Opinion: 7 Important—But Negative—Leadership Lessons from President Trump

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Donald Trump makes a trademark gesture at a 2016 rally in San Diego. Photo by Chris Stone

By Chris Jennewein

Libraries are full of the leadership lessons of America’s most respected political, military and business leaders.

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From “George Washington’s Leadership Lessons” to “Cigars, Whiskey and Winning: Leadership Lessons from General Ulysses S. Grant” to “Steve Jobs: Ten Lessons in Leadership,” there are thousands of books to help you master your professional life.

We can learn a lot for President Trump too — but only if we use him as an example of what not to do. Sure, he’s built a successful branding business, and even a few buildings in his early days, but much of his life is full of cautionary tales we can learn from.

Here are seven leadership “lessons” drawn from the past two years:

1. Always tell the truth

Whether it’s President Obama’s country of birth, Muslims cheering 9/11 in New Jersey or vaccines as the cause of autism, our President has a seemingly limited regard for the truth. In fact, he’s a big fan of conspiracy theories, often sharing them on Twitter. It’s great reality television, but not a useful tactic in normal life. For most of us, stretching the truth — let alone actual lying — will ultimately destroy relationships and careers.

2. Advance preparation is key to success

Trump reportedly told friends that he made up facts about trade during a meeting with Canadian Prime Minister Justin Trudeau. One supposed fact was a trade deficit with our northern neighbor when in fact there is a surplus. Making up facts may work for a supremely confident salesman, but not for most of us. It’s better to study up before an important meeting.

3. God is in the details

In his ghost-written book “Trump: Think Like a Billionaire,” he famously said that “it can be smart to be shallow.” Many of his shoot-from-the-hip polices show a profound disregard for the details. Whether it’s health care, transgenders in the military, steel tariffs or tax reform, the President doesn’t sweat the details. But in real life, it’s the details that ultimately determine success or failure. It’s hard work to master the nuts and bolts of a complex project, but most of us must do that to be successful.

4. Check the facts, but listen to your gut

Many problems are so filled with grey areas that it’s important to listen to one’s gut. But knowing the facts can help inform that gut. For Trump, however, it’s usually the other way around. Impulsive actions like the blanket steel tariffs have to be carefully walked back by staff, causing confusion (and often a big drop in the stock market). Listen to your gut, but only after learning all that you can.

5. Show loyalty to those you lead

Whether its criticizing Atty. Gen. Jeff Sessions on Twitter or chewing out long-time confidant Hope Hicks after her Congressional testimony, Trump appears to be the prototypical “boss from hell.” Perhaps it’s his decades as head of a family business, in which you can fight and still be family. But most of us don’t work in a family business. As managers and leaders, we need to support and develop those who work for us.

6. Deliver bad news in person

It’s hard delivering bad news to a person being fired. Trump delivered this news weekly on “The Apprentice,” but in the Presidency he delegates. FBI Director James Comey learned via news reports, Secretary of State Rex Tillerson by Twitter and Chief of Staff Reince Priebus when he was left at the airport as Air Force One departed. It’s courageous to deliver bad news in person, cowardly to delegate it and cruel to do it publicly.

7. Treat your adversaries with respect

Nicknames like “Pocahontas,” “Crying Chuck” and “Sleepy Eyes” draw laughs. They may even intimidate. But when the joke wears off, you may have an enemy for life. For most of us, treating our adversaries with respect is the best course. Be nice to those on the way up; you may need their help on the way down.


Chris Jennewein is editor and publisher of Times of San Diego.

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