What Qualities To Look For In A Boss? The Things My Favorite Boss Did

I find myself thinking about a lot of the negatives associated with project management and the workplace, even without meaning to. Delays, problems, issues, disputes, claims, manipulative people, standing up for yourself at work and other similar topics are what many of my articles are written about. There’s validity behind all of these topics for sure, but there’s a lot of good we can discuss at work, too – in project management and beyond. How you feel at work often comes down to who your coworkers are. The most important coworker of them all, though, is your boss. I imagine that there’s very few people who love their job but can’t stand their bosses. Today, we are exploring the question of “What are the qualities to look for in a good boss?”. I will answer by examining my favorite boss and the seven qualities he possessed!

A Bit About The Best Boss I Ever Had

When I graduated college, I was hired as an Asst. Project Manager at a construction company that did public works projects (bridges, highway, etc). I was assigned to work for a Project Manager who’d been working for several years at the other end of the state on one of the toughest projects this company ever did. He stuck it out until the end, despite commuting several hours per day and working insane hours. My new boss had a reputation for getting the job done.

He always was so level-headed and even-paced with all of the work he did, so I was surprised to learn that he’d handled such a tough project for so long. After getting to know him better over the two years I worked with him, it became more and more obvious.

I could be suffering from confirmation bias here, as it was my first job out of college and the first boss I ever worked for. In comparison to a bad, manipulative boss I worked for later on, this guy seems like a titan of the industry.

In any case, let’s get into what a good boss actually looks like.

What Qualities To Look For In A Good Boss? The Best Boss I Ever Worked For Had These Seven Characteristics:

When it comes to spotting a great boss, we first must know what to look for. Some things are obvious, while others are appreciated more or less depending on personal experiences from the past. Here are the qualities my favorite boss had:

  1. Level-Headed & Grounded
  2. Well Organized
  3. Leads From The Front
  4. Keeps You Up To Date
  5. Helps You Grow Your Skills
  6. Understands What Your Job Requires
  7. Genuinely Cares About You

Let’s talk a bit more about these characteristics below.


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1. Level-Headed & Grounded

A bad boss is volatile, emotional and is all over the place when it comes to managing their operation. Nobody likes working for a boss like that – coworkers will begin to dread even interacting with them, let alone working with them closely for months or years on end.

The first boss I worked for handled work exactly the same way no matter what was happening. While he could be abrupt and short at times with certain people, he kept his composure in a vast majority of situations.

This includes when I would make a mistake. Our company was extremely busy and I was brand new – there’s no way I’m not going to make some. Thankfully, he focused on me fixing the mistake, not making it.

Two must-have qualities to look for in a boss are level-headedness and being grounded.

One of the most important qualities to look for in a boss in personal organization

2. Well Organized

A sure sign of a good boss is their ability to stay organized. If a boss is organized, it means a few positive things.

First off, an organized boss has a clear vision of what’s actually going on in the workplace. They have their arms around all of the work that needs to be done, where each item falls in the priority and know exactly what should be happening right now.

Secondly, if a boss is organized it usually mean that they care about their performance. Who wants to work for a boss that doesn’t care how well they’re doing their job?

My first boss kept things fairly simple – legal pads and a smartphone for the most part, but he’d always be referencing and updating his to do list every day.

3. Leads From The Front

In my experience, a hallmark of a bad boss is to “lead from behind” – that is, to give directions and have high expectations, but not do much of the real work themselves.

While a boss is supposed to give direction to their employees by definition, there’s an element of leadership that a good boss carries with them.

They’ve done the work before, they’ve been in tough spots, they have some ‘war stories’ and they’re not afraid to roll up their sleeves when the going gets tough.

My first boss was exactly this way. Since I was a new guy in a busy department, I stayed late regularly to keep up – he was always there late, too. Later than me sometimes.

A random example of his dedication is when we were inspecting a bridge in a rural area. We were over two hours away from our office and it was close to days’ end already. We needed to get some measurements on this bridge – unfortunately this bridge spanned over a small stream.

