The Q&A session you always wanted to have with your boss

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I’ve seen my share of holiday office parties and happy hours, where everybody has had a few cocktails, and suddenly the entire department is hugging and singing “Sweet Caroline.” For those few hours everybody thinks they’re friends with everybody else, and the normal facade of professionalism drops. And people are more honest than usual. Perhaps more honest than they should be. (“I never liked Glen from technology, but I really like you, Felicia. I really, really do.”)  And then the next day everybody goes back to being their buttoned-up selves.

Now, the one good thing about those kinds of gatherings are that people are saying things that they’ve been holding back. You get a better sense of people and see that they have their own opinions about the company and its policies. It’s a breath of fresh air! But experiencing that type of honesty isn’t always easy or common.  For the sake of your career, we’ve got a guest blogger today who is that honest.  Author Hank Gilman calls himself an accidental manager, meaning that he’s someone who rose through the ranks of his profession without setting out to be the boss. That’s why he knows the mindset of everyday workers like us and also understands the quandaries new mangers find themselves in. Fortunately, he’s answering the questions many workers have but can’t ask.

So skip the appletinis at the next happy hour and listen to Gilman’s advice instead.

I’ve been a boss in the media business for more than two decades now. It’s kind of simple job in the sense that there are only a few basics involved in doing it well. (Other than not being a sociopath.) You give feedback. You hire. You fire. You dole out raises — or you don’t. It’s a great gig, really. The pay is good and your troops pretend, for the most part, that they like you. Unfortunately, employees don’t have it so easy. They have no clue, much of the time, what makes their supervisors tick. And, as a result, they worry too much about what the heck their bosses want from them.  I recently wrote a book called “You Can’t Fire Everyone: And Other Lessons from an Accidental  Manager.” The few people that read an early version—the ones that report to me anyway — said pretty much the same thing about various parts of the book. That is: “I didn’t know you thought THAT!” I had no idea I was so mysterious. But, in that spirit, here are some questions, and answers, from me that will help you tap the inner-mind of your boss and, hopefully, manage your career a little better as a result.

Feedback: Should I ask my boss for more?

Yes.  But proceed with caution. Just between us, I’m not the biggest hand-holding guy on earth. I guess that’s because, back in the day, I never liked spending much time with my bosses. I figured the less I was around, the lower the odds were they’d stick me with projects I wasn’t keen on. (It’s the out-of-sight-out-of-mind thing.) Here’s the way I looked at it: I came up with ideas, did the research, and wrote the stories. If they were published and I got raises, that was enough feedback for me — thank you very much. That said, there are a few things you should know.

First, many bosses are spineless and actively avoid confrontation. Nor do they like to deliver bad news. It’s human nature. Basically, your supervisor won’t feel compelled to give you feedback unless you’ve done a terrific job or totally choked. (The later because they really have to.) Unfortunately, it’s the stuff in the middle that you need help with.  So, you’re going to have to ask. Nothing wrong with finding out how you could have done a better job on a specific project. Tossing around ideas is always great fun. The caveat?  Don’t be whiny and needy on a frequent basis. Many years back, I had a writer who felt compelled, every other day it felt like, to walk into my office and ask why he wasn’t getting enough feedback on his work. I think I finally cracked and said something like,  “Ok, here’s some feedback. You don’t come up with many good ideas. And when you do the stories aren’t good enough to publish.” Well…he asked.

Can you be friends with your boss?

Maybe. In an old episode of the TV show, “The Office,” Steve Carell’s character, Michael, said to a new employee, and I paraphrase, “My number one job is being your friend.” If only. Sure, people who spend a lot of time working together become friends, even if it’s a boss-employee thing. That’s the way it is. But there’s a silent code of conduct: You should not expect a raise because of the friendship; you should never take advantage of that friendship for better assignments or a promotion (or expect either); you shouldn’t anticipate employment in perpetuity. If you follow the code, you’ll be OK.

