8 red flags of bad bosses [+interview tips]

Three things will disproportionately influence your career: how good you are at your job, how fast your industry / town / country / network is growing, and how good your boss is. Most people only take action on the first one and leave the other two to chance.

This is often a mistake. While there might be good reasons to work in an industry / town that isn’t growing, there are no good reasons for spending time under a bad boss. Not only will it severely limit your career growth, but even if you are not too ambitious, it will also drain your energy and affect your personal life.

What’s the deal with bad bosses?

Some bad bosses are selfish psychopaths, but most are well-meaning yet bad at their job. Most got there because they were good at their previous role which didn’t involve managing people or because they were loyal – but neither will make them a good boss.

A well-meaning boss is arguably more dangerous than a psychopath one – with the latter, at least, you know that he can hurt you. But the former can harm you too, for example by wasting a couple of years of your career (often the early ones, those with the largest impact on your trajectory and thus lifetime outcome) or by making you undergo frustrating situations that will teach you the lesson that it’s not worth caring – a lesson that will be hard to unlearn and might become a handicap for life.

Here are some non-obvious red flags that you might be dealing with a bad manager:

• He is vague
• His career stagnated
• His subordinates’ career stagnated
• His subordinates are in a bad mood
• He isn’t ambitious nor sets ambitious goals
• He never works overtime or always works overtime
• He procrastinates or avoids addressing important questions
• He doesn’t have boundaries or respect his subordinates’ boundaries

Let’s see them one by one.

He is vague. He will create misunderstandings and grey areas, and you will be on the receiving hand. You will misunderstand what he wants, you will not be told what matters, and as a result you will lose a lot of time and gain a lot of frustration.

His career stagnated or he is never in a good mood. The former means he didn’t understand what matters in business. The latter means that he didn’t understand what matters in life. Either way, if you work for him, you will learn the wrong lessons or fail to learn the important ones.

(You might think: what if I’m not ambitious? In that case, does it matter if my boss’ career stagnated? It might. While there are exceptions, a boss whose career has stagnated is a red flag for a lack of management skills, and if so, you will be on the receiving end of unclear tasks, unrewarded efforts, chronic lack of budget, and other frustrating experiences. This doesn’t mean that managers whose career stagnated do lack management skills – there are plenty who are great – but it does mean that it’s a  red flag, and you should further ascertain whether it stagnated due to lack of ambition or lack of skills.)

His subordinates’ stagnated, and so will you. Yes, you might be the exception, but even then, you’d do much better working for a boss whose median subordinate doesn’t stagnate. (Note that by “stagnated” I do not necessarily mean their career – if you care about personal growth instead, look if their personal growth stagnated.)

His subordinates are in a bad mood, and so will you, if you end up working for him.

He isn’t ambitious nor sets ambitious goals. On the one hand you probably do not want to work for someone so ambitious that he will hurt your personal life. On the other hand, you do not want to work for someone that sets excessively conservatives goals, for he will lack the windfall to reward you or create room for growth.

He never works overtime or always works overtime. In most businesses, every now and then there will be problems or opportunities requiring urgent attention. A boss that never works overtime could be a boss that ignores them, and one that always works overtime could be a boss that isn’t able to prioritize or delegate, and thus will fail to work on the important things. You don’t want to work for either. 

(Note, again, the “could.” A red flag doesn’t mean that it’s bad. It means that it could be problematic, and if it’s a problem you care about, you want to dig deeper to know whether there indeed are problems. Red flags aren’t conclusive and yet not to be ignored.)

He procrastinates or avoids addressing important questions. Problems grow the size they need for them to be addressed, and a boss that procrastinates is a boss that will have large problems on his hands. When they will finally explode, you’ll be within the blast radius.

He doesn’t have boundaries or respect his subordinates’ boundaries. A boss without boundaries is a boss without values, and one that doesn’t respect his subordinate’s boundaries is one that won’t let you have values. Either way, someone you might want to avoid, proportionally to how important your values are.

