Top 5 Insights from Managing 100 Projects

In a quarter century of project-based work, you eventually learn (through many mistakes) that there are certain areas which consistently elevate projects. Sometimes that means going from Failure to Success, and other times from Good to Great! You learn that a flawless plan is only perfect until reality throws a curveball—because who knew that "everything going according to plan" was more of a wish than a guarantee? As Mike Tyson would say "Everyone has a plan until they get hit in the face!"

So, let's talk about a few key insights that can make all the difference. From embracing uncertainty, to harnessing the power of emotional intelligence (because AI / robots haven't taken over just yet), focusing on value over just ticking boxes, turning data into engaging stories, and daring to take calculated risks—these are five lessons that have turned project mishaps into successes.

1. The Illusion of Control: Embracing Uncertainty in Project Planning

In project management, there's a comforting allure in meticulously crafted plans, detailed schedules, and comprehensive risk assessments. We often believe that by planning every minutia, we can control the outcomes. However, the reality is that projects are inherently uncertain, influenced by countless variables—market fluctuations, stakeholder changes, technological advancements—that are beyond our control.

By clinging tightly to rigid plans, we may inadvertently set ourselves up for frustration and setbacks when the unpredictable occurs. Instead, embracing uncertainty means acknowledging that change is not just possible but probable.

KEY TO IMPROVEMENT:

• Recognize that flexibility, rather than rigidity, is the true strength in project planning.

When we shift our mindset to view the project plan as a living document—one that evolves with new information and circumstances—we empower ourselves to adapt proactively. This doesn't mean abandoning planning; it means planning for adaptability. Incorporating iterative reviews, contingency buffers, and decision points allows us to respond gracefully to the unexpected.

TIPS:

• Implement Rolling-Wave Planning: Focus on detailed planning for immediate tasks while keeping future plans at a higher level, refining them as the project progresses.
• Cultivate an Agile Mindset: Encourage a culture where change is anticipated and seen as an opportunity rather than a threat.
• Enhance Communication Channels: Regular check-ins with stakeholders ensure that emerging changes are identified early and addressed promptly.

2. The Human Element: Prioritizing Emotional Intelligence Over Technical Expertise

Technical skills and methodologies are foundational in project management, but it's the human element that often determines success or failure. Emotional Intelligence (EI) — the ability to understand and manage one's own emotions, as well as recognize and influence the emotions of others—is a critical, yet sometimes overlooked, competency.

High EI enables project managers to navigate complex interpersonal dynamics, foster strong team relationships, and handle conflicts effectively. It also contributes to better stakeholder management, as understanding motivations and concerns leads to more effective communication and collaboration.

KEY TO IMPROVEMENT:

Realizing that projects are executed by people, not just processes, and investing in relationships yields tangible results.

When we prioritize EI, we're better equipped to inspire and motivate our teams. Empathy becomes a tool for understanding team members' perspectives, leading to higher engagement and productivity. Recognizing signs of burnout, frustration, or disengagement early allows for timely interventions that keep the project on track.

TIPS:

• Develop Active Listening Skills: Truly hear what team members and stakeholders are saying, both verbally and non-verbally.
• Practice Empathy: Put yourself in others' shoes to understand their viewpoints and challenges.
• Provide Constructive Feedback: Offer feedback that is specific, actionable, and delivered with respect, fostering a growth-oriented environment.

3. Value Over Deliverables: Shifting Focus to Outcomes Rather Than Outputs

It's easy to become consumed with ticking off tasks, meeting deadlines, and producing deliverables. However, without aligning these activities with the underlying value they are supposed to provide, projects can become exercises in bureaucracy rather than vehicles for meaningful change.

Focusing on outcomes means keeping sight of the "why" behind the "what." It's about understanding the impact the project is intended to have and ensuring that every effort contributes to that end goal.

KEY TO IMPROVEMENT:

Understanding that delivering on scope doesn't necessarily equate to delivering value.