For you corporate ladder-climbers out there, the bigger problem is when you become the boss and have to supervise your friends. Back in the 80s, when rock bands like Huey Lewis and the News ruled the airwaves for some reason, I was named the business editor of the Sunday Boston Globe. My pals in the newsroom seemed like they were ready to throw a party. Come to work late? Check. Longer lunches? Check. Softer deadlines — or any deadlines? Check. Well, I’m exaggerating a little, but not much. Some of them actually thought those things. I was tested immediately. A close friend turned in a poorly-written story that she must have wrote on the subway on the way to work. I figured out pretty quickly that if I didn’t fix it, it was my job that would be on the line.  So, I re-wrote the story and she bitterly complained to my boss. I think she said, among other nasty things, that I was an idiot. But as far as my boss was concerned, I passed my first test.

(Note to future bosses: It’s either you or them, and it might as well be you.) There’s kind of a happy ending to all this, by the way. We remained kind-of-friendly. She invited me to her wedding. I think I ended up at the “cousins” table, though. As Antarctic explorer Sir Ernest Shackleton once said, “Loneliness is the Penalty for Leadership.” Yup. He was right.

Do bosses get angry when you ask for a raise and resent you forever?

No. Not the good ones anyway. This is one of the great myths of the boss-employee relationship. Now, I’ll confess, I never asked for a raise in my 35-year work-life. Partly because I was always afraid of getting fired– and partly because I always felt lucky to be paid to write about people who were actually doing more important things than I was doing. But that’s just me. No one is going to think badly of you or have you escorted from the building. You’ll get the raise because you deserve one and your boss wants to keep you happy; or your boss might tell you that money is tight and be patient, which is often true. Or, in an act of ultimate feedback, she’ll just say “no,” wave you off and quickly take a phone call. (Even when the phone’s not ringing.) Then you’ll know it’s not a raise you should be worried about.

If you get a job offer– and tell your boss you’re considering it– should you polish up your Linked-In profile?

No. That’s another myth. It’s certainly a pain in the rear when one of your employees comes in with a job offer in hand. But it’s a little flattering in a way. (I know a few of our competitors that nobody will recruit from.) It also lets us, the bosses, figure out how much we really want you.  And it helps you figure out how much you really want us. Just don’t do it on a serial basis if you really do like where you work.  Because if it is an “I can get a raise out of this” trick, it works only a few times. And only if you’re a bona fide star. And, before I forget, don’t ever tell your boss about a job offer and not be prepared to [accept] it. There’s a good chance you might not like the response. Like: “What a great opportunity! Keep in touch.” They might not view you as an “A” player or may not like you or both. Or they had their eye on someone on the outside and you just helped them, as they say in the National Football League, clear out some cap space. Just pointing that out.

Hank Gilman is the deputy managing editor of Fortune. This blog is inspired by his book, “You Can’t Fire Everyone: and Other Lessons From an Accidental Manager.” (Portfolio / Penguin) On sale now.

50 Comments
  1. Wow…good information to know.. well I did ask for a raise and got it, thank God. I think that if you know you are a good employee and bring something to the table, you will have little to no problem getting what you ask for. Ask and ye shall receive… maybe a yes, maybe a no, maybe a wait. But at least ask is what I say.

  2. An interesting thing happened at my current job a few years ago. Somebody accepted a position here, showed up for a day, and then never showed up again. It turned out, this person never resigned from their previous job, and just used their vacation to see what it was like here. I was sort of surprised by this action. (I think if you give in your resignation, you’re done at that job, personally. They might resent you if you stay.)

  3. Why is Bosses will not consider applicants who are over 60 for some reason or another? Isn’t that age discrimination. They say you don’t meet their qualifications or you did not pass the assessment test.

    • “non discrimination on age” is only an advertised proclaimation,it is not the policy adapted when it comes to real hiring time,and no authority can follow up or object in any way against that discrimination,it is just like your right of trying to get the best value for your money,no one else can interfere.

  4. This was an interesting read. I am looking for a different job, but it is not because of the pay. I just don’t like my current job or some of the people I have to work with on a daily basis.

    • I had the same dilemma about 6 months ago. My boss loved me but he was scared of his employees and upper management. I was being harassed for helping him out and he was doing nothing to help me b/c he was scared himself. And upper management wasn’t onsite at my job so they weren’t aware of what was going on. I believe he was doing things he wasn’t supposed to be doing and got in to trouble. Hence, his fear. When I went to him to let him know I was resigning, he never countered or offered me a salary increase of anything. He was angry at me because he said he had other plans for me. I realized it was all about him and he didn’t care who got hurt in the process. Well, the day I resigned so did his team leader. and He got in to quite a bit of trouble for that. I am doing more work at my new job but I really liked my job that I had previous. In the end my well being was more important than his feelings. After I left it turns out they fired one of those employees.

