A Case For Oversight-Free, On-The-Clock, Personal-Interest-Driven, Professional Development

Previous drafts of this article went into a bit of detail about why I feel I’m qualified to voice my opinion on this topic, but just a few minutes ago I thought better of getting so granular with my credentials, so I hope you can believe me when I say that if you work for a small company where the owner maintains a stranglehold on upper-management positions so that they can be filled with people matching a very specific profile (for instance, sharing a last name with the owner), I am here to tell you that you’re not crazy for thinking that they’re slowly killing their company. Small companies designed around a familial legacy have some deeply ingrained issues with change, and often these issues will put a glass ceiling above non-relatives and a selective filter on the memories of upper management. In short, the soft spot for nepotism is also a blind spot for people and ideas whose time has come.

Par exemple, I have personally experienced an owner laying claim to the credit for increasing annual gross sales by more than 400% over 5 years, when in fact the lion’s share of said credit should rightly have gone to the employee who, while waiting for the owner to come to a decision on an unrelated topic, took it upon themselves to prototype a website redesign to replace the current one, which was about a decade behind the times. When the owner found out that a more modern version of the website existed, though not in a publicly accessible or already-deployed format, they went ballistic. E-mail rants about approved vs. unapproved projects and needing to tracking how employees spent their time, in some cases minute-to-minute, spewed forth from his outbox for days. Things got even worse when it came to light that this same self-starting employee had devised a way to slightly modify the code that runs the website and turn it into a wiki-type application for storing and organizing internal data and documents.

In my time observing this and similar events, it’s become common knowledge that the owner lags behind employee ideas by an average a 3 years. From the day an employee makes an objectively good suggestion, be it a customer-facing project or for internal use only, the owner first hates the idea, then forgets about the idea, then decides that their latest idea is the bee’s knees, and the employees are left looking at the original suggestion e-mails and design documents from 3 years ago, hanging their heads in disappointment and wishing it didn’t take so long for these things to come back around.

Even in the midst of all this managerial torpor, the employees at this company still, from time to time, suffer a bout of inspiration. Sometimes it’s about software. Sometimes a new product. Sometimes a marketing opportunity. But in almost every such brainstorm that transpired while on the clock, the outcome has been a stern talking-to about the dangers of pursuing unapproved projects. The owner loves to know how people are spending their time, and so would prefer that you ask for and receive permission when you need to think about something for a bit before you take action.

This is the crux of one of the largest problems at this company: the owner demands that the employees innovate and drive growth, and then expects that the moments of inspiration can be summoned at will. Unfortunately for the employees at this company, innovation doesn’t really work that way. The owner has become a manager without a plan because they’ve stayed wrapped in the comfortable blanket of code that runs the company infrastructure (which they wrote in the late 80s), and now the world outside is moving in ways that they couldn’t have expected or predicted. To quote something someone not me once said, “It’s amazing what you try to control when you feel like you don’t control anything.”

In the last decade, all of the things that have pushed this company forward have been dreamed up and executed by someone besides the owner. In all that time, none of the ideas started out as approved projects, and all ended up being designed and built years after originally being proposed. There have been compromises, lackluster approaches and finales, and nothing has been pulled off as well as anyone originally envisioned it. Credit where credit is due, the product lines that have made the cut in that time also had to be adopted by the owner, but actually selling them, B2C-style, has nearly entirely been the job of his employees.


Much of what I’ve described has probably sounded pretty specific to the company in the story, but I am convinced that the world can’t possibly have only one aging business owner who’s not ready to retire yet and is still trying to live by the map that got them where they are even though they long ago passed the edge. Directionless wandering punctuated by lashing out at employees makes a corporate culture of foot-dragging and doing just enough to not draw attention to yourself. Standing out means risking your neck, and there simply isn’t a good reason for that kind of whimsy.

So what happens when an employee or two simply decides that, provided their coworkers think the outcome of a given project would be of value to them, they are going to do whatever they think will help the company and the owner can just get over it? Well, in this case you end up in quite a few meetings about how disappointed in you the owner is, but the completed projects never go away. The ambition may get you in trouble, but if the work is good enough a manager would have to be actively working toward sinking the company to actually fire people. Business owners are the final word in whatever happens; that is their prerogative and their right. Genuine awesomeness, though, cannot be denied.

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