Of course, there are exceptions, as with any rule of thumb. But they do not mean that following the rules of thumb above isn’t useful nor that ignoring them comes with risks.

And of course, few bosses have no red flag at all. Is it worth working for one that only has one or two? Your call. But do not hope, “maybe the red flag is wrong;” instead, ask yourself, “will I be okay with it?”

How to probe for red flags

The best way to probe for these red flags is during the interview process. Unlearn the idea that an interview that doesn’t convert into a job offer is a failure. If you discover that the work environment won’t be a good fit for you before you start working there, that’s a magnificent success.

Always, always! talk with your potential future boss. Ask open-ended questions such as “what does a day working here look like” and follow-up with questions such as “what will my tasks look like once I’ve finished the onboarding period.” Look for red flags of vagueness and avoidance. Then, ask questions such as “how often do people work overtime here” and “who was the last person that left and why.” Probe for the red flags above.

If you have ambitions, mention them with your future boss. If he feels threatened or doesn’t care or any other problem, you want to know about it now. Ask him, “what will it take to get there and, if I do all of that, how likely is it that I will succeed?” Of course, you cannot overly trust his answer, but regardless of its contents, the way he answers it (with care? with dismissal?) will give you great insights into his nature.

If you have boundaries or ambitions, make sure you mention them with him. If they won’t be met, the right moment to know is before you get hired. Many believe that it’s more important to “land the job” to “get a foot into a good company / industry” and that “if there’s any problem, I’ll just jump ships” but the reality is that people working for bad bosses always stay too long: they’re afraid of what a 3-months job experience would look on their CV or didn’t want to look like fickle. And they are right, it won’t look great! Working for a bad boss is a trolley problem where you lose whether you quit early or remain longer. The moment you have to decide whether to pull or push the lever, you already lost. Hence the importance of appropriately probing whether one’s future boss will be a bad one, even if it means asking uncomfortable questions, and even if it might mean not landing the job.

Of course, if you’re already working for a bad boss, I suggest you immediately cut your losses by looking for another job – inside your company or outside of it (though beware of the former – bad bosses cluster).

Results, not words

Try to also interview a few of your potential future colleagues – not just because you want to know who you will work with, but also because you want to know what working for your future boss could look like. Are they tired and resigned? Or cheerful and energetic? Are they satisfied? What’s the one thing that frustrates them the most?

You can either formally interview with them or spend some time with them by the coffee machine or at the coffee opposite the street. Feel free to walk by the office when most people are getting out, stopping a few people, and explaining that you’re interviewing with the company and wanted to know how it feels like to work there. Yes, it’s awkward, but working for a bad boss is awkwarder.

To sum it up

Most people underestimate the likelihood of ending up working for a bad boss, mostly because they define it as “selfish psychopath” and not as “someone who will hinder my professional and personal growth.” This leads them to underestimate the need to interview their boss during the hiring process. 

Instead, candidates should proactively and extensively probe for red flags during their interviews, front-loading any problems and misalignments. If they really like the company but their future boss exhibits multiple red flags, it’s sometimes possible to side-step it by getting hired by another team of the same company. But never start working for a bad job with the idea of “it will only be a while” – it most often isn’t. Or, “it won’t be this bad” – it will often be worse.

A last thought. In school, we learn that if we work hard, good things will happen to us. In a company, if we work hard, good things might happen. A great boss ensures that they do [1], and that’s something worth proactively looking for.

Notes:

[1]: I believe that every manager should live by the commandment “always be fair.” It’s not banal, once one accepts that it’s not intentions that matter but results. For example, if an employee performs well at his tasks, it is only fair that he is rewarded. But many managers are too conservative or incompetent, and cannot reward the well-performing employee. Needless to say that you want to work for a boss that will treat you fairly, and that requires more than finding a genuine person.