Project planning is a critical element to the success of most tech shops. Outside the “run and maintain” activities that we perform to keep our operations churning along, much of what we do is designing and delivering projects of varying degrees of complexity. Projects might range from simple deployments of new tools to complex multi-month enterprise software rollouts that cost millions of dollars.
Having the right tools and people to deliver projects successfully can be a crucial asset to tech leaders. After all, a great strategy is nothing without the organizational capacity to implement it through successful project execution.
Understanding the Approaches and Tools
One of the challenges for leaders in project planning and management is the myriad tools and approaches available. Like too many aspects of technology, relatively simple concepts are shrouded in confusing names like Agile and Kanban, and practitioners might have opaque titles ranging from PMP to Scrum Master.
One of the better definitions of project management is that it’s the knowledge, skills, people, and tools used to deliver something of value. If you consider anything of value that’s been delivered in your professional or personal life, you likely did things like:
- Clarify and refine what you were trying to accomplish
- Consider the time, money, and skills you might need to achieve that objective
- Formally or informally write down the key steps required to get to that goal
- Create some tracking mechanism, like a simple note or to-do list, and use that to execute your objective
- Adjust your effort based on the feedback from your tracking mechanism
This is the essence of effectively executing projects. Whether you’re managing to implement a friend’s birthday party or a complex multi-year technology rollout, the basis is the same.
While this might seem overly simplistic, as leaders, our job often involves simplifying complex technologies and processes to find tools that help realize our vision. When assessing project management approaches, test potential options against the simplified bullets above to determine how that approach will make your teams more effective.
Critical Path versus Agile
Traditionally, complex projects were planned with a focus on identifying and tracking the critical path. This series of tasks must be completed before subsequent steps can be executed. Consider building a house. Until the foundation is completed, builders can’t install the framing, and until the framing is completed, the roof can’t be installed. In this case, completing the foundation is part of the critical path for building a house. Conversely, installing the light fixtures would not affect the ability to finish building the house and would not be on the critical path.
The critical path also identifies the minimum amount of 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 project management style were developed through complex infrastructure programs, where one can ultimately define most of the steps required to deliver the outcome and then build relationships between them. With these relationships defined, a level of effort can be assigned to each task, and the timeline will expand or contract as these times are adjusted.
This approach requires significant planning since all tasks must be identified, linked, and the level of effort estimated. This level of diligence is critical for projects where life and limb might be at stake, or hitting a date is imperative. However, this level of detail creates significant overhead, and there’s a risk that the project plan quickly becomes outdated if a team isn’t diligently updating each task as it’s completed.
This additional effort has driven a significant change in how projects are planned and executed, particularly when the critical path is less important or the exact tasks and sequencing are unknowable. 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 might not be known beforehand.
There’s also a compelling case for a streamlined version of project planning and execution when the task at hand doesn’t require the overhead of a critical path-based approach.
Unfortunately for tech leaders, what’s a simple and intuitive process has become obfuscated with jargon like Lean, Agile, and Kanban. In too many environments, obtuse terminology has made good practices less accessible, resulting in using the terminology as a mask for ignoring formal project management discipline.
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 that’s the system’s foundation. Originally developed for automobile production, Kanban is as simple as a whiteboard or section of wall divided into three or more columns when applied to technology projects.
As you mature in a Kanban-style approach, you might start grouping tasks into sprints or other units, but if you’re new to Kanban, begin with the base 3-column system.
Team members write tasks on sticky notes and paste them into a “Pending” column to get started. If you’re using an Agile method, this column might be called “Backlog,” but in all cases, this is the repository for every identified activity that needs to be completed.
The next column reflects in-progress tasks, and once someone is actively working on a task, they simply move the sticky note out of the Pending column and stick it in the in-progress column. If you’d like additional accountability, that individual can write their name on the note.
Once a task is completed, the person that “owns” the card moves it to the “Complete” column.
Most project managers and leaders find this so shockingly 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 the volume and distribution of cards. If the Pending section continues to grow while Complete remains static, it’s visually apparent that there’s a potential problem.
- Physically adding cards to the board often triggers a discussion about other tasks that might be needed, creating a natural method for regularly updating, adding, and consolidating activities.
- Project management becomes a “team sport” versus a specialist activity that requires unique knowledge and access to special (and often costly) 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, overburdened, or struggling to complete a card that doesn’t seem to be advancing.
- The visibility and simplicity of a Kanban board naturally creates a degree of competition. There’s an immediate reward for moving a card to the “Complete” 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 provides the most benefit if your team is in the same physical location.
A Hybrid Approach
For many tech leaders and practitioners, the uncomplicated structure of a Kanban board might seem overly simplistic. Kanban is more focused on workload and progress than the timeline, so it can be challenging to identify where a project sits in terms of its overall schedule.
However, project management need not be a binary choice where one is forced to choose between approaches. Managing complex projects using a critical path approach abstracted from the details of day-to-day tasks is perfectly reasonable.
With this approach, a complex task like “Execute performance testing” might be planned as a single element of the critical path. When the testing team begins, they could employ a Kanban board that breaks “Execute performance testing” 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 overall project manager to quickly assess progress on the “Execute performance testing” task. They can merely glance at the team’s Kanban board and assess a completion percentage that’s likely more accurate than the typical “What percentage complete are you?” question thrown in an email or status meeting.
Sophisticated organizations can even automate some of this reporting, 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 best suited for their needs.
Leading Your Programs Effectively
For tech leaders, the execution and progress of a project can feel distant, obscured by complex tools and terminology. Too often, we’re forced to “trust the system” and rely on red/green/yellow charts or reporting that seems deeply rooted in data but is based on flawed “gut estimates” of how far critical tasks have progressed.
Like all tools, project management systems, and professionals are only as good as the data they’ve gathered and consolidated. Tools like Kanban boards can provide a more visual representation of progress. Still, it’s also incumbent on the leader to ask challenging questions and ensure they’re getting the whole story of a project.
Your project managers should be able to answer questions like:
- What risks are you most concerned about?
- What areas outside your control could impact the project, both positively and negatively?
- How confident are you in your plan’s estimates (dates, effort levels, completion percentages)?
- Which areas or teams are struggling? What can you do to help them along?
- What resources are you missing?
- What has surprised you thus far?
The content of the answer is just as important as understanding the data that drives the answer. For example, if you ask about risks and merely get a recap of some bullets off a status chart rather than an assessment of why that risk is worth monitoring, that may indicate a problem.
Perhaps most important is the ability of your team to articulate where they need your help. If your team and tools can provide you with concise, pointed insights to understand when, how, and where to leverage your leadership abilities, then you likely have the right team for the job.
Tune the Project Machine
As your teams mature, ensure that you capture successes and failures and use that feedback to execute future projects better. When deadlines are missed, or beaten by a significant margin, take the time to assess what contributed to that outcome. Were the original goals too aggressive? Did the scope or understanding of the objective change? Were resources more or less capable than initially assumed?
Perform this exercise without recrimination or attempts to assign blame for any failures. If you, as a leader, make it clear that the goal is to create higher performance in the future versus highlighting wrongdoing, you’ll have better engagement and participation from your teams.
This effort has an exponential payback. As you refine 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.
