How to Be a Boss

How to Be a Boss2017 update: We still stand by this advice on how to be a boss (and links have been updated) but you may also want to check out our latest discussions on being a boss

How do you be a boss — if you’ve never been a boss before? What changes do you have to make to your working style, attitude, and more? Reader Y has a great question.

I received a promotion last year at my job and I have had some trouble adjusting. I am generally a lighthearted jokester in the office and I find it hard to delegate work or to have my coworkers recognize/ respect my new position. Even though it has been a year, I was wondering if there is any way to turn this around?

Congrats on your promotion, Y! We’ve talked about how to step up your wardrobe to be seen as more managerial, how to delegate to your assistant, and whether you should be friends with subordinates — but we’ve never really talked about the changes you have to make when you become a boss.  (Update: and I just found this post on how to become a leader — knew I had one in the archives somewhere.)

When I started managing people, I remember this being kind of difficult as well — particularly because I was basically a middle man between my boss and my subordinates. My “big sister” instincts kicked in and I basically tried to protect the subordinates. I tried to make sure that they didn’t turn in work that made them look bad. I tried to give them super advance warning of projects and deadlines, since I had always hated when people dumped projects on me at the end of the day. If my boss had harsh criticism for the subordinate I tried to filter that and spin it so my subordinate got the constructive criticism minus the stabby feeling.

All of this sounds, well, Nice in retrospect. The truth is I spent a lot of time that couldn’t necessarily be billed, and maybe coddled my subordinates a bit too much.  With some distance, I’d have given myself these tips on how to be a manger — I can’t wait to hear advice the readers share.

– Be friendly, but be professional.  Put another way:  “be ok if you’re not liked.”  After all, how many bosses have you really and truly liked?  You can be liked by your friends. You don’t want to be hated — I think that usually speaks to you being a lousy manager — but it’s hard to be your subordinate’s best friend one minute and dumping hours of legitimate-but-not-fun work on them the next.

– Dress for respect — particularly if some of your subordinates are older than you.  Think blazers, structured pieces, classic shoes.  Whatever your hair and makeup routine is, strive to look put together above everything else.

– Protect your earned respect by being mindful of what you do near the office.  For example: in my dating days I never brought my suitors near the office.  Don’t go drinking with friends near the office and talk loudly about your job.  You may even want to consider salons near the office to be off limits — the last thing you want is to give someone a huge project and then be seen getting a mani/pedi near work.

– Be very clear on what work product you want before you assign it.  This may take a bit more time before you assign it, but it’ll help you come across as certain, it’ll help you be clear in assignment and feedback, and ultimately it will aid your reputation as a good manager.

– Give good feedback — for both you and your subordinate.  Tell him or her what was good about the work — but also what could have done better.  What would have made it more helpful for you in the long run?  What were the additional steps that you had to do to make it helpful to your boss — and could the subordinate do those steps the next time?

I think those are my main tips.  Readers, what’s your advice for Reader Y — how did you learn to be a boss?  What did you change when you started managing others?

(Pictured above: Greatest Boss mug, available at Cafe Press for $13.49.)


  1. I am NOT sure how good a boss I will be, but the manageing partner has been buggeing me to hire a new associate to handel my overflow, and do a little tax work also. I do NOT want a sniveling young guy who will make me do all the work. FOOEY ON THAT!

    I have been SO Snowed under with all of my casework and my docket runneth OVER! FOOEY! Even the 2 judge’s at the Comp Court look at me like I am the HUMAN DYNAMO with all of the case’s I have. There is a new judge there that is handeling my judge’s over flow so mabye there are alot more cases EVERYWHERE! YAY b/c that mean’s more billeable hours and more firm profits for the managing partner. When I told him alot of my clothe’s are getting worn out on the subway, he said to take a cab to court. I said the cab’s were grungie and the cabbie’s all stare at me thru their mirror’s (some with food in their mouth–FOOEY). I asked if he could take my clotheing allowance up to 75%, and he said he would think about it, but he would put a $15,000 annueal cap on it. I have to talk to my dad to see if this make’s sense b/c onley he know’s the annueal total of my clotheing. I think I will need for him to include acessorie’s now if I am to get the full VALUE, but I will have to talk to dad. He did call me and said that he was sorry for being so pushey. YAY!!!!!

