I'm an owner / CTO of a consultancy, and this point always frustrates me. We are only 12 or so employees, and we're all very comfortable with one another (we'll have game nights at the office, watch the GSL, etc). Still, when me and my partner have a 1:1 or talk to the employees, about 80% of them will not tell us their concerns or things they need.
It's a huge problem for us - we are very interested in spending our money on benefits, etc. that people care about, rather than just guessing, but it's virtually impossible to do this. Story time:
We had a designer leave recently (I <3'd him, awesome guy) to go work somewhere else, and a huge part of his decision, in the exit interview, was about a difference in health insurance between the two places. We had met with him 2 months prior EXPLICITLY to ask him (and other employees) if they wanted us to pursue any changes to health insurance, and were universally told that our existing benefits in that regard were fine.
We have since modified our health insurance to be just fantastically good, because apparently this was a concern (and we've had to forego a few other things in order to be able to afford it). But the point is, this is a guy that I was friends with, and he just would not tell me what weight to give the health insurance benefit vector.
It's maddening because I'm a very data-driven guy, and for whatever reason I can't get good data on employee concerns to save my life. Does anyone have any pointers here?