Is your boss a prison warden or a party host?

Prison vs. Party

Here’s a scary tale from the real world:

When I was just starting out as a legal secretary, I worked for two lawyers who I referred to as Good Boss and Evil Boss.

Evil boss would never look for a file – he would yell for me to immediately find a particular FILE – which would be on his desk where he kept all of his working files.

In addition he would go through my in-box after I had left the office and rearrange the stack, move his work up and add new post-it notes with different deadline dates.

Three drafts to any document was the absolute minimum, and he often wanted to see the previous drafts for him to check my work. Consequently, my wastepaper basket was very organized.


The old leadership style of “I’m the boss, you must do whatever I say” is being challenged by a different style which is more about supporting people to let them create results.

While the old leadership style reminds me mostly of a prison warden, exercising absolute power over his wards, the new leadership role is completely different. It’s about making people like their jobs. It’s about realizing that people are in fact free to leave at any time.

In short, the new leadership style reminds me much more of the host of a party. Here’s how the two roles compare:

Prison warden Party host
Treats employees like prison inmates Treats employees like valued guests
Decides when people arrive and how long they stay Invites people – they decide whether to show up and for how long
Orders must be followed to the letter Can’t tell my employees what to do
Harshly punishes wrongdoers Focuses on acknowledgment and fun
Thinks employees must be watched or they don’t perform Knows employees want to do good work
Is in control Creates the setting – employees create the actual content
Work is a deadly serious matter Work is a lot of fun
Wants to control you Wants you to succeed

The good thing is that the prison wardens in the business world are being hit hard by Leadership Darwinism and are slowly losing their followers to better, more modern leaders. They’re left with only those employees who enjoy this treatment or those without the drive or the skills to find new jobs.

It’s all about freedom

So good leadership is like hosting a party. Why is that?

The answer is freedom. I believe that freedom is a basic condition of life. We are (mostly) free to choose.

When you go to a party, nobody can tell you what to do. Nobody can tell you what to think. Every time somebody gives you an order, you decide whether to carry out that order or not. You make the choice.

If people tried to give you orders, you’d quickly leave and probably never attend that particular person’s party again.

If you accept that we are free to choose, and that nobody can give anybody orders, then any order becomes instead an invitation. “Do this” is then the same as “I invite you to do this, but you choose whether or not to do it”. And this means that the leader is now a host, who has invited somebody to work towards some goal.

This is also true at work. Your boss has only as much power over you as you grant him.

The only power your boss truly has over you is the power to fire you. Take away this power, and you’re free.

Here are a few ways to do just that:

  • Live a low-rent life. Control your fixed expenses so that being fired is not an immediate financial disaster.
  • Increase your skills so it will be easier for you to find a new job.
  • Remind yourself that quitting or being fired from a bad job or a bad manager is not embarassing.
  • Remember that sometimes losing a bad job is the best thing that can happen to a person.
  • Remember how much more fun it is to be happy at work – and then find a job you can love.

So if your boss is of the prison warden variety, it’s time to get out of Cell Block D and go work for a boss who knows how to make work fun.

If you liked this post I’m pretty sure you’ll also enjoy these:

7 thoughts on “Is your boss a prison warden or a party host?”

  1. Most bosses would be in favour of “Freedom” provided that the employees are responsible enough to handle freedom. Sadly, not many employees are responsible enough to be given Freedom.

    After all no boss enjoys bossing people around. If employees are responsible enough to not be policed, it leaves the boss more time to focus on her own thing.

  2. I think you’re partly right Nikhil, but the important thing to remember is that most employees like being given responsibility and tend to live up (or down) to the expectations managers have of them.

    Treat employees like responsible adults capable of making decisions for themselves and they mostly will be.

    Treat the like mindless serfs who must be micro-managed every step of the way and they will be just that. Or they will quietly leave.

    So it’s not just a matter of giving responsible employees freedom. It’s also a matter of teaching employees responsibility by giving them freedom.

    Would you agree?

  3. Thank you for this. I have passed it along to a friend and colleague. It really made me think!

  4. I dont agree with Mr. Nihil.

    Employees are not responsible enough means justifying the prison warden role. Employees have entered the organization through interview and they are not behaving respobsibly.

    Interviewer is wrong if employees are not responsible enough.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.