    • Aren’t there a few young lawyers on here looking for work? Who wouldn’t want E11en as a boss?

  2. I don’t know that what I changed in my work behavior when I started managing people would be all that valuable:). It takes time to figure out a managerial persona and approach. At the highest level, you are now responsible for results, and for people, and you have to learn to balance the two.

    Learn to coach. Learn that you have to repeat yourself. Learn that people want you to be good at your job, unless they are jerks, and then you manage them very tightly. Learn that the good people want to be seen truly more than they want praise.

    There’s more:)

  3. Anonymous :

    Small rant. I’m a very curvy person with an exaggerated hourglass figure. Because it’s nearly impossible to find sheath dresses that fit without massive (and expensive) alterations, I normally stick to wrap dresses with A-line skirts for work. Today I wore one with a high neckline, 3/4 sleeves, A-line skirt down to my knees, dark color, thick/lined fabric. As an extra precaution, I bought a size up so it wouldn’t be clingy. I can literally grab several inches of loose fabric at my waist while I’m wearing it. Result? Someone I don’t even know comes up and tells me she’s surprised I can “get away with” wearing a “sexy dress” to work.

    Sigh. Excuse me while I go hide under a bulky cardigan.

    • Don’t hide. Anyone who would come up to a stranger and make a comment like that is being rude at least, and possibly a bully by trying to make herself feel better at your expense. Think about it – why would anyone say something like that? She wasn’t helpfully letting you know you had a tear or something; she was just criticizing. Anyone who goes out of her way to criticize a stranger’s appearance has her own issues, and should be ignored.

    • TO Lawyer :

      Agreed don’t hide. I’m sure your dress is perfectly appropriate. Some people just have messed up ideas about office wear and make inappropriate comments because they like to make other people uncomfortable.

      Example – my boss’ 60-something law clerk who thinks my knee-length pencil skirts, 2.5 inch heels and dresses with a belt to cinch my waist are too s3xy and inappropriate. On Monday, she pointed out my shoes (which were the same colour as my blouse) to a male law clerk and said I was too coordinated and was trying to impress him.

      I think you just have to ignore those people. You went to extra lengths to make sure your dress was appropriate and I’m sure you look fab!

    • Don’t hide! I heartily agree w/what Eleanor and TO Lawyer said. That coworker didn’t say what she said out of kindness; it was a microaggression, and definitely to be brushed aside.

    • NWanalyst :

      Sounds like cattiness to me. There are many people at my work to whom I could make that comment, but I never would. Because it’s mean and inappropriate to say something like that, in those words.

      If someone came up to me and made a comment like that, I would actively avoid them in general. Strictly speaking, I think this might border on harassment, since she actually approached you and brought up the sexy factor…

      • Yes, I agree, sounds like cattiness and jealousy, and agree on the bordering on harassment as well, since the DRESS obviously isn’t “sexy”, but your BODY is perceived as “sexy” in it, and commenting on people’s bodies at work is just not appropriate.

  4. Anonymous :

    Perhaps it would help reader Y to separate times for joking and times for being the boss. Contrary to Kat’s experience, I have had true friendships develop with very good bosses that I respect. It is ok to have good relationships with coworkers, but everyone (including you) needs to know when you are wearing your “boss hat”. At first, it may help to say something like “Ok, let’s put on our job hats on” or “ok, let’s get down to business” to break up the joking. It may feel a bit odd and cliche at first, but if you change your tone and start talking about work, everyone will pick up the tone and focus. Be exra serious and determined when you switch so everyone gets the message loud and clear. As they say, fake it until you believe it.

    • Senior Attorney :

      I used to be the lighthearted jokester, and honestly, at some point one just has to give that up if one wants to be taken seriously at work. I’d suggest Reader Y work on developing some gravitas at work and saving the joking for after hours.