With no change of clothes, he waded into the 2-ft deep stream and took the measurements. He didn’t consult or ask us first, he just did it himself. That was one of the many moments I recognized him as a great boss to have.

One of the most important qualities to look for in a boss is the ability to lead from the front.

One of the most important qualities to look for in a boss in the ability to communicate

4. Keeps You Up To Date

A good boss will provide their team with as many updates as they can. Many businesses move at a fast pace and it’s easy to get behind. A good boss will take the time to communicate with their team about important events as they happen, along with any changes to their focus and plans.

Great bosses are good at communicating effectively, too. They have proficient skills in one-on-one conversations, saying things clearly, emailing, etc.

This helps employees feel more like a team that has a sense of purpose, not just people who have to work together. Camaraderie always boosts workplace happiness and performance.

My first boss would stop by my office every couple of hours, just for a minute or two in some cases. Our jobs had us traveling around the state and working in the office, too – even if we were both in separate locations, he’d touch base once or twice per day.

I was copied on emails routinely, but not so many that I didn’t know what I was supposed to do next.

Even though I was new, young and making plenty of mistakes, I was still made to feel like an important member of the team. A great boss will make sure you’re kept in the loop.

5. Helps You Grow Your Skills

A good boss understands that you’re an individual person with your own career and life. Good bosses don’t feel the need to hold you back or keep you in a position you’re not satisfied with.

Even if they want to keep you on the team, they’ll at least understand that your skills increasing can only help the performance of the group. In turn, they’ll make sure that you’re constantly developing.

At best, a bad boss won’t care about your personal development. Worst case, really bad bosses go out of their way to limit your development for their own reasons – ego, selfishness (wanting you to help them), etc.

Every week, my first boss would give me something a little more challenging than the week before. It made sense, because I was getting my workload done a lot quicker as I got more experienced in the position.

When something was above my pay grade, I was often asked to sit in on a conference call or a meeting. After it was over, he’d take a few minutes to explain the specifics on what was important and why the meeting was needed.

Over several months, I was proficient in many more aspects of the business than when I began. In turn, my boss tried to give recognition and credit when it was due. I felt more confident and motivated, which made the following week even better.

6. Understands What Your Job Requires

A terrible boss just wants to give you as much work as humanly possible so they don’t need to think about it themselves. You may be doing the work of two people, yet your boss may still ask ignorant questions, like “what do you have on your plate right now?”.

A good boss makes sure that they understand what their team members are actively working on, as well as what they’re responsible for. They know what deadlines are looming in the near future and roughly how long each task is supposed to take.

My boss and I had a weekly meeting where we’d go over my to do list. He’d help steer me in the direction of what he wanted done first, which types of tasks I should group together and which items can wait.

This was extremely useful to me. As a new employee, I lacked the perspective to effectively prioritize all of the tasks I have on the list. My boss made sure I knew how to keep track of work that needs to be done by the end of the week and which items are most important.

By doing so, he’s also making sure that I’m working on what he sees as most important, too. The opposite scenario would be if my boss had no idea what I was working on, then ran to me last-minute so we can race to finish something on time.

7. Genuinely Cares About You

Last but not least – a great boss will genuinely care about you as an employee and coworker.

Sure, bosses don’t need to be your best friends or stand-in parents, but a good boss will care about you on some personal level. Even if your boss only cares about you as a coworker, they’re still spending 40+ hours per week with you – that’s a lot of time. Having a genuine relationship at work will only help.

In contracting, it’s no surprise that having a few drinks is customary after a long week of work. My boss, along with many others, would take the time to hang out for a few hours after work on a Friday. These couple of hours every so often would pay off big-time in the form of bonding and personal relationships.

In addition to the points above, a good boss will take the time to have at least a basic relationship with you on a personal level.

It’s my opinion that of all the qualities to look for in a boss, genuine caring is the root quality for all the others.

In Summary

So, back to our original question of “What are the qualities to look for in a good boss?”. In my experience, any boss who has several of the qualities above is going to affect your work life and career in a positive manner. Though it was only two years of my career, I had a great boss with all of these qualities during my first two years of work. I hope this article has been helpful and informative! Thanks for reading.

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