Terrible Bosses: The 5 worst types of delegators

terrible bosses

We’ve all read the advice. You need to delegate more. You need to free up time to focus on the important stuff. Don’t waste your time doing $10 an hour of work. Whether you run your own business or manage a group of people, being an effective delegator is the key to being able to grow and be successful in your career.

And yet, I keep on coming across people who are terrible bosses and terrible delegators. People who create more damage and create more work for everyone when they try to delegate. In this article, I have identified the five most common types. Let’s see how many of these you have worked with in your career.

The Superficial Delegator

This terrible boss will always give vague instructions. He doesn’t quite know what he wants, and he is horrible at explaining what he needs. He will say something like, call and book a hotel for the event next month. He won’t sit down and explain what type of room he needs, how many people will attend, or which factors need to be considered before booking.

All instructions are vague, and the delegator expects whoever is on the receiving end to execute the plan flawlessly, even though no clear goals have been set. Superficial delegators tend to be people who should have never been put in a position of responsibility. They tend to be charming and are good at wooing their superiors which explains how they get positions of responsibility.
However, they are incompetent and are terrible at inspiring the people who work for them. They call themselves “a big picture person” when in fact, they don’t have a clue of what they are doing.

The Serial Delegator

This is the type of person that goes around assigning people tasks. She loves creating work for people, even if the job is a waste of time. Her need for delegating is connected to her underlying needs to create more drama and problems.

I once worked with one of these types. Whenever I saw Mrs. Serial Delegator approaching, I would go into hiding. She was the type of person that always had a long list of tasks. There was no prioritization of the tasks. Nor did she care if a particular person was the right person for the job.

There was no end goal or vision of what needed to be done. The purpose was to assign tasks for the sake of delegating tasks. Whether the job was launching the new product next month or pick up her dry cleaning, the task seemed to have equal weight in her books—both functions needed to be completed.
Serial delegators tend to lose their credibility very quickly. No one takes them seriously cause they don’t inspire.

Eventually, people ignore or avoid them. The only people that listen to these terrible bosses are newbies that want to impress with their work ethic. But after a month or two, they too become disillusioned when they realize that there is no purpose in what the delegator is pursuing.

The Dismissive Delegator

Dismissive types are probably the types of terrible bosses that annoy me the most. This is the type of boss who is incapable of listening to feedback. He assigns a task, and the person given the job asks questions and points out difficulties in executing the work.

A proper leader’s job would be to listen to the problems and suggest possible solutions or an alternative course of action. The dismissive delegator does not want to listen. He quickly dismisses the situation as if everything is fixable. This is not my problem; go figure it out. People working for him become disillusioned rapidly, wondering if he should be even in charge of that department.

Dismissive delegators love to talk about themselves and how they could fix the problem quickly if they were in charge. They reminisce about the good old days when they solved all the problems. But deep down, they are just insecure and incapable of problem-solving. So they push the problem onto someone else.
Last year, I was involved in a construction project for a new factory. Several of the subcontractors (including my own company) were facing significant technical difficulties. We needed to consult the owner of the facility to help advise us through these problems.

Every time we tried to raise these problems with the owner, he would dismiss the problem with a condescending attitude. He acted as if people were looking for excuses to avoid the work. Eventually, one contractor after the other just abandoned the project.

I went back to the site six months later. The project had not progressed much. The supervising engineer had left the project and been replaced with someone else. The company’s CFO was complaining that the project had gone way over budget and that the project was only half-finished. And I bet the owner was still dismissive of the problems.

The “Everything can be Fixed with Money” Delegator.

These terrible bosses are quite common among first-time business owners and solopreneurs. Need a website done? I have no clue, but I’ll find someone that knows WordPress. Need to run Google ads? Just pay an agency to do it.
And the list goes on and on. Now, don’t get me wrong. A business owner should not be fiddling about with a WordPress site all day. But what I see quite commonly is that these delegators never take the time to educate themselves on the basics.

As a result, they cannot assess if a particular web developer is suitable for the job. Meanwhile, the web developer realizes how clueless the customer is and starts overbilling for trivial tasks since no one holds them accountable.

If you want to run Facebook ads, figure out what you are trying to achieve and how much money you are willing to spend. Otherwise, you will fall victim to every agency out there that charges a retainer without ever bothering to optimize your ads.

If you decide to hire a lawyer, make sure you know some basics about the law. If you hire an accountant, you need to have a good idea of your numbers and the ongoing tax laws in your country. If you give blank cheques expecting people to fix your problems, these people will take advantage of you, and they will not resolve your problems.

The Micro-Managing Delegator

Micro-managing delegators tend to procrastinate on delegating. They believe that they could probably do a better job than anyone else, so why delegate it in the first place?
When they do manage to hand off a task, they immediately regret it. For example, Mr. Micro Manager might ask one of his co-workers to craft an email response. They end up re-writing the email because it was not quite what they wanted.

Micro-managing delegators can be self-destructive terrible bosses. Their obsession with keeping all the tasks close to them leads them to feel overwhelmed all the time and convinced that only they know how to complete a task.

Their business is never able to grow because they never manage to hand off tasks effectively. The top-performing employees become disillusioned with the micromanaging and leave. Ironically the only employees that stick around are the people that need hand-holding. This ends up re-enforcing the micro-manager’s belief that only he can do a task correctly.


Among the types that I have identified, I have at some point been every one of these types. I most probably relate to the micromanager as I have always been wary of handing off tasks. But there have also been times where I was handing out assignments for the sake of assigning them without really knowing what I was after.

Closing Thoughts

As a final remark, I believe a delegator is only effective if he has figured out precisely what he needs and how he plans to achieve this. Superficial delegators are incapable of formulating their thoughts. Dismissive delegators may have a vision, but they cannot find a path to the goal.

And the types that throw money at problems will quickly go out of business if they believe that every challenge can be focused on with extra money.

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