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Ryan Paugh graduated from Penn State in 2006 with a Bachelor's Degree in Journalism and a minor in Business. After working in corporate communications, freelance writing and reporting, he co-founded 
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New here? Employee Evolution is dedicated to helping the Millennial generation answer the hard-hitting questions that come with the biggest transition of our lives. Be sure to visit our about section for the full story. Since you're here, check out our best articles in the archives. We've also put together a list of some Millennial-friendly employers on our jobs page. Any questions? Feel free to contact us.
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.
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- 1 Pingback on Jan 25th, 2008 at 5:21 pm
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Pretty good questions. These also would come in handy if you get a chance to talk to any prospective coworkers in the department
2 problems though:
1) A lot of positions (especially entry-level) that I’ve applied for don’t even give you a chance to interview with your supervisor before you are hired. You usually wind up interviewing an HR rep, or another supervisor who’s been designated as an interviewer.
2) If you have a new boss replacing an old one, you won’t get a chance to dig up their dirt before they take over.
I’m fortunate to have a fantastic boss. I actually interned for him (in a different capacity) 8 years prior to me working for him. That being said, I’ve also had a boss that I am convinced is bi-polar, and having to manage those expectations were, well…odd.
My question is regarding something i anticipate happening in the next quarter at work. There has been rumor that there will be a change in manager’s within our department circulating throughout the division.
Any ideas/suggestions on how to adjust and warm-up to the new boss quickly, or while he is still transitioning into the new position. I am fairly new so it’s not like I can talk about my long years of experience within the department and help guide him into his new position. I’ll try and do this but I only have so much experience, and my counterpart has been in the position for over 4 years - so most experience-related question are always directed towards her?
Any suggestions?
On the same note - I would like to ask a bit of advice on how you suggest approach the following problem: I have been looking for the right blog to comment on this, but I will just do it her and hope someone could help me with some of their insight and experience…
I was “hoooked-up” into my position at work by my counterpart. She was responsible for my training when I first started the position..She was a very meticulous and detail-oriented trainer. so much so, that my training lasted close to three months, when it could have gone for about a month. Nonetheless, I was thankful for that, rather overly prepared than not prepared enough, right??
But what I notice in hindsight is she really made a point of reiterating 100 times over that I was the “young guy” and she was the “20-year corporate veteran.” She made a clear distinction saying, I am the giant, if you know what I mean.
Well, now I’m coming up on my 1-yr anniversary in the position. I am really making an effort to break out of that shadow because I am looking to apply for other positions within the company - so I want to really make a name for myself.
How do I do so when I have a motor-mouth counterpart constantly raving about her every move and making a clear distinction between my experience and hers? I have made an effort to take alot of initiative - and actually hold an edge on her because I start work two-hours before she does..
What else can I do to emerge out of that shadow??
I would appreciate any suggestions …
Andy:
That’s a good point. There’s a lot of instances where you won’t even get to see your manager until day one. And I think that’s unfortunate for both parties. All I could suggest is to navigate the interviewer toward telling you what your boss is like, but I guess you’ll never really get the full scoop.
The replacement boss scenario sucks too. But you can still approach them with these questions to get a feel for what the relationship is going to be like. Then you can at least prepare for whatever you’re going to have to deal with.
Gustavo:
My suggestion is that your go out of your way to offer help to this person. Changing managers is not only a stressful experience for the employees, but it’s also a stressful experience for the new manager. So once the rumor is confirmed to be true and you find our who the new manager is going to be, email them, call them, send them a meeting request, whatever…even though they’re busy, I’m sure they will appreciate the effort you’re making to make the transition easier.
Any other ideas for Gustavo?
excuse my typos..
Ryan, thank you for your words - can you tell me a bit more on meeting requests? Can anyone set up meetings within a corporate office? In my experience, all of my meeting invites have been proposed by managers and that is usually what I have seen and heard as typical protocol. Is it appropriate for staff to request meetings around the office?
Gustavo:
The meeting request idea is discretionary. I don’t know how your office works, but when I started out, I was certainly allowed to request time with my manager. But I’ve also learned that everywhere is different. I think in most scenarios however, the worst that is going to happen is that they say no.
As for your overly-ambitious and sometimes overbearing counterpart. I’d just suggest that your worry more about yourself and less about her. Find a strength that you have, but she doesn’t. Capitalize on that strength in the office and I think you’ll start to emerge out of the shadow.
