Agile Milestones for Creative Endeavors (Part 1)

At Cardsmith, we spend a lot of time thinking about project management. I’m not just referring to making project management faster, more responsive, and more rewarding. We also reflect on what it means to “manage” a project and, beyond that, how we define and categorize projects themselves. One type of endeavor we’ve given a lot of thought to is the big, ambitious, uncertain kind: launching a startup, designing an invention, starting a band. These sorts of projects are, by their nature, creative and nonlinear. They’re volatile and unpredictable, coming together sporadically, prone to wild deviations and changes of direction. When a person embarks on these projects, they have a general sense of where they want to end up, but they’re not sure exactly how they’ll get to the destination. Often, they trust the process to take them there. We call these projects “creative endeavors.”  
Creative Projects
Creative endeavors necessitate an agile approach, one that allows a person to iterate, learn, and revise along the way. Yet, as is the case for traditional projects, goals and milestones are essential. Project milestones are extremely valuable for creative endeavors, keeping a creator, innovator, or startup founder motivated and focused on results. In these situations, however, traditional project management approaches to milestones may be less than useful—but that doesn’t mean you shouldn’t use them. Here’s why: What Is a Milestone? The word “milestone” used to refer to a real object: a stone along a path that was used to measure the distance, in miles, to a particular destination. The purpose of these stones was to tell a traveler, simply, how much farther they had to go. milestone 1 mile to holt In project management terms, milestones mark progress towards a goal. It pays to map them out. Milestones help you see the path—how far you’ve come, how far you have to go—even if the exact route is uncertain. That’s why they’re so important for creative projects. During creative projects, we need to remind ourselves of the value of completion. It’s all too easy to get caught up on the juicy, creative process, doing what we love—creating—that sometimes we lose sight of the fact that we need to finish the project and reach our destination. One of the fundamental reasons creative projects are so uncertain is because they’re frequently so long. When a project is lengthy, recognizing accomplishments along the way keeps us motivated. Milestones show us that, if nothing else, we’re making progress. Milestones behind us also help us solidify our learning. Many things can (and do) happen along the journey that can slow us down or make us rethink the trip: “is it really worth it?” And yet, as we travel, we learn. Perhaps we got a flat tire at mile 16, causing a significant delay. So we learn, from our past mistakes, to always carry a spare. Perhaps most important, milestones ahead can motivate us to keep an idea in motion, to push that creative project forward. Milestones can challenge us to accomplish things that we didn’t think we could accomplish. And when we see those accomplishments in rearview, we grow more inspired. Reasons Project Managers Use Milestones Here are seven major purposes milestones serve in traditional project management, along with a few comments on how each may or may not apply to creative projects and other creative or otherwise unfamiliar projects: 1. Milestones help you understand the structure of a project. When you come up with significant achievements or progress steps along the way to project completion, you have to project into the future, forcing you to think about what is actually necessary to do along the way. For creative projects, you may need to replan and reset your milestones from time to time as you learn, but these movable milestones still illuminate,—and may in fact give you an even better sense—of the framework you’re creating. 2. Milestones monitor status: “Are we on track, ahead, or behind?” In truly unfamiliar creative projects, like a startup or a biotech research project, you probably won’t be able to plan out a timeline with an exact scope or result. At some point, you will need to either change the scope or change the timeline. I’ll revisit this topic in more detail in my next article—stay tuned. 3. Milestones motivate. Without them in sight, you might not take the extra effort sometimes needed to achieve them. When you’re tracking an idea in motion, milestones challenge your assumptions: let them push you, especially in creative pursuits! 4. Milestones help you plan ahead for resource availability. Most people are working on multiple projects at any given time. Milestones, when time-phased and reviewed for estimated end-dates, can forecast when and how projects get handed off. For instance, you want to make sure your contract graphic designer is available when you need her, so it can be super useful to have a milestone to monitor for when all inputs (content, ideas, branding) are ready for her to begin. 5. Milestones are often used to communicate high-level project plans to customers, investors, managers, and anyone doesn’t need to (or want to) know every detailed task. This is also true for creative endeavors, but be aware of the double-edged sword of deadlines: people who see the milestones could consider the milestones more solid than they may actually be. In agile projects, they might be more like mile-pumice-stones. They are a little lighter. 6. Milestones identify accomplishments. It’s important to recognize each accomplishment not only for the sake of morale, but also to understand what’s been achieved and thus what the team is capable of achieving in the future. For example: “We figured out how to design our first iOS app, so we now have more confidence when it comes to planning the next one.” Or: “We ran a successful marketing campaign that yielded 100 new users, so now we know what that takes and have a measure to improve upon.” 7. Whether made or missed, milestones can be used by stakeholders outside of the project team to judge that team’s past performance… or lack thereof. In teams founded on trust and respect, we should hold ourselves accountable to do what we say, and at the same time we need to consider missed milestones opportunities to improve rather than sticks to hit each other with. Keep your eyes on our blog for the follow-up to this article, wherein I’ll take you through a recent project—I mean creative endeavor—at Cardsmith that made us rethink how we used milestones.
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