Black Friday Sale! 50% Off All Access

The 7 Easiest Ways to Insult Important People We live in an increasingly thin-skinned world, and some of the most successful people are the worst offenders. Here's how to avoid getting on their bad sides.

By Steve Tobak Edited by Dan Bova

Entrepreneur+ Black Friday Sale

Our biggest sale — Get unlimited access to Entrepreneur.com at an unbeatable price. Use code SAVE50 at checkout.*

Claim Offer

*Offer only available to new subscribers

Opinions expressed by Entrepreneur contributors are their own.

Brooklyn is a great place to be from. People tell it like it is and wear their hearts on their sleeves. What you see is what you get. And your so-called friends have no problem ripping you apart one second, then giving you a bear hug and saying, "You know I love you, man" the next … and really mean it.

Since I grew up there, I'm very thick-skinned. It's nearly impossible to surprise me, rattle me or insult me. On the contrary, I tend to take abuse as a sign of affection. The theory is, if you didn't care, you wouldn't bother to give me a hard time.

Even if you do somehow manage to rub me the wrong way, I have no problem letting you know and giving you a chance to explain.

Unfortunately – and I say this with deep humility – most people are not like me. You can insult them and never even know it. And whatever relationship you had or were hoping to achieve will simply evaporate like it never even happened. I know that because, like those I grew up with, I tend to speak my mind and let the chips fall as they may.

Related: How to Think Differently to Succeed in a Complex World

To make matters worse, the cultural trend is definitely moving in the thin-skinned direction. Political correctness is rampant. You can offend people without even realizing it. And all too often, they're not man or woman enough to let you know.

That's why I despise political correctness and don't appreciate being around thin-skinned people.

That said, if you're trying to impress or cultivate a relationship with a potential mentor, a senior executive, an important client, a venture capitalist – those who are accomplished or think they are and perhaps take themselves a little too seriously – here are seven things you probably shouldn't do if you want the relationship to continue.

Ask for their help and don't follow through. People are always thanking me profusely for taking the time and sticking my neck out to help them. I think that's nice, but the truth is, the only appreciation I really need is to see you get something out of it. That's why I do it. But if someone goes to bat for you and you don't follow through, that's likely to be the last time they lift a finger to help you.

Invite them to your daughter's wedding. Yes, this does happen occasionally. Some people are so warm and appreciative they feel sort of an intimate connection. Sadly, if the feelings aren't reciprocal – which they usually aren't – it puts them in an awkward position and nobody likes having to feel awkward. In all likelihood, they'll make up some excuse to decline the invitation and then suddenly become very scarce.

Related: 9 Reasons Why Most Startups Fail

Offer to buy them lunch. I once helped an associate get a CEO job right before the company's IPO. The guy made millions. What did he do? Offered to buy me lunch. That says that what I did for him was worth about $10. It also assumes I would want to go to lunch with him, which I didn't. A nice bottle of wine or a simple heart-felt "Thanks, I owe you one" voicemail would have been far more appropriate.

Overstay your welcome. I mean this in a broad sense. Just make sure you have a reasonable understanding of the value they're providing you. That way you won't abuse the privilege. If you're not sure, just ask them.

Try to BS or sell them. On the one hand, I'm virtually unoffendable, if that's even a word. On the other hand, I have a built-in BS detector and you can't sell me, either. I don't care how charming you think you are; don't even try. Those who've been around the block a few times will see right through it and they won't appreciate it one bit.

Waste their precious time. When I was in the corporate world, I didn't have time to breathe. Then I started my own company and now, I'm happy to say, I have time to enjoy life, give advice and mentor folks. It's truly gratifying. But there are a lot of self-important people out there who think their time is way more precious than yours. Just be aware.

Put them on some dumb email list. What goes through people's minds that makes them do something so annoying, I can't even begin to imagine. But it happens way more often than you'd think. I know they mean well, but it's so not cool, it isn't funny. And all it does is ensure that, from then on, your emails go straight to the spam folder.

Sure, it would be great if everyone in the world was open and genuine, nobody offended anyone, and we all just got along. Funny, but in my experience, it always seems to be the thin-skinned PC people who say that sort of thing. They're also the first ones to feel offended or outraged at the drop of a hat and cut you off without a word of warning.

Related: An Entrepreneur's Guide to Personal Grooming

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at stevetobak.com, where you can contact him and learn more.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Making a Change

This All-Access Pass to Learning Is Now $20 for Black Friday

Unlock more than 1,000 courses to fit your schedule.

Health & Wellness

How to Improve Your Daily Routine to Strike a Balance Between Rest and Business Success

Here's how entrepreneurs can balance their time and energy to prevent burnout.

Business News

The Two Richest People in the World Are Fighting on Social Media Again

Jeff Bezos and Elon Musk had a new, contentious exchange on X.

Business News

Barbara Corcoran Says This Is the Interest Rate Magic Number That Will Make the Market 'Go Ballistic'

Corcoran said she praying for lower interest rates and people are "tired of waiting."

Money & Finance

Why Donald Trump's Business-First Policies Trump Harris' Consumer-Centric Approach

President Donald Trump's pro-business agenda is packed with policy moves encouraging investment to drive economic growth. The next Congress has a unique opportunity to support entrepreneurship and innovation, improving U.S. competitiveness with the rest of the world.