This is a nice list, but like Andy said, you don’t get to interview your boss beforehand. If you did get to do this you probably wouldn’t want to because it would come across very self-entitled.
Furthermore, your boss changes all the time, and your boss’ boss changes too. I’ve already had three bosses in two years of working and my boss’ boss just changed again with a (nother) reorg.
I think all you can do is hope for the best. Choose a job in an area you like and work for a company that has a corporate culture which fits you. Try to get a great boss at the beginning, but if you can’t try to transfer to another team/section in a year or hope that your boss does. Realize that the workplace is so dynamic your job can change almost every six months. Learn to deal with change.
@Ryan, In the interest of full disclosure I wondering if you can tell us how many job interviews you’ve actually been on and how many jobs you’ve had since college.
thank you Ryan - really appreciate/value your advice.
Monica:
I think your attitude is great, the workforce is a dynamic place, ever changing, etc. But patience will only get you so far. It’s important to truly understand what you don’t like about your boss in order to learn how to navigate it. Even if you’re already in a position and a new boss is transferring in (like Andy pointed out) you can make an effort to learn about that person, find out if they’re going to suck as a boss and take things from there. In other words, we proactive or you’re not going anywhere.
I also don’t think you’ll be though of as entitled by asking these questions. I think the entitled thing comes from us asking about raises, benefits, vacation time, etc.
Anonymous:
I can’t count the number of job interviews I’ve been on. Let’s just say “a lot.” If you can keep track of the job interviews you’ve had after college you’re either really good, or you’re just not trying.
As for jobs: one large corporation, a small business and now a startup company. I’ve had many bosses in my short time. Some good, some bad…
I also like Chinese food and Van Halen…just for full disclosures sake
It’s impossible to tell from interviews….people may put on an act if they want you to be in the position or are desperate for help…
Hey Ryan,
I thought the whole point of the article was to provide questions you should ask your future boss during your interview with a company. It’s definitely self-entitlement if you go into an interview and essentially interview your interviewer. It comes across as “I think I’m going to get this job already, let me see if I like you now.”
I agree, in an ideal world we’d get to choose our bosses. In the real world we kind of get to choose our bosses by hopping around jobs and transfering units. But as our bosses are doing the same, it’s impossible to have a great boss all the time. To me, waiting a year before changing jobs or teams is not waiting patiently at all - it’s being proactive about your career.
I’ll definitely be evaluating my future bosses on some of the things you described, but I would never use this information for a first interview. Sorry.
Dan:
I agree that it’s hard, but I don’t think it’s impossible. Desperate people will lie just to fill the position, but that’s not everybody. There’s also something to be said about how they answer the questions. If it’s with a hint of uncertainty there’s probably going to be some erratic hours involved, high-stress situations, etc.
Monica:
I don’t agree. I think an interview is a chance for both parties to ask questions. That’s why interviewers open the floor to you once they’re done probing. And asking questions like the ones above are not entitled. They’re about the environment you’re going to work in. Pretty important stuff even if you’re not trying to find out if your boss sucks.
Don’t be sorry for your opinion. You’re very right in many ways. I just believe that keeping your interests in mind from day one has nothing to do with entitlement and an interview is not just a chance for you to get a job, but a chance for you to see whether or not you really want the job.
I have to side with Dan, it’s really impossible to tell for sure, but I do think if you can get some good responses to these questions that it will help immensely. When I was interviewing for my current position, they flew me in for the interview in the evening and me and my now boss went to a local restaurant and sat at the bar, ate & drank and talked for 3 hours. It was very low key and I got a good insight as to what type of boss he would be. I was right and he’s great.
In my previous job, my new boss took me to dinner at Ruth’s Chris steakhouse. The evening was a more formal and hence so was our working relationship, not bad, but we never really connected.
Obviously there are no hard and fast rules, but if you get your new boss to let their hair down, you’ve got a chance to make at least an informed decision.
btw, I like Van Halen and Chinese food too.
Another thing to consider: although the disposition of your boss is important, there are other things to take into account when choosing a job. It’s possible to have a fantastic boss but still have a crummy job, and vice versa.
And to extrapolate on my earlier point of sometimes not having the option to choose your boss, it’s situations like these that make being well-connected vital. If you have good connections within your company, chances are you’ll either know or know somebody who knows your incoming boss.