      And as an interim measure while you’re still working on it, I like Anonymous’s idea for signaling “time to be serious” by saying something like “let’s get down to business.”

    • ExcelNinja :

      as long as you don’t say it’s time for business socks :)

  5. Trying to encourage someone to change a “bad attitude” threadjack:

    Thought about going anon for this, but thought the better of it. Might as well own up to my having major difficulties with my mother about this issue.

    1. My mother has this habit of body-snarking and appearance snarking. Primarily other women, and on my friends. This has led to some amount of conflict because I will defend my friends and call my mom on her BS. I don’t believe that her being “family,” exempts her from the requirements of being a decent human being.

    Example: after one of my friends got married, my parents and I were looking at her website (personal blog, which included some wedding photos). I was one of the bridesmaids and I was busy identifying everybody in the photos, and all my mother could say was, “that bride is HUGE. why didn’t she lose weight before the wedding?” Me: [Vigorously defending my friend, challenging my mother on what she said].

    End result: my mother screaming like a banshee at me and me telling her that I was leaving because she doesn’t get to talk to me like that. Also, my father calling her a b—-, and blaming her for ruining my visit. Good times, right?

    2. In school, my mother and I occupied completely different social strata. She was the “town beauty” and has always been (conventionally) beautiful. No awkward phase. (I look nothing like her, was an invisible geeky type, and have only recently learned to not be so awkward now that I’m in my 30s.) Because she was treated so very differently — it really opened my eyes as to how different her experience and worldview was from mine when my uncles bragged to me (ugh!) about how people (mostly men who were friendly acquaintances, coworkers, fellow students) would just *give her things* (gifts, trinkets, free tickets, favors, offers for connections, recommendations, help, etc.) . Not because of anything she did, but merely because she was beautiful.

    As much as it pains me to say this about my own mother…I suspect that she (subconsciously) views those who are less conventionally beautiful as someone who’s existentially inferior on some sort of unbreakable, set-in-stone hierarchy that’s so obvious it’s unspoken.

    Have any of you ever dealt with this from someone you love?

    I recall people posting about how to deal with racist relatives, and this is a similar problem, but harder to pin down, because there are so many off-the-shelf resources to address racism, and far fewer ones to address this ..look-ism and body-snarking.

    I am hoping to have a good …initial chat with her about these issues to frame the problem and probe why she does it. It doesn’t always come out; but it’s like a casually cruel thing that slips out, revealing what she really thinks about my friends. Any ideas about how to approach this subject, and to try to offer continuous encouragement to get her to not be so nasty about my friends (and other people’s apperances in general)?

    • Senior Attorney :

      I don’t think it’s realistic or reasonable to think you are going to be able to get her to see the error of her ways.

      I do, however, think it is highly appropriate to set a boundary and say “Mom, I love you but I’m not going to listen to that kind of talk [about my friends].” Repeat as needed and if she persists, you get up and leave the room.

      The benefit to this approach is that you aren’t [overtly] making her wrong or calling her a non-decent human being, which is guaranteed to get her riled up and defensive. You are just telling her that this topic is not open for discussion with you because you don’t like it.

      Good luck!

      • Senior Attorney :

        Forgot to say I don’t think probing why she does it will be helpful. Just let her know that henceforth any such talk will send you scurrying for the exit, and then back it up each and every time.

      • Sydney Bristow :

        I’ve never dealt with this type of issue before, but I agree. I think saying that each time it comes up and following through every time could at least avoid her screaming at you. Maybe if it happens enough she would start to consider looking at her actions and thoughts, but I’m not sure that is likely. I think before you could reach a place where you discuss the issue in generalities you need to at least be at the point where conversations aren’t turning into her screaming.

      • I like this, as I’m dealing with similar comments/ worldview from my MIL and I’m worried about its effect on my daughter. I know I can’t change MIL, so I like the straightfoward approach of “You cannot talk about people that way in front of me or DD.” and then leaving the situation if she persists.


