Ask These Questions to Make Sure Your Boss Won't Suck

Published by Ryan Paugh on January 25th, 2008 in Employment | 28 Comments

It would've been nice if someone told me that there are early warning signs that determine whether or not your boss is going to suck. I had to learn the hard way.

Unfortunately, that's the case for most of us. As early as the first interview, we're so consumed by how we're perceived by the company that we don't take the time to look at who we're going to work for; even when they're sitting directly across from us.

In an interview, the questions you ask are just as important as the questions your potential boss asks you. They can determine what the relationship will be like and they can determine whether or not working for this person is really right for you.

What time do you typically get into the office?

If your potential boss can't at least answer this question with a hint of certainty, it's hard to say whether or not you can count on them to be there when you need entry-level support. It's understandable that throughout any given day, meetings, lunches and workshops will keep any boss from committing a daily dose of their time. I've learned that the morning is usually the time to get the guidance you need out of your manager.

When I worked in corporate communications, my boss was missing in action for the majority of my 8-hour days. If I needed to meet with her, it was up to me to catch her while she ate breakfast and read the morning news. Otherwise, my day was going nowhere.

Having a boss that can't commit to what time they will show up in the morning is dreadful. And unless of course they can commit to meeting you at some other habitual point in the day, you're not going to get the attention most entry-level workers crave during their early career.

What time do you typically leave the office?

Just as important as when your boss gets into the office is when they leave. If they're someone who never stops working, it's probable that they'll have a hard time understanding that you do.

Penelope rarely turns off work mode. Her hours are erratic and it completely clashes with my ability to have a "work-life" and a "life-life." Luckily, I'm not in a position where getting fired concerns me. Unfortunately, most people are.

If you hope to have a life outside of your job, unpredictable bosses are the worst. You'll either spend hours waiting for something they may need rather than calling it a day, or you'll leave at a reasonable time and get blasted the next morning when it turns out that something important came up and you weren't there.

What type of person do you like to work with?

Having a manager who knows exactly who they want working for them is crucial. First off, it says a lot about their character. And secondly, it shows that they'll know how to get the best out of you if you're hired.

A boss who knows who they want to work with shows that they know enough about their own strengths and weaknesses to choose people that will work well on his/her team. When I was an intern reporter for a collection of community newspapers back in New Jersey, there was one editor that I consistently did assignments for. She was overburdened with hard-news (borough council meetings, crime reports, etc.) and because they were such high priority, her feature/soft news stories were suffering.

Seeing that I was such a great people person, she realized that she could leverage my abilities by using me as a feature news writer. I went out and met with people around the town she covered, found the stories and covered the pieces of the news that were missed because of her workload.

What is your boss like?

The people that your boss has to deal with will inevitably play into how your boss deals with you. If their boss is really demanding, you may be seeing less of them, but more challenging work. If their boss if more lax, you'll probably see more of your boss, but less challenging work during your day-to-day.

How you deal with the answer to this question all depends on what you are looking for most in a job. We'd all like to have both challenging work and a manager who is always around to help, but you'll never find that perfect balance.

Accept that fact. Then decide whether or not your boss's boss is going to make your job better or worse.

How do you like to communicate with your employees?

When I look back at my first part-time jobs as a baker/cook, a gas station attendant and a liquor store employee, what I miss the most is the face-to-face communication I received on a daily basis. To me, nothing beats the value of that kind of personal attention.

Both the corporate world and entrepreneurship have been tough. Communicating the way I like is sometimes impossible. Blackberries and laptops are essential in order for us to stay connected…it sucks.

So first, face the fact that 75 percent of our communication is going to be electronic. Next, make sure that your boss does make an effort to communicate with you in person. If they don't you'll unavoidably become disconnected and you won't like it.