 87% user adoption within three months—significantly higher than industry averages.

Implementation Steps: – Identify key stakeholders and influencers early in the project lifecycle – Develop tailored communication strategies for different user segments – Create immersive training experiences that build confidence with AI tools – Establish success metrics focused on adoption and usage, not just technical implementation

Managing AI Project Risks

AI projects face unique risks that require specialized management approaches:

Technical Debt Management

AI systems can create significant technical debt if not properly managed. In one RPA implementation, we established a “refactoring Friday” where 20% of development time was dedicated to improving existing automation rather than building new features. This practice prevented performance degradation and reduced long-term maintenance costs.

Ethics and Bias Monitoring

I recommend establishing an Ethics Review Board for AI projects with significant decision-making impact. During a predictive analytics implementation for operational planning, this board identified potential bias in historical data that could have reinforced existing inefficiencies if not addressed.

Expectation Management

AI projects often face inflated expectations. Creating an “AI Reality Index” that plots stakeholder expectations against technical feasibility helps identify perception gaps before they impact project success. During executive reviews, I use this tool to realign expectations and maintain realistic project scope.

Case Study: From Failure to Success

On a recent project integrating AI-powered document processing for a major corporation, the initial implementation failed despite strong technical execution. The primary issue? Poor project management practices specific to AI.

When we reset the project, we implemented the practices outlined above, particularly focusing on:

  1. Redefining success metrics based on business impact, not technical capabilities
  2. Establishing a cross-functional governance team with weekly touchpoints
  3. Breaking the implementation into eight smaller releases with clear business value
  4. Creating a specialized change management program for end-users

The result? A successful implementation that delivered $1.2M in annual savings and 40% improvement in document processing times.

Conclusion: The Project Manager as AI Translator

The most valuable skill for AI project managers is serving as translators between technical possibilities and business realities. By implementing the practices outlined above, you can bridge the gap between AI’s promise and practical business implementation.

In my experience leading AI initiatives across multiple industries, I’ve found that excellence in AI project management often delivers more business value than marginal improvements in model accuracy or technical sophistication. As enterprises continue their AI transformation journeys, specialized project management approaches will become increasingly vital to realizing the full potential of artificial intelligence.


Rosario Fortugno is a Senior AI Project Manager with 15+ years of experience leading complex technology initiatives. He has orchestrated RPA, machine learning, and AI-powered projects across healthcare, energy, and resources sectors, delivering measurable business impact through strategic project leadership.

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