    • Maybe I am more cynical, but my mom is in her late 60s and I don’t think she is capable of significant change, especially with something that is fundamental to the way she experiences and perceives the world. I think if the real issue is how your mom talks to you about how you look (not your friends), then maybe you two can work on your communication (my mom and I both enjoyed and benefited from “You’re Wearing that? Understanding Mothers and Daughters in Conversation”). But it sounds like you really want to change her basic views and judgments. I don’t know how realistic that is. It doesn’t mean you can’t correct her (thinking of responses to racists grandpas, that kind of thing). I just wouldn’t expect any real change.

      • My mom used to snark on me in the same way, but I put the kibosh on that more than a decade ago, so that’s not a major issue. Now, she only offers up the occasional (1x/year) , “hey, I notice you sometimes wear your hair in a bun, and I think it’s less attractive than when you let your hair down,” to which I reply, calmly and quietly, “my hair in a bun is attractive to me and makes me happy. I put making myself happy infinity times more important than trying to be attractive to hypothetical men, you, the CVS clerk, etc.” That shuts her up.

        Maybe I’m more optimistic. My mom is in her mid-60s and I do know people in her age-set who have been able to change. She’s been able to change certain other things about herself, so I have a little spark of hope that she’ll make *some* improvement in this matter.

        • i haven’t read all of the comments on this yet, so maybe you got this further down in the thread, but i agree. i do think people can change, and i think in this situation, you could help your mom to see how these comments are hurtful (to anyone who might be listening, but also ultimately to her) and help her to change her way of thinking about the world. And I also think finding out the “why” behind her thought process would be the key to this.

    • Diana Barry :

      My mom is similar about body size and gender-related norms. I have a daughter who is thin and small and a son who is tall and was chubby as a baby, and she would make comments like “It’s so great that Daughter is so thin and Son is big, it would be awful if it were the other way around!” Gah. Luckily, she has backed off on it as the kids have gotten bigger and more aware, but I think Senior Attorney’s approach of “this topic is not something I will tolerate” is a good one for when people say these kinds of things.

    • The first thing I thought of here was aging: nobody is gorgeous enough to get free stuff from men forever, and this is obviously a huge part of your mom’s sense of worth. Is she hitting out, so to speak, because she’s losing at her own game?

      I have a lot of issues with my own mom too, and I go back and forth on whether it could ever help to address things directly. One option I do see for you is to make her realize that she values her own daughter who is not living up to the beauty standard (so you say), so does she think other people’s daughters are less loved or whatever due to their supposed flaws?

      • I don’t know if she thinks that other people’s daughters are less loved. I think that one of the reasons why she is extra snarky about my friends is because she views them as my s#xual competition (never mind that I’ve been with the DH forever…)

        I do know that aging has been hard on her, and that her attitudes make it harder for herself to deal with aging. This pains me, because I love her and want her to get more out of life (and be more respectful when she mentions my friends.)

        • so this is why i mentioned earlier upthread that the comments are ultimately hurtful to her. she is further supporting the idea that traditional beauty should be recognized and strived for every time she says something negative about someone who doesn’t fit those norms. Some of that attitude has to be getting to her as she gets older.

    • My family and to an extent most everybody of the same ethnic background does this to me and basically to every individual ever.

      My father’s first question about family friend’s daughter after her first semester at Harvard was, “did see get pretty in college?”

      Not only is it body snarking, it’s the assessment of a woman’s worth as only tied up in her appearance that bothers me. I’ve discovered it’s affected me and my familial relationships enough that I’ve been drawn to Brene Brown’s books and therapy.

      No tips or suggestions, just wanted to add that I truly hope that more women like the community here will continue to try to fight these destructive patterns.

    • Thanks to all who’ve replied to my post. I agree with those that it might be tough to try to change her attitude (or even her behavior). The screaming thing is something that I think I have to deal with separately — she’s done this before about other stuff, and it’s just inappropriate in general and unproductive.

