AI Driven PM: Fulfilling the Promise of Lessons Learned

In the realm of project management, the perennial challenge has been not just to navigate the present but to learn from the past in a way that illuminates the path forward. Chapter 12 of my book "Project Management That Works" presents a narrative on risk assessment, a process traditionally encumbered by subjective judgments and cumbersome methodologies.  I presented a way to turn lessons learned into a risk assessment that could provide actionable insights.  It is here, at the intersection of aspiration and reality, that artificial intelligence (AI) and machine learning (ML) emerge not just as tools but as transformative forces, making the ideal of learning from past lessons a tangible, impactful reality.

AI and ML: The Vanguard of Realizing Lessons Learned

The essence of AI and ML in project risk management is their unparalleled ability to digest and synthesize vast datasets, encompassing both the successes and missteps of past projects, to offer actionable insights rather than mere classifications of risks. This marks a paradigm shift from the conventional practice of categorizing risks as high, medium, or low, towards a dynamic model where risks are not just identified but understood in the context of their historical outcomes and mitigated with precision.

Proof of Concept

In my book, I delve into how my project management team undertook the meticulous task of gathering, organizing, and analyzing insights gained from the past three years. The crucial element we sought was the impact of each lesson, be it in terms of time delays, costs, or other significant effects. To leverage these insights, we crafted questions aimed at new project managers embarking on projects, designed to identify potential risks early on. A positive response triggers a report with actionable advice for the project manager.

For example, a common issue is "vaporware," where a vendor offers a not-yet-complete solution, seeking customer investment for development. The risk assessment process includes questions like, "Have you seen a demo of the product?" Followed by, "Was the demo live, recorded, or a PowerPoint?" If "PowerPoint" is chosen, the report suggests the project manager verify the product's completion and user base directly with the vendor. A positive vendor response mitigates the risk; a negative prompts discussion with the project sponsor.

This method illustrates the power of applying past lessons to new projects. However, its effectiveness is tempered by the labor-intensive nature of maintaining and aligning the risk assessment tool with the organization's needs, requiring constant diligence and discipline.

Transforming Lessons Learned into Proactive Risk Management Strategies

1. Automated Compilation of Lessons Learned: Through AI, the exhaustive process of gathering and categorizing lessons from past projects is automated, ensuring a comprehensive repository of knowledge. This database becomes the bedrock upon which AI and ML build to forecast risks and recommend mitigation strategies.
2. Contextual Analysis and Prediction: ML algorithms, trained on historical project data, can predict the likelihood and impact of potential risks with a nuanced understanding of context. This approach transcends the binary nature of traditional risk analysis, offering a spectrum of insights that reflect the complex interplay of various project factors.
3. Customized Risk Mitigation Actions: By integrating lessons learned, AI-driven systems provide tailored risk response strategies that are both specific and actionable. Unlike the generic responses of yesteryear, these strategies are grounded in the empirical evidence of what has worked (or not) in the past.
4. Dynamic Adaptation to New Information: As projects progress, AI and ML continuously refine their predictions and recommendations based on real-time data, ensuring that the risk assessment is not a one-time exercise but a living process that evolves with the project.

Key Takeaways for Embracing AI and ML in Project Risk Management:

• From Reactive to Proactive: Leveraging AI and ML enables a shift from reacting to risks as they arise to anticipating and neutralizing them before they impact the project.
• Precision in Planning: The depth of analysis provided by AI and ML allows for more precise contingency planning, moving beyond arbitrary allocations of time and resources.
• Empirical Foundations for Decision Making: Decisions on risk mitigation are made with the confidence of empirical data, ensuring that the actions taken are proven most effective.

A Vision Realized Through Technology 

The integration of AI and ML into project risk management is not just an upgrade; it's a fulfillment of the long-held vision of truly learning from past projects. By turning the abstract into the actionable, AI and ML actualize the potential of lessons learned, offering a roadmap that is both informed by history and tailored to the unique contours of each new project.

In this new era, the words of George Santayana resonate with renewed significance: "Those who cannot remember the past are condemned to repeat it." With AI and ML, the past is not just remembered but becomes a guiding light, transforming risk management into a strategic advantage that propels projects towards success with the wisdom of experience as its compass.