      • Just to clarify..when I say he loved me I meant he loved my performance. Not that he was in love with me. After I read my reply it seemed as though he was in love with me. lol

  5. Good catch, Andy. I saw the same thing. This _is_ a good read, but when mistakes like that are made (especially by a Write/Editor … and HIS Editor!) it kinda takes the sheen off it. Maybe we should edit for the Globe!

  6. Someone else beat me to it, but “MUST HAVE WROTE”?

    Were you really an editor?!?

    I think I understand why she was unhappy when you re-wrote her story.

    • Also, in Feedback: Should I ask my boss for more?: paragraph 2, should be “latter”, not “later. Love to proofread!

  7. My employers haven’t given us a raise in 2 years. And we do not get any sort of feedback as far as the quality of our work. They are also the ones who set the employment/employee standards for large corporations. I asked for a raise a few years ago, and had paperwork to show the pay scale in our area. I did get a raise but am still not up to the pay scale in our area. I know they value me and my work is great but now I am afraid to ask. Any suggestions?

    • Been at this company for 4 years. You get one raise a year no matter who u are, no matter how hard you work or how much you do. Now this company has taken extra hours away because of staffing was an issue well it isnt anymore. Still get that same money and you feel like it isnt worth the time any more for that same money. You drive almost 50 miles one way for this job every day.Got interview tomorrow with another company after work tomorrow. A associates position. Should I talk to my boss and see if there is a raise even though people are here?

  8. Must have wrote?! I pray that this mistake was just an oversight and that you aren’t running around saying other crazy things like, “I seen,” “he don’t,” and “have ran.”

    You had such great content, but I can’t think of anything else now! LOL

  9. Very good!! But, regardless of the raise, I don’t have my raise at least 3 years now.

    How do we deal with Bosses who want our works then throw out our good name in the trash and replace with his/hers?

    How about Bosses who bully us around? Here is the truth scenario… Afraid of our work is taken by our boss… we send an invitation to everyone to demo our good work. Our boss calls us in the office, and tell us to cancel the meeting. However, he/she asks to send back our work to him/her. Hours later, he/she send out the demo invitation under him/her self as the project manager/owner.

    What do we do with this kind of bosses? Is there existing any thing call “the judgement day”?

    • Yes – copy your boss’ boss and other team members and frame it as you’d appreciate their collective feedback before rolling out the full-scale project – or as a “meeting before the meeting”. It’s a non-threatening way of sending a message to your immediate boss about sharking your work.

    • Do your homework on these types in order to develop strategies. Read “The 48 Laws of Power.”

      Law 7: Get others to do the work for you, but always take the credit.

  10. Andy, Todd, there are many more grammatical errors in this article than “must have wrote.” Com’ on fellas. This is how many, many people write in the 21st Century, and as a boss, he’s writing to appeal to as many people as possible with some common sense ideas.

    You would find more agreement from me had you noted this author’s silence regarding routine meetings successful managers set with their reports. Many successful managers communicate clearly the department’s goals and expectations to their staff in routine meetings, at least once a month. Two meetings a month are more appropriate, one departmental meeting so everyone is “on the same page,” and one individual meeting with each staff person to discuss individual performance and progress. After two or three of these meetings, it becomes routine for everyone – manager and staff – and everyone comes to expect them. Call this the ultimate ice-breaker. Additionally, routine meetings tend to forestall the “hand-holding guy.” He will always have one to look forward to. By the way, the manager’s manager should be involved at least once a quarter in the departmental meetings too to ensure the department is going in the right direction and to gauge the department’s morale. (Yes, even we successful managers need a “course correction” every so often!)

    Perhaps another example of good advice from this editor might have been WHAT goals to set for his writers to give them a clear sense of direction. A couple examples of clear expectations would be;

    1) as writers (and editors) representing a well-known big city newspaper, we should use good grammar. Please be mindful of your P’s & Q’s. Therefore, I expect to see an improvement in your grammar in the upcoming articles please.

