Micromanagement

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If you don't trust the people who work for you, you're going to fail. This is a pretty simple equation, but one that's commonly misunderstood by most people, especially entrepreneurs, and especially entrepreneurs whose job it is to lead people. 
 
That's because most people confuse delegation with trust. Or rather, they don't put trust into the people they delegate out to until it's too late, setting those folks up for failure. That, ultimately, sets the entrepreneurs/leaders up for failure, and usually leaves them questioning where the hell they went wrong. Or, worst-case, blaming their underlings for their demise. 
 
Those are two great words—"underlings" and "demise"—aren't they? I mean, you rarely get to use them in the right context so I feel pretty good about shoehorning them into one sentence. 
 
Anyway, here's how that happens and how to keep it from killing you. 
 
The entrepreneur, the true entrepreneur, is the one who came up with the idea, got it working, and learned, tweaked, pivoted and scrapped over and over again until people started paying for it. This is a BIG DEAL. This is the baseline definition of an entrepreneur: People who get other people to pay for the crazy bleep they come up with out of thin air. 

And this is good. This happens to be my favorite part of entrepreneurism. The Holy-Crap-Someone-Just-Handed-Me-Money-For-That moment. Honestly, I don't even care about the money, it's the switch that gets flipped in the brain that signifies the quantification of worth—but I digress. 
 
So at some point entrepreneurs can't do everything themselves, and they have to start bringing other people on to carry out some of the more mundane tasks—and by mundane I mean anything that the participation of the entrepreneurs themselves isn't 100% critical in carrying out successfully. 
 
This is also good. The problem is that any true, good entrepreneur thinks that EVERY task requires 100% of his/her participation to be successful, so he/she often do one of two things: 
 
  1. Hire people and underload them. 
  2. Hire people and train them to do things EXACTLY the way the entrepreneur does them. 
This works a ridiculously small amount of the time. In some situations, the entrepreneur has to hire drones, people to do cookie-cutter work usually related to manufacturing the product. But in most startup cases, entrepreneurs should be hiring right—and by that, I mean they're going out and finding people who are smarter than them to offload tasks in the hopes that those people will execute those tasks better than they could themselves. 
 
But then those same entrepreneurs browbeat them, cajole them, or otherwise convince them that the only way to be successful at those tasks is to do them EXACTLY the way they did them or think they should be done. 
 
This is because entrepreneurs can't give up their babies. In other words, they fought so bravely and worked so hard to get to that money-exchange moment that they're convinced any deviation from the process they developed over that long and winding road will eff things up, instantly and forever. 
 
Entrepreneurs. This. Is. Not. The. Case. 
 
It is at first. There's always a learning curve. Your startup, if it's done right, should be doing new things in new ways and have its own process, language and muscle memory. It can be hard to teach, but at some point entrepreneurs have to recognize when that training period is over, and then let the employees be the brilliant people you thought they were in those seconds before you pulled the trigger on hiring them. 
 
If you don't, they'll resent you, or they'll shrink away into whatever role you've carved in stone for them, and you'll stagnate. Or they'll quit, and you'll have to do it all over again. 
 
Don't make this mistake. At some point in an apprenticeship, pull your employees aside and tell them the warranty period is over, and you expect them to show up and execute your vision in new and exciting ways. Let them make their mistakes, because they'll compensate for them 10 times over down the road. 
 
If you can't do this, then you hired the wrong people, or maybe you're just destined to be a middle-manager. Because honestly, middle managers are the only ones who have time for that kind of micro-management anyway.