Let's consider a software program that isn't very intuitive or easy to understand. First, show your employees that you understand their concerns. Even if you're running a daylong or extended training session, make sure you encourage open communication and let them know individual coaching could be available should they need it. Provide them with some visibility into the analysis and rationale that led to how you chose this particular software. This can help put their concerns into context and lead to better teamwork in adopting it, especially if they see it's for the greater good.
Next, it's important to know your audience to decide which types of training to use. For a particularly tricky piece of software, start by leading an initial session. This way you can make sure you address why it's important to introduce this new platform, showing what it can do and—most importantly—how it will benefit users in their day-to-day work. To help in this effort, you may want to encourage an HR rep or department manager to ask a vendor to organize a custom event for your staff. Vendors will often offer a demonstration for free, especially if it's in a webinar format.
Then, use videos to your advantage. If your employees have differing schedules, a lot of them will be more receptive to training if they can fit it in when convenient. On-demand videos also free up time for one-on-one coaching and reviewing the analytics from tracking software. Also, you won't have to redo an entire presentation for any employees who were out of the office for the initial presentation.
Consider custom training, which can take into account your employees' collective base level of knowledge and move forward from there, so they don't feel as though their time is wasted with the basics. No matter the method, be upfront about the plan's objectives, content, activities and assessment. If the employees are going to be assessed on how much training they've completed or how well they apply it moving forward, they have a right to know. Even if there's some grumbling at the beginning, a surprise would likely be worse.
Calculating ROI for a training method gives you a chance to see how well it worked and how you can adjust it for the next time. But how do you measure it?
Look to training-tracking analytics to help you with this task, as you can see who has completed which parts of the training. This can give you some perspective if you keep track of mistakes following the official deployment; if someone errs more than once and he or she hasn't completed the training, you can weigh these mistakes against those of others who finished.
On that note, tracking these mistakes can help you measure ROI to see how effective your methods were to the group. To prevent mistakes, however, give your employees a chance to prove their knowledge prior to deployment. Rather than typical quizzes, which can seem a bit immature, provide them with a trial period so they can make some mistakes and feel their way around without your business suffering consequences. You might even be able to provide a "sandbox" sort of play environment in which they can do so.