I know that many of my readers are either current or aspiring business leaders.  Having a leadership position comes with many benefits:  self-satisfaction, higher pay, the opportunity to make more of an impact in business and the world, and the opportunity to leave a meaningful legacy.

Don’t miss updates on Procurement & Supply Chain, Subscribe here!

Like just about anything with attractive advantages, there are disadvantages.  One such disadvantage is the vulnerability of your reputation and legacy.

There is a lot of professional and personal scrutiny that leaders have to endure.  A leadership position brings with it certain standards of behavior.  And if those standards aren’t met by a leader, the public will be far less forgiving compared to how they may react if a non-leader behaved identically.  As the saying goes, “the bigger they are, the harder they fall.”

A leader certainly can make – and survive – business mistakes.  When you take business risks and break new ground over the course of a career, you can earn a veritable pass when some risks don’t pay off and your reputation will remain largely intact.

History’s best leaders have made major business mistakes.  That’s because they didn’t play it safe.  Because playing it safe never results in game-changing breakthroughs.  Middle management in companies everywhere is filled with people who are scared to make decisions, always play it safe, and will never be a household name.  So, as a leader or aspiring leader, expect to make business mistakes if you have any desire to be remembered as a great leader.

But, if you want to be a great leader and leave a great legacy, there is one type of mistake that you should never make.  If you make such a mistake, you will have a hard (or, more likely, impossible) time overcoming it.

No self-respecting subordinate would want to follow you.

No self-respecting board of directors would want to hire you.

No client would want to be associated with putting money in your pocket.

What type of mistake am I talking about?

A moral mistake.

Though many people think moral mistakes are easy to avoid because there is a clear distinction of right and wrong, by the volume of celebrities, sports stars, politicians, government officials, and, yes, business leaders who make them, it is clear that there is not nearly enough guidance for avoiding moral mistakes.  The following are some examples of moral mistakes to avoid at all costs if you wish to be, and leave the legacy of being, a great leader.  Some of the examples are also illegal activities but are included because they too represent mistakes that are almost impossible to overcome:

  • Making comments that can be construed as racist
  • Making comments that can be construed as sexist
  • Making insensitive comments about a physical disability or someone with that disability
  • Making insensitive comments about a mental disability or someone with that disability
  • Making insensitive comments about a religion or someone who practices that religion
  • Making insensitive comments about a sexual orientation or someone with that sexual orientation (inluding using the word “gay” as an adjective in a negative context)
  • Making insensitive comments about an ethnicity or someone who is of that ethnicity
  • Making insensitive comments about individuals in less prosperous financial situations
  • Engaging in any activity that is egregiously wasteful (including the waste of money, food, etc.)
  • Engaging in any activity that harms animals or promotes the harm to animals
  • Engaging in any activity that is environmentally irresponsible
  • Engaging in sexual harassment
  • Participating in an act of prostitution
  • Engaging in adulterous activity
  • Embezzling money or otherwise obtaining financial benefit through fraudulent actions
  • Initiating any type of unwanted, aggressive physical contact with others, ranging from pushing to spitting to hitting, etc.
  • Making fun of or downplaying the seriousness of sensitive topics like rape, molestation, death,  domestic violence, etc.
  • Using sexual, profane or other inappropriate words or gestures in an environment where children could hear those words or see those gestures, either in person or via a media broadcast

It is important to remember that today’s world is very technology-driven.  Any thing you say or do can be recorded and shared with anyone in the world via ubiquitous smart phones and the Internet. And by its very nature, that “evidence” might never go away, possibly eternally inhibiting your ability to leave a positive legacy no matter what you’ve done in the past or what you will do in the future.

Just this week, I encountered a video that was being passed around on a social network.  This video was of a sporting event where a spectator was, over the period of more than 10 minutes, repeatedly making obscene gestures that were caught by the television network’s camera.  I was horrified to realize that I had met the offender as he is also an entrepreneur who has attended some of the same events I have.

There is a risk that this guy could essentially have all of his clients decide to not be associated with such behavior and pull their business from his successful company which, heretofore, has built a very respectable reputation.  He could literally lose everything.  He should feel fortunate that neither the video nor the accompanying article mentioned him by name and the activity was probably too obscene for some people to share with their friends and some news sources to share with their readers/viewers, limiting how widely seen it becomes.  He may have dodged a bullet that could have destroyed everything he had worked for in his entrepreneurial career.  It still could – remember that once a photo or video is on the Internet, it may never go away.

Let’s hope that he learned from this close call and will never make such a stupid moral mistake again.

So, as you climb the ladder of leadership in your career, remember that there are some mistakes you can make and get away with.  Those are the mistakes that are just part of business.

But if you want to leave an impressive and untarnished legacy of leadership, don’t let yourself ever make a moral mistake.


Charles Dominick, SPSM, SPSM2, SPSM3

Charles Dominick, SPSM, SPSM2, SPSM3 is an internationally-recognized business expert, legendary procurement thought leader, award-winning entrepreneur, and provocative blogger. Charles founded the Next Level Purchasing Association in 2000, oversaw its incredible growth, and successfully led the organization to its acquisition by the Certitrek Group in 2016. He continues to blog and provide advisory services for the NLPA on a part-time basis as he incubates his upcoming business innovations. Charles is also the co-author of the wildly popular, groundbreaking book, "The Procurement Game Plan: Winning Strategies & Techniques For Supply Management Professionals."

More Posts