This happened to me once, I knew from experience the boss coming in was going to be a complete jerk…hence I was able to formulate my “escape plan” a bit earlier.
Scott:
The situation you describe is a much better way to get to know a new boss. I once got flown down to Atlanta for an interview. They took me out, introduced me to team members and it really gave me a feel for what the place was all about. I didn’t get the job in the end, but that was okay with me. I wasn’t really thrilled about moving to Atlanta anyway.
Now I’m in Madison…go figure.
Andy:
Connections within the company you work for are invaluable. If you’re going to be getting a new boss, it’s great to have fair warning from your peers if they’re going to be a pain.
I’m also glad you mentioned the other factors that go into the job hunt. Just because the boss sucks doesn’t mean the job sucks (and vice versa). But it’s important to be prepared (if you can) and know what you’re getting yourself into from all angles.
Gustavo – I think I was in a position similar to yours, and though I was aided by some fortunate circumstances that opened up, I can relate to your frustration.
When I started my current role, I did not have the background in the industry that all of my coworkers had. That wasn’t a problem, I offered to the team more technical experience than they had ever had at their immediate disposal. In no time at all I had a working knowledge of the industry, yet they were nowhere near the technical knowledge that was beginning to be expected. Because of this “rising star” type aura around me, the most senior guy within the group was the one I sat next to, and the one I constantly bothered with my questions. This is the “go to” guy for the special projects, sensitive clients, etc etc. He’s on every pilot program, he has his hand in every pot, and has all the contacts in the world.
Fast forward a year, and I’m not longer asking him questions every 5 minutes. I’m his permanent backup, and while he’s still the go to guy, I’m steadily taking his the load off his plate. It all happened quite naturally, and I couldn’t have been happier. But the problem was, as you say, he’s still the guy who lets everyone know “I was on the team that made that process” or “I was the one who brought in the first client to do xxxx” which is very similar to what I believe you’re saying.
What you have to do is offer a niche. I still offer my technical expertise, he offers the path of least resistance. It’s been a great team, and though I am not at all a “look what I did” type person, I fear that the right people wouldn’t see the effort I had put in because I was in the shadow.
Fortunately for me, at this point, a senior manager who worked closely with both of us had moved into a new role. She had the perspective and the filter, so to speak, to see through to the actual accomplishments and was about to offer my path to make the move within the company that I was looking for.
I think this is what you need to find, because I’m assuming that you do not report to this person, they are just a senior individual in your role. Your boss, or the manager of a group you work closely with, etc, these are all the people that have the clarity to see what exactly you have done, but also serve as your launching point to explore new roles within the same organization.
Frankly, the two qualities all good bosses share is 1) confidence in themselves and 2) kindness. I can work around most other things.
Self confident bosses don’t hold you back. You don’t have to tip toes around them or try to trick them into believing that your ideas are their ideas so they would approve them.
Kind bosses don’t go out of their way to slap you in the face or make sure you know that they are the boss. When I say “kind” I don’t necessarily mean “nice” (although that’s good, too). I don’t need my boss to blow sunshine up my skirt. However, over the years I have worked for some real pieces of work that were just plain mean.
Ryan,
You bring up a great point. It’s definitely important to get a feel for your potential boss before accepting a position. Asking about start and end times could be a bit tricky, especially if you’re interviewing with your immediate supervisor. I would suggest a more indirect approach. If you want the job, the last thing you want to do is give the appearance that you’re questioning his or her judgment before you’ve even been offered the job.
What types of things would you like for me to bring to your attention and what types of things would you like me to handle on my own? What’s the best way for me to get necessary feedback on time-sensitive projects? (this could help address the boss who was missing in action).
What’s the best way to share my input? Some people prefer email, others a quick chat in the hall and even others would rather set up a formal meeting.
What does success look like for this position? I’ve turned down more than a few positions because the person who would be my immediate supervisor had unrealistic expectations for the role. If I take a job, I want to know I’ll have a chance to be successful.
I completed a guest post on the same subject recently.
The questions I recommended:
Ask them what their management style is?
Are they silent? Do they have to think about it? Are they vague? Do they mention words like ‘supportive, approachable or decision maker’?
Ask them when they last took forward an employee suggestion or idea?
Are they struggling in their answer? Is the example worthy of a great manager? Bad managers don’t follow up on employee ideas. If they do provide a worthy answer, it shows they are supportive, approachable and they listen. A great manager removes all obstacles to help their staff do the best job possible.
