Microsoft did not respond to CRN questions Thursday about whether CEO Satya Nadella or other Microsoft executives have reached out to Belichick about his Surface usage.

Microsoft paid $400 million to the NFL in 2013 to put Surface tablets into the hands of coaches and players on the sidelines.

The five-year deal has made Microsoft "The Official Sideline Technology Sponsor of the NFL."

In situations like the one with Belichick and the Surface, "you better move heaven and earth to make sure that person has a positive experience," Grosfield told CRN. "If they’re having a negative experience, it may be simply because whoever is working with them on the technology doesn’t understand what the issue is. 

"Maybe it doesn't have to be a poor experience for this guy. Why wouldn’t you bring your expertise to bear as a provider or vendor, to make sure that a high-profile customer is shouting from the rooftops, 'Hey, I love this stuff'? That's a heck of a missed opportunity."

For all technology solutions, "the issue is one of both setting it up properly and training the people how to use it. And then listening to users," said David Wrenn, vice president at Branford, Connecticut-based Microsoft partner Advanced Office Systems. "Nothing is static in this world, so once you put it out there, you probably need to tweak it, so it works according to what the end user's hopes are."

Rick Jordan, director of sales and strategic alliances at Toronto-based Tenet Computer Group, a Microsoft partner, agreed that it’s "extremely crucial" for technology providers to be responsive when they get wind of user frustrations.

Jordan said that Tenet Computer Group stays proactive by regularly gathering and reviewing analytics of how their solutions are being used by customers.

"After every month we look at the analytics to see, are they using it? Are they not using it?" Jordan said. "We want to make sure we retain these clients."