Project Planning and Delivery

The planning and delivery of projects is the most critical work we do in software engineering. Generally, all other work we do is in support of our ability to deliver working software. Some aspects of this process are under the control of engineering teams and some are not, but regardless, we have an interest in making the process go as smoothly as possible.

Planning and delivery practices may include specific project and product management methodologies, scheduling activities, team rituals, communication conventions, the creation of various software artifacts, and tools such as version control systems (VCSs). Engineering managers have a central role in negotiating these practices and helping them to work in the best interest of the engineering team and company.

This chapter will focus on project planning and delivery from an engineering management perspective. We will learn how engineering managers can approach planning and delivery across a variety...

Why do we need project planning?

If our goal as engineering managers is to deliver working software, not plans, we may question why we should bother with plans at all. Fundamentally, the purpose of planning is to reduce risk during project delivery. Without plans, we face significant risks of misalignment, miscommunication, and rework. Plans help us to avoid situations where team members have differing understandings of goals, constraints, and expectations. They help us to avoid wasted effort from misunderstanding what to deliver in what sequence.

Plans allow us to think through objectives beforehand in the hope of being prepared for delivery. Plans are useful when they preempt conflict, direct efforts in harmony, and align expectations. Plans are not useful when they waste valuable build time or provide a false sense of security, for example, by missing unknown unknowns.

Given the understanding that plans have useful features but are not foolproof, we can judge that they are...

Setting the stage for planning and delivery

In Chapter 4, we learned how engineering managers can assess what their work environment does and does not provide, fill in the gaps left by that, and set the stage for good architecture. Project planning and delivery are similar in that engineering managers can begin in the same way.

Depending on your work context, project planning may begin before, in parallel to, or after technical design work. The advantage to having technical design prior to project planning is that you can benefit from the discovery and information gathering already conducted. If planning occurs prior to technical discovery, only high-level planning can be done due to the lack of detailed systems knowledge.

To set the stage for planning and delivery, we will begin by assessing the environment and your role in that environment, as we did in the last chapter. From there, we will look at project goal orientation. Let’s get started.

The environment

Engineering...

Project planning

Project planning encompasses a wide range of activities in preparation for a project. Depending on your workplace customs and the project size, this may include scoping, budgeting, estimation, prioritization, assigning roles and responsibilities, creating timelines and roadmaps, setting milestones, and many other supporting tasks.

Regardless of what your responsibilities may be during the coming project, planning is the engineering manager’s opportunity to set expectations with their project stakeholders, contributors, and themselves. Resolving expectations early on during planning helps to avoid misunderstandings and unpleasant surprises later when the project work is underway. Inward expectations to set for yourself and your engineers are prioritization and roadmapping. Outward expectations to set for the project contributors and stakeholders are estimations and risks. In this section, we will introduce these four elements of the planning process in sequential...

Project delivery

In project build phases, an engineering manager’s focus is on maximizing the healthy productivity of their engineering team. In other words, you want to help the team move quickly while taking action to prevent burnout. In this section, we will learn these two aspects of project delivery: techniques for moving quickly and techniques for avoiding burnout. These goals can share the same solutions or complement each other, so they are interleaved through the following delivery topics: project kick-off, good user stories, and removing friction.

Project kick-off

The project kick-off is how you initiate your project. It is often a meeting or a series of activities to announce and begin work on a new project. For engineering managers, project kick-off is an opportunity to set up the project for success by aligning the team and creating some excitement about the goals.

Whether or not you are tasked with organizing the kick-off activities yourself, your aim...

Project problems and solutions

Every project has its share of speedbumps or unexpected events. Here we will introduce two of the most common project problems along with different methods of resolving them.

You need to do more with less

Sometimes you need to find a way for a project to do more with less. For example, you might reach the end of estimations, and when you present them to your leadership team, they say Great, you think you can do it in 6 months—we need you to do it in 3.

One approach to this is to use the project management triangle. This method involves balancing three constraints: scope, time, and budget. Sometimes this is stated as You can have it good, you can have it fast, you can have it cheap; pick two. So, for example, if you need it fast, you would aim to negotiate a reduced scope or an increased budget.

In practice, you can often come up with additional levers and compromises to do more with less. When reducing scope is not an option, consider...

Summary

In this chapter, we learned how engineering managers can lead their teams through project planning and delivery by doing the following:

• Begin setting the stage for the project by understanding your environment and what you must provide to accommodate and support your team in that environment
• Finish setting the stage by evaluating and capturing opportunities to advance your engineering goals during the project
• Produce effort estimations with awareness of the amount of flexibility permitted in your plan, then break down work into small units and capture any assumptions you are making that impact the effort
• Prioritize the features of your project with stakeholders so you understand their relative importance and know what may be dropped if needed
• Address potential risks in the project by identifying them, organizing them into a matrix, prioritizing them, communicating them, and remediating them
• Put together a roadmap or timeline that captures sequential...

Further reading

Project methodologies and estimation

• Project management in software development (https//hackernoon.com/project-management-in-software-development-key-questions-answered)
• Project management methodologies cheatsheet (https//afroant.com/2021/08/18/project-management-methodologies-a-cheat-sheet/)
• Estimation checklist (https//github.com/togakangaroo/estimation-checklist)

Prioritization

• In Chapter 14, see the section on prioritization for an introduction to different methods of prioritization and how to choose a method
• How to prioritize using these 9 mental models (https://www.ejorgenson.com/blog/how-to-prioritize-using-these-9-mental-models)

Risk assessment

• See Chapter 11 for a further introduction to managing risk
• How to run a pre-mortem (https://www.antmurphy.me/blog/2023/4/13/pre-mortems)
• Klein, Gary. “Performing a project premortem.” IEEE Engineering Management Review 36.2 (2008) (103-104. https...