As Roundpeg has grown, we’ve had our share of growing pains. The latest was adapting our project management system to accommodate the volume and size of the assignments we were taking on.

When I started Roundpeg, I created a spreadsheet with a simple numbering system to track active and inactive projects. Both digital and paper records were identified the same way allowing us to find original work files, project notes and contracts even 11 years later. The system worked fairly well until recently as the complexity of our new projects required multiple  members to be involved different phases of a project. It was hard to get a complete picture of a project and things began to fall through the cracks.

It was time to grow up and get a real project management system. But which tool? There are so many project management tools out there and they range price from free to hundreds of dollars a month. It wasn’t just the pricing that was confusing, it was all the  features and the changes we would need to make in our day-to-day routines. So how did we pick the right one?

1. Asked around. I reached out to owners of digital agencies locally and around the US through LinkedIn groups. Messages posted in discussion groups resulted in a list of tools with helpful implementation tips and the pros and cons of each.
2. Talked about where our system was failing. We identified areas of weakness, particularly requests between team members, which were often sent via G-chat with no other record. We looked for a  tool which would allow us to capture communication between team members.
3. Looked for tools which would fit our system. It’s hard to get people, me included, to change their behavior even slightly. Many of the tools we looked at would have required adding multiple new steps to our process. Although they had great features, I knew we would struggle with too many changes at once.
4. Found an intuitive interface. While I knew it would take time to become completely comfortable with the new tool, it was important that the basic functions, like setting up a new project, be fairly easy so we could get started right away.
5. Kept one eye toward the future. We needed this tool because we hit a critical point in our development. We expect to continue to grow, and we needed a tool which could grow with us.
6. Set a reasonable budget level. Yes, there are free tools out there, but as you grow up as a business, you need to be prepared to pay for the tools you use to run your business. I was willing to spend up to $100/month, but fortunately found something we really liked for less.
7. Kicked the tires. We actually tested several tools at the same time.  It was a little tedious and time consuming, but the side by side comparisons, made it easier for us to see which one was best for us.

After careful consideration, we selected Do. Created by the team at Salesforce, it’s affordable, easy to use, and has lots of features which have streamlined our process.  Once we selected the software, we needed to make it a part of life at the ‘Peg

1. Took time to train everyone. This seems obvious, but when a tool is intuitive, it is easy to think you can skip this step. The training sessions gave us a time to find weaknesses in the tool and talk about how we would handle some of our special cases.
2. Made it part of the routine. We start every week with a project meeting. Now we record notes and assignments during the meeting so things don’t fall through the cracks.
3. Evaluated existing systems. Not everything you do is necessary. Implementing a project management system is a great time to let go of routines and task which no longer add value.

The hardest part of this process is using the systems long enough for it to feel natural. It is still easier to walk down the hall and ask Allison to look at something rather than put it into Do, but in the long run, I know the discipline will give us a foundation on which to grow.

This transition was much easier because Josh Brammer shared his project management expertise. He helped me evaluate different tools and identify functions which would streamline our processes in ways I had never imagined.