There are three things we consistently advocate for when we start rolling out an LMS:
1. Define Your Measurement And Reporting Strategy In Advance
Make sure you have your measurement and reporting strategy defined in advance, and make sure you can deliver the analytics you need without investing too much time. If you don't have this thought through in advance, you'll not be able to engage your organisation properly, and this will negatively impact the rollout. If actually obtaining the information is time consuming or burdensome, you will come to regret the new system. Ideally, you'll have a few different groups that you are providing progress and engagement to. For example: students, instructors, or executives and each of them should have a tailored view of how things are progressing, which answers the questions they typically have. If the distribution of this data takes more than just a few minutes, you probably need to examine how to make this more efficient.
2. Evaluate Your Content
Many of our customers think they can quickly repurpose offline, or instructor-led content into quality, eLearning content without too much effort. While this is technically true, we've found that organisations that treat a new system rollout as an opportunity to evaluate their learning content tend to have better success overall. You've already spent plenty of time evaluating and implementing a new system, why not do the same for your content? Fresh or simply updated content will help students and other stakeholders engage and avoid the "oh, it's a new interface, but it's the same old stuff" eye-roll reaction!
3. Do Not Underestimate Administrative Work
Don't ignore the administrative work that will need to happen within, or around, your new LMS. Many LMS options are great for students, but ignore the plight of the administrators; things like reporting, workflow, communications, and student data. Keep an eye on how many spreadsheets you're using around the office and make sure this isn't growing out of control.
Our experience has been that when these three things are nailed, the rollout and implementation of a new system tends to be much more successful and enjoyable.
Good luck!