I don't want to redirect your original discussion much so I will keep this brief, but if you are a traditional software company that plans to branch into distributing and servicing open source software, make sure you deal with your sales staff in addition to your technical staff.

In fact, you should probably do it first. All your IT preparation in the world won't save your business if you don't properly take care of the mechanisms and people by which you make money. Figure out that new sales compensation plan!

I wrote a blog entry on this a couple of years ago called "Adjusting to a more open world: Understanding and overcoming resistance to open technologies".

New headcount isn't a total answer, but it's often a part of the answer. If the current staff doesn't have open source savvy, imposing it from the top down is going to be a bit difficult - particularly for IT managers that aren't particularly open source savvy themselves.

Make sure your next few hires are developers or admins with open source smarts -- preferably contributors who not only use open source, but actually have a pedigree.

There's no magic "open source pixie dust," though -- just like any other goal, if you want your IT shop to use open source more aggressively, then make it a metric of success. Sit down with your staff and set realistic goals and decide what components of your infastructure you want to use open source for.

Also, reach out to the projects that are strategic -- be present on the mailing lists and even offer to pay travel to have key members of a project come to your shop and give advice. (Many open sourcers are consultants, after all... so they'd likely be open to helping out for a fee...)

Engage with companies that support and sell open source software, and ask them to assist you in your transition.

Send your staff to open source conferences if possible, so they can meet other people using open source.

Finally, don't expect it to be an overnight transition. The open source movement has grown slowly, and open source adoption doesn't happen overnight in most shops.

Adopting open source may not be as big a leap as many analysts and consultants make it out to be. Many IT executives that I talk to have been "shocked, shocked I tell you" to find that open source is alive and well within their organization, and has already been widely employed to solve tactical problems. Sometimes this has been in order to avoid the costs (and so, the sales and procurement cycles) associated with many traditional commercial vendor solutions, and sometimes it has simply been because the open source solutions are more accessible and effective. One of the most common examples of this is the recent world domination of “wiki’s”, which propagate throughout organizations and establish effective documentation and knowledge management systems (KMS). This stands in stark contrast to the Herculean (and by-in-large unsuccessful) efforts organizations have endured over the years to implement commercial KMS.

Admittedly, the use of open source “wiki’s” is a far cry from adoption of unsupported open source operating systems such as (non-commercial) Linux and core ERP (such as Openbravo) or CRM (such as SugerCRM) applications, but most IT organizations are already much more open source savvy than most executives might expect. Indeed, the biggest barrier to adoption of open source software may be the institutional relationships with traditional vendors, the imbedded nature of enterprise license agreements (ELAs), and the largely false security of preferred providers. The most proactive approach an executive can take towards open source adoption might be to sponsor an internal discussion about what is available, what has already been successfully utilized (internally or elsewhere), and what might be the best or most strategic deployment strategy for the organization. It might also be wise to keep the analysts and management consultants at arms length, since this approach flies in the face of many of their traditional recommendations (such as the mythical “Off the Shelf / No Customization” mantra).

Conferences and training are always a good idea, but many IT executives may want to look internally to their own resources for answers, since those very practitioners (not industry analysts, management consultants, or big commercial vendors) are most responsible for open source innovation and adoption to start with.