    2) for you “subway” writers, your articles need to be a little longer than it takes to write between two subway stops, and it needs to be more engaging for our readers than three-word sentences (the simplistic sentences one would write traveling only two subway stops) – otherwise, I’ll be forced to use a my red pencil to make my corrections to your article at the “cousins’ table” at your wedding!

    3) and here as a hypothetical scenario – due to the recent downsizing of our hypothetical big city newspaper, we will need to increase the number of articles you folks are writing. Unfortunately you will need to prepare to help produce articles for our colleagues over in the Local News, Political Affairs and Neighborhood Buzz departments. This is scheduled to take effect next month. So in addition to the 5 articles per week you’re putting out now, we’ll need one article for each of these departments beginning next month. I can either assign one of you these tasks on a rotating basis, or you can pool you’re resources and share the load. Otherwise, I’m open to ideas on how you want to accomplish this. As a light-hearted incentive, here’s five bucks from my wallet for the first person to come up with the idea we can all agree on, which will meet this new demand!

    • Well said, and I totally agree. Correct grammar is not always required if the writer is trying to be informal in his/her tone. The read came across as rather conversational because of this.

      And your reply, Dieter, I found it amusing. Glad someone on here can keep up. That someone would get all whiny because of a rewrite, especially in that business, is shameful.

  11. But first ask how well I have done; If you get a positive word out of your boss like Exceptional or doing excellent job.On behalf that may I have a raise in Salary? Ask them those 2 questions while massaging there shoulders and asked @ the same time w/a cheerful voice?

  12. I work in const. I’ve not ever asked for a raise, however this is good info. I’m a great worker too.

  13. Great article. I happen to be friends with my boss. And the boss over both of us is such a nice gentlemen that he doesn’t get paid so we can have a check. And in fact, he’s nice enough to remind us of that fact, oh I’d say maybe 4 or 5 times a month. Needless to say, I don’t ask for a raise. lol

  14. <> Wow ! This is a “poorly-written” verb conjugation that was used by an Editor of Fortune Magazine and it is a glaring mistake to many readers. Maybe the Editor wrote the statement on the subway.

  15. Great article – enjoyed the candor, good humor and down to earth conversational style.

    The grammarians in our midst are obviously unaware of the alternative past perjorative speculative subjunctive. Their English teachers must have not wrote about it…

    To ‘have written’ implies an action that was complete at the time of reference – this speculative subjunctive tense implies that the writer was not even finished at the end of the subway ride… ;)

    It is an excellent part of the conversational editorial style – such is the license of the art :)

  16. OMG, you were a boss in the media business for over two decades? Does that include having to know grammar? You wrote–capitalizations mine–that “A close friend turned in a poorly-written story that SHE MUST HAVE WROTE ON THE SUBWAY on the way to work.”

    Hello-o-o-o!!! The correct grammar is “that she must have WRITTEN”. Furthermore, “poorly-written” is NOT hyphenated.

    Signed: A most disillusioned Christie Wagner

  17. We all make grammatical errors from time to time, BUT

    1. “Must have wrote” is such a painful and obvious error.

    2. You claim to be a professional writer/editor, so the reader expects more from you than from other bloggers.

    3. One of your themes is the poor quality work turned in by other people. Such irony!

  18. Is it appropriate, to ask the person who just interviewed you for a job, that you did not get, for any suggestions to make your next interview better? Suggestions s/a: dress, interview, education…

  19. Great post. Even though we can’t crawl into the mind of our superior, there are context clues as to what they’re thinking. As for the gray areas, I would hope that person would be able to talk to their boss to get an answer or resolution to the problem.

    I write regularly for a career tips blog. The topics we write about are centered not only on career search advice, but suriving the office and how to get through the work day; much like what this blog is trying to accomplish. I put together a post about different personality types in the office, and how to get along with them. It’s a good read, and encompasses a range more broad than your cube-mate – http://onlinecareertips.com/2010/12/are-you-the-grinch-at-work-deciphering-personality-types-and-how-to-work-with-them/.

