Cowboys and Drones: two modes of operation for small business
emeaentrepreneurs.com
emeaentrepreneurs.com
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?
So many times it boils down to insecurities in the people managing. If you need to degrade the other to not feel inadequate, you shouldn’t manage people.
- 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
—-
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…)
As you grow, it’s tempting to fix every issue using the ‘cowboy’ method. It’s fast. It’s efficient. It leads to good results. But the number of things that need a cowboy fix grow exponentially, and cowboy fixes only ever fix that one thing, while system fixes fix future issues too. As you adapt from cowboy to drone, it’s easy to skew too much to one side or the other. No matter how good your systems are, sometimes stuff just needs to get done pronto. But sometimes you need to take a step back and trust that the system you built will do its job, and trying to jump in to speed things up will only make everything worse.
Yes it does. It matches both sides negatives and positives step for step from beginning to end.
This remark is sort of fascinating.
But this concept is too broad (and interesting) to only apply to a scaling startup. So I was thinking beyond this narrow focus - to the downsides of cowboys in other situations or contexts. I didn't explain this sufficiently.
1st: Intro. Does lean cowboy, admiring what a cowboy does while merely stating what a system does. drone +0.5 cowboy +1
2nd: Positive aspects of systems. Doesn't mention cowboys by name but last sentence does describe negative effect of cowboy by saying "not that". drone +1
3rd: Positive aspects of cowboy. Notably shorter than 2nd. cowboy +1
4th: Negatives of both drone & cowboy. Why each does not respect the other, from the individuals perspective. drone -1 cowboy -1
5th: Positives of both from a small business owner perspective. drone +1 cowboy +1
6th: Cowboy incompatiblity with growth. cowboy -1
7th: Summary, positives of both, negatives of both, both are necessary to some degree at dofferent times in different contexts. drone -1+1 cowboy -1+1
total drone +1.5 cowboy +1
Huh, Cowboy actually gets an entire paragraph dedicated to nothing but the negatives of cowboy (6th), and no matching paragraph dedicated to nothing but the negatives of systems.
Even the intro leaning cowboy positive doesn't cancel 6th out since it's not dedicated to negatives of systems, it only says positive things of both, but is more positive to cowboy.
And everything else cancels out.
In total, it's actually more critical of cowboys than systems.
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.
You can put the interfaces of those activities into a process, so you insulate the rest of the company from their randomness. But you can't formalize the activities themselves.
More often however, cowboy entrepreneurs are either pushed to by boards or otherwise takes in "experienced" people from large organizations that honestly often became "seniors" by cargo-culting knowledge about how "big business" should be run.
Writing this, i realized that this is a tangent on that Founder Mode essay by Paul Graham.
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.
Indeed. One sentence in TFA stands out
"As you adapt from cowboy to drone..."
Systemantics thinkers (Gall) would say that optionally you can move the other way too. In fact that happens when old systems are broken up into gangs of cowboys (much apropos DOGE etc). Only bad systems are ones that "cast themselves in stone". We prefer modular systems of smaller systems and if you put a process in place, it should be as easy to remove, adapt or replace that process.
SE tells us, never build highly coupled systems where changing one small bit causes problems in unrelated subsystems.
All this is to say there are such things as "flexible systems", which are designed to be more like cowboys than steel machines. A good example is an "operating system", where the essential purview is to frictionlessly run other systems. Parts can be set running, and just as easily terminated if they don't work, need bypassing, or the org grows.
I am absolutely a cowboy and I understand that this is a pejorative when spoken by a drone or a manager who only wants drones, yet this article does not attack me.
This article does not pick a side and is not disparaging anyone. Simply this dynamic of opposites does exist, and using some more clinical terms would be less honest and less accurate by hiding or downplaying the emotional element which is a real part of the thing they wish to express.
The drones don't see me as "a bit more individualistic and self propelled" they see me as "cowboy".
I think the very point was to show that the negative thing, whichever one you consider negative, is actually unavoidable and you are also exactly the same negative, so maybe not so negative. So it wouldn't be useful to avoid the very thing you aim to discuss.
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.
Though that may be the right response in many scenarios, sometimes it's better to just accept the risk of it happening again, as the preventative measure may be worse than the disease. Especially when considering the combined, stifling effect of a historically accumulated wealth of such measures.
I mean, while this is an important consideration to have, I fear that all too often it's used as an excuse to ignore the issue altogether until a later date, especially by management.
Prevention doesn't necessarily mean the issue is prevented from recurring, but that the outcome is prevented. It could be building a self-healing check that intervenes on a given symptom to auto-repair a known fault. It could be firing off a warning that this issue will happen again soon, so whoever is on call isn't caught by surprise. It could be shunting a known outage into a specific maintenance window, so customers don't notice it.
Prevention is ideal, sure, but sometimes the best you can do is a preemptive response.
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.
But the UK is the most populous English-speaking country in Europe, and the second most populous in EMEA as a whole (after Nigeria), and the only English-speaking G7 member in the region. If an EMEA-based company is looking to do business with UK customers (which I don't doubt is a less enticing prospect than it was, thanks to Brexit), it would be advised to avoid associating itself with the word "cowboys" in anything other than a literal sense.
The article does not pick either type as the better one. It only says that each sees the other as a problem, but both have both positive and negative facets, and both are necessary, and whichever one you are, you are actually a source of both positive and negative forces, and so is the other.
…or maybe I’m just paraphrasing what the article said, I’m not really sure.
That's not necessarily the case, actually. You will be slow so you may make outdated decisions and you will try to "cover everything" in advance, which means you may well cover the wrong things. "No plan survives contact with the enemy".
A business case-in-point is Nokia vs Apple. Nokia was caught completely off-guard by the iPhone and they then spent years planning their response (down to the usual comprehensive technical design specs covering every details) while Apple was churning one new version of the iPhone almost every year.
Perhaps a similar scenario is playing out with SpaceX vs Arianespace (Ariane 6 design started in ~2012 with first flight in 2024, "only" 12 years later).
The slow approach might look like it's trying to "cover everything", but sometimes it's just trying to account for the things that could break, so that 1) they don't end up dumped on other people's heads as externalities, and 2) the total ROI is actually positive.
Which model is more appropriate and to what degree, really depends on the context. Technology is often a good case for the "fast" model, but since this subthread is making this an US vs. Europe thing, it's only fair to point out that the "slow" model works better when the general public is on the receiving end of the business or political activities.
The situation is Europe is not really demonstrating that the "European/slow model" works "better"... At the moment what we're seeing is legacy systems and companies slowly falling behind and decaying everywhere with a glacial pace of change.
Process is not free. The bad decision may well be to invest in the process rather than invest in cleaning up after the cowboys.
It takes time, labor and money to run whatever process structure you're using. There are many, many cases where various processes grow in scope of things they cover that it reaches a point of absurdity and the cost is greater than the cost of just cleaning up after the cowboys when they screw up. But because the costs are diffuse, hard to quantify and efforts to quantify them are rife with places that less than honest people can inject subjective judgement processes are often allowed to grow in scope or cost until they are so massively huge that the absurdity is undeniable.
The current disrupters don’t care about improving the administration or delivering something. They’re civil servants like the Vikings were looking to improve monastic efficiency.
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.
Today will be a productive day, new opportunities will arrise but be careful what you wish for, a mistake will be made and come with a much needed moment to reflect as a blessing in disguise.
As a kind of, before things can improve, first they have to get worse.