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Lessons Learned from Switching Project Management Systems

March 22, 2018 Macy Fontaine

mojo-blog-Lessons Learned from Switching Project Management Softwares

As the new Project Manager for Mojo Media Labs, I knew when I joined the team in December that one of the biggest pain points the team was having was a need for a new project management software. They had been working in Trello which is great for the agile and scrum methodologies that we use, but was lacking in a few departments that were hurting the team more than it was helping. Right off the bat, I started doing some research into new systems that could help improve our productivity and  better manage timelines and deliverables.

This can be a daunting task for any organization so I’ve broken down the steps that we went through to help us transition into a new system and provided a few lessons learned along the way. You can do it!

How do I know if I need a new project management software?

While this may seem like the easiest step in the list, it can actually be deceptively difficult to determine. It can be extremely frustrating to work in a tool that doesn’t meet your needs or expectations, but immediately scrapping it and starting over isn’t always the answer. My first tip is that new isn’t always better. I recommend that you to take a step back, watch and read some tutorials on the software you’re currently using, and determine if you need to adjust how you’re using the tool to make it more effective for the team.

I’ve worked with an agency before that was utilizing a project management tool that had all the capabilities to meet their needs, but was being used ineffectively and inappropriately. By simply making sure we used the tool the way it was intended to be used, we were able to track projects, workload, and timelines through the existing tool without having to make the switch to something new.

If you’ve done all you can to make the tool work for you but it just isn’t cutting it, then it’s time to move. Start by listing out the capabilities you need from your tool and determining if your current tool can accomplish this. Are you sacrificing a mandatory capability for other capabilities that are nonessential? For us, we needed more robust task management with a portal for our clients and great visibility for our teams. Trello was great at keeping us agile and providing visibility into sprint progress, but it just was not what we needed when it came to task management and client visibility. This isn’t surprising because according to a study done by GetApp, “one in five (19 percent of) respondents cites task management as the most important feature” of their project management system. We knew it was time find something new that would meet these needs and I began the search for our new hub.

Okay, I need a new project management system. How do I go about choosing one?

I would say that the best place to start is with the list of capabilities you made when you were evaluating your current project management tool. Take that one step further and determine which kind of collaboration tool your team would benefit most from. Forbes did a great job of outlining the different types of collaboration suites available so I definitely recommend you look over those options to get an idea of what will work best for your team and the types of projects you work on. For us, we were primarily using a kanban chart in Trello with makeshift task lists on each of the cards. We decided that we needed to switch to a tool that provided both Gantt chart and task lists as the primary view due to the nature of the projects that we work on (I was secretly thrilled because I LOVE checklists).

Project Management System

Next, make a short list of tools that you want to trial. There are tons of ways to compile this list and great articles out there that can be a jumping-off point. Be sure to also use word of mouth and take recommendations on which tools to try. Take a look at the cost of the tool and weigh the benefits it will bring the team. Niki Gallo Hammond, a senior project manager with technology firm Jackson River recommends you "Factor in the time you'll save, errors avoided, and opportunities previously missed."

Once you’ve made this list it’s time to demo. Almost all tools will provide you with a free trial period to see if you like the tool. We took a dummy project that was representative of a typical task that we perform for our clients and I did a test run of all of the tools on my list. It will become pretty clear which ones suit your needs and which ones don’t once you have that project in the tool. Here’s another lesson learned: If it isn’t immediately better than what you have, scrap it and look elsewhere. There’s no use in trying to make something work if just doesn’t suit your needs. I spent too much time trying to configure other tools to fit my needs. When I found Teamwork, it clicked and was the obvious winner.

Great! I’ve chosen a new project management system. Now what?

This is easily the most daunting part of the process in my opinion. My biggest tip is to outline and project plan your implementation plan. Create a list of what needs to be done from importing task templates to training the team and delegate where possible. This is a big undertaking and can become overwhelming if you feel like you’re steering the ship alone.

Another thing to keep in mind is timing. We work in month long sprints so it was natural for us to update and transition for the new month. A couple things to consider are clients in the onboarding phase, where your projects are in the process, and your team’s workload. The last thing you want to do is transition everything and actually decrease productivity due to training, getting used to the tool, and potential loss of information housed in your current tool.

Do a little research to see if you can get in touch with a product representative who can help you manage the transition. Most of the time they can help with the physical process of setting up the team in your new tool and can give you great tips on how to streamline the transfer of information. The ability to upload tasks, projects, and client either directly from your existing tool or from an excel file will be a lifesaver. Don’t do it manually unless you absolutely have to.

The last part of implementation is training and adjusting once you get the team involved. Set aside time to train the team on how to use the tool and provide demos for their most common uses and views. Once the team is in the tool, be open to suggestions and questions regarding the software while keeping a running list of items to adjust based on their feedback. This is a work in progress and you need your team to know that their questions and concerns are being heard. Make adjustments when they make sense and provide a lot of mentoring and training to help them get the hang of it.

While switching to a new project management software can seem like an overwhelming process, you can learn from our experience to develop your own plan to tackle the transition. Take it step by step, remember the lessons we learned from our experience, and you’ll soon be reaping the benefits of using a tool that suits your needs.


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Macy Fontaine

Macy Fontaine

Macy Fontaine is a graduate of Texas A&M, class of 2015, from Houston, Texas. She holds a BA in marketing and her experience working with agencies focuses on building processes and operational efficiencies for both digital and traditional marketing efforts. She began her career focusing on digital marketing strategy development here in Dallas, and branched out into account and project management. Macy has worked with clients ranging from national restaurant chains and retailers to local businesses on projects encompassing web design and development, paid media, in-store print advertising, direct mail, email, SEO, and paid media.

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