I recently had the opportunity to visit with OPDA technology alliance, a group of private businesses that provide sounding boards for each other. Imagine having to face a migration to Office 365 or the ever growing challenge of email security on your own. OPDA helps members face those challenges with support.
Because OPDA members don't compete with each other, they can speak freely, knowing the advice and experience they provide others won't threaten their own business. That noncompete requirement for members may explain why C-level executives often participate directly.
Where do you find such a group for your needs? From what I've seen, it may not be easy to find such a technology alliance. But ones I’ve attended include the Millennium Alliance and the Channel Company, as well as OPDA. I suggest you search for local events for whatever title you have; that's a good way to locate relevant groups.
IT admins may want a bit more technical depth to their conversations and shared experiences. Conferences like TechMentor and Ignite let you rub shoulders with peers. But they may prove to be beyond your budget. If so, you might be able to meet up with like-minded IT professionals at local user groups, which are typically free to attend. You can do a search for a user group that fits your needs.
Microsoft also appreciates the need for a shared experience to assist folks in gaining confidence through the experience of others. Thus, it recently released a new free subscription offering, Microsoft IT Pro Cloud Essentials, with extended trials on Azure, Office 365, and the Enterprise Mobility Suite plus access to experts through a free support incident along with training to help round out your skills.