Disclaimer: I am currently between jobs, so i have to stay very generalistic on this.
1. Which types of content should be ready for digital learning?
I do believe that digital learning is great for a lot of topics. I am sure, though, that some types of content should be offline or blended, especially when it comes to leadership and communication topics.
2. Who is supposed to learn digitally?
Are we talking all kind of hip GenY types, or do we include well educated and digital-savy employees, where a slow start with "how to use digital tools" is in order? Can all employees access all content, or is the content supposed to be limited to the area of expertise (can the bookkeeping lady study html?) Does everybody have access to the necessary tools? How do we get the learners on board?
3. How exclusive/company specific are which types of content, and who can provide them?
Save money and effort with some run-of-the-mill classes, eg on standard software, where possible. Get the right people on board early on to start with some great, specific trainings which meet the users need in company-specific knowledge early on. If possible, enable social learning / sharing (eg of interesting articles, blogposts, podcasts among the learners) - and make sure to decide if everybody is allowed to share or only certain roles (HR, Management,...)
4. What is the timeframe?
How long does it need to implement the first steps, which content comes first / last? How often does the content have to be reevaluated? Does it make sense to come up with "degrees", courses with a specific order and time frame? How can content be provided "just in time", and found easily when needed? How can we differentiate between content that needs to be delivered "just in time" and long-term and in-depth learning?
5. All about the dough
What budget is needed for the perfect solution, what would cheaper B and C options look like? What cost components need to be observed (LMS, standard courses, company-specific courses, updates, necessary hardware). Is learning on company time, or private time (=does the company pay the employees to study, or just cover course costs?) Can the costs be spread over time, eg starting with limited content and then adding to it, if the budget does not enable the full solution at first step?