Starting Point: Microsoft Word
Although Microsoft Word is a great tool for everyone to do daily, generic word processing, it is not a good tool for the creation and maintenance of corporate information (like technical content, business processes and marketing content). Information in Word is not ready for the future - it can't be easily converted to other formats like HTML or eBooks.
On the other hand, XML is a format for the future. DITA XML is an OASIS approved standard schema for technical documentation and the DITA Open Toolkit (DITA-OT) has transformations that can take your content to almost any deliverable.
Creating and maintaining content in the DITA XML format is often a culture shift in companies/departments. It can be huge to move away from a document-centric approach to an information-centric, search-based approach (think Google-based searching for specific pieces of information). But the new approach helps information developers (writers, SMEs, etc.) be better positioned to create searchable 'document' deliverables, for now (PDF/HTML) and in the future (HTML especially mobile-optimized sites, e-books for tablets, etc.)
Find the words that articulate why Word is not the best solution for delivering the company's information. Identify the pain points, whether that's the creation time or the lack of control of content when it is copied from one document to another.
TIP: Use terms or visions that resonate with the company - it could be cost savings, the ability to reach new markets (via the Web) or the reduction of errors.
Word is one tool, DITA is another tool. There are many other tools, some that work with both Word content and DITA benefits. You need to find out what tool will help you the most in your situation. What are your limitations and how do you think you can overcome them? Do the research.
You can spend nothing on tools (the DITA-OT is 'free') but beware that you'll invest heavily in time and in learning. You'll benefit from understanding in detail what the tools can do but you could be hampered by the time it takes to learn and code as well as by the number of errors and corrections you'll make.
You can hire a consultant (big or little; local, from other areas of Canada or international) to help you get there. The benefits of this approach are that you learn from someone with experience and your project can avoid some pitfalls that come with inexperience. However, issues around this approach are the fund requirements. Documentation teams tend to be underfunded, making the request for money a huge hurdle. In these cases, use metrics to prove the return on company investment and do your research on both the tools and the consultants.
Define a small project that has specific issues and goals. For example, the current approach does not reuse content (content is written fresh all the time) and you can only output a PDF file from your Word source. The goal for the pilot is to realize at least 10% reuse of content and to output a PDF and an HTML file from the XML source.
It's a good idea to measure the current state so you have something concrete to compare with your results. Counting words created vs. words delivered is a good way to get a metric that doesn't change.
During your pilot, communicate with your stakeholders. They want to hear about your progress, your issues and your results. Don't hide away while you do this or people might become suspicious of your work. Keep them involved and get them excited.
Record your Lessons Learned - the mistakes and the good points. You want others to learn from your pilot project and not repeat past errors. Use these as training points for others in the company.
Follow the company's process for documenting your change in direction. Get the approvals you need, including buy-in from the IT department.
Decide how much conversion of legacy content you'll need to do, based on the company's requirements and the usage of that content. Describe how writers and content contributors will get trained and how the maintenance effort should work.
Install the needed components, whether that's just an XML editor or a full blown Component Content Management System.
Convert content, if that's your approach. Write in the new way. Train those who need training. Learn and share with others.
The company's content can be managed - effectively and efficiently. Bring on the future!