What factors do you consider when putting together a dept training plan?

I designed and developed training for MS for about 10 years. The most successful approach I found was to

1. Perform a business needs analysis - many businesses have required compentencies or skills for people in different job functions at different stages in their careers. Even smaller companies likely have a set of expectations, and expected level of proficiencies in job roles, or product/technology 'expertise.' Also, interview people already doing the job, and ask what they needed to know six months ago to be more effective/performant in their job. Also consider the future direction of the business (e.g. what skills/knowledge is required to grow the business).
2. Perform a skills gap analysis - Assess the current level of skills, compentencies, etc. What skills and how proficient are people with those skills today. What do they know about x. (For example, we were primarily targeting CS grads for tester roles, and we from interviews with new hires, college boards, etc that testing techniques and approaches are barely covered in most programs. We also learned that while most new testers knew the general concept of techniques such as equivalent partitioning of data, few were competent enough to decompose complex data sets into equivalent sub-sets for a given task.) (Another example might be internal tool training, or processes, etc.)
3. Design targeted training sessions - that addresses the skills/knowledge gap.

For teaching new concepts I would structure each lesson as follows

• 5-10 minute analogy introducing concept (ideally with something they can relate to)
• 5-10 minute demonstration of practice/skill
• 20 - 30 minute practical exercise
• 15 - 20 minute discussion of lessons learned and new ideas (This is the part where student move from 'application' to 'analysis' in Bloom's taxonomy.)

Few additional thoughts

• Don't spend a lot of time in the classroom on theory, provide additional material to explain theory
• Keep lessons short, no more than 1 hour spent on a specific topic/concept
• Separate 'soft-skills' from more 'technical' skills
• Make it hands-ons, many people learn a new skill by doing (anyone can read how to rebuild a carborator, but it is quite different to actually do it successfully)
• Encourage collaboration/teamwork on finding solutions to problems
• Make training fun!