Building a Loving Organization

  • “All I do is work, my work-life balance is a mess.”
  • “Silicon Valley brogrammer companies do not understand or value diversity.”
  • “Most startups fail.”
  • “Recruiting is difficult, it’s such a competitive market we have a hard time finding the 10Xers we need to crush it.”
  • “I can’t figure out if yoga or alcohol are more effective at helping me deal with work stress.”

What is going on? Why are these challenges so pervasive and persistent in software product development?


Many interesting problems and valuable opportunities are too large in scope and too complex to be addressed effectively by individuals. We build collections of individuals with defined roles and processes that define how they should interact. We build organizations.

We are conditioned from the time we are children to invest heavily in measuring individual performance: grades, the SAT, class rank, time for the 100 yd dash, swipe left/swipe right. Given that we construct orgs to address interesting and valuable problems it makes perfect sense that we try to understand and measure how well they perform. “We can’t manage/improve what we cannot measure!” finds us immersed in headcount plans, revenue, pricing, feature velocity, bug find/fix rate, page views, up rounds, down rounds. As we declare winners we pour back over the data, how can we reproduce this success? And often we fail. Why?

Maybe we are not measuring the right things. Maybe we are not thinking the right way about what to value in building orgs.


To write about love is to risk being misunderstood. To write about love in a professional context to risk being thought odd. Bear with me.

In modern English we overload the word “love” to mean several different important things. What we’re after here is Webster’s definition 4a: “unselfish loyal and benevolent concern for the good of another.”

In other contexts this is not difficult to see and understand, like a parent’s love for his/her child or charitable donations of time and money. But we rarely think/write/speak about the importance of love in building and operating an org.

Traditional leaders of successful tech organizations are praised for level headedness, consistency, discipline, accumulated knowledge, understanding and performing well in a culture that values heroes , where a hero is — by definition — an individual that performs better than her peers. They talk about recruiting in terms of finding “10X” players, they say stuff like “A players recruit A players, B players recruit C players.” They blather about “meritocracies” in defense of their confusion about why they continue to hire too many young, white men.

It’s as if we just generalize the way we measure individual performance to measure that of orgs, including the assumption that within orgs measuring individual performance differences is key.

But orgs must measure and optimize attributes that are different from that of individuals. High org function requires, e.g. that the individuals in it communicate, plan, and and collaborate effectively — that the individuals invest heavily in supporting each other.

Suppose we were building a new org, and from the outset we recruited people who are not only competent individuals, but we understand them to have “unselfish loyal and benevolent concern for the good of another.” When we interview them we don’t just test if they can write decent javascript on the whiteboard, or some superficial notion of whether they are “team players”, we examine how they, in their personal (as appropriate), academic, and professional lives, have committed to the success of others. It’s a Loving Org.

A Loving Org does not see any trade-off in the performance of an individual and the performance and well being of the org, therefore a A Loving Org tolerates no assholes. A Loving Org does not declare 10% of itself underperforming and in continuous need of replacement. A Loving Org does not recruit young white men disproportionately. A Loving Org naturally helps individuals manage work-life balance because it truly cares about them.

The Loving Org recognizes that individuals perform best when they are recruited for the right reasons, feel safe and supported by not just leaders but all of their colleagues, and that there is nothing more rewarding than teaching and supporting others and succeeding together as a team.


I have good news and bad.

The good news is that Loving Orgs can reach extraordinary levels of real productivity while team members revel in their lack of artificial stress and drama. The benefits of a Loving Org accrue in many critical areas like:

  • Culture
  • Diversity
  • Recruiting
  • Product Development Process
  • Work/Life Balance

I look forward to exploring each of these further with you here over the next weeks.

The bad news? Not everyone has the self awareness and emotional strength to approach their professional life as a loving individual. We have not traditionally screened for such so many existing orgs include people lacking the capacity. It can be difficult to teach the benefits of a loving approach, especially to people who have learned to value their contributions in competition with their colleagues, those that look to *win* as opposed to those who win by investing in building harmonious and supportive orgs.

One of the things that is so cool about the startup experience is the opportunity to define culture in terms of what the founding team values. Are you a founder/leader who understands the value and power of welcoming only people into your org who understand and demonstrate love as a fundamental personal principle? I’d love to hear more from you in the comments.


Carty Castaldi has been loving his colleagues and building great software in Boston for a long time, he’s founder and CTO of It’sMyHealth.