top of page

Startups: 3 Bad Leaders, 3 Good Leadership Lessons

“Who’s the worst leader you ever worked for”? That’s the question posed to me recently by a senior HR executive. I did not answer immediately, reflexively. I almost said a name but hesitated because another came to me, then another and yet, another still. Epiphany. Many of the people I have worked for in my long career have not been good leaders. Many have ranged from mediocre to horrible, especially CEOs. But, as you can learn from failure as you can from success, you can learn from bad leaders as you can from good leaders

Bad Leader 1, The Tantrum

My startup CEO was mercurial in behavior and judgement, arrogant in opinion, dismissive of the senior staff and morally duplicitous. He once threw a Rolex (of course) watch across the office, just missing his terrified secretary. His leadership style was Darwinian: let the wolves fight amongst themselves and the best vice president would emerge. He had a long standing affair with a young woman in the office (yes, he was married with children). He attacked anyone that he deemed to be a potential threat to his position. He lost the respect of the executive staff, dampened the sharing of new ideas and created a talent drain at all levels.


You cannot “manage up” with such an insecure and volatile personality. Eventually such a leadership personality resents your stable, professional behavior and will make you a target. Attempting to manage up in this scenario will impact your own leadership effectiveness. If you are working for this type of leader, you should move on to another opportunity.

Bad Leader 2, The Elitist

This Senior Vice President was resentful of anyone that did not have what he thought was the only correct career path (meaning, like his). Anyone outside his linear frame of reference was suspect and diminished. He openly dismissed a non-Ivy league education as worthless. His misogyny was barely subsurface and his jealousy of other’s camaraderie drove him to physically reassign office seating, including entire teams. He lost the office and became isolated and ineffective. No one, absolutely no one respected him and not a single person kept in touch with him post-employment.


Never project an elitist, exclusive attitude. Do not be threatened by different backgrounds nor team camaraderie. Promote these and engage your team and they will help you lead. You will learn something new.

Bad Leader 3, The Violator

This startup CEO was brilliant, well educated, charming, kind and inclusive. He engaged everyone on a personal level, spent time to chat with the most junior employees. He was a pillar of his social community. So why is he on this list? In a time when most everyone is tolerant of character flaws, do not judge someone’s private life and forgive most any transgression in the pursuit of a unicorn IPO, this man crossed a line accepted by all. His transgression sent him to prison and his future leadership opportunities were effectively eliminated.


It is not just what you do at work, but what you (should not) do outside of work that will prevent you from leading in the future. It will also mitigate or even destroy your previous leadership-driven positive results. Some personal behavior is beyond professional redemption. Act accordingly if you wish to continue to be an effective leader.

Every leader you work for offers an opportunity to learn, even the bad ones. And it is beyond the obvious “do not do what they do”. The lessons they offer are deeper than the manifested symptoms that can destroy a company.

Throwing a Rolex is not just a temper tantrum, it is an abundance of disrespect for your team, management by fear, fear of not appearing smarter, stronger and greater than anyone else. Good leaders surround themselves with smart people and listen to them, empowering everyone including themselves.

Dismissing others’ accomplishments, education and career path is not only narcissism, it is a lack of empathy and a badge of insecurity and uncertainty. Be secure, be confident yet respect and welcome diversity of experience. Seek it out.

Online activity at work that crosses a moral and legal line is not just giving in to base impulses, it is, again, a lack of respect for others and will destroy your legacy. Your private life is just that, but it can, once public, negatively impact your effective as a leader, now and in the future.

The lessons are there from bad leaders as well as good.

4 views0 comments


bottom of page