Avoid the Trap of a Bad Job With a Good Boss

“People don’t leave bad jobs, they leave bad bosses.” (Or so the saying goes.) Does that mean you should stay in a bad work situation if you have a good boss?

I once worked for a terrible company. All the traits of a toxic work environment, with senior employees bullying the junior staff, a micromanaging CEO, and workloads that would make anyone’s head spin.

The thing that made all of this bearable? My boss.

I stayed at the company for a long, long time. But in the end, a good boss couldn’t offset the bad. I knew I deserved better.

If you’re in the same situation, you need to weigh much your boss can “protect” you versus the negative impacts of the job as a whole.

Benefits of a good boss

There’s no doubt that a good boss can make a world of difference at a job. Whether it’s making a bad situation better, acting as a sounding board, or advocating up the food chain on your behalf.

I got along really well with one of my former bosses. She was the ultimate listening ear (and commiserated with my gripes). I could complain to her about anything and talk about my dreams for improving the situation. She provided mentorship and helped me climb the ranks within the company.

But at the end of the day, a good boss is more than a work friend. A good boss knows how to navigate challenges and conflicts — and doesn’t avoid them. They’re supportive, skilled leaders that create a positive and productive work environment.

You may like your boss, but that doesn’t mean your boss is a good boss. Or, your boss’s hands are tied and they don’t have the power to enact real change in a bad environment.

In these situations, friend-bosses might make the job palatable but they don’t offset other factors that make the job a bad job.

Signs that your boss can’t overcome the negatives

Sometimes companies can get themselves out of a rut and the bad things will self-correct. New employees will be hired and the bad ones will be fired. An economic downturn might mean that the company is struggling financially and things are more stressful internally, but the company pulls through.

Or the company recognizes its own shortcomings and is really committed to change management. (If this is true, you’ve found a unicorn employer since most don’t have that much introspection).

If your boss makes a bad situation tolerable and you see signs of improvement, it might be worth sticking with the job. Especially since job hunting is exhausting.

But there are some telltale signs that things won’t get better, and they usually have to do with the company’s core essence of “who we are and what we do.”

1. The company’s products or services aren’t good

Maybe twenty years ago a company could skate by with mediocre products or services. Not in today’s world. Today’s buyers have nearly unlimited options and a quick Google search will point them in another direction.

It’s one thing if the company knows that its products or services aren’t up to snuff and is trying to improve. It’s another if the company isn’t aware, doesn’t have the resources to match what competitors offer, or doesn’t care.

If you don’t have a good sense of what customers are saying, try to learn. Look at reviews. Or look at your company’s support tickets, if you have access. If all you see are complaints, that’s a bad sign.

Companies can only last so long with bad products or services — even if the price is right. Eventually, they’ll lose business, won’t earn any repeat business, or their reputations will prevent them from earning new business. In the Age of the Internet, word spreads.

2. C-suite leaders are problematic

Not all people who hold leadership roles are cut out to be leaders. Some lead out of ego and others fail upwards into a role.

Bad leaders can be a death sentence for a company. From lack of vision to poor decision-making to favoritism, these people don’t have the company’s best interests in mind.

Look for communication from your company’s c-suite. Is it clear? Do you know what direction the company is headed? Does your company always seem to be chasing the “next shiny thing” or does leadership have a very firm grasp of the company’s mission?

If the leadership team collectively makes bad decisions, or the CEO holds too much power to single-handedly dictate the company’s path, that’s a bad sign. True leadership should never rely on one person’s decision-making abilities since no one can be right all the time. True leadership wants to do right by its customers and its employees.

3. Your boss can’t protect you or help you grow

Depending on the organization’s hierarchy, there’s only so much your boss can do.

Take the example of my former boss that was a great listener. It was great to get things off my chest (like work therapy), but she couldn’t actually do anything. The company was beholden to a few toxic employees and the CEO was arrogant and out of touch.

Your boss may want to help, but can’t. These bosses can’t shield you from other managers, toxic employees, or decisions made by the company’s leaders. They don’t have the ability to fix broken processes or systems that might be stressing you out.

Or maybe you want career growth and are caught in the company’s red tape. You can’t get promoted or upskill in your current role — and there’s nothing your boss can do. Even if your boss sees your value, your career might stagnate if it’s not recognized by the rest of the company.

4. The company is struggling

The economy will always have ups and downs, and a good company can weather the storm. Or something new emerges on the market that causes a massive disruption in the company’s business.

And if it looks like the company is in trouble, you should not go down with a sinking ship.

Not all companies are transparent about their financial situations. But you can look for signs, such as:

• Slowed sales
• Lack of hiring
• Budget cuts

You may also feel the pressure through increased micromanagement. Your boss or your boss’s boss wants to make sure that everyone is as productive as possible when times are tough.

If you sense that the company is having trouble staying afloat, your boss may have zero ability to save you from a layoff.

Do your due diligence

If you get along with your boss and things don’t feel that bad, how do you know that the job is worth leaving?

Taking on a new job is a risk, absolutely. You could end up in a similar situation, or (even worse), end up with a terrible boss.

If you’ve started looking elsewhere, there are a few ways you can assess a potential new boss during the interview process.

Treat the interview like a two-way street. You’re interviewing the new boss as much as they’re interviewing you. Pay attention to the questions asked. Come prepared with your own questions, such as “How do you measure success in this role?” or “How do you plan to support me during onboarding?”

Check Glassdoor. Look at employee reviews on Glassdoor. They usually paint a fairly accurate picture of the company overall, especially factors like leadership or work-life balance.

Contact other employees. Use LinkedIn to find current or former employees and send them a quick DM. Sometimes Glassdoor lacks reviews for smaller companies. Or you can ask a question about your potential new boss, specifically.

Prioritize yourself, not loyalty to your boss

If you like your boss, the decision to leave might feel difficult. You don’t want to leave your boss in a lurch, or have the feeling that you’re “in this together.”

Loyalty to your boss is admirable, but you should always put yourself first. The company will always put itself first, no matter how much your boss may try to protect you.

Your career is a journey. And if your boss is really a good boss, they’ll want you to do what’s best for you. Ask your boss to be a reference or write a LinkedIn recommendation for you.

And if your boss gets upset that you want to move on, well — then the relationship was only about work, and not about you as a person.

You can read more about the future of work and why work shouldn’t suck on my Substack.