Plan on Planning: Experience is Your Playbook

Project planning is an underappreciated art form, sometimes viewed as an unnecessary oversight that undermines the team’s autonomy. However, when done thoughtfully, planning lays the foundation for lasting success on both the individual and team levels. Good planning doesn’t just benefit the project—it provides clarity, security, and reduces stress for the entire team. Experience plays a key role in developing an effective plan. Whether you're managing people or tools, having a solid plan can make the difference between project challenges and overall success. Experience can be drawn from a variety of situations that may not be directly related to the project at hand.

What 'Planning' Really Means

The purpose of planning is to provide the tools for clarity. For a project leader, who has the starting point, ending point, goals, and contingencies in mind, the journey may seem clear. However, for team members, the road can often be hazy, conceptualized only in day-to-day tasks, which can make long-lasting projects seem daunting and endless. Creating a plan that outlines goals, milestones, timelines, necessary tools, and testing processes helps the team visualize the path ahead and ensures a sense of confidence that, when everyone does their part, the team will move forward. By setting clear expectations from day one, you ensure everyone stays informed and motivated through tangible progress.

Just as a project has a linear timeline from start to finish, it also includes another dimension: perpendicular lines of communication, affectionately known as 'dependencies' or support channels. Anticipating and documenting these dependencies is a valuable step to ensuring different aspects and milestones of the project connect and flow smoothly. By documenting these connections, knowing who to contact, understanding turnaround times, and addressing bottlenecks, a well-documented plan can help the team avoid unnecessary delays and maintain momentum by diverting resources when necessary.

Internal Tools and Processes

Another critical component of planning is finding or developing the right internal tools. Are there systems in place to track progress? Are there tools for feedback, collaboration, and issue resolution? The documented plan might benefit from including the development and testing of these tools to ensure smooth execution during the project. Additionally, establishing a consistent process for testing will help produce consistent results at all stages of the project. Defining how the team approves work, especially when tasks are completed across teams with members who may not be in constant contact, is an important element to address. Outlining how blocked issues will be managed is also necessary for keeping progress on track when issues inevitably arise.

Using Experience as the Guiding Light

Experience is the ultimate guide in project planning. Whether you’ve led projects in finance, healthcare, construction, or technology, the ability to foresee challenges and opportunities grows with every project you lead or actively participate in. Successful project plans come from leaders who have experience and know how to avoid potential pitfalls, or have experience tackling obstacles with creative solutions and minimal resources. All industries have their own unique aspects but share common elements of managing people, tools, and dependencies. With experience, you can anticipate the needs of your team and project, enabling you to plan ahead for obstacles and capitalize on opportunities.

While your project may have a defined timeline, it's also important to ensure consistent communication throughout the project’s duration. Just as the project moves forward, so too should recognition of progress. Regularly celebrating small wins—whether it's hitting a milestone, completing a sprint, or wrapping up a productive week— keeps morale high and reinforces momentum. People thrive on balance, and recognizing these moments allows the team to decompress while staying motivated. If you don’t provide the team with an opportunity to stop and catch their breath, they may seek self-relief in less constructive ways. —if you've ever toiled away on a seemingly endless project, you know what I mean.

Things to Consider While Developing a Plan:

• • What’s the starting point? What is the current state of the project?
• • What’s the end goal? Define what success looks like.
• • Who will be involved? What capacity can they participate in, and will they need onboarding?
• • What tools are needed? Determine whether the required tools exist or need to be developed for the project.
• • Is any additional training required? Does everyone understand their scope and responsibilities, and how their efforts will serve the team?
• • Are there major milestones? Outline periodic celebrations, announcements, and check-in points.
• • Are the steps well-defined? Can each step be broken down into more specific tasks?
• • What is the structure of the work? Is there a defined working methodology (e.g., Agile, Waterfall) to ensure cohesive contributions? How will team members submit work?
• • What is the margin of variability in work? When multiple team members are working in different styles, how much flexibility or margin of error do you want to allow to ensure consistent results?
• • What will be the project format? Does the team understand the format of deliverables, reporting style, and expectations for each phase?
• • Who is the point of contact? Ensure that when issues arise, there’s a clear chain of communication at each stage.
• • Who needs to be in the loop? Is there an overarching team, department, or person that needs to be informed of the undertaking or progress?
• • Are the project boundaries defined? Are there integration points that need to be clarified with other teams or departments?

Study and learning are important, but true growth happens through practical application. Present ideas, propose initiatives, and observe how timelines unfold and where pitfalls emerge. The more you lead projects or get involved, the better you’ll become at planning effectively, and anticipating various challenges. Experience is the guiding light that helps you navigate the project planning process and equips you with the skills to lead teams to success.