Simplified project planning

Project planning is a critical element to the success of most technology shops. Outside of the “run and maintain” activities we undertake to keep our operations running, much of what we do is design and deliver projects of varying degrees of complexity. Projects can range from simple deployments of new tools to complex enterprise software implementations that last several months and cost millions of dollars.

Having the right tools and people to successfully deliver projects can be a crucial asset for technology leaders. After all, a great strategy is nothing without the organizational capacity to implement it through successful project execution.

Understanding approaches and tools

One of the challenges for leaders in planning and managing projects is the numerous tools and approaches available. Like many aspects of technology, relatively simple concepts are shrouded in confusing names like Agile and Kanban, and professionals can have opaque titles ranging from PMP to Scrum Master.

One of the best definitions of project management is that it is the knowledge, skills, people and tools used to deliver something of value. If you consider something of value to have been delivered in your professional or personal life, you've probably done things like:

• Clarify and refine what you were trying to accomplish
• Consider the time, money and skills you may need to achieve this goal
• Formally or informally write down the key steps needed to achieve this goal
• Create some tracking mechanism, like a simple note or to-do list, and use it to execute your goal
• Adjust your effort based on feedback from your tracking engine

This is the essence of effective project execution. Whether you're implementing a friend's birthday party or a complex technology launch that takes several years, the foundation is the same.

While this may seem overly simplistic, as leaders, our work often involves simplifying complex technologies and processes to find tools that help realize our vision. When evaluating project management approaches, test potential options against the simplified items above to determine how this approach will make your teams more effective.

Critical Path versus Agile

Traditionally, complex projects were planned with a focus on identifying and monitoring the critical path. This series of tasks must be completed before subsequent steps can be performed. Consider building a house. Until the foundation is complete, builders cannot install the structure, and until the structure is complete, the roof cannot be installed. In this case, completing the foundation is part of the critical path to building a home. On the other hand, installing light fixtures would not affect the ability to complete construction of the house and would not be on the critical path.

The critical path also identifies the minimum time required to complete the project, since these tasks must be completed before other dependent tasks can be completed.

Many of the techniques for this style of project management were developed through complex infrastructure programs, where you can define most of the steps needed to deliver the result and then build relationships between them. With these relationships defined, a level of effort can be assigned to each task, and the schedule will expand or contract as these times are adjusted.

This approach requires significant planning, as all tasks must be identified, linked and the level of effort estimated. This level of diligence is essential for projects where life and limb may be at risk or where it is imperative to reach a deadline. However, this level of detail creates significant overhead, and there is a risk that the project plan will quickly become outdated if the team does not diligently update each task as it is completed.

This additional effort has driven a significant change in the way projects are planned and executed, especially when the critical path is less important or the exact tasks and sequence are unknown. This has been particularly impactful in technology implementations and software development, where you are often developing something uniquely suited to the circumstances at hand, and all the steps and dependencies may not be known in advance.

There is also a compelling argument for a simplified version of project planning and execution when the task at hand does not require the overhead of a critical path-based approach.

Unfortunately for technology leaders, what is a simple and intuitive process has become overshadowed by jargon like Lean, Agile and Kanban. In many environments, obtuse terminology has made best practices less accessible, resulting in the terminology being used as a mask to ignore the formal discipline of project management.

Simplifying project planning

One of the best tools for simplifying project planning is the Kanban board. Loosely translated from Japanese, Kanban means “card you can see”, and this is the basis of the system. Originally developed for automobile production, Kanban is as simple as a whiteboard or a section of wall divided into three or more columns when applied to technology projects.

As you mature into a Kanban-style approach, you can start grouping tasks into sprints or other units, but if you're new to Kanban, start with the basic 3-column system.

Team members write tasks on post-its and stick them in the “Pending” column to get started. If you are using an Agile method, this column may be called “Backlog”, but in all cases, this is the repository for each identified activity that needs to be completed.

The next column reflects in-progress tasks, and when someone is actively working on a task, simply move the sticky note out of the Pending column and paste it into the in-progress column. If you want additional responsibility, that person can write their name on the note.

Once a task is completed, the person who “owns” the card moves it to the “Completed” column.

