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The Entrepreneur's Curse: Watching The Watchman! Your company wouldn't exist without you, but once you begin hiring you've got to get out of the way and let your employees do their jobs.

By Issamar Ginzberg Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


Once upon a time, a long time age, there lived a wealthy man named Eugene Moneybags. He was quite wealthy for his time and station in life, being by far the richest man in his little village, and one who could afford the type of toys that were out of reach of most people of his background -- certainly of everyone within a day or two of travel from where he lived.

Eugene was always looking for ways to further advance his reputation as a sophisticated gentleman. And so, he purchased a strong, white, muscular Lizzipian horse -- a truly unique find, and one that was not usually owned by someone like Eugene. He paid top dollar for his horse, and proudly rode it home to his village, so everyone would see that he, Eugene, was a true gentleman who understood the finer forms of the high life.

But there was a concern that haunted Eugene. He was worried about the possibility that along with word spreading about his prized racehorse, so too did chances increase that horse thieves would hear about it. The thought that they might try to sneak in during the hours of darkness and steal his horse made Eugene shudder. So, to ensure that his prized possession would not be stolen, or come to any type of harm, Eugene did what any smart and wealthy person would do; he hired the top builders to come and build a huge, comfy, protective barn for his horse. He bought the finest oats for his horse to eat. And a special "horse Jacuzzi" was built, in the most advanced style of the day. To top it off, Eugene had a stone and metal fence and gate built around the perimeter of his property, to keep those with nefarious motives at bay.

Hire an expert.

But even so, with all this having been done, Eugene was still a bit concerned; perhaps what he did was all very nice in theory, but just maybe thieves would break in anyway, though all these protections. He was concerned that his horse was so valuable that it would all be for naught, and that one morning he'd wake up to find his barn empty and the horse stolen. And also gone would be much of his money and his reputation for having risen above his upbringing to true sophistication. So as he drank another glass of wine (that he didn't appreciate all that much for its taste, even though the bottle was fancy and the wine was expensive), he wondered what could he do to make sure that the horse would be there every morning when he woke up.

Eugene has the perfect answer. He sent a messenger to the big city to ask the constable in charge for the most muscular, stern looking, watchman that could be found. He promised to pay top dollar to have said guard move to his village and become the personal guard of his special horse, now named Purpled Royale XII.

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The watchman who accepted the job at the constables' recommendation came to the village to become the guard.

Eugene felt that this guy was the right person for the job. He instructed his horse watchman to spend every moment in "profound thought;" this would serve to ensure that the watchman was able to stay alert, sharp and awake to ensure that his ultimate duty, watching Purpled Royale XII, was properly done.

Sleepless nights.

Satisfied with his hire, Eugene went into his master bedroom and lay down in the luxurious Egyptian linens, to sleep and rest up from his long day.

But Eugene could not, as hard as he tried, fall asleep. So after two hours of tossing and turning, he put on his robe and slippers, and went outside to check on his precious horse -- perhaps his watchman had fallen asleep after all.

Related: Entrepreneurs, Have No Fear of Trusting Your Employees

The guard was wide awake. "What are you thinking about?" Eugene asked the guard. "Something deep, to keep you alert, as we discussed?"

"Certainly, sir!" answered the guard, bowing slightly to Eugene. "Here's what I'm pondering at the moment: when someone eats a bagel, what happens to the hole in the center? Where does it go during the "bagel eating process"? It wasn't eaten, so it should still be there ... and yet, it disappears into thin air!"

It was the perfect response for Eugene. He, left satisfied that the job was being done well.

Toss. Turn. Another hour passed, and Eugene still could not fall asleep.

So, he put on his slippers and went back downstairs, out of the mansion and over to the gate where his newly hired horse security superhero sat, hopefully watching out for the safety of his dearly prized horse.

Demand honesty.

The guard was awake, with an expression of deep, intense focus clearly visible on his face.

"Watchman! What are you thinking about now?" he asked

"I'm thinking about…" The watchman hesitated.

"Go on…" Eugene encouraged.

"How can it be," continued the watchman, "that a man such as yourself spends so much time, energy and tremendous effort into buying a prized racehorse; builds a strong fence and stable to ensure its safety from thieves; hires the best watchman he can find, cost no matter; pays said guard extra to think deep thoughts all night -- and still that man can't fall asleep at night? How can it be? He should be able to sleep peacefully, knowing that his horse is as safe and secure and will be there in the morning when he wakes up!"

Related: 11 Things Smart People Don't Say

I love this fable as a great example of explaining some of the interesting reactions that happen when entrepreneurs and business owners hire a consultant or speaker, or outsource some job that has to be done to someone with expertise in that topic.

Don't be Eugene.

For many of those business owners, instead of being relaxed in the knowledge that they have offset much of their worry by paying an expert good money, they "super-supervise" those very same people they hired to do the work. Now, being in touch with your hired help is appropriate, and you certainly want to make sure that what they are doing is in line with your vision and expectations. But once those are discussed and agreed to, do not micromanage to the extent that the expert becomes nothing more than a "follow my exact instructions, don't color outside the lines," teenage, part-time, summer wait-staff worker.

In my experience, experts have two types of clients: The ones who want to understand what is being done, and why it's being done in that way ("Please explain to me why you use that style font?"); and on the other side, clients that don't care much about why you decided on a specific promotional giveaway, they just want it "done well and done now."

In the former case, being a consultant who works on an hourly (as opposed to project) retainer, I'm only too happy to explain what I'm doing and why I've chosen that particular path forward -- or why I wrote an email a specific way -- because it gives the client the opportunity to internalize a strategy for future use and other applications, and it takes time. It's a true win-win; I get paid to teach what I know, and they get additional insight that lasts a lifetime.

Related: 5 Lessons a Boss Should Learn From Employees

In the latter case, in theory it's not a problem to work that way -- and it's something which I've done many times. However, the truth is that a client should want, should crave, to have input into their product; it's their product and it's their investment to propel their company forward.

Another person can come up with a name, a brand, a story, an ad, a sales pitch, a PR pitch, and whatever else on their behalf, true. But it is the owner who is ultimately the person behind the product, not the outside hired help, be they autonomous experts or "robotic parrots," who do and repeat exactly what they are told. If the boss doesn't care at all, that's an unhealthy sign. A lack of enthusiasm or desire to be involved is something that employees and clients pick up on. Sort of like a restaurant owner who never tastes his own food, or cares what the menu offerings are.

There's a balance that every business owner should have, to hire the right people, and to be involved, while letting the people they hired actually do their job. It makes for better results, a better relationship, with an expert who can use their full mind and range of expertise to improve your business.

Be it help with product development, advertising, a Kickstarter campaign, a legal issue, copywriting, photography for your product, try to remember that you are supposed to be doing what you do best while letting the horse watchman -- the expert you hired -- get it done.

Because that's the reason you hired them ... remember?

Issamar Ginzberg

Entrepreneur, Columnist, Lecturer, Venture Capitalist and Consultant

Lecturing on three continents and with hundreds of thousands of entrepreneurs reading his advice each month, Rabbi Issamar Ginzberg certainly is the "purple cow" in the world of marketing strategy and business development. An expert on marketing psychology both offline and online, Rabbi Issamar uses his unique style and background to connect the dots and formulate strategy for entrepreneurs, execuitives and nonprofit organizations. He has lectured and consulted for companies like Google, National Geographic, the Jewish National Fund and major organizations in the USA, Israel, Europe and Austrailia.

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