The first Cultivate Conference, produced by O'Reilly, was a beautiful thing that has potential to inspire  empathy-challenged technology geeks to be warmer and more empathetic. But even the conference speakers seemed divided on the best ways to promote culture within the enterprise.

Like a kid in a candy store, I listened to a room full of engineering geeks discuss the value of culture in technology companies and heard several speakers explain ways to do it. I hope the event was successful enough that O'Reilly continues it next year and beyond, because the topics are rarely discussed in geek circles and it seems there are too few engineers capable of enterprise leadership.

Beauty First

Kate Matsudaira of PopForms.com spoke about her journey from "flaw in the foreground engineer" to "possibility first leader." She started talking about one of the largest sources of pain for the engineering community: a successful project in which individual engineers were not recognized for the specific effort they put in.

Then she had the good fortune to work with a professional coach and see the other side. The reality, she explained, is that while it is  "wrong" not to recognize individual effort or performance, fixing the problem is not fundamentally aligned with the best interests of the enterprise.

Matsudaira recognized that any attempt to improve the metrics for delivering praise to engineers was more flawed than the problem she was trying to address. Measuring value in hours, lines of code, imputed quality, numbers of features or any quantitative metric rarely tells the whole story.

She had learned a basic truth of medium-to-large size teams - the better you are at your job, the less people seem to be aware of it. What she took from this lesson was that something she called "possibility creation" dialogue creates better results than "disaster prevention" dialogue. Matsudaira rounded out her talk by touching on the value of "informal power" (or influence) and discussing how leadership is more of a decision than a position.

Then the Beast

Patty McCord, a consultant who has worked with companies like Netflix and SimplyHired, spoke about her journey from empathy-first HR professional to truth-first leader in a talk entitled "Leading by Logic." McCord started by talking about "the appeasement oriented" HR mentality -- one of the greatest sources of pain for the human resources community. Left unchecked, she said, it encourages people to take advantage of the system.

McCord praised the engineers reliance on the "lens of truth" and noted how this "truth first" perspective can correct the constant stream of "whining" that comes from people afraid to call out what is self-evident to the engineers. Claiming "judgement will always trump everything," the lesson McCord imparted was that corporate cultures based on truth and logic are more efficient than ones that suffer fools and tolerate poor hires.

Not So Fast

McCord's message was powerful, which is why it got the most spontaneous applause from the audience. But this might not be a good sign as much as it was a sign that she was inciting a mob. Going and telling a room full of engineers that binary thinking should be celebrated, that HR professionals more often than not waste time and placing yourself in a position of judgment is good for the enterprise is risky, at best.

Masters of Balance

Several other speakers -- Tim O'Reilly of O'Reilly Publishing, Scott Chacon of Github and my personal favorite Michael Lopp of Palantir Technologies (and Apple) -- spoke about Principles First leadership with an insatiable curiosity to find layered truth that changes with context in search of optimizing organization design and cultures against values rather than end states.

It would be oh so easy to walk out from the day and believe that people walked out with the siren-song of truth in their head and a borg-like desire to crush all opposition to efficiency.  But if I want to hold myself accountable to the possibility first lens that I ask the other geeks to embrace, I must remind myself: Faith in awesomeness will beat the certainty of doom. It's just a matter of time.