It was at the annual holiday party when I discovered I was no longer interested in listening to what my employees told me.

In line at the buffet, I bumped into the significant other of one of our engineers and asked her how he was enjoying the team. She said since he joined he was generally happier and came home after work feeling energized. Tilting her head down and then looking up with a slight smile, she said that as a result her life had improved as well.

As the founder and CEO of Braintree, I'd always asked for transparent feedback from everyone on the team. If this was a direct criticism of me, even better. My goal was for us to build an exceptional company; to do this, I needed to have data about what my team was thinking and feeling. As I'd discover, however, getting it wasn't always easy.

Why transparency is important... and elusive

To open channels for feedback, I started by doing the obvious: holding weekly town hall meetings, checking in with individual team members in person and by email and constantly asking for input from everyone. At first, this was a revelation. I quickly discovered that everyone always has a pebble in their shoe--something, big or small, that nags them on the job. Unaddressed, these annoyances inevitably lead to backbiting and office politics. Startups are chaotic and difficult enough without this added layer of corrosiveness. The good news is that fixing many of these concerns was usually fairly easy. Sometimes just mutually acknowledging an issue existed was all that was necessary to be rid of it.

There was just one problem. No matter how hard I tried to get the best data on my employees' satisfaction, I inevitably ran into a basic fact of human nature: the difficulty we all feel in communicating honestly with one another. Being ruthlessly honest is risky, awkward, and uncomfortable--for nearly all of us.

On a personal level, for instance, who wants to hurt a friend's feelings by telling him a new tie looks terrible? In the professional realm, stakes are often much higher. Especially when a superior is involved, telling the truth gets tricky. "We have a deep set of defense mechanisms that make us careful around people in authority positions," explains Cornell University professor James Detert, an expert on organizational silence, in Harvard Business Review.

Studies bear this out. A recent survey of more than 15,000 workers in 19 countries showed only about half actually challenge their boss by voicing their opinion and sharing ideas. Among 18 to 24-year-olds, nearly 60 percent admitted to being "yes men" (and women). The price of all this silence? Real issues go unaddressed, tensions escalate and company culture suffers.

Hunting for the perfect feedback tool

But how do you overcome that human tendency to self-censor, especially when superiors are involved? I started exploring different ways to get more honest, direct input from my employees. Results were mixed, at best.

1. Take it to the cloud

A number of cloud-based applications--examples include Salesforce's and 7Geese--have simplified and automated the process of giving and getting feedback. Whereas having a face-to-face meeting or sending an email out of the blue to your manager might be intimidating, providing regular updates online is relatively painless. Nonetheless, it's still hard to be brutally honest with someone, online or off.

2. Going anonymous

Facilitating anonymous feedback can help avoid some of this stickiness. This can be as simple as having a comments box at work (or the online equivalent) or as elaborate as custom-made employee satisfaction surveys. (Some of the cloud-based tools, above, also allow for anonymous feedback.) Still, especially in a small company, "anonymous" input often has fingerprints on it. At the same time, surveys can be a blunt instrument. Not every opinion gathered is equally credible or equally valuable.

3. Crowdsourced feedback

Third-party job review sites help get around at least some of those limitations. The best known example is probably, where users can post feedback on their company and position (including salary), without disclosing their names. For managers, it can be eye-opening--and often humbling--to search for your company on Glassdoor. The caveat here is that these reviews can lack context and hide ulterior motives.

4. Radical transparency

Bridgewater Associates, the world's largest hedge fund, is well-known for its obsession with "total honesty and accountability." All meetings, for instance, are recorded and can be viewed by any employee, as long as confidential material is not discussed. But I wasn't quite ready to go this far. My goal was to boost honesty, not eliminate privacy.

Finding feedback where you least expect it

It was after all of this searching that I ended up at that holiday party. Speaking to my engineer's significant other that night, I realized what people say when they go home from work is usually the rawest and best form of data possible. This was the data stream that I wanted to capture: Were team members going home feeling fulfilled, energized and happy about what they did while working? Granted, getting at this data point isn't an exact science, either. You can't go around systematically interrogating people's partners without coming off as intrusive (at best). Likewise, there's always the possibility you'll get lip service. (Interestingly, some organizations do conduct more formal "spouse surveys," like the Armed Forces' Military Spouse Employment Survey, which looks specifically at how military life impacts spouses' employment prospects.)

Ultimately, though, what worked for me was a casual approach. When the chance came up at company events to chat with employees' significant others, I always took it. That feedback was gold to me, and I made it a point to act on it. Even the little things could end up making a big difference. Once, a colleague's spouse told me, "She loves what she does. But her computer is driving her crazy!" I had no idea how disruptive this was. We got her a new one and she was ecstatic.

Deeper still, I saw time and time again how caring--asking questions, taking an interest, responding--opened closed doors, created softness where there could have been harshness and forged enduring and resilient relationships. The surest path to honest feedback turned out to be this simple act, which really shouldn't be a huge surprise. More than any employee survey or online tool, the gesture of caring opened lines of communication and helped build a company that we loved as much as our customers did.