There are lots of ways for management to go wrong, but if you feel like this article describes your small business, here are some low-hanging fruit:

- Have you sought out management coaching, or are you trying to become a good manager by trial and error?

- Do you treat your employees as trusted, respected professionals (meaning: people who might know better than you)? Do your employees treat one another that way? Do they give you that same respect?

- When you've made a mistake, big or small, how do you discover it? Do your employees and co-founders feel safe and secure enough to give you frequent negative feedback? Do they trust that you'll act on it?

- Do you have the time and resources to provide good management for all of the employees that you're directly responsible for? Have you been properly hiring, promoting and delegating to spread out that workload as the team grows?

- Leaders are just team members whose job is to produce decisions, in the same way that a software engineer's job is to produce code. Are you actually doing your job, by consistently producing high-quality decisions? Who's keeping track of that?

- Your most impactful responsibilities are hiring, firing, promotions, setting salaries, and choosing how to balance quality against speed. Are you giving all of those decisions the care and effort which they deserve?

- given a likely predisposition to action, a Cowboy may also sometimes lack the experience/oversight to spot reasons why the system is as it is, and miss downsides or unintended consequences of their disruption

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Also, there are also many, many times that you would want a system and ‘drones’ to be in charge - like anything involving detail with life-changing downsides. Y’know, things like radiotherapy administration, airliner QA, pharmaceutical production, etc.

As such, changing the nomenclature to be less negative about the group of people who do important but routine work would help discussion and dissemination of this concept. Maybe “disruptor” and “deliverer” might work better?

(We should also note that this is a subset/simplification of Belbin’s team roles…)

This by the way is why most big ERP, BPM,RPA projects fail. Once the pretence is codified it turns out the emperor never had any clothes.

A good "cowboy" is one that gets the job done but can also build a sustainable, changeable process in their wake.

A good "drone" is able to spot ineffective parts of the system/process and change it.

As an aside, I really dislike the cowboy and drone nomenclature.

Is stuff actively on fire? You want a Cowboy, and you want one NOW. You need that fire put out, you need stuff back online and work resumed. Once the fire is out, you need a Drone, someone to dive into the systems to determine what caused the issue in the first place, and ensure systems are designed to never let it happen again.

For larger orgs, you want Drones on the day-to-day. Focus on iterative, incremental adjustments and improvements. A new feature here, a pipeline upgrade there, a bugfix every sprint. But you also need those Drones to become Cowboys when systems are hindering their productivity, to get something over the finish line when a system is arbitrarily blocking the path forward without valid reason. You then need those Cowboys to revert back to Drones to engage with malicious compliance on bad systems, to surface those problems up to leadership and get them dealt with.

The best performers are neither drones nor cowboys, but both as needed. It's always about balance.

Words like “drone” and “cowboy” are used in a way completely removed from any useful context. Neither real drones nor real cowboys resemble them, even metaphorically.

Rather than insight, each concept is based on a fashionable trope. The tropes are strung together. It’s the essay equivalent of sample code.

Few people are all creative and unstructured. The ones that are can’t hold jobs. But also, few people in the technical world can survive by “following processes” since all the processes are wrong. No one has the patience and skill to specify a real and also effective process. Instead we proceed via heuristics. We all do.

“Cowboys” are not people who create trouble with their creativity. Instead ad hoc problem-solving may or may not have disruptive affects, and people who wish for no trouble are like children wishing it would never rain.

So a business owner who describes their operation as "more cowboys than drones" to a British audience may not be conveying quite the message they intend.

One is not more important than the other.

Entrepreneurs are cowboys in this analogy. But it's more than just being willing to figure things out on the fly. An entrepreneur sees something that doesn't exist yet and breaks all the rules in order to bring that thing into reality.

Think of any successful startup. Or think of Steve Jobs or Bill Gates. They're bullshit artists with a penchant for finding talent who can make reality match their lies so that they're not lies anymore. Without them, the word would be a very stagnant place.

But, for every successful Jobs, there is a Tim Cook. For every Bill Gates, there's a Paul Allen.

The problem with the visionary entrepreneurs is they make for terrible managers (drones). They're great gamblers, great at taking big risks, but they just keep doubling down until eventually things blow up in their face, unless they're constrained by an excellent manager.

Look at SBF or Liz Holmes. I truly think they're cut from the same cloth as Jobs and Gates in terms of being willing to bullshit their way to the top. But they never appreciated why they needed "drones" (talented managers) to keep things in check and tell them "no" when their visions were truly batshit.

I'm not sure anyone is truly great at both. Being great at one tends to blind you to the other.