If your current productivity software was a candidate applying for a job, I'd imagine you'd describe the applicant as frustrating, time-consuming, rigid, antisocial, and maybe "old-school." Definitely, too expensive for what they're really doing. Not exactly a flock of adjectives that would indicate a good fit.
Shouldn't we apply most of the same criteria for hiring employees that we use for productivity software? Certainly, productivity software's job expectations have changed so it's at least time for a new job description. Personality-wise, I might look for a candidate that's easy to work with, social, quick, and can jump into any situation and help. Not to mention energetic and (dare I say) fun to work with.
One prospective customer of ours is a 15,000 employee health care company. They're making their decision about which software to choose by putting different choices in front of a lot of different cross-functional employees and scoring based on a number of use criteria--including how easy the software is to use and how much the employees liked to use it. The IT department stripped several applications of their branding so they could perform this as a "blind taste test." Since everyone was going to use the software daily, they saw this process as critical. They also strongly felt like the software's values needed to reflect their culture, since culture was a key ingredient to this company's success.
Ultimately, it's time for a whole new set of productivity metrics as we move from personal productivity to social productivity. Isn't it time to take a good, hard look at your existing "productivity software" and think about having an intervention?