5 lessons in leadership I learned from some of the worst bosses I experienced

I’ve been very fortunate throughout my career in that I’ve worked with and for some wonderful companies, had some fantastic mentors and some first-rate colleagues! They provided me a solid foundation in leadership, business and communication that I use to this day. But if I’m honest, I have learned as much if not more from the horrible bosses in my life as I did from the shining stars. Working for or with some of these people was so painful, if not downright traumatizing, that it burned into my psyche the importance of NEVER doing these things. I encourage you, if you are working for ‘that guy/gal’ to a) Get out! Get out now! And/or b) take heart that even the worst of bosses may be teaching you something valuable.

On the other hand, maybe you ARE that guy/gal. If you see yourself in any of these examples, then that alone means you still stand a good chance of changing. Unless they are a dyed-in-the-wool sociopath, most people behave badly out of either ignorance or fear. Unfortunately, there is also a tendency for people to become addicted to their perceived power and stop seeing the people they lead as human beings. Sadly, the ones these people hurt the most end up being themselves, because you can fool the world but usually your own conscience will convict you. If any of these ring true for you, consider talking to a professional and changing the course of your leadership – which is also your legacy.


1)      The Truth-Challenged

Almost every leader has to struggle with how much information to provide their employees. Those who decide that less transparency is best usually cite competitive vulnerability or lack of employee ability to understand the information as reasons for keeping information close to the vest. As a leader that’s up to you, but there is a line between discretion and outright lying. I remember on business trip my colleague and I were traveling with our boss, who told us employees that we had to stay at one (cheap and shoddy) hotel, which unfortunately was booked so HE would be staying at the 5-star down the street. Little did he know that we were close friends with the company travel agent and quickly made a call to determine whether that was true (it wasn’t). Lying about things may seem to be the simple and expedient path but being caught by your employees in a boldface lie can damage your credibility forever. It’s not worth it!


2)      The Drunk

Most people enjoy a social cocktail every now and then, or maybe even more than one. To each their own, but if you have developed a dependence or an addiction to a mind-altering substance there is no way this won’t affect your career. I had a wonderful and charismatic mentor at one point in my career whose impact on my life was immeasurable. Unfortunately, this person also drank. A lot. Whenever we would meet, they ensured alcohol was involved and they would keep it flowing, turning every event into a party that others might not have wanted to attend. Worse, there were times when we’d have long conversations and they would give me assignments and then clearly not remember them later. They would show up smelling of alcohol and their behavior was erratic and unpredictable. This is heartbreaking because many times alcoholics are high achieving, sensitive and just plain awesome individuals who deal with stress or latent perfectionism by numbing it out. But once it turns into an addiction they become very hard to work for/live with and until they recognize it’s a problem life for everyone involved becomes a tornado of destruction.


3)      The Bully

We’ve all experienced a bully at some point in our lives. This is the person who belittles you, demeans you or is basically just a jerk to everyone in order to get what they want. The bully likes to throw you off guard and try to catch you up. Bullies are usually fearful people who think the only way to stay ahead is by keeping other people down. They will prey on your weakness and leave you feeling exhausted and demoralized. One of the happiest days of my life was when I was finally laid off by my bully (note…the only way to deal with a bully is to stand up to them, but when they own the company it doesn’t mean you will survive the stand-off…and that’s okay). Bullies think it’s okay to swear at you, yell at you and blame you for their own inadequacies. My favorite bully line? “I don’t understand what you’re even doing around here…our culture is terrible and people are all leaving. Why don’t you do your job and fix our culture?”


4)      The Narcissist

The Narcissist and the Bully are related but separate. Whereas the Bully may not have gotten enough hugs growing up, the Narcissist probably got too many. These folks believe to their core that they ARE the smartest, most important people in the room and you exist to serve them. Their ego knows no bounds and you are simply along for the ride. When you encounter a narcissist with a noble vision, it can be exhilarating as the power of their convictions can carry you and the company through a storm and leave you committed to achieving the greatness they know they are destined for. Just know that Narcissists are incapable of giving back, so these relationships usually end up in the painful realization that the only one the Narcissist truly cares about is themselves and you are at best a valuable tool to achieving their goals and if you lose your utility you lose your place in the sun.


