A Sure Fire Way to Succeed at Failing: Hire the Wrong People

Matthew Caiazza
2 min readNov 5, 2019

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Advice from The Failure Guru for entrepreneurs on how to tank your company

Hiring and retaining great talent has always been difficult for those who are striving to build a profitable and enduring business. However, since you ultimately want to tank your business, how can you ensure that you hire the wrong people to help you achieve your goal? One may think that is easy to do…just hire somebody woefully under qualified for every position and just like that you will fail! But wait…would you rather be a flash in the pan failure or would you rather fail in an epic manner? If you are looking for a quick way to fail, don’t waste your time reading this. The Failure Guru’s advice is for those who want to go big or go home. It’s advice for those who want to f%$& up big-time.

So, hire people who are qualified. But while interviewing, make sure you both develop a quick connection with one another. Let that person sell you on why they should hire you. Hiring people that you are able to personally connect with is a great way to surround yourself with people who worship the ground you walk on, because after all, as a leader it is important to be liked. If you are not liked no one will be willing to put up with your micro-managing, no one will crave your attention and above all, you won’t have people around to validate your ideas, strategies & objectives. In other words, you won’t be able to surround yourself with people who tell you what you want to hear.

Because some people are really good interviewers they may be able to fool you into thinking they like you (which is probably easy in the first place) so I have used a great question towards the end of the interview that really puts them on the spot. At the end of the interview, after I have stopped talking about myself and my company, I ask, “So…enough about me, now why don’t you tell me about me.” If they can get through that question without stumbling, you’ve got yourself a winner.

Takeaway: Just as important as hiring a qualified person is hiring someone with whom you have formed a connection. That connection will ensure loyalty and retention which will become important once everyone figures out that you are really trying to take the company down, otherwise, you won’t have anyone around to blame when it implodes.

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Matthew Caiazza
Matthew Caiazza

Written by Matthew Caiazza

I am an entrepreneur and CEO who is passionate about helping businesses and helping others.

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