Acceleration over Position

The single biggest mistake I see at early stage startups is focus on position rather than acceleration. If you’re engaged in an iterative process—such as integrating new data sources, or on-boarding new customers—and your team isn’t moving fast enough, then one of the worst mistakes you can make is to achieve short term goals in a way that doesn’t improve your ability to execute on long term goals. In other words: Whatever it is that you need to get better at, prioritize getting better at that thing, not on achieving “victories” that won’t increase your rate of delivery on future iterations.

Just when we shelter under paper, the rockets come at us sideways.

—Meat Puppets, Backwater

As a software engineer, the chief manifestation of this mistake I see up close is the accumulation of technical debt. Some amount of debt is natural; and, in fact, the amount of debt may reasonably increase over time (implying a tech deficit), so long as the team’s ability to deliver increases at an even greater rate. But if each new integration, customer, etc. is no faster or easier than the last, then you cannot scale any faster than linearly (O(N)), which is typically not good enough for a startup with limited runway; nor, indeed, for any initiative in a competitive market, since somebody else will soon be better at this (whatever “this” is) than you are. If you’re not actively tracking your debt vs. delivery rate, it's likely that your acceleration is negative, meaning your ability to scale isn’t even linear.

When institutional debt—technical or otherwise—interferes with acceleration, a common response is to hire more people. Surprisingly, this makes the problem worse, not better. This principle is sometimes called Brooks’s Law:

Adding manpower to a late software project makes it later.

—Fred Brooks, The Mythical Man-Month

The inclination to expand the team, even when management is intellectually aware of this principle, stems from a misunderstanding of the root cause of the problem. The issue is neither position, nor velocity, but rate of change in that velocity. If you’re going in the wrong direction, then doing that faster makes things worse, not better. A more intuitive phrasing of Brooks’s Law may be the old joke (whose origin eludes me, but please do enlighten me in the comments):

We're losing money on every unit, but we'll make it up in volume.

If the reason you’re not moving fast enough is that you’re accumulating tech debt faster than you’re acquiring reliable automation, then hiring more people is like trying to “make it up in volume.” You’re only making the problem worse.

A lot of Deeply Nested readers will be familiar with the tribulations of trying to deliver market value in the face of accumulated tech debt, bureaucracy, or other institutional inertia. Aside from tech debt, the most common form I’ve seen in person has been badly structured deals, the architects of which are often long gone by the time I arrive. Deal structuring is an underrated art form. If you’re in the process of signing a new customer to a long-term support contract, take care what concessions you make: They will have a real impact on your life (or at least, the lives of your teammates) for years to come.

If it feels like you’re spinning your wheels faster and faster, but not getting anywhere, then it’s likely you’re not understanding the actual impediments to progress. These are often several degrees removed from easily observable metrics like delivery or integration time, instead amounting to things like code complexity or customer support burden. The only way to defeat these impediments once you’ve identified them, as far as I know, is head on. The direction of your velocity is more important than its magnitude, and its derivative acceleration is more important than either. If your weapons are pointed in the wrong direction, you’re liable to suffer more damage from friendly fire than you inflict on your opponents.

If you agree with this sentiment in principle, but simply can’t afford the time to make fundamental changes, then it’s time to move on. You’re like a passenger on a sinking ship who can’t stop bailing water long enough to plug the holes in the hull. So, at some point, you have to ask yourself: Is this boat sufficiently maneuverable to reach a safe harbor before it sinks? You might as well take drastic measures, when the only alternative is going down with the ship.