Protecting Selflessness in Startups

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Building a shared sense of purpose is easy when the company is young. There is plenty of work to do and not enough people to do it. As such, selflessness is easy because you’re a small search party, a tight group of renegades out to prove the world wrong. This creates high cohesion that cements individual sacrifice. 

If the team is young, there’s another dynamic at play. The young are fresh, helpful, inquisitive, and need the experience. They are willing to prioritize learning over earning and are inclined to be selfless. 

Outside of the confines of a small team, selflessness can quickly lose itself in the din of high growth. As a company expands, existing employees get more experience and more experienced employees come onboard. In the name of efficiency, experience and expertise team up to create processes. However, if not managed properly, that efficiency can come at the cost of selflessness. 

Soviet Tanks & Molotov Cocktails

Some years ago, during my regular visits to EZ Texting’s Kyiv offices, I struck up a conversation with a group of engineers. The conversation meandered to how Kyiv had changed (this was a few years after the Maidan revolution). One of the engineers shared an eye-opening personal story. 

From the office, this engineer could see smoke coming out of the Maidan. On YouTube, he saw army tanks rolling into Kyiv’s town square. Almost immediately, he left the office and proceeded to the scene of the unrest. Once at the town square, he “borrowed a Molotov cocktail” to throw at a tank. 

I nodded in acknowledgment, barely hiding my surprise. Here was a smart engineer, one of the best we had, and his thought process told him to take two seemingly illogical actions.

First, take life-threatening risks and walk into violent political unrest. Second, use a Molotov cocktail to stop a Soviet-era tank. This engineer believed his truth and was cocksure he’d fight a tank and win. For someone with this level of disregard for personal safety, I had flown halfway around the world to ‘motivate’ him to give a sh*t about Americans getting their text messages on time. 

My only hope to get him to care was to be honest with myself and direct with him. 

As much as I’d like to believe the mission is everything, a company is a for-profit enterprise that exists to enrich everyone who partakes in it. This truth is lost in the current Silicon Valley speak where mission-oriented is tossed around like cheap candy to give us the sugar high of doing something meaningful with our lives. 

In reality, I’m here to do a job. That job is to further the goals of the enterprise. Everything I do is here to serve that purpose. If I do it right, I’ll make myself and those around me a lot of money. 

There is some vainglory that comes with this kind of ambition. The aspiration is to be a Richard Branson and not delude myself into thinking I’m the Dalai Lama in pants. 

Selflessness in Professions

Selflessness makes us better at our jobs. It is the willingness to help when someone is struggling. When you see something falling through the cracks, it is the desire to call it out and fix it. Most importantly, if you see someone trying their best, it is the willingness to help them over the finish line. 

A thriving profession depends on mentoring, sharing, and apprenticeship. Without the systematic transfer of knowledge, the collective skill of the group atrophies. The profession needs selflessness to perpetuate itself. The professional needs selflessness to grow themselves.

Professional Selflessness is Different from Personal Altruism

When talking about selflessness, the conversation often skids into altruism. Using altruism as a proxy for selflessness is not only a disservice to truly altruistic endeavors (donating a kidney to a stranger, fighting a Soviet tank for an idea) but to the challenging task of encouraging selflessness in a corporate setting. 

Altruism and selflessness require removing ourselves from the center of our narrative and empathizing with others. Altruism is about personal sacrifice, while selflessness is about being generous with our time. You can expect selflessness. You can only hope for altruism. 

When the mission is clear, so is the need the selflessness. A uniformed organization (army, police, and the likes) is a good example. Be it patriotism or protection of the community, the expectation of personal commitment to a larger cause is clear. This expectation becomes harder for private enterprises, especially startups. 

Solving for Selflessness

Solving for selflessness is hard. It requires appealing to the hearts and minds of people and prioritizing influence over authority. The natural first move to get people to be more selfless is to create a PR machine that repeatedly and in multiple forums encourages them to do so. There is truth to this. 

Constant reminding of values builds culture. Showcasing and rewarding examples of selflessness creates a virtuous loop for more selflessness. But it’s easy for the calls for selflessness to sound hollow when working towards a singularly capitalist goal. You’re asking the employee to remove themselves from the center of their narrative while working for an organization that solely exists to further its financial objectives.

Selflessness as a Ground War

Narratives asking people to be more selfless can fall short if not supported by making it easy to be selfless. You do this by focusing on the friction that gets in the way of that selflessness. 

