Day 4 - Successful projects without all the pain

By: Kirstin Slevin (@andersonkirstin)
Edited By: Jessica Ulyate (@julyate)

Projects are an unavoidable part of our work in tech and we’ve all seen examples of the good and the bad. Good projects look like a cohesive effort towards a clear goal, a reasonable amount of planning, meeting the challenges that come up, and camaraderie all along the way. In contrast, poor projects look disjointed and disorganized. They become even more frustrating when given the dreaded ‘behind schedule’ designation, when there is confusion as to why the project even exists, when nobody is sure what they should be working on, and when it devolves into endless meetings. This is only a small set of common project pain points.

While almost all of us will be involved in or leading projects from time to time, most of us are not full time specialists in managing projects nor do we usually have the assistance of a dedicated project manager. So how then can you set a project up for success, while keeping as much time as possible for all the other things you do?

To begin to answer this, we should first start with defining what a “project” is. A project can be defined (and indeed is, by the Project Management Institute) as “a temporary endeavor undertaken to create a unique project service or result.” A project should have a reasonably clear start, middle, and end. Moving an application from a company data center to the public cloud is an example of a project. Establishing and practicing a security incident response team is also project. On-call support is not a project - it’s an on-going activity that is not expected to end. However, establishing a revised on-call structure and response processes to meet holiday business needs could be considered a project. Now that we know what a project looks like, let’s talk about important practices.

• Start with a charter; A project charter is a simple but critical foundation for a good project. It should answer questions like: Why are we doing this? Who is involved and who are the stakeholders? How will we know when we’re done? How we will we know if we were successful? As the old saying goes, “An ounce of prevention is worth a pound of cure.” A solid charter can do wonders to guide the project and help keep everyone on the same page. But do note that starting with a charter assumes a decent upstream process that prioritized this project in the first place; if you’re not sure you have that, first work to make sure prioritization is clear and in order.
• Breakdown the work; the charter should give a good idea of what you want to accomplish at a high level and next you want to begin to break that down into smaller pieces of work. Keep this simple to start - an hour of focused attention at a whiteboard can get you far. You’ll continue to refine more as you go, and things will inevitably change, but laying out the broad strokes of how to get towards the goal and more detailed steps for the shorter term work, is a must.
• Set up some basic work tracking; Now that you’ve broken down the work, you want to make that usable. This means perhaps moving the plan you whiteboarded into a shared document, task tracking tool like Jira, or a project plan. Stick with something that is familiar to you and your team. It’s important that everyone can see the plan, collaborate, and keep it updated; beyond that, advanced features are often less important and an easy way to get distracted.
• Provide regular updates; Once your project is in motion, it’s important to distill a snapshot of the project regularly and share with stakeholders. Even if no one asks for these updates, even if you’re not sure anyone is looking at them, do this anyway. Providing regular updates ensures that you take a step back from the day to day view of the project and look more widely at how it’s progressing. A simple format should include: key milestone or estimated completion date, likelihood of hitting the date, top priorities for the next one or two weeks, and notable call outs.
• Celebrate wins; With the project progressing, there should then be some solid achievements along the way. These can be simple moments, like a ‘Hello, world!’ from an application being moved to the public cloud. Take the opportunity to celebrate and bring attention to these achievements. The goal here is to help keep the enthusiasm high. Don’t underestimate the motivation and satisfaction that can be achieved by doing this.
• Model behaviors, always; No matter what your role on the project is, you have an opportunity to make the project more successful, and certainly a more enjoyable experience, by setting a positive example. Get the team together to break down some more of the work, proactively share an update on your work, or call attention to a win from the team. Often, the difference between a tedious project and a gratifying one is in the way the team acts towards the work and towards each other.
• Learn something for next time; Ongoing retrospectives are a great practice that gives the team a regular opportunity to look back, reflect, and improve. Good retrospectives though require strong facilitation, time, and follow up which may not always be possible. At the very least, you should look back in some way at the end of the project with the team and generate ideas for how a similar project could go better in the future.

We are all likely to be involved in or managing projects from time to time and we want to do as effectively as possible. A few key practices, used throughout the life of the project, can go far towards setting the project up for success.