Develop Skills to meet Expectations, How to

Knowing the required outcomes will often be the first stage of any skill development process.
Without knowing the end point then any skill development journey will be subjective, so this does need to be well defined from the start.
Using SMART goals will help to clarify required these expectations. Effective communication of the goals, which will be a two-way process of listening and explaining, is needed if they are to be actioned appropriately and without any misunderstanding from everyone concerned.
To support the process, make sure adequate (which also means clear and concise) documentation is provided, including interim targets where applicable, and make sure it is fully accessible to those concerned - planning is an important aspect of this process.
Allow for a feedback mechanism to be open and transparent so that any barriers or issues which prevent or reduce the smoothness of the skills development journey can be more readily addressed and overcome.
Issues do arise over uncertainty of actions or outcomes, lack of confidence at certain stages, and how successful someone is in undertaking a skill, so constructive feedback along with guidance and support will go a long way to helping in achieving expectations.
Within all of this try and make the development of skills process as enjoyable and engaging as possible.