Ask them when they last praised an employee or team and why?
If they haven’t ever done this then be wary. Bad managers withhold praise. One of the biggest staff motivators is praise from their manager.
Ask them for their opinion on individual development and training?
Have you ever been denied a professional development opportunity, because your own manager said that it would take too much time away from work? Is that why you are thinking of moving roles? Bad managers ignore professional growth needs, whilst great managers support their staff’s development.
Ask them when they asked for feedback on their management style and what were the results?
A good manager will always be looking to improve their performance and style and one of the best ways to do this, is to ask their staff for feedback. If they have asked for this feedback, ask how have they used it to improve their style?
Ask for their views on delegation. How do they delegate? Do they delegate? Do they micro-manage?
Great managers build trust in their staff. A quick and easy way to do this is to delegate pieces of work, which uses and exploits individuals’ strengths, all with the right level of control.
Andrew
For Monica,
Actually, I don’t find it self-entitled at all to ask questions of your perspective employer. People often lose sight that an interview is a two way street. It is a time for the employer to see if you are a good fit for the company, but also for the potential employee to find out if the company and boss will work for them.
I think that when it comes to interviews, the potential employee is so focused on “getting the job” that they don’t ask about things that are important to them and would make a difference once they are apart of the team.
Denita:
I think you’re right. In fact, I believe that asking questions makes you a more desirable employee. I think what Monica was getting at is that my questions in specific aren’t fitting to ask a perspective employer. Which I disagree with, but is of course up for discussion.
As you point out, asking questions about things which are important to you can make you a better part of the team (if you get hired). Not only will you be better prepared for whatever is coming your way, but you’ll have your expectations aligned right where they belong.
Sometimes I think people walk into a job with expectations that are totally unreasonable. So maybe asking more in-depth questions of the perspective employer is the answer. Maybe not. I’d like to know what others think.
Denita,
Ryan’s right - I don’t disagree with asking questions to potential employers, but I took what he wrote very literally. I don’t agree with all of these questions (specifically one, two and four), nor asking five questions in a row to your future boss while you’re trying to get a job. I do agree with uncovering this information in some way, via the company website or though asking 1 or 2 questions to several interviewers/recruiters, not just your future boss.
The tolerance for questions depends on the industry, the location, the company, and the type of person your future boss is. Whenever I’ve been on an interview team, the men in the group have a negative perception of people who “interview the interviewer,” or do anything else that comes off as “cocky” in their eyes.
I also think you hit on some magic words: You don’t think it’s self-entitled to ask those questions. In an interview, it doesn’t matter how you think you are perceived; what matters is how your future boss perceives you. Your boss could be old school or he/she could be nice and open - you have no idea though walking into that interview.
A better way to find some of these things out is to ask people at the company questions like, “What time do people normally come and go? What kind of mentorship programs are available?” I stand by what I said earlier: bosses change too quickly to get hung up on your current boss. Between bosses, team lead-type bosses, boss’ bosses, I’ve probably averaged a new one every two months during my career (I’m 24, so not that long of one). I think it’s more important to join a company where the atmosphere fits your needs - that atmosphere is more likely to attract the type of people you would want to work for.
Monica,
With the questions one should have a short list of things that are the most important to them. If asking 3-4 questions is an annoyance to the interviewer that should be taken into consideration as well, especially if this is the person that they will be working for.
I actually agree with Ryan about asking the interviewer about the amount of time your are expected to work and also your boss’s working style. It may seem annoying, but is very important. You may or may not have exposure to people outside of the interview team to ask before being hired. You want to know up front that they expect someone to work 70-75 plus hours a week, when you are an 8-5 only willing to work occasional overtime type of person.
I don’t know how one would evaluate the environment of an organization without actually working there or knowing someone who does. I have only learned to ask questions because I have been through some terrible bosses in my career (I am 31 and have been working since I was 16). Some of the terrible bosses I exposed myself to could have been avoided by asking good questions. Working for a terrible boss can make your life hell no matter how long they are in the position, even if it is only two months.
I would actually add a couple of things to Ryan’s question list: How would you describe your current team members? And, What positive characteristics does the most effective person on your team exhibit? If they have nothing nice to say about anyone on their team, I have no reason to think I would be any different and I cut my losses and move on.