I've not tried implementing GTD in an environment beyond 2 people (ie, my wife and I), so am not speaking from experience. That said, a few thoughts come to mind:
- Keep in mind that GTD is intended to encapture whole-of-life, not just one's work context or work-related areas of focus. My suspicion is that if you try and implement company-to-person, it would be very hard to implement effectively. I think much better to aim to have each person at the company over time adopt GTD themselves
- I'd suggest that you try and take the same approach that is typically discussed - ie, start simple, and let it build naturally from there
- I think the most effective way to get widespread adoption would be to aim for a viral approach. That is - staff who aren't on GTD will begin to see others using it, hear the GTD terms being used, and want to get on board themselves
- On the back of the above - I'd suggest you work closely with the chairman, the others she is working closely with, and a few more people who you think will jump on board - and get a strong team of users who will be advocates of the GTD system. This would primarily be you spending time with that core group to train them, help them not make mistakes that you presumably made as you were first implementing, etc
- Start an informal weekly or biweekly discussion group where GTD adoptees come and share their wins and their struggles with GTD
- Get permission for anyone who wants a copy of the book to get one from you/HR, etc for free. The reason for this - if someone isn't enthusiastic about implementing GTD in their life, there is no way they will succeed
- Once your advocates are going well on their personal implementation, move onto more formal training offerings - this would be first-come-first-served, again to create an air of desirability and scarcity about adopting GTD, which will encourage more people to want to do it
I'd suggest you don't have a 'hard and fast' approach to what tools people use - some will like paper, some electronic. The main thing is for you to be an expert on the pros and cons of the various options. Individual style and personality will be primary influencers for what is best.
What an awesome opportunity you have! Good luck with it
Do, or do not. There is no try.