Preparing for 365

Brett, I'd be happy to have a chat by phone about this and our experience. I'm in Sydney and have a very long background (back to 1982) with Federal government. We are implementing O365 now, having had on-prem SharePoint (2010 > 2013) since 2012 and working with O365/SPO since August 2016. We've had Yammer since 2012 as well, we did nothing to roll it out, it just grew by itself (with some light supervision and maintenance so it didn't get out of control).

From a collaboration point of view, the ATO is likely to be similar to us - lots of users on email and using network file shares (plus personal drives). This is a long legacy that's hard to break.

I'll assume you will want to move users off personal drives to ODfB, and off network file shares to SPO.

Depending on your current SP on-prem architecture and if it's been customised, you may need to take a different approach with SPO.

From a collaboration point of view, you may need to consider what users will naturally want to use, versus what they will find strange and counter-intuitive; Teams may fall into the latter category unless they have an internal chat system already. One approach might be to focus first on 'one for one' equivalent services (email to email, SP to SPO), and then start to extend the options as required.

Send me a message here if you'd like to chat by phone.

Thinking aloud here are a few comments! I think it comes down to what does the organization want to achieve, what are its goals and how can Office 365 help. Organization culture and preparedness, adjusting to Office 365 and the toolset it brings is also important. Be aware that Government tenants (if that’s what you will be on) won’t necessarily have the latest features.

Yammer might be a great testbed, since you're already involved with it, with the concepts of collaboration and what the Yammer folks call the "outer loop" for driving teamwork. Check out the recent Build your outer loop: What's next in Yammer blog post for details.

You may find the biggest barriers are more to do with not the technology, more how adaptable staff are and the resources you put behind it.  Training is very important, champions etc, look at the Adoption Guide for lots of practical tips and guidance for putting a framework around your Office 365 adoption.  If you are looking for inspiration, this collection may be of interest as well - Microsoft Office 365 Productivity eBooks Collection.

I'd suggest setting up an Office 365 dev tenant, if you haven't got one, you can grab a 5 user one year one for free.  If you are still getting up to speed, try out new features, since you use SharePoint on-premise, if you haven’t already, try out modern teams sites and communication sites, as well Office 365 Groups, Microsoft Teams etc.

Also, see some of the items in the "Microsoft Ignite 2017: Productivity Management" learning pathway in the new Microsoft Tech Academy. 

Hope that helps a bit.