Usually I tend to split my work into 6 main work streams:

1. Collecting as-is data
1. Mapping IT assets: collecting existing IT assets to understand what IT manage and to get a hint how.
1. Information model: information entities and their relations. Helps to understand interaction between business units and level of integration from business perspective. Information model is also being used as an input to Information management.
2. Applications and products : applications (internal development), External products and relations. Will be used for different aspects as well as mapping to core-context model.
3. Technologies, Databases and servers : collect data about technical component and their relations. Used to understand what stand behind each application/product and to find out if resources are balanced (from usage point of view) and if new technologies (such as virtualization) are applicable.
4. Communication infrastructures : same as technologies, but focused on communication.
5. DRP : current design recovery plan.
6. Information security : what procedures and IT assets are in place to support information security.
7. Information from externals: what type of information the enterprise is getting from externals, in what format and how the data is being handled by the enterprise.
2. Information management: how information is manage, who own information, who use it, what is each information availability, etc'
3. Program of Work (POW) management : what is the current (if exists), how POW is being prepared, who is involved in this effort, what are the inputs for the process, is the POW address IT needs or just business needs, is it multiyear plan, is the plan enable prioritization and control, do we have milestones, deliverables and time tables, etc'
4. Budget management : who current budget is build (centralized or separated between business units), how the process is being done, who is involved, what are the inputs, is it multiyear budget, do we have breakdown of budget chapters, is the budget structure represent the major areas of expanses, is the structure enable management queries regarding budget behavior, Can we optimize budget without changing IT deliverables, etc'
5. IT equipment procurement management: are there any policies regarding procurement (Tender, predefined suppliers, how the process is done, where), what are the relations to other business units (when IT purchases), how IT physical assets are managed, any retire principles for IT equipment, etc' 
6. Project management : is there one and uniform process for IT project, is the project follow PRINCE2, PMBOK or any other project management methodology.
7. IT infrastructure management (ITIL) :  checking who much ITIL is implemented (even if its not ITIL explicitly) . Are we implementing any management of Incident, problem, configuration, release, change, capacity, financial, availability, continuity and service level.
8. Governance: mapping the IT against governance frameworks such as COBIT.
9. IT organizational structure and Human resources management. Existing structure and how it should support current tasks, one shop or shop per business unit, duplicated teams, location of teams  in hierarchy, are teams located in the same physical location, compensation per role, etc'.
10. Training / Education : Current training and education plan or opportunities available, are they per role, are they address known gap in worker knowledge, are they related to POW, etc'
11. IT management - supporting forums:  Are there any IT or enterprise wide forums that serve IT needs or IT is involved in, what is the perception of IT, is the CIO has CEO support, what is the CIO location in organization structure, etc'

2. Understand the business, future direction and who it impact IT
1. Business capabilities : what are the functions performed by the business to reach goals and objectives. Including new capabilities (or changes in capabilities) that support new business directions, or any business change. Used to see alignment between IT and business needs (current and future)
2. End-to-End business processes (Value chain): mapping main processes that generate value to the enterprise. Used to see interaction and integration between business units.

3. Understand new technology future IT directions and how they can Impact the business.
4. Create TO-BE architecture: Creating new architecture (blueprint or high level architecture) based on business directions, new technology options, key finding from IT assets mapping and IT as-is mapping.
5. Identify gaps between as-is and to-be: list all gaps in each element that we mapped in the "AS-IS"
6. Translate gaps into a roadmaps with dependencies and assignments : group gaps into projects, write one page of project high level analysis, assign resources to projects and  creating a road map (taking in account dependencies )

Then I translate the work streams data into a word document with 6 main chapters:

1. Executive summary. Actually I'm writing different executive summary for each audience using  relevant linkage to document paragraphs. I found out that although it's more work it proves to be more digestible.  This way I can use different lingo and sharp different aspects of the strategy for each audience without rewriting the entire document and with ability for adjustments on the other hand.
2. Description of the as-is + to-be. Describe the data as it was collected from different roles. This part should hold just facts. I'm using it to build my findings on top of agreed facts.
3. Analysis : TO-BE based on analysis of collected data.
4. Blue-prints and Principles : based on the analysis what need to be done, and which principles should be followed by the enterprise.
5. Roadmap : Translate blueprints and principles into defined projects with assignments and dependencies with other projects and resources.