q American View: Dispatches from Boot Hill - Business Reporter

American View: Dispatches from Boot Hill

Merry Christmas from the American Southwest. Business Reporter’s resident U.S. blogger Keil Hubert has just published a new book about ‘office cowboys’, and offers a look behind the scenes on its development over the last year (along with a way to get his book for free).

Let me put a disclaimer right up front: this entire column is about my newest book and how it came to be. I promise to get back to business, technology and security news with next week’s column. This week, I want to answer several questions that I’ve received about my new e-book since it went live on 8th December.

First up, the book is called Office Cowboys: Cautionary Tales from the Cubicle Frontier. The entire point of it is to discuss how to deal with those people in the office that believe (against all logic and evidence to the contrary) that the organisation’s rules just don’t apply to them. They’re special, darn it! They have a destiny! They play by their own rules! You know the type: the anti-social and confrontational people who stubbornly won’t do what they’re told… even when it’s in their best interests. Those people in the office who refuse to cooperate with their co-workers, who constantly disrupt other people’s activities, and who openly flaunt management’s authority. You may have a special slang term for them (if you do, please post it down in the comments). In the American Southwest (or, at least, the parts of it where I hang out) we call these sorts of folks ‘office cowboys’.

I actually started this project back in in July of 2013 with a column [1] called ‘Cowboys in the Cubicles’. I’d planned for it to be a one-off piece, but that didn’t happen. I came back to the topic two weeks later with a follow-up column titled ‘Concerning Critters and Cowboys’ and capped the series off as a trilogy the next week with a conclusion piece called ‘Reining in the Office Cowboys’. I thought I was done flogging that dead horse in 2013, but the topic never stopped bugging me. I think it’s because this sort of annoying employee drives me absolutely mental everywhere I go.

The one thing that you can guarantee about an endeavour involving people is that there will be drama. If nothing happens to instigate legitimate conflict, someone in the office will inevitably start some drama just to fill the silence.
The one thing that you can guarantee about an endeavour involving people is that there will be drama. If nothing happens to instigate legitimate conflict, someone in the office will inevitably start some drama just to fill the silence.

Maybe this isn’t a thing in the UK. Y’all have a global reputation for being some of the most polite, charming and dignified people on Earth. God knows, every time that I’ve visited the UK, I’ve been impressed with how y’all conduct yourselves. [2] Maybe the ‘office cowboy’ phenomena is just an American thing. Or maybe it’s something that we excel at, given our cultural conceit around pig-headed individualism. If it wasn’t already abundantly clear from our pop culture exports, we have this problem in spades. Pretty much every company you’ll ever work at has at least one of these yahoos, and most workplaces are saturated with them. When the ‘office cowboys’ are at the bottom of the totem pole, they’re the bane of management’s existence. When they’re the ones actually running the show, they can be an absolute terror to everyone.

I think that’s why this topic has stuck with me. It used to drive me absolutely apoplectic during the ten years I spent running an IT department. It continued to vex me in all my different jobs as a freelance consultant. These belligerent and destructive individualists are everywhere, like fire ants at a Texas picnic. The majority of the ones I’ve known ran roughshod over their fellows until they either got themselves fired or else left the organisation in a snit. Some profited from their audacity, others stagnated. Few of them ever tried to change their anti-social ways.

After I finished my book on understanding office cultures back in April, I started sketching ideas for a new project. Nothing immediately came to mind, so I decided to give myself a month to let my subconscious work on it. Lost Allusions posted to the Amazon Kindle Store on 22nd April. When I returned to my notes on 23rd May, I realized that I’d just written ten cowboythemed columns in a row – a pretty sure sign that my subconscious wasn’t done with the ‘office cowboy’ theme. That became the focus of my next dozen columns. In the end, I chose 19 of my 27 cowboy-themed columns and one extended column draft [3] to make up the core of the new manuscript.

As I’ve done with my other books that [4] the columns in this compendium make up about half of the overall text. The rest is made up of commentary about the stories and how they fit into the book’s overall narrative. In this project, I aimed to introduce what an ‘office cowboy’ is, then explore whether it’s a matter of culture of personality. I illustrated some different variations on the concept, then explored what it’s like when the office culture allows these antisocial types to run amok. I closed with stories about a culture where the ‘office cowboy’ was running the entire show. I ended with some practical advice on how a leader can deal with this sort of disruptive employee.

WITHOUT resorting to illegal workplace violence. Real life isn’t an action movie.
WITHOUT resorting to illegal workplace violence. Real life isn’t an action movie.

All told, it took me a little over eight months from start to finish to put the book together and to polish it until it was releasable. One issue that tripped me up during assembly was a need to make sure that I’d been clear enough explaining the allusions in the column titles. Every column that had appeared on Business Reporter had a humorous reference in the title, but the tie-in to the reference wasn’t always as clear as it needed to be.

For example, the first column in the book is a caustic piece on the consulting industry titled For a Fistful of Billable Hours. It’s an allusion to Sergio Leone’s 1964 classic Western For a Fistful of Dollars. That allusion was pretty straightforward: if you’ve ever been around professional consultants, you’ve probably worked out that their ultimate goal is to bleed you for every billable hour possible – not to actually solve any of your problems.

Other columns were a lot vaguer. The one I wrote on personality attributes and tied to Marlon Brando’s 1961 film One-Eyed Jacks was so tenuous that in needed an extended post-script explaining what the heck I was thinking at the time. That’s also one of the reasons why I’m a bit late getting this introduction posted: I didn’t have a film or book title to reference for the introduction itself.

