Beyond Plans and Processes: Lessons in Project and Program Leadership

Introduction

I have over 20 years of project management experience, predominantly in the financial services sector, with a particular focus on the insurance and reinsurance industry. Throughout my career, I've had the opportunity to manage a diverse range of initiatives—from small, high-impact projects with lean teams to complex, multi-year programs across various functions and geographies.

Based on my experience, I would like to share in the following sections observed patterns (what works) and anti-patterns (what might not work so well) around methodology selection, selecting the right person for the job, the importance of a strong core, and risk, expectation and scope management.

Agile vs. Waterfall: Choosing the Right Approach

Not One Is Better Than the Other

One of the most persistent debates in project management is Agile vs. Waterfall—which is better? The reality is, neither is inherently superior. They are different tools designed for different contexts, each with its own advantages and disadvantages. The key to success lies in understanding when to apply each approach based on the project's needs.

Understanding Agile and Waterfall

Waterfall is a linear, sequential approach that works best when the scope is well-defined from the start, such as in regulatory requirements that set a clear deadline with penalties for non-compliance. It is also ideal when requirements are stable and unlikely to change, the delivery timeline is fixed with little room for iteration, and regulatory or compliance-driven projects demand detailed documentation and strict phase gates.

On the other hand, Agile is an iterative, flexible approach designed for projects where requirements evolve based on market dynamics, customer feedback, and learning. It is well-suited for fast-paced environments that need continuous delivery of value. Agile teams thrive on collaboration, adaptability, and incremental progress, starting with a minimum viable product (MVP) that is improved iteratively. This approach is particularly effective for complex problem-solving where the final product is not fully defined at the outset.

Throughout my career, I've often encountered situations where senior management attempted to introduce late changes under the guise of Agile, while still expecting all the originally planned items to remain in scope and the deadlines to be met.

Common Misconceptions About Agile

A common misconception about Agile is that it means no planning, when in reality, Agile involves continuous planning in smaller cycles rather than all upfront. Another myth is that Agile is inherently faster; while it can deliver value sooner through incremental releases, the overall speed depends on factors like team maturity and project complexity.
Some people mistakenly believe that Agile allows for scope creep, potentially being misled by the word "Agile" as a synonym for flexibility. However, when Agile is implemented correctly, it actually manages scope changes through controlled processes like backlog prioritization.

When to Choose Which Approach

Resources: The Power of a Strong Backbone

While tools, methodologies, and frameworks are important, the true backbone of any successful project is the team behind it. More specifically, it often comes down to a core group of three key people—a focused leadership unit that drives direction, decision-making, and delivery.

However, success doesn’t come from just having people in these roles—it’s about having the right mix of skills and expertise. One of the most critical lessons I’ve learned over the years is that this leadership team must have a balance of strong business knowledge and technical expertise. Without both perspectives, project plans risk being based on wishful thinking rather than grounded in reality.

The Core Leadership Team: A Triad for Success

1. The Project/Program Leader (Strategic Navigator)

   • Role: Responsible for the overall delivery, stakeholder engagement, risk management, and ensuring alignment with strategic objectives.
   • Value: Provides the big-picture view —understanding how the project fits into the broader business goals while keeping execution on track.

2. The Business Expert (Value Driver)

   • Role: Deeply understands the business domain, including processes, customer needs, and regulatory requirements.
   • Value: Ensures the project is delivering real business value, not just outputs. They help translate strategic goals into actionable project objectives.

3. The Technical Expert (Feasibility Anchor)

   • Role: Brings deep technical knowledge, assessing solution feasibility, system design, and technical risks.
   • Value: Prevents the project from drifting into unrealistic technical assumptions, ensuring the solutions are scalable, secure, and technically sound.

Together, this triad forms the strong backbone of a project. Each brings a unique perspective, and their collaboration ensures balanced, realistic decision-making.

Achieving the right balance in project planning is crucial to avoid falling into the trap of overly optimistic assumptions. When projects are driven solely by business goals, they might focus heavily on ambitious targets without considering technical feasibility. Conversely, when projects are driven solely by technical considerations, they may become overly complex and lose sight of the business value.