  20. In my past experiences with most companies if they find out your looking for another job or have a job offer they fired you or found a way to get rid of you. Can you be friends with your boss? My answer is no and if you think he is your friend then your wrong. I have given blood sweat and tears for former companies and have gotten crapped on in return. Right now i would rather go on another deployment then go out and get a job and be treated like a dog. But what goes around comes around.

  21. I’m with you Pittsburgh. A real Irony and shameful. This is a classic example of mediocre bosses. Often we hear employees complaining about this kind of supervisors, usually we hear them say things like “My boss is an idiot; I can’t believe that he is a head of department.” Sad but true.

    Corporate America is infested with these types of “professionals”. To understand this particular case we must focus our attention to Balderrama’s line “Author Hank Gilman calls himself an accidental manager, meaning that he’s someone who rose through the ranks of his profession without setting out to be the boss”.

    It is that simple, the typical case of a very lucky man…

    • Yes I had a boss that I would describe as a big bully plus does not help at all when it comes to create/develope in the work place but would rather sink it to the bottom possibly along with himself which I find very dangerous This exboss of mine is the General Manager of First Transit in Boca Raton who needs to be removed, resign, retire or be fired immediately

      • And just for that, the whole bus company which is First Transit needs to pull out and be removed along with the General Manager at Century Village in Boca Raton, Kings Point in Delray Beach and Employees Shuttle at Miami International Airport. If there’s anybody out there in South Florida that can make this happen. Then let this happen as soon as possible so that a local South Florida bus company can take over the shuttle service and this could slowly but surely start the recovery in create/recreate jobs and hire/rehire more shuttle bus drivers.

  22. I have a good one for you all but I know my boss reads many of the articles here. I hope he reads this one and sees himself and can become better at his job since I do about 60% of his and 100% of mine. Sometimes you have to learn that, as the author wrote – As Antarctic explorer Sir Ernest Shackleton once said, “Loneliness is the Penalty for Leadership.” Yup. He was right. —- I agree, but for most of those lonely leaders who are getting paid a cr*p load of money out there – the loneliness comes from their ‘LACK’ of leadership. If you are a manager reading this then I have a bit good advice for you – Learn to Lead but don’t bully, learn to listen and don’t interrupt by trying to equate your story with your employee’s it minimizes them and give the kind of feedback people need during the course of the year and DON’T wait until a person’s annual review to use it as a corrective action measure. Good feedback and mentoring will help managers grow good future leaders. Just some food for thought from a NON-manager.

  23. How about people that don’t do anything and get everything. They walk around getting the best and easiest things to do. Throwning everybody under the bus and they come out smelling like a ROSE. The company is so big that you don’t know where to turn without losing your JOB. And that is the way the Boss got his job. Forgeting about the work and sweat that people are doing and not being reconized, or even just Thanked for a good job done.

  24. The Peter Principal states that people rise to the level of their own incompetence. I’ve worked for bosses that knew about as much about the business as the interns and even less about people. Seeing them screw up was funny, but we had to make it right in the end, not them. Great bosses aren’t your pals, they’re your teachers. I became a manager by watching how the good ones did it, asking questions, and learning as much as I could. I’m still learning.

    • Sallie, I am with you and Richard. Good leaders are those who provide the feedback. Many do rise to the top for the wrong reasons and but like you many don’t. You are right, boss are like parents, they are there to teach and be the boss not your friend. Learn that early on. Being friendly doesn’t mean you are friends. It is a job and in the end, their job is more important to their livelihood then yours. For those of you who see that your leaders lack in leadership, seek out other members of the company that can provide that mentoring to you or you may have to leave the company to seek them out. Work isn’t always about the money but when you see the wasted dollars paid to managers/leaders who fail to manage or lead then it is frustrating. Those who wish to move up the chain, learn from postings like this and don’t end up as the butt of someone’s post. I am a new manager and like Sallie and Richard, I have had great leaders so I hope I can pass on what I have learned to someone else.

  25. Great info…. I work for a company that no one cares, not even when a great job is done. They are the ones that get all the credit,however dont do a thing.

  26. The good mentors who instructed me gave general guidelines and delegated leeway to accomplish de facto tasks providing wisdom and value added. They also protected me politically and kicked me in the rear as required. My bosses also wisely shared good people skills through example and reminiscing.

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