Helping people like their job or career more is a worthwhile goal. After all, even the smallest uptick in the percentage of people happy with their job would have huge benefits for society. From the mental health of those involved and their sense of fulfillment, to the wider goals of economics and productivity, keeping people satisfied at work means we all win.
One of the biggest factors that impacts that outcome is your boss. In a lot of ways, it’s the biggest factor: A good boss can make even the worst job enjoyable, and a terrible boss can turn your dream career into a living nightmare.
One of the key points of my book, My Boss Is a Moron: Strategies to Manage Up and Thrive in Any Workplace is that most “bad bosses” are coming from a place of ignorance or incompetence rather than deliberately going out of their way to make your life miserable. While that doesn’t do you much good when you’re in the depths of an awful situation, it does give me hope that this is a fixable problem.
Some will argue that there’s little management training in today’s world because that training relies mostly on soft skills and most businesses neglect them, but I disagree with that. Sales and client services are also reliant on soft skills, and yet companies will throw thousands at even the slightest potential for increase in those arenas.
I remember a very funny, albeit slightly depressing, story from an HR manager who once got in touch with me. This person worked at a company that claimed it had a phenomenal training budget for managers. They apparently had run a cost analysis on said training budget, and found out that the company spent more on seemingly everything — from flowers for the reception, to snacks for the kitchen to, inexplicably, a magician for its Christmas party — than on management training. (I was assured he was a very good magician, but he was sadly overshadowed by the actual staff, since they turned out to have their own disappearing trick: people quitting in droves.)
So if better management training isn’t in the cards for most companies, it’s important to start controlling the factors you can, which includes understanding yourself as an employee. The best place to start is by identifying how you like to be managed. If you can figure out what type of management works best for you, you can start factoring that into how you approach your work and your career.
Here are four steps to help you determine how you like to be managed:
- Identify your motivators. We’re all motivated by something. For some of us, work is simply a financial transaction — the size of the paycheck is what matters. For others, the motivation could be having a healthy work-life balance. Some of us believe passionately in the mission of what we’re doing, and as long as we have enough to live off of, we’re happy. Alternatively, you could hate your current role but it’s a stepping stone to what you do want to do, so you’re happy to “suck it up” to achieve the end goal.
One of the first things to understand about yourself is what gets your juices flowing — and be honest. Because if you know what motivates you, you’ll start to be able to understand, a) what you want to achieve and, b) what you’re willing to put up with to achieve it.
Produce a list of the things that keep you motivated and get you up in the morning. Then use that list to guide every decision you make about your career, and your interactions with your boss. If your boss is reasonable (even vaguely), I would highly encourage you to tell them what it is that motivates you. - Assess your working style. A lot of management/report clashes come from a simple incompatibility of personalities, rather than incompetence. Understanding the type of people you work best with is an incredibly valuable piece of homework, to hopefully ensure you collaborate well with those around you. As a starting point, there are lots of different online work personality tests and articles that’ll help you gauge what type of management style might suit you. Some are surprisingly insightful and can give you a good idea as to the type of manager that will work best for you. However, you can look deeper than this.
Try finding a quiet room and do a little self-reflection. Ask yourself: How do I like to work? Do I like working with the same three people, or mixing it up? Do I prefer working collaboratively, or do I prefer to work on my own? Equally important is to think about which parts of the job weigh on your soul and make you miserable. We all have tasks we relish doing and some that we would quite happily never touch again. Spend some time thinking about this, and in a tone-setting conversation with your boss — ideally early on in a new job, or even during an end-of-year review — try to communicate what you’ve discovered. These details may also help diffuse issues that come up during the year, since you might be able to use your preferences and tendencies to inform the type of projects you’re given, or how you function within a team. - Reflect on past experiences. Write down a time when you were most happy at a job. (If you’re a glass-half-empty sort of person, you can approach this as finding a time when you were the least miserable.)
Now write down the factors that you think might have contributed to that feeling. Perhaps it was a specific project, a certain person, or a work environment — but for whatever reason, it functioned well for you. Your observation can be as mundane as feeling better working next to a window, or with plants on your desk. Add this to your notes (mental or physical) about what motivates you most at a job.
It may feel like your boss should be intuitive enough to work out what motivates and encourages you, but it’s unlikely they’ll discover that on their own. And if writing down a cheat sheet and discussing it with them makes you a more productive and happy employee, then it’s absolutely in your (and their) best interest to do so. - Ask your friends and colleagues. It can be tough to be honest with yourself, and it can be quite tricky to spot the trends and the patterns of what you enjoy at work, and what you don’t.
Luckily, this isn’t something you need to muscle through on your own. Ask your colleagues, friends, or family — anyone who knows you well — one simple question: “How would you manage me if you were my boss?” I think you’ll be quite surprised by how accurately they would be able to answer.
At the end of the day, you can’t control whether your boss suddenly becomes a management prodigy — but you can control how well you understand yourself and what you need to thrive. By identifying your motivators, clarifying your working style, reflecting on what’s worked in the past, and asking the people who know you best, you’ll give yourself the tools to navigate even the trickiest workplace dynamics. The more self-awareness you bring to the table, the easier it becomes to shape your career — on your own terms.
Excerpted and adapted with permission from My Boss Is a Moron: Strategies to Manage Up and Thrive in Any Workplace (Hay House, Sept. 30, 2025) by Ben Askins, published by Hay House, LLC. Copyright (c) 2025 by Ben Askins.
