AI Experiments in Project Management

My current exploration with AI is to find ways to assist our teams in using the new Jira/Confluence software rolling out in our City. Right now, I have been experimenting with using it to build projects.

Our city has not had formal project management software in the past. Projects have been managed independently using whatever methods our staff found available or useful. Much of it operates off institutional knowledge, emails, network folders full of files, OneNote, etc. It is exceptionally difficult to track, measure, and even collaborate on projects in this state. It makes sense to institute a unified project management system for our teams at every level. However, the implementation of software, including a new way of working, has its challenges.

It can feel daunting to be told to scope out your entire project in a new system, no matter how skilled you are at leading the project. Many of our staff are in this situation right now, staring at a blank screen, not knowing where to begin. It's not because they don't understand their project or the tasks that need to be done. It's mostly because it's a new tool, and the page staring back at me is blank. All the ideas are in my head, but how do you quickly get them entered into a Jira project that your manager will understand and approve?

This is a job for ChatGPT, Claude, Bard, Perplexity (Llama seems too cute to perform serious work), or maybe Bing (though I'm not as enthralled with Bing in this capacity). In my experiments, I mainly use ChatGPT because I have some plugins I like and a persona built out that is working for me.

First, I start with a discussion. Since ChatGPT already knows me, the work I do, and the tools I use through my custom profile settings, I explain my project using language I might use to explain it to my coworkers. I give it any relevant information, including links to related resources or data (I use the web pilot plugin), timelines, and specific significant milestones I want to document. This conversational task is much easier than "enter your project in Jira."

Before submitting my prompt, I ask ChatGPT to outline this project's epics, tasks, and subtasks, also providing summary descriptions for each. Sometimes I ask for suggested timelines for each issue as well if I am wanting a little guidance in that area.

If I am feeling confident about the information I have provided, I click submit and watch my entire Jira project outline appear before my eyes within moments. My screen is no longer blank. I have the start of a project framework I can enter into Jira.

If I am not feeling as confident about the information I provided, I include "Ask me for any additional information you need" at the end, and we continue our conversation with me answering the questions before getting my Jira project outline. This is helpful when tasked with a project that is new or unfamiliar to me. It can also help if you aren't sure you articulated your project well.

Once I have my initial outline, I review it carefully to see what changes must be made. This is where human expertise is needed. All chatGPT has done for me is get me started by providing an outline. Now I can start picking it apart. I sometimes ask ChatGPT to add missing items or change some of the items it outlined. I continue conversing until I feel I have a solid framework for my project. The lovely part is ChatGPT doesn't get tired or need a break, and most importantly, ChatGPT doesn't judge you. I can keep asking it stupid questions all day long (or night which is more the case for me), and it is always pleasant, polite, and helpful even if I am hangry, tired, or frustrated.

So there you have it, and you might be thrilled with that amazing assist. A project outline in just a few moments when it might have taken hours and hours to develop on your own without help. It also doesn't have typos and understands yours if you do. But this isn't the stopping point. ChatGPT is willing to stick it out with you all the way to the end. You never need to feel alone in project management again!

The next step, after getting over the joy of having a project outline, is the frustration of copying and pasting all those project items into Jira.

No worries. ChatGPT to the rescue again.

Simply ask ChatGPT to create a CSV file you can use to import your project and within moments, you have what you need to use the external import feature in Jira to create your project. Using the CSV and import tool, you map your fields to the fields in your project, click submit, and boom, your project is magically in Jira.

I'm oversimplifying this last piece a bit since you will likely need to have an administrator help you import the file if you don't have those permissions. You may run into a few hiccups where the fields you need to map are not available but I've done this successfully with a test project, and the idea has legs that are willing to run.

And once your project is in Jira, you keep that conversation going with ChatGPT on the regular. You can ask it to help you build your confluence pages or make recommendations for a new task that needs to be added or with suggested timelines. Ask it anything. It's now your partner in project management.

I'm hoping to post some examples soon but I'm getting pressure from humans right now to back away from the computer to play some golf. I feel good about it because ChatGPT is taking away the fear of "how will ever get all this work done if I go play golf on my day off" and replacing it with "don't worry, it's not going to be as hard or take as much time as I thought because I have my own AI assistant helping me."

This also makes me realize how executives of the past found all that time to golf. They all had assistants at the ready doing the busy work for them. ??