
I've taken these lessons from my experience in higher education implementing systems like Workday®, Slate®, and Symplicity® as well as new initiatives like a large scale internship program for a career center.
But as all projects come with similar challenges, I think they apply more broadly.

Let me know what you think or if you have any you would add as a "top lesson learned".
#1: Short-Term Timelines
You need the week by week detail of a project plan only 3-4 months in advance. If you try to build the whole thing out on a project lasting 6 months or more, you'll waste time making updates to all those details versus waiting to fill them in until closer to that date..
#2: Plan High-Level
You need a clear high level project plan. If you only have one with lots of detail and the high level plan is buried in it, it doesn't work.
#3: Ensure Understanding
Your project team should clearly understand the project plan. I can't tell you how many times I've seen a misunderstanding of the project plan cause major issues on a project. You need the project team members to explain the project plan back to you to make sure you have understanding. Don't take a "Yes I understand it" as an answer. It's too risky you're not on the same page.
#4: Don't Depend on the Vendor
As the customer of a vendor, you need your own project plan. You can account for the vendor's plan, but their plan is more narrow. The internal plan needs to have details of things like: testing, training, user experience design, documentation, operations planning, communications, stabilization phases, and uptakes of the technology based on the operation cycles.
#5: Buffers
Build in buffers in the project plan for things to go wrong. This seems obvious but too often I see it missing in a plan.
#6: Take Breaks
Have agreed times for project shut-downs during long projects. Use this time to catch up of dropped tasks and, most importantly, schedule in required breaks where everything stops. These kinds of actions support the goal of not burning out project team members.
#7: Plan, Plan, Plan
The plan stage is critical on projects. If the project involves an implementation partner, you have to be ready when they show up. It's like being neatly packed with your boxes labeled and ready when the movers arrive. Packing (and the inevitable decluttering and downsizing) that happens before the move determines a lot of how smoothly the transition will go.
#8: Prioritize End Users
Build in user experience design into the project plan and include it early. The order must be People, Process, and then Technology.
#9: User Acceptance Testing
Build in user acceptance testing into the project plan and include it early (same reason as #8).
#10: Get in the Details
A project manager must be somewhat in the weeds. That might not be a popular opinion, but that's what I've seen work. The PM needs to understand the technology or initiative by having some amount of hands-on experience. They need to trust but verify if the work is actually complete.
Project Management Support
Being the project manager can be an isolating position. Be sure to seek out support inside or outside your organization to dissect pesky problems or brainstorm new solutions as needed.
In some situations, bringing in an outside perspective is most valuable way to proceed in your project. For those who ask, we provide free discovery calls on a limited basis. Consider reaching out to mine the expertise of those on our team on how to best proceed or approach your project.
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