By realigning our focus, we ensure that we're not just completing tasks but actually achieving the desired business objectives. This might mean adjusting features to better meet user needs, even if it deviates from the original plan. It's about being outcome-driven rather than output-driven.

TIPS:

• Define Clear Objectives: Establish measurable goals that articulate the value expected from the project.
• Engage Stakeholders Continuously: Maintain an open dialogue to ensure the project remains aligned with stakeholder needs.
• Be Willing to Pivot: If a deliverable no longer serves the intended outcome due to changes in context, don't hesitate to adjust or eliminate it.

4. Communication as Storytelling: Engaging Stakeholders Through Narrative

Traditional communication methods—status reports, data charts, technical jargon—often fail to engage stakeholders on a meaningful level. Storytelling, on the other hand, is a powerful tool that can convey complex ideas in relatable terms, making the objectives and progress of a project more compelling.

By framing project updates within a narrative, we can highlight the journey, celebrate milestones, and contextualize challenges, making the information more digestible and memorable.

KEY TO IMPROVEMENT:

Recognizing that facts inform, but stories inspire action and commitment.

When stakeholders understand the narrative arc of a project—the challenges overcome, the collective efforts, the anticipated triumphs—they are more likely to feel connected and invested. This emotional engagement can translate into greater support, advocacy, and resource allocation.

TIPS:

• Craft a Project Vision Statement: Articulate the story of what the project aims to achieve and why it matters.
• Use Real-World Examples: Share anecdotes or case studies that illustrate the project's potential impact.
• Visual Storytelling: Leverage visuals—infographics, videos, prototypes—to bring the narrative to life.

5. The Risk-Taking Mindset: Encouraging Innovation Through Calculated Risks

Risk is often perceived negatively in project management—a hazard to be minimized. However, without taking risks, innovation stalls, and opportunities are missed. The key is distinguishing between reckless risks and calculated ones.

Encouraging a risk-taking mindset involves creating an environment where team members feel safe to propose bold ideas, experiment, and even fail, as long as valuable lessons are learned.

KEY TO IMPROVEMENT:

Embracing calculated risks is not a liability but a catalyst for innovation and growth.

By shifting the narrative around risk from fear to opportunity, we unlock the creative potential of our teams. This approach can lead to breakthroughs that give the project a competitive edge or solve longstanding problems in novel ways.

TIPS:

• Establish a Risk Management Framework: Identify, assess, and prioritize risks, formulating response strategies that balance potential benefits and drawbacks.
• Promote a Learning Culture: Celebrate lessons learned from failed experiments as much as successes.
• Allocate Resources for Innovation: Dedicate time and budget for exploratory initiatives that could enhance the project.

Final Reflections:

These insights are interrelated, each reinforces the others to some degree. Embracing uncertainty requires strong emotional intelligence to navigate the human aspects of change. Focusing on value over deliverables naturally leads to storytelling as a means to communicate that value. Encouraging calculated risks necessitates a culture that values outcomes and trusts its people.

At the end of the day, Effective project management is less about rigid adherence to plans and more about dynamic leadership that embraces change, values people and their work, plus fosters innovation.

By internalizing these principles, we elevate our role from task managers to strategic leaders who guide our teams and stakeholders toward shared success in an ever-evolving landscape.

Please let me know your thoughts in the comments. I can also provide a cheat sheet to the key points and tips on request.

#ProgramManagement #ProjectManagement #LessonsLearned #ITLeadership #BusinessTips

David Apollon serves as the Managing Director at 9Nation Inc., a consulting firm established over a decade ago to assist organizations with specialized IT and strategic projects, including ERP, CRM, PMO, and cloud-based implementations. With two decades of experience, David has successfully led more than 100 corporate programs, projects, and PMO initiatives. For further information or to connect, he can be reached through LinkedIn at https://www.dhirubhai.net/in/davidapollon/