Trump’s business prowess was cited by many of his backers as the main reason for their support.  Detractors said his business success was not due to his business savvy, but was more likely due to the millions left to him by his father.

Entrepreneur Magazine published an article back in October of this year called 22 Qualities That Make a Great Leader. Please read it, it’s a great piece!  I thought it would be interesting to see how many of these qualities are possessed by our new President-Elect, Donald J. Trump.  Let’s get started!

  1. FOCUS

Given Trump’s susceptibility to being “Baited by a Tweet,” and the nature of his “majoring in the minors” responses, I think this is an easy call. FAIL!


At first glance we might assume, given his bombastic nature, that he exudes confidence. I disagree. I believe his over-the-top behavior is a defense mechanism for deep-seated insecurities.  Confident people don’t need to defend themselves against petty charges.  They also seek out strong subordinates that will challenge their decision making, not simply validate it.  Confident people don’t feel the need to tell others how great they are.  FAIL!


I don’t feel the need to examine this closely.  When it comes to medical and financial records alone, Trump is one of, if not the most secretive Presidents in our history. FAIL!


Integrity is impossible without honesty.  According to just about any fact-checking organization associated with the election, honesty has been a problem for Mr. Trump.  FAIL!


Adam and Jordan Bornstein, authors of the wonderful piece in Entrepreneur, use quotes to exemplify what they meant by each quality.  I will use a few of their selected quotes here and below: “People always say I’m a self-made man. But there is no such thing. Leaders aren’t self-made; they are driven. I arrived in America with no money or any belongings besides my gym bag, but I can’t say I came with nothing: Others gave me great inspiration and fantastic advice, and I was fueled by my beliefs and an internal drive and passion. That’s why I’m always willing to offer motivation—to friends or strangers on Reddit. I know the power of inspiration, and if someone can stand on my shoulders to achieve greatness, I’m more than willing to help them up.”

—Arnold Schwarzenegger, former governor of California

There is no question that Trump motivated his base to go to the polls, pulling off, (possibly with Russia’s assistance), the most unexpected win since Truman beat Dewey.  But there is a difference between motivation and inspiration.  During an IRS audit a tax examiner, (and fear of prison), can motivate you to pay your taxes, but my guess is you won’t feel very inspired.  Schwarzenegger talks about inspiring others to help themselves.  Trump’s motives are clearly to convince his followers to help him get elected, and not much else.  During the Primaries and the General Election, if Trump highlighted a follower by bringing them on stage, it was usually, if not always to have them heap praise on him.  That isn’t inspirational.  FAIL!



“You must love what you do. In order to be truly successful at something, you must obsess over it and let it consume you. No matter how successful your business might become, you are never satisfied and constantly push to do something bigger, better and greater. You lead by example not because you feel like it’s what you should do, but because it is your way of life.”

—Joe Perez, cofounder, Tastemade

I do believe that Trump has a passion, and he certainly obsesses over it.  Unfortunately, that obsession is himself over anyone and anything else.  Sad but true, so technically a PASS!


I couldn’t think of any innovation that Trump had championed, so I Googles “Trump Innovations.”  All I found was an article by Forbes discussing how Trump would be “A Disaster for Innovation.” We will call that a FAIL!


Ok, stop laughing, this is serious . . . He’s going to be our next President!  FAIL!


Here is an amazingly applicable quote! “It’s inevitable: We’re going to find ourselves in some real shit situations, whether they’re costly mistakes, unexpected failures or unscrupulous enemies. Stoicism is, at its core, accepting and anticipating this in advance, so that you don’t freak out, react emotionally and aggravate things further. Train our minds, consider the worst-case scenarios and regulate our unhelpful instinctual responses—that’s how we make sure shit situations don’t turn into fatal resolutions.”

—Ryan Holiday, author of The Obstacle is the Way and former director of marketing, American Apparel

Trump’s tweets have proven over and over that he acts or reacts with little thought to the consequences, intended or unintended.  FAIL!


If Nonwonkiness was a word, Trump would be the prime example.  “Who is Donald Tump” will never be a Jeopardy answer to “He is widely known as the Policy Wonk President.”  FAIL!


The bad comb over combined with the orange glow of a spray tan fails to shout authenticity.  As for the “He tells it like it is” refrain that commonly comes from his supporters . . . If much of what he was saying wasn’t found to be a lie, I’d agree with you.  FAIL!


Trump has admitted that his circle of trust is small, rarely extending past his older children.  Beyond that, Trump is open to your suggestion if and only if you are suggesting that he is absolutely right, as always.  FAIL!


This one is fairly easy.  Trump is decisive in the same way a bridge jumper is decisive in committing suicide.  As I said earlier, he often makes decisions with little thought to the consequences.  PASS!


“We all provide something unique to this world, and we can all smell when someone isn’t being real. The more you focus on genuine connections with people, and look for ways to help them—rather than just focus on what they can do for you—the more likable and personable you become. This isn’t required to be a great leader, but it is to be a respected leader, which can make all the difference in your business.”

—Lewis Howes, New York Times bestselling author of The School of Greatness

You have probably heard his advocates say that he’s very nice in person.  Something one only needs to say about someone that isn’t very nice in general.  In Trump’s own books he points out that he wants those he deals with to respect him, but more than that he hopes they fear him.  That’s not very personable.  FAIL!



The only empowerment extended to staff is the authority to ask for his approval.  FAIL!


Again with the laughing . . . FAIL!


Trump just announced on Christmas Eve that he is closing his charity.  Records indicate that his last contribution to his own charity happened in 2008.  After an event to raise funds for Veterans during the Primaries, Trump had to be shamed, by the press/media, into actually making those donations.  It appears clear to me that donations are just another tool Trump uses to get a desired result for himself.  FAIL!


Trump is persistent in his unconventional approaches, even in the face of logic, truth, and negative repercussions.  PASS!


“It takes insight every day to be able to separate that which is really important from all the incoming fire. It’s like wisdom—it can be improved with time, if you’re paying attention, but it has to exist in your character. It’s inherent. When your insight is right, you look like a genius. And when your insight is wrong, you look like an idiot.”

—Raj Bhakta, founder, WhistlePig Whiskey

Trump’s ability to separate the important from the unimportant is easily described in a tweet.  FAIL!


The number of times that Trump and his team disagreed on a given subject, on TV, on the same day, indicates communication isn’t a strong suit.  There are other great examples as well.  FAIL!


Ok, the laughter is absolutely getting out of control!  Settle down now!  FAIL!


“It takes real leadership to find the strengths within each person on your team and then be willing to look outside to plug the gaps. It’s best to believe that your team alone does not have all the answers— because if you believe that, it usually means you’re not asking all the right questions.”

—Nick Woolery, global director of marketing, Stance Socks

Since I’m not privy to insider conversations, I am unable to conclusively discern between restlessness, as articulated in the quote above, and what has been described as utter chaos within the Trump inner circle.  So, I’ll call this one a PASS, but I suspect otherwise.


Ok, by my count that’s 4 passes and 18 fails.  That’s a score of 18% on a 100% scale.

Is the scoring subjective?  Sure, opinions will vary greatly on this, so I want to know how you scored it!  Please leave a comment with your thoughts!



The kind of person, (along with their qualities), we select to occupy the Oval Office matters.  It is reflective of who we are as a society and the values we hold dear.  I fear we have collectively failed this cycle, only time will tell.

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