5)      The Politico

This may just be the worst of the bad bosses in terms of the emotional disruption. These folks see work and life as something to be ‘spun’. They don’t trade in power or information so much as relationships and they are very, very good at imitating actual leadership qualities in order to build alliances. You can tell a true leader from a Politico by their fruit. Do they sow unity, growth and respect for people or are those just words that precipitate backbiting and coups? Typically these people use flattery and rhetoric to gain allies but eventually their true colors emerge as they begin to reveal hidden agendas masked as ‘strategies’ and lies couched as ‘spin’. If you have a boss who has thrown their boss or other peers under the bus, stay clear. Do. Not. Trust. Them.


Although these were the worst of the worst, here are some other bad boss examples to avoid:

The boss who always wants to promote ‘friendly competition’ between employees in order to drive performance (patronizing at best and downright destructive at worst).

The boss who blatantly IM’s and texts people while in a one-on-one with you, is unprepared for meetings with you or does other things that make it abundantly clear that you or your time are just not that important to her.

So thank you, horrible bosses, not only for the years and years of anecdotes and column-fodder you provided me, but also for showing me the value of honesty, respect, integrity, patience, gentleness, joy, kindness and self-control. 




“Please stop ruining your company” – HR’s role in dealing with difficult bosses

I have been fortunate enough to have been asked to speak at my SHRM chapter in May and the topic will be HR’s role in dealing with difficult people.  Human Resources professionals have consistently been growing into a strategic presence in organizations and we are often relied upon at the senior planning table to help articulate, conceptualize and implement plans to achieve organizational goals.  This is an absolute win and I have seen how organizations benefit from having us be part of the process.  As most people have experienced at one point or another in their lives, however, even the best laid strategic plan will fail in the hands of toxic people.  This is truly where a skilled HR professional can bring maximum value to their role.  

But it’s not easy.

Anyone who has been in a senior HR role for any amount of time will have experienced the ‘bad boss’ phenomenon.  It starts with rumblings or maybe an employee or two in your office talking about what a ‘jerk’ such-and-such manager is.  Further investigation reveals that yes, the manager in question is not upholding corporate values and is inconsistent, disrespectful or even downright mean.  Although this is not pleasant, it is somewhat routine for a seasoned HR professional (or great consultant/coach) to address first or second level managers on their conduct.  

But what do you do when the toxic person is the most senior executive, owner and/or your boss?  I have spoken to countless HR professionals and this is probably the number one reason why great HR people leave organizations.  For that matter, it’s the number one reason why any great people leave an organization.  From an HR perspective, this can be one of the most challenging and stressful experiences to deal with.  There are many different ‘difficult people’ profiles an owner can fall into but as a very general rule these people are: Highly driven, perfectionist, high need for control, intelligent, somewhat blind to their weaknesses, capable, achievement oriented and tending to take things very seriously.  Frankly, these skills are necessary for entrepreneurs and almost any owner or CEO will have these traits to an extent.  The ‘difficult’ part comes in when one or more of these attributes outweighs others or eclipses their social/emotional intelligence.  That is the recipe for toxicity.

When the owner of the company is creating a culture that is drastically undermining the mission of the organization there are only three outcomes: 
1)    They will realize what they are doing, become willing to change their approach and do so
2)    They will realize what they are doing, become willing to change their approach but be unable to do so
3)    They will refuse to acknowledge the destructiveness of their behavior and refuse to change.  

Usually the ‘realization’ comes from a series of very predictable pain points such as employee turnover, customer loss or other negative feedback.  This is a critical point of impact for the HR profiessional.  Often, we will be the ones requested to present this information to the owner.  This is a very vulnerable position and needs to be handled carefully.  It is my experience that until this pain point is reached, change is unlikely.  More often than not, the HR professional, as messenger will be the focus of the owner’s discontent with the feedback.  Just because this is uncomfortable, does not mean it should be avoided.  There comes a time in everyone’s professional career where we must weigh out what’s right and wrong as well as whether we are willing to continue in a situation if it doesn’t change.  In other words, working with the toxic owner also will produce a pain point spurring action.

Once the owner realizes their problem and becomes willing to change the HR professional is again a valuable asset.  We can either provide access to coaching or sometimes we are the coaches and this will be both challenging and rewarding.  

There are also the situations where the owner does not acknowledge a problem with their behavior and to the HR professional and much of the organization the behavior is intolerable.  When this happens, unfortunately there are not many alternatives.  IF the behavior is truly egregious the company’s future success is in jeopardy.  It is sometimes worthwhile to stage an intervention with other key executives in the company to try to force a realization on the part of the owner but if that does not produce a desire to change, it may be time to select a new opportunity.  

In the end, becoming adept at helping bad bosses become great leaders is one of the most important contributions of a talented HR Professional.