Ramji's Sisyphean task was evident last week in Portland at the Open Source Conference (OSCon) and will likely be fuel for chatter at next week's LinuxWorld gathering in San Francisco. (Disclosure: Computerworld's parent company IDG sponsors LinuxWorld.)
In Portland, Ramji, who runs the Open Source Software Lab for Microsoft and is the company's director of open source technology strategy, gave a 15-minute presentation highlighting Microsoft's work with open source, the company's first code submission ever to the PHP community and a $100,000 (£50,000) investment to become one of only three Platinum sponsors of the Apache Foundation (Yahoo and Google are the others).
Then it turned ugly.
The first questioner from the audience wanted to know what it would take for Microsoft not to claim patent infringement violations in open source code.
His inquiry was followed by whoops, whistles and thunderous applause.
The next question was about trust, as in why should we trust you this time? And the next referenced what the questioner called the "Office Open XML debacle" and accused Microsoft of using its power to buy international standards.
Ramji, dressed in a Firefox T-shirt like it was a virtual bullet proof vest, is used to the machine gun fire and didn't shy away. He mentions cultural change that he has to facilitate within proprietary-minded Microsoft, trust built within an 18-month working relationship with Samba creator Jeremy Allison and others, and the need to provide more clarity around patents and the company's work to address shortfalls in US patent law.
As he left the stage, he invited people to the back of the room for more questions, which becomes a six-deep ring of fire that lasted nearly 30 minutes.
"People stopped and wanted to ask more questions," he said later during an interview. "They thanked me for being here, appreciated the change agency work that my team has the privilege of doing outside the company."
Ramji, who took on the open source post in 2006, says listening is the start. "It lets us start to look at what divides us and what we can do to come closer together. What I said today may not be the be-all and end-all, but we have more than started the conversation, we are opening the next chapter."
That next chapter, he says, includes speaking and actions.
And if Portland is any indication, the speaking part is actually working.
"At its heart there is a lot of bad blood, but I'm proud to see Microsoft stepping up to the plate," says Ben Hengst, a Linux developer for Powell's Books. Hengst says he feels Microsoft is willing to change but that the open source community has ideas about how it should change. In essence, they are tired of being talked at and want a part in defining change.
"Animosity? Yes. But we want to get them going down the right path," Hengst says. "The biggest piece of change I saw was Sam on stage with a Firefox T-shirt and without fear of getting fired."
Ramji, a veteran of five start-ups who has a bachelor's degree in cognitive science and interests that range from history to physics, says he has a long leash. "What helps is that I have business responsibility. It is not strictly advocacy. I can tie what we are doing to good outcomes for the company."
In Portland, he announced Microsoft was contributing a patch to ADOdb, a data access layer for PHP. The code contribution to the PHP community was a first for Microsoft, and Ramji had to work with Microsoft's legal team to fit the work around the Free Software Foundation's GNU Lesser General Public License (LGPL). Last year, the LGPL was a dead end for Microsoft.
But it wasn't all altruism, Ramji says the code makes it easier for PHP developers who routinely develop on Windows to actually deploy their applications on the platform.
"Those kinds of innovation are what lead companies like IBM to contribute to open source," he says. "You have to find an operational business framework - legal, financial, development - that lets you move forward methodically. You can't be a corporate-level contributor and have everything be ad hoc."
As part of the plan, Microsoft earlier this year published 30,000 pages documenting APIs and communications protocols that its products use to connect to Windows Server 2008 and Windows Vista (including the .Net Framework). Last week, Ramji announced 100 protocols from its Communications Protocol Program would move under Microsoft's Open Specification Promise to ensure they could be used without fear of patent infringement.
The business side of the relationship is a reality many understand Ramji brings to his change efforts.
"We feel that if we fight Sam we weaken him," said Russell Nelson, the licensing approval chairman at the Open Source Initiative. "But it is going to take Microsoft time to figure out what they can execute. The biggest problem is that open source people feel under attack, under siege."
Ramji says he battles on two fronts, those within Microsoft that see open source as a threat and the open source side which sees Microsoft as a villain.
When asked which faction is softening faster he is careful not to speak for the other side.
"I have gotten to the point where I'm backed by great organisational management," he says. He points to new chief software architect Ray Ozzie, who talks about the importance of open source, and Ozzie predecessor Bill Gates, who Ramji says is fully connected with where Ozzie is driving Microsoft.
"Guys like Bill Hilf (GM of platform strategies) and Bob Muglia (senior vice president, server and tools division) have a vision and there is other executive sponsorship from places like the legal team and the sales team. People who see this is going to help our business," he says.
Ramji has delivered keynote addresses at more than a dozen open source events. "People are passionate. They ask questions and I am willing to take them. They say they appreciate the work that I do and they say they are seeing some changes in Microsoft."
Whether they see that change as positive or not will be the difference between Ramji being at open source's Thanksgiving table or on it.