This problem resolved itself late one evening thanks to Netflix. While browsing new (to me) old movies to watch, I came across Giuseppe Colizzi’s 1969 Spaghetti Western Boot Hill.  When I opened the IMDB page on the English-language version of the movie, the plot synopsis read:

‘Victims of oppressive town boss Honey are offered help by an unusual alliance of gunmen and circus performers.’

Maybe I’ve been living in Texas too long, but when I read that the ‘town boss’ in the movie was named ‘Honey,’ this is immediately what I visualized. Turns out … not so much.
Maybe I’ve been living in Texas too long, but when I read that the ‘town boss’ in the movie was named ‘Honey’, this is immediately what I visualized. Turns out… not so much.

I figured that was perfect. In a way, that’s what the entire project is about: victims of an oppressive ‘office cowboy’ (presumably you, the reader) are being offered help (via the book) by an unusual character (me) who blends dry academic theory with unconventional Texas-style humour. That’s pretty darned close to ‘an amalgamation of gunman and circus performer’. Add in the fact that the term ‘Boot Hill’ is an American slang term for the graveyards where gunfighters were buried in the Old West, and the movie reference was a perfect allusion. [5]

All of the stories that appear in Office Cowboys really happened. I was present for all of them. So, in a sense, they are like news dispatches from the days of field reporting. Just… slightly obfuscated. I had to edit several of the columns to obfuscate the people, places and companies involved. I’m not the least bit interested in the ‘name-and-shame’ approach. I may be a journalist, but I’m not a muckraker. The stories are real, and the characters are all anonymised. I want you to learn something useful from the stories – there’s no additional value to be gained from figuring out who the blackguard AngryEssexFishmonger47 really is.

There’s also the problem of why it took so darned long to turn about 80 pages of column drafts into about double that in an extended argument. If I’m honest, the actual first full draft was ready back in late September. I tried to devote one day a week to the project all the way through the summer. I stumbled when it came to finding an editor, and then applying all of the recommended edits. In the end, I wound up excising about 10 per cent of the original manuscript and significantly re-wrote the ending.

As much as I’d like to claim that this is what I primarily do for a living, no one is paying me to write books for a living (yet!). I have to fit these projects in wherever I can carve out time, after all of the other major life maintenance issue get sorted. Most of the time, that means I get to apply whatever time I didn’t spend crafting a new weekly column on Saturday afternoon. Sometimes that’s an hour, sometimes less.

If the stock photos for these columns ever start to seem bizarre, please understand that decision-making starts to get strained and desperate at three in the morning.
If the stock photos for these columns ever start to seem bizarre, please understand that decision-making starts to get strained and desperate at three in the morning.

Finally, there’s the issue of pricing an e-book. I set the original cost of my first e-book to £3 since that was the average price of a pint in London at the time. The logic was that if something I said in person helped someone deal with an issue, he or she would express their thanks on Friday after work by treating me to a pint. I never wrote these columns and certainly never assembled the books to become a filthy-rich celebrity writer. Each column is an attempt to argue an idea while entertaining the listener or reader, same as we’d converse down at the pub. My goal has been to write pieces that were at least worth a pint. [6]

So, that’s all of that, then. Office Cowboys is available now on Amazon’s global Kindle Store. If you’re part of the Amazon Kindle Unlimited programme, you can get it for free… at least, for the next month or so. If you qualify – or if someone gets you into the Unlimited programme for Christmas – you may as well snag my book while you’re waiting for the newest Stephen King bestseller to download. Hopefully something in it will give you an effective countermeasure to use on your own ‘office cowboys’ wherever you work.

Merry Christmas, everyone.


[1] Over on the old Business Technology site.

[2] Along those lines, I’d like to apologize – again – to the young couple that I terrified out of their wits late one winter night by offering them a loud and unexpected ‘Howdy!’ My Geordie host was quite insistent (once he stopped laughing) that such… boisterous… greetings are considered unseemly, especially in the dark of night and from a foreign stranger.

[3] I never actually published the ‘Hurricane Frieda’ piece in column form on Business Reporter, but it wrapped things up nicely so I built the book’s conclusion around it.

[4] Shameless plug time! Those were (in order): Why Are You Here?: A Curmudgeon’s Guide to IT Interviewing, High Tea Leadership: Leading IT Teams in Non-Tech Organisations  (also available in print), In Bob We Trust: Lessons Learned From Terrible Bosses (soon available in print) and Lost Allusions: Making Sense of Dysfunctional Company Cultures.

[5] Useless trivia moment: I grew up in a city two hours south of Hays, Kansas – the town where the original ‘Boot Hill’ cemetery was established.

[6] I realize that the recent fluctuations in the USD/GBP exchange rate have screwed up that price point. Sorry about that.

Title Allusion: Giuseppe Colizzi, La Collina Degli Stivali (a.k.a., Boot Hill) (1969 Film)

POC is Keil Hubert, keil.hubert@gmail.com
Follow him on Twitter at @keilhubert.
You can buy his books on IT leadershipIT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store.

Keil-Hubert-featuredKeil Hubert is a retired U.S. Air Force ‘Cyberspace Operations’ officer, with over ten years of military command experience. He currently consults on business, security and technology issues in Texas. He’s built dot-com start-ups for KPMG Consulting, created an in-house consulting practice for Yahoo!, and helped to launch four small businesses (including his own).

Keil’s experience creating and leading IT teams in the defense, healthcare, media, government and non-profit sectors has afforded him an eclectic perspective on the integration of business needs, technical services and creative employee development… This serves him well as Business Technology’s resident U.S. blogger.

Keil Hubert

Keil Hubert

POC is Keil Hubert, keil.hubert@gmail.com Follow him on Twitter at @keilhubert. You can buy his books on IT leadership, IT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store. Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant. Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

© Business Reporter 2021

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