Unrelenting Simplicity

One of the most important jobs that a leader has is to fight entropy within their organization. More specifically, their job is to not allow their organization to be apathetic about adding complexity. Meaning, whenever someones adds something to a system, they do so without taking into consideration how it affects everything else. This behavior is the status quo for most businesses, especially large corporations (no wonder why they move so slowly). Teams will add a feature here, add a feature there, and over time, the product and codebase becomes a spaghetti monster. The insiduous thing about having an apathetic attitude towards complexity is that its consequences compounds. Each addition may seem harmless, but because most environments consist of interrelated and dependent elements, the system’s complexity and its abstractions increase in a non-linear fashion.

I recently listened to Dharmesh Shah (HubSpots Co-Founder and CTO) on Lenny’s podcast [1] and he put it well:

“The third stage is you’re fighting complexity. And that’s the thing that you will crumble under your own weight over time absent some external intervention. And this you see all the time and it shows up and manifests in different ways which is everything gets more complicated. You need more layers of management, more head count, more this, more that, more everything. Everything becomes harder. You become slower and it’s a slower death because you have more scale, but it’s eventual death. Complexity does kill companies, maybe not as quickly as other things, but much more reliably than other things. This is why it’s never too early to plant the seeds of simplicity, put them there, make them part of the kind of culture of the organization. We have a guiding principles around the ‘fight for simplicity’. The message we’re trying to convey is simplicity is worth fighting for. One, it’s important. But the other thing is that it requires fighting for. It will be a fight. The universe is working against you and it will take calories to fight for that simplicity because everything, even well intentioned people will introduce complexity because that’s the natural way of the world. We want more tiers in our pricing. We want more knobs and dials in the product.”

“We had a rule in the HubSpot product as the product grew in the early years that every time you added what we thought of as a knob or dial called a feature, you had to take one out somewhere else. This goes to the sort of binary heuristic; it forces you to think about it. The other mistake I think people make in product all the time. We measure the cost of the feature based on the cost of implementation. That’s the first order thinking. Second order thinking is the maintenance of that feature. The third order thinking, which is the most nuanced and most important is the other cost that that complexity adds. So when you go from product number one to product two, it’s going to cost us X to develop. What now happens when you go from product 1 to product 2, you have added dimensional complexity to your business. What i mean by that, it’s not an incremental increase. Every decision you make has to be made to the lens of now we have 2 products. We just hired an engineer, do they work on product number one or number two? Do we spend 5 minutes talking about one or two? Now every chart that you ever had now has to be viewed through the lens of product one and two. And this applies once again every level of abstraction.”

In other words, adopting a mindset of unrelenting simplicity.

Unrelenting simplicity means:

Unrelenting simplicity is the closest antidote we have for curing apathetic complexity. It doesn’t completely address it, but it’s a powerful heuristic that one can use to constantly keep entropy at bay.

Practically, creating an environment of unrelenting simplicity is the leader’s job, usually the CEO. There are a few reasons for this:

  1. No one else cares enough about the system as a whole, most are concerned with their own little silo.
  2. Unrelenting simplicity requires a firm decision maker that is willing to make a bet that’s usually unpopular.
  3. There’s a formula when it comes to pushing for something within an organization. You have to believe that the expected value of what you’re pushing for outweighs the potential political backlash / downside. To increase the chances of someone pushing for change usually means reducing potential political risk. The people with the lowest amount of political risk are the executives; you’re not going to fire yourself. The exception is when there’s a board. When the board is risk averse and just wants to maintain the status quo, executives will exhibit the same risk-averse, indecisive behavior. For most contributors, the the potential backlash is usually greater than potential upside.

But to be relentless all of the time is exhausting. Most have to work really hard and manage burnout to do it well. There haven’t been many leaders who could always put their foot on the gas and demand simplicity at all costs. The only one that comes to mind is Steve Jobs. There can only be one or two Steve Jobs in a generation. For everyone else, it’s just a matter of willpower and discipline.

[1] Spotify link to the podcast here.