Most managers and project leaders find this so surprisingly simple that they dismiss this approach as almost childish. However, there are several distinct benefits to Kanban:

• Checking project status is as simple as looking at the board and instantly seeing card volume and distribution. If the Pending section continues to grow while Completed remains static, it is visually apparent that there is a potential problem.
• Physically adding cards to the board often sparks a discussion about other tasks that may be needed, creating a natural method for regularly updating, adding, and consolidating activities.
• Project management becomes a “team sport” rather than a specialized activity that requires unique knowledge and access to special (and often expensive) project management tools.
• The immediacy of the physical board provides a natural focal point during team status discussions. Each card can be reviewed, assigned, or updated, and it quickly becomes apparent if an individual is stuck, overwhelmed, or struggling to complete a card that doesn't seem to be moving forward.
• The visibility and simplicity of a Kanban board naturally creates a degree of competition. There is an immediate reward for moving a card to the “Completed” column.

For distributed teams, there are dozens of tools that duplicate Kanban boards, which can be used to collaborate with remote workers and partners. However, a physical board offers greater benefits if your team is in the same physical location.

A hybrid approach

For many technology leaders and professionals, the straightforward structure of a Kanban board may seem overly simplistic. Kanban is more focused on workload and progress than schedule, so it can be challenging to identify where a project is in terms of its overall timeline.

However, project management does not need to be a binary choice where someone is forced to choose between approaches. Managing complex projects using a critical path approach abstracted from the details of daily tasks is perfectly reasonable.

With this approach, a complex task like “Run Performance Tests” can be planned as a single element of the critical path. When the testing team starts, they could employ a Kanban board that divides “Run Performance Tests” into dozens of cards.

This allows the team responsible for executing a complex task the freedom to manage the approach and assignment of work within their team and domain of expertise. The Kanban board also allows the general project manager to quickly assess progress on the “Run Performance Tests” task. They can simply take a look at the team's Kanban board and assess a percentage of completion which is probably more accurate than the typical “What percentage of completion are you?” question thrown in an email or status meeting.

Sophisticated organizations can even automate some of these reports, using tools like Microsoft's PowerAutomate to update the overall project plan when tasks on a digital Kanban board are completed. These integrations can streamline reporting and management, allowing your teams to work in the tool that best suits their needs.

Leading your programs effectively

For technology leaders, project execution and progress can feel distant, obscured by complex tools and terminology. Too often, we are forced to “trust the system” and rely on red/green/yellow charts or reports that appear deeply rooted in data but are based on faulty “gut estimates” about the progress of critical tasks.

Like all tools, project management systems and professionals are only as good as the data they have collected and consolidated. Tools like Kanban boards can provide a more visual representation of progress. Still, it's also up to the leader to ask challenging questions and ensure they understand the full story of a project.

Your project managers should be able to answer questions like:

• What risks are you most concerned about?
• What areas outside of your control could impact the project, both positively and negatively?
• How confident are you in your plan estimates (dates, effort levels, completion percentages)?
• Which areas or teams are experiencing difficulties? What can you do to help them?
• What features are you missing?
• What has surprised you so far?

The content of the response is as important as understanding the data that guides the response. For example, if you ask about risks and just get a recap of a few items on a status chart rather than an assessment of why this risk is worth monitoring, this could indicate a problem.

Perhaps most important is your team's ability to articulate where they need your help. If your team and tools can provide concise, timely insights to understand when, how, and where to leverage your leadership skills, then you likely have the right team for the job.

Adjust project machine

As your teams mature, be sure to capture successes and failures and use that feedback to better execute future projects. When deadlines are missed or exceeded by a significant margin, take time to evaluate what contributed to that outcome. Were the original objectives too aggressive? Has the scope or understanding of the objective changed? Were the resources more or less capable than initially assumed?

Perform this exercise without recriminations or attempts to assign blame for any failures. If you, as a leader, make it clear that the goal is to create better performance in the future, rather than highlighting irregularities, you will have better engagement and participation from your teams.

This effort has an exponential return. As you improve your ability to execute projects successfully, you can take on more ambitious strategic goals with the confidence that your team, approach, and tools are up to the task.