The pitfalls of imbalance are significant. Projects that are too business-heavy may be filled with ambitious goals and aggressive timelines, but without technical validation, they risk constant delays, scope creep, or outright failure. On the other hand, projects that are too technical-heavy might focus on technical perfection, over-engineering solutions that don’t deliver meaningful business value or miss market opportunities. When business and technical teams work in silos, critical dependencies are missed, and communication breakdowns occur.

Project Management vs. Program Management

While the terms project management and program management are often used interchangeably, they represent distinct disciplines with unique objectives, scopes, and leadership requirements. One of the key challenges in the industry today is the inflationary use of the term "Program Manager", which can dilute its true meaning and create confusion around roles and responsibilities.

What Is a Real Program—and What Is Not?

A program is not just a large project or a collection of smaller projects. It is a strategic initiative composed of multiple interrelated projects that:
- Aligns with broader business goals of the organisation, ensuring that all projects contribute to a common strategic outcome.
- Requires integrated management to oversee dependencies, risks, resources, and stakeholder expectations.
- Delivers business value and measurable outcomes, beyond just the sum of individual project outputs.

Example of a Real Program: IFRS 17 Implementation in an Insurance Company
This initiative encompasses several projects, including updating financial systems, changing actuarial models, integrating with reporting tools, and managing compliance workflows.

What Is NOT a Program:
- A Big Project: If there’s one clear deliverable, even with multiple workstreams, it’s likely just a large project.
- Example: Developing a new policy administration system with multiple teams working on UI, database, and APIs is still a single project because the goal is singular.
- Multiple Unrelated Projects: Just because several projects are happening simultaneously doesn’t make it a program. Without shared objectives or dependencies, they are simply a portfolio of projects, not a program.
- Example: Running a marketing campaign, implementing a CRM system, and launching a new product—all separately managed—doesn’t qualify as a program unless there’s a unified strategy linking them.

Why Mislabeling Matters

• Role Confusion: When every big project is called a "program," organizations risk assigning program managers without the right skills for strategic coordination.
• Inefficient Governance: Applying program-level governance to non-program initiatives adds unnecessary bureaucracy.
• Misaligned Expectations: Stakeholders may expect program-level benefits (like transformation or strategic change) when the initiative is simply operational.

Common Mistakes: The PMO Trap

Another common pitfall is thinking that program managers — or even project managers — are just there to manage risks, actions, issues, and decisions (RAID logs). While these are important, they represent only a fraction of what’s needed for effective leadership.

One mistake I’ve often observed is assigning a PMO resource to act as a project or program manager, assuming that strong governance skills are enough. While PMO professionals excel at frameworks, reporting, and risk tracking, these skills alone are insufficient for effective project or program leadership.

A strong program manager doesn’t just react to issues—they anticipate obstacles before they become problems. They connect the dots between projects, identifying emerging risks, resource conflicts, and strategic misalignments early.

Moreover, success isn’t just about managing schedules; it’s about inspiring teams and securing their commitment to the program’s goals. Program managers must build trust and credibility with delivery teams, fostering a culture where challenges are surfaced early, and solutions are co-created.
Program managers operate at a level where they must make tough decisions—balancing competing priorities, managing stakeholder demands, and navigating trade-offs between scope, cost, and time. They must also influence stakeholders without direct authority, relying on persuasion, data-driven insights, and strategic alignment. A PMO approach may focus too heavily on process compliance, missing the bigger picture around strategic alignment, team dynamics, and proactive leadership. This can lead to projects that are technically well-managed on paper (great status reports, detailed RAID logs) but struggle to deliver meaningful business outcomes because leadership lacked the vision or authority to steer effectively.

Risk, Expectation, and Scope Management: Keys to Success

Successful project and program management hinges on three interconnected pillars: risk management, expectation management, and scope management. While they are often treated as separate disciplines, they are deeply intertwined. Poor expectation management can create scope issues, and unmanaged scope creep can escalate risks. In my experience, mastering these areas is what differentiates a project manager who simply tracks tasks from a leader who drives outcomes.