Friction is good, it moves you forward. But too much friction can create roadblocks to sharing and thereby to selflessness. Unchecked friction in collaboration creates apathy, the real culture killer. 

Instead of boiling the ocean to encourage selflessness, it makes sense to invert the problem and protect against apathy. This has a two-fold advantage. First, it acknowledges that a startup is a for-profit enterprise not optimized for altruism. Second, it boxes the problem and lets you focus on setting guardrails around good behavior instead of micromanaging interactions or giving grandiloquent talks about vision. 

Apathy, The Silent Culture Killer

Apathy and friction share a mutual affinity. The more unnecessary friction an organization has, the more apathy is encouraged. The more apathy is allowed to fester, the more friction it creates. 

Here is how it happens:

  1. We become highly skilled and specialized. 
  2. We stick narrowly to our domains. 
  3. Scale adds process, which adds friction to daily interactions.
  4. A “not my problem” mindset sets in.
  5. We silently disengage from the team.
  6. We get comfortable with diffusion of ownership.
  7. Apathy takes hold.
  8. Nothing gets done.

These changes often go undetected for long periods until a major catastrophe reveals them. However, early signs of this apathy are easy to detect. There are increased departmental silos. These silos create their processes. The processes live in perpetuity long after being rendered useless and usually sunset only after causing a major accident. 

Even the best processes are acts of friction. They exist because there is a need for multiple people or systems to work. They provide a safe framework to move an organizational goal forward. It is a way to communicate, and group communication is an act of managed friction. 

Unwatched processes, however, can take a life of their own. Peter Drucker calls this “organizational obesity.” He contends that in companies with such bloat, processes have to prove their ineffectiveness to be killed. Warren Buffet calls this the “institutional imperative”-the tendency of companies to engage in activities for their own sake.

An Approach to People First Process Reviews

To fight the self-serving tendency of processes, we must review them. Many formal and informal frameworks help do this. The formalism presented by the likes of Computer Scientist Leon Osterweil asks for a code-like review of software processes and constantly monitors the gap between process design and execution. 

Applying software engineering principles to process design doesn’t scream easy. The other approach, recommended by Drucker, while structured, considers the people aspect of reviews. Reflection is an emotionally demanding exercise; the more constraints you put on it, the less people will want to do it. 

Drucker offers a more pragmatic take on the matter. He recommends having processes demonstrate their effectiveness at regular intervals, starting with asking the simple question, “Is this still worth doing?” 

One way to do this is to break down processes to their checklists and review them frequently. A checklist done well is precise, efficient, and easy to use. Breaking down the process into tasks that must be done makes it easy to inspect. The mechanical act of reviewing the checklist will force a team to be intentional about their daily work and where they spend their time. 

It may sound counterintuitive, but checklist reviews work. Instead of fighting apathy seeping into the culture by grand narratives and presentations, focus on the daily, the now. Create a culture of reflection and rumination by building a framework that allows a candid, dispassionate look into why we’re doing what we’re doing and is the way we’re doing it the best way to do it. 

Start by asking, “if you didn’t already do this, would you still do this today?” Doing so will require an explicit acknowledgment of the “why” in the collective psyche. This quest for knowing the “why” will create a vibrant, selfless organization that doesn’t give in to dogma or dogmatism. 

Don’t Wait to Prune Waste

Once you’ve identified a process causing unnecessary friction, dispose of it ruthlessly. Not doing so right away will cause emotional and physical exhaustion in your team. It will kill team morale, the bias for action, and rot your culture like gangrene. This rot, of course, will only reveal itself at the aforementioned catastrophe.  

My trip to Kyiv became focused on the little things and the significant changes. I focused on the small issues, like improving wifi, video conferencing between the US and Kyiv, and big stuff like cloud provisioning of testing resources. Purchasing little items like Google Chromeboxes and Apple TVs turned out to be a challenge as neither Apple nor Google have an official presence in Ukraine. Our local partner had to send someone with cash to the local store to buy the equipment in the secondary market. But, if I didn’t show extreme responsiveness in solving their minor issues, I’d lose their trust in resolving the big challenges. 

Finally

Process review and reflection requires a healthy dose of contrarianism, a willingness to experiment, and the drive to execute. It requires a pervasive entrepreneurial mindset that puts people ahead of process and structure, gives them autonomy and accountability, and respects their expertise and time. 

Standardizing meaningful review and mindful reflection assumes an adaptive environment that enables them. It takes an open culture that encourages risk-taking and individuality and discourages group thinking. Selflessness thrives best in such environments.