Welcome to the Whirlwind: Tips for Managing Multiple Projects at Once

Posted by Lauren Foiles on Jul 13, 2017 9:06:26 AM

When I first started working at Beyond20 almost three years ago, I often found myself finished with my daily activities and ready to go home right around 5 PM.I shared an office with the doyenne (my new favorite word) of IT Service Management (ITSM), AKA the co-founder and President of the company, whose list of daily activities and obligations made my stupid list cower in comparison.

I’d often feel guilty about leaving the office at a normal, human hour while my bionic, super-human boss remained there, working for hours to come. I’ll never forget her advice to me, which I now pass on to every person who joins the B20 team: “The whirlwind will come for you soon. Enjoy this time while it’s here, because you’ll get swept up soon enough.”

Fast-forward a few years to PMP certification, a handful of ITIL Intermediate certifications, and a not-insignificant number of train wrecks (there’s always a learning curve, right?), and you’ll find me sitting here as a Project Manager at Beyond20. Currently, I’m managing not one, not two or three, but upwards of ten software implementation projects at any given time. We move at a clip here at Beyond20. It’s invigorating and rewarding to say the least, but you can’t pull it off without some varsity level organization and drive. So, while my nostalgia for the days of giving my undivided attention to a couple customers or projects at a time is real, I’m grateful to have picked up some life-changing organizational skills as I’ve learned to navigate that infamous whirlwind. Here are a few things I’ve found the most impactful:

1. Be Organized

I realize this seems like the most cliché Step One that could ever exist and I’m slightly disappointed in myself for writing it, but it’s so true! When you have 10+ projects with multiple points of contact for each, plus a technical team carrying out the work on each one, it becomes impossible to successfully make mental notes and actually remember to come back to them. Instead, get a small moleskin notebook, sit down on Monday, and write out each of the next ten working days on its own separate page. That way, when a customer says, “Hey Lauren, we don’t quite have that deliverable ready for you yet. Check back in when I get back from my vacation on July 6,” you can simply flip to July 7 or 8 in your notebook and quickly write a reminder to ping so-and-so on that deliverable. Then close that email window and get it out of your brain so you can go back to being jealous about that person’s vacation.

If you find yourself with a recurring task for different customers or projects (which tend to pile up until you have time to knock them all out), create a separate list for those items somewhere visible. For example, when our sales team has received all signed project documents, they then officially hand off that contract/project to me. I must then spin up the SharePoint site and all relevant folders for each, add all project documents received thus far to the SharePoint site, then add them to our time keeping system. It’s the same thing every time, and while these tasks are by no means difficult, the challenge lies in making time to get them done. I get this official hand-off from sales anywhere from 5-10 times a week, and rarely do I have time to stop whatever I’m doing at that exact moment to start/complete this process. So, what did I do? I ordered a tabletop whiteboard easel on Amazon for $7 and drew some ‘lines’ (admittedly crooked) onto a table to keep track of each of these new projects and their recurring tasks. It sits right in front of my face so at any given time I can see how many of these contracts I have open tasks for and can easily add new ones to the list without interrupting the flow of whatever I am currently working on.

2. Use Visual Aides

If you can’t tell by now, I’m a very tactile person; I function better when I can physically see, write, or interact with things. While online tools and applications are extremely helpful (I swear I work at an IT company), nothing beats good old fashion post-it notes and wall calendars. Managing a bunch of resources and projects and trying to forecast workload for the next few months? Get a few large whiteboards and list out one- or two-week increments in each column and then add a row for each resource you’re planning for. You can then cut up post-it notes and map out who is working on what projects and when - easily creating your own version of Project Server.

If arts and crafts were never your thing, there’s one other benefit to employing a visual table like this. Online tools are great for sharing information when bosses and colleagues are out on the road, but a visual board in the office gives your workmates the ability to walk by and see for themselves which projects “Jeff” will be working on August 7 - 18. You may just end up with one less email in your inbox.

3. Don't Reinvent The Wheel

This is a staple of every ITIL/Scrum class, and it definitely applies to managing multiple projects at once. You’ll find that the majority of your projects follow the same lifecycle or workflow each and every time. Prioritize the creation of a template set, which contains all of the documents you’ll utilize throughout the project lifecycle. That way, when it’s time for a project kick-off or status meeting, you won’t need to go scrambling to create a new document. Keep this set of documents somewhere convenient and always update them with enhancements or modifications as you need them.

This shouldn’t exclusively apply to document/deliverable templates. This rule can work for managing a large portion of your email correspondence. Do you always send out a very similar set of instructions/documents to a customer after the project kick-off meeting? Great! Then spend your time crafting an extremely clear and concise email, then save that email in an Outlook folder. Next time you have a kick-off, go find that email template, add any necessary extras or specifics, and send it off.

4. Set Realistic Expectations

Setting realistic expectations with both colleagues and customers is a skill that takes some time to get comfortable with. As service providers, we’re always inclined to jump when a customer says so even if it’s not to their benefit. A customer will respect you more if you set a deadline a few days after their ideal timeline, but deliver upon that deadline as agreed. When managing multiple projects at once, take advantage of realistic expectations. If a customer is transparent with you regarding their availability and lets you know they can’t read your deliverable for 1.5 weeks, flip in that moleskin notebook to 1.5 weeks from now, write a reminder to check in with them, and then merrily skip on to your next task. This removes the unnecessary burden of having to check in or send unnecessary reminders so you can focus on tasks with more imminent deadlines.