Just a few thoughts for your consideration, Mary:
-- Identify critical path tasks and corresponding performance required in the new PM system. If your new PM system offers lots of functionality, identify the essential components for your initial roll out and training. Introduce short-cuts and "bells and whistles" later.
-- Identify business processes / critical path tasks performed by humans that need to be changed given new PM system functionality (or identify PM system functionality that needs to be modified given business processes). Some steps may be eliminated or added. Develop job aids for new performance.
-- Identify prior to rollout the most proficient computer / software users who are competent with on-site business processes / tasks. These should be people who "get" and "enjoy" using PM software systems. Use this group to be your "PM Software Experts" and your feedback loop.
-- Train your "PM Software Experts" first. After training, ask them to identify what they think is the best sequence for introducing, teaching the new software, based on functional areas that are to be rolled out. Ask them to identify potential problems that on-site end users may have with the new system and what might be done to prevent or mitigate.
-- Make "PM Software Experts" available after vendor training to clarify, provide hands on and to observe and document where end users are experiencing difficulty. Ask them to provide observations on end user difficulties, confusion, etc. as well as software technical issues.
-- Plan for multiple OTJ training for skill acquisition by on-site end users, especially if the new system is significantly different. Most effective learning takes place OTJ from colleagues because end-users are more comfortable asking questions, and most importantly, because training takes place in the context of job performance, not in the context of introducing a new PM system.
-- Test for performance in the new PM system.
(1) Run reports and compare to previous performance. For example, new PM system may have different step for moving a prospect from lead to applicant, and that prospect may "disappear" if new process is not followed.
(2) Check end user assumptions. End users may be susceptible to "I thought it would automatically do this" with a newer, more powerful PM system. For example, if new PM software generates emails and populates certain fields, but not others, confirm end user understands what they need to enter.
(3) Test, test, test. For example, for leasing module, submit a test lead and see how it is processed, what emails you receive, etc. Test one week after training.
-- For training materials / job aids, less is more. Job aids are preferable to manuals for most end users, and most will only want and use what they need for their specific performance in the new software.
-- Develop a clear process for addressing and documenting problems with the new PM software (including issues that affect business processes): Who is called, how is the issue tracked, is the issue limited or portfolio-wide. Clearly communicate the process during roll-out to your PMSE team, regional and property managers, as well as to your PM software vendor.
-- 30 days after roll-out, plan informal, casual observation of on-site end-user performance to identify issues and gauge acceptance. For example, ask leasing agent to demonstrate entering a lead, posting rent.
-- Identify the benefits to end users and communicate during roll-out: What's in it for them: why and how with the new PM system make their jobs easier.