Risk Management: Proactive, Not Reactive

Risk management isn’t just about filling out RAID logs—it’s about fostering a proactive mindset throughout the project lifecycle:

• Early Identification: Spotting risks before they materialize into issues. This involves not just looking at technical risks but also considering stakeholder dynamics, resource constraints, and external dependencies.
• Continuous Monitoring: Risks evolve as projects progress. Regular risk reviews with the team help catch emerging threats early.
• Response Planning: Every identified risk should have a clear mitigation or contingency plan, prioritized based on its impact and likelihood.

Expectation Management: The Art of Alignment

Managing expectations involves a continuous mutual exchange with key stakeholders, ensuring their vision aligns with project realities. Misaligned expectations are often the root cause of dissatisfaction, even when projects technically meet their objectives. - Clear Communication:Setting realistic timelines, costs, and outcomes from the start.
- Stakeholder Engagement: Involving key stakeholders regularly to validate assumptions and course-correct when needed.
- Transparency: Being upfront about risks, challenges, and potential trade-offs.

Scope Management: Controlling Change Without Stifling Agility

Scope management is where many projects stumble, especially when Agile methodologies are misunderstood. A common pitfall is confusing agile flexibility with uncontrolled scope changes — also known as scope creep.

Scope creep refers to uncontrolled, unplanned changes that are introduced without proper evaluation, often driven by shifting stakeholder demands. This can lead to missed deadlines, budget overruns, and a diluted project focus. The root causes of scope creep typically include poorly defined requirements, weak change control processes, or stakeholder pressure to "just add this one thing."

On the other hand, Agile, when done right, is a disciplined, iterative approach that embraces change within a controlled framework. This methodology enables adaptability while maintaining a clear focus on business value. Mechanisms such as backlog prioritization, sprint planning, and clear acceptance criteria ensure that changes are evaluated thoughtfully and integrated effectively.

Smart Approaches to Project Delays

When a project faces delays, the instinctive reaction might be to add more resources and schedule additional meetings. However, this approach is often counterproductive. Adding people to a late project follows Brooks’ Law: “Adding manpower to a late software project makes it later.” New team members require onboarding, which diverts time from experienced contributors, increasing workload instead of reducing it. Moreover, not all tasks can be parallelized, meaning additional resources may have little impact on actual bottlenecks. Instead of accelerating progress, this increases coordination overhead, creating more dependencies and complexity.

Similarly, scheduling more meetings does not inherently lead to better outcomes. Meetings disrupt deep work, forcing key contributors to shift focus frequently. This constant context-switching reduces efficiency and leads to fatigue rather than meaningful progress. Excessive meetings can also delay decision-making, fostering a false sense of action instead of addressing root causes.

A more effective approach is to identify key risks and key contributors, then take deliberate action to protect their time and remove blockers. Many project delays arise not from a lack of effort but from unresolved risks. Addressing these early—whether through technical validation, process adjustments, or clearer decision-making—prevents last-minute surprises. Additionally, every project has a handful of key individuals who drive the majority of progress. If their time is fragmented by unnecessary meetings and distractions, the entire project suffers. Ensuring they have focused working time enables them to resolve critical challenges and maintain momentum to avoid further delays.

Conclusion: Reflections and Final Insights

Reflecting on over 20 years of project and program management experience, particularly within the dynamic financial services industry, I've realized that while methodologies, tools, and frameworks evolve, the core principles of effective project leadership remain constant. Successful projects are not just about ticking off milestones—they're about delivering real value, managing complexity with clarity, and leading people with purpose. Throughout my career, several recurring themes have stood out as critical to project and program success: balancing strong business acumen with technical expertise, understanding that Agile is disciplined and not a free-for-all, proactively managing risks and expectations, and relying on a strong core team of key individuals.

Ultimately, project and program management is about people as much as it is about plans. No matter how sophisticated your methodology or detailed your risk register, success comes down to how well you engage stakeholders, inspire and lead teams, and adapt to change. The best project managers navigate ambiguity with confidence, align diverse stakeholders around a common goal, and drive delivery without losing sight of the bigger picture. As you take on new projects, programs, or broader strategic roles, focus not just on what you’re delivering but also on how and why. That’s where the real value lies.

Author

Alberto Desiderio is deeply passionate about data analytics, particularly in the contexts of financial investment, sports, and geospatial data. He thrives on projects that blend these domains, uncovering insights that drive smarter financial decisions, optimise athletic performance, or reveal geographic trends.