Why is managing people so hard?
When I think hard about this question, it isn’t actually that big of a mystery.
This is probably my 92nd attempt trying to record this video. And, if managing myself is hard, then it stands to reason that managing someone else is probably magnitudes more difficult.
I think that the very idea of managing people tends to be tied with this idea that somehow we are overseeing this chessboard of employees where we can just choose which piece to move and then it will move exactly as designed and only in that way.

But in reality, we’re living in this giant ecosystem where lots of things are happening in lots of different ways and it’s very “messy.”
People aren’t robots. And we as managers aren’t robots.
Learning how to manage people is skill number seven on the Eight Essential Skills To Be A Successful Entrepreneur.
Why Is It So Hard To Learn How To Be A Great Manager?
Managing people is a very difficult skill to learn.
It’s hard to learn because there are not great feedback mechanisms to know when you’re doing well, and when you’re doing poorly.
If you’re doing poorly, you don’t typically know it until time has passed and lots of bad things have happened to you.
This is unlike Sales Skills for example where you try to use that Sales Skill on a sales call and it either works or it doesn’t work. You know when to go back to the lab to retune your Sales Skills.
These managerial skills lead to things like a poor company culture. They lead to things like poor morale, which will erode the company from the inside slowly over time, like rusting a hole in a bucket. You’ll feel it later and have trouble going back and pinpointing the initial causes.
Managing people is incredibly difficult.
Key Areas To Manage To Become Better Managers
1.) Managing Ourselves
I really like this quote by Peter Drucker, one of the original consultants. He said something along the lines of “It is not yet proven we can manage ourselves, much less manage other people.”
And this gets really to the crux of it- one of the first key skills of managing people is managing ourselves and this includes managing our emotions on some level (because if we’re spun up and anxious and angry about other things in the business and we talk to an employee, there’s a high chance we actually direct them on accident).
So that’s one of those key things is managing ourselves as much as possible.
2.) Managing Clear Expectations
Number two is actually having clear things we’re managing our employees towards doing.
So if we haven’t done the previous step of getting systems and processes put together how is the employee supposed to do things accurately?
If the expectations and training are not clear it is VERY VERY difficult.
Lessons From Supernanny
I oftentimes recommend newer managers look at Supernanny the TV show. I think it’s streaming currently.
A nanny comes into a house with some kids who are being very unruly, and she helps turn them around.

What’s really interesting about this is the process she uses is very similar to management best practices.
Those include
- Knowing what the expectations are
- Communicating very clearly to the people you’d like to follow those expectations to ensure they understand those expectations and nothing is standing in their way to stop them from being able to achieve those expectations.
- When they don’t follow them (because they won’t because they’re not sure if you’re “serious”) you reinforce how important it is that they follow them or they’ll have consequences.
- Follow through on the consequences you’ve laid out.
If you follow this pathway, it’s very easy to help employees understand what is expected of them.
Now some employees might just decide that following your rules is too much work. They don’t want to do that job. They can self-select for that and find another job that is a better fit for them.
But many employees would be happy to do what you’d like them to do if they just knew clearly what that was!
This is the process to get them there.
So managing people is very, very difficult.
3.) Manager’s Mindset
And I would say that there are a few things that happen in the process of becoming a better manager.
Extreme Ownership
One is that we need to take Extreme Ownership. This idea comes from Jocko Willink’s book (he was a Navy SEAL).
He helped evaluate Navy SEAL commanders.
Bad Commander
What he found was that the commanders who came in after a training mission complained about everyone else in their squad – How their artillery guy wasn’t there on time – The other guy didn’t do his job and hated his job.
The ones that basically threw everyone under the bus and took no accountability for themselves tend to NOT be good managers.
Good Commander
The ones who actually come in and take personal accountability for all those actions had the chance to become better managers.
What that looked like would be instead of saying that the artillery guy wasn’t where he was supposed to be, they would take responsibility and say “I must not have communicated clearly where he was supposed to be at what time or he would have been there.”
They have to take that accountability for themselves and what impact they had on an interaction.
As a manager the instant you start doing this you recognize that even though you don’t have full control over everything, if you act like you do, it always gives you learning lessons to execute on for the future, to make things better and better.
Seinfeld’s Girlfriends Theory
Number two is that as employers, we can become jaded. Sometimes we’ve had some tough experiences with employees.
If we think back some of those might have been our fault. But it’s easier just to point the finger at employees and say it was them. They were the problem.
This is where you get jaded very quickly and go into what I call “Seinfeld’s Girlfriends” territory.
So on the show Seinfeld, Jerry Seinfeld was always having a new girlfriend and always breaking up over the smallest possible sort of reasons.
She was a “close talker”. She had small hands. She made him wear a puffy shirt.
There are lots of small reasons to break up.
He’d go find a new woman and it wouldn’t be long before he would be breaking up with her for a different minuscule reason.
So as employers, it’s easy to all of a sudden find the fault in the employee that justifies the firing, and repeat the process over and over again.
But we haven’t done our work to make it a quality work environment and really get clear on what are the basic requirements for the job, what are the non-negotiables, and then how is that job done – it’s really hard to manage people.

Standing Out As A Great Manager
So a little bit of interesting Q&A you can do.
I like to use focus groups of people around me.
Going about your day-to-day life ask people you know about their work life
- Ask them how many great managers they’ve had. People who helped develop them took care of them and made them into better employees.
- Ask how many horrible managers they’ve had. Managers who were abusive yelled, and didn’t set up fair structures.
Most people actually leave a manager and not a job.
I would imagine this to be a higher number of poor managers in my experience than good managers.
Then you can have Okay Managers – How many weren’t really good or bad they were just sort of there.
Use this as a reference to see how big of a chance of an opportunity it is to become one of these great managers.
People love to work for great managers!

In this time when hiring people can be really really hard, great managers have much less difficulty hiring people because of their positive work environment.
So learning how to hire, train, manage onboard, and develop people is one of the key skills to be a successful entrepreneur, and is one that cannot be neglected if you’d like to scale to another level without having a constant stress of hiring, firing, and micromanaging employees.
Best of luck to have a great day.
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