      As I read through the replies and think about this subject, I also understand a little better why I react the way I do to certain things. (e.g. when I read magazines that have articles like, “how to hide all types of figure flaws,” I get irritated and really recoil against that. The chirpy advice to wear certain types of pants, pant-hems, and shoes to try to approximate tallness (and thinness) just reminds me too much of my mother’s commentary. )

    • I have a similar mother and a similar story and I found this book to be helpfil: Will I ever be good enough? Healing daughters of narcissistic mothers.

      I don’t talk to my mom about what I view as her shallow, appearance-obsessed personality. I try to ignore comments she makes about my appearance. I ignore comments about my friends’ weight and my friends’ husbands’ weight. I try to enjoy the parts of her I can, I keep my distance, I don’t ask her opinion about my clothes, shoes anything, and I try to see and value people for who they are not (only) what they look like.

      It’s not easy. But being confrontational would, in my case, just make it worse.

      Good luck.

      • I do think that it is important to remember, not as an EXCUSE but just in an effort to understand “why”, that our mothers in their 60’s (my mom is 67) are this way because they grew up in the 50’s and 60’s. Unless they happened to be on the cutting edge of feminism…then they are reflecting the reality of *their* felt experience.

        In other words, we get upset because we see them “tying a woman’s value to her appearance” when the fact is, when our mothers were 20? A woman’s value WAS tied to her appearance. Now, maybe some people still do, but we get angry about it, we rail against the societal constraint. In our mother’s time, it wasn’t acknowledged as a wrong thing. And, your appearance/weight really WAS considered the “reason” for negative things in your life. If you gained some weight and your husband left? Well what did you *expect*? Again, I am not at all saying this was right or okay, but what is so easy for us, now, to forget, is that it was REALITY for our moms.

        Just like dealing with someone raised in an era when racism was widespread, this does not mean you excuse or allow the comments. But I think unlike racism, which is pretty universally decried at least on an outward level (there is still plenty of racism, but while apparently it is still really funny to have advertisements that riff on rape and kidnapping, I don’t think that an ad making fun of lynching would go over very well).
        So, I think that when you were indoctrinated from birth that your worth actually IS tied to your appearance, and that if you let yourself “go”, bad things really WILL happen and they really WILL be your fault; and then people are telling you, that’s not acceptable anymore but from looking around you at the media it sure still SEEMS to be true…If you’re old you’re worthless, if you’re fat you’re a joke, and if you’re attractive you’re a sex toy.

        I think it’s hard to change a deeply held view when it actually still appears to be the dominant societal view.

        I like the idea of simply putting a hard boundary that you aren’t going to tolerate this type of talk. But recognize the history.

        Marital rape was still legal in almost every state when I was a child.
        I’m only 37.
        The world was a very different place for our mothers.

        • Very true. I’m 57. And I remember so clearly, at the age of 12, listening to my teacher talk about something called, “Women’s Liberation.” Even so young I got goosebumps, and knew that it mattered. However, I was in California, Northern California to boot. So we must have been in the earliest wave of change. If you can imagine then, growing up female in more conservative parts of the country, only 5 years earlier, how it must have been.

          I always feel that the women who grew up in that era gave up so much that it takes a very evolved person not to resent younger women who are saying that it was all unnecessary sacrifice.

          • Thank you to the anons, Aon, and Lisa for their wise, late-night posts.

            They explain so well why my mother’s worldview is what it is. And they remind me to try to be kinder when I approach this topic with her.

  6. Blonde Lawyer :

    Ugh CNN reporting shots fired on Capital Hill.

  7. Anonymous :

    Finance TJ re IRAs

    I need to roll over my 401K with a former employer to an IRA either with the same company (a “wealth management company”) or another place like my bank (USAA) or somewhere else (Fidelity?). How do I decide where my IRA should live? FWIW, I will be the only contributing to this new IRA for the next two-three years – my employer does not have a retirement plan that it will contribute to, or that I could contribute two on my own (USG in temporary position).

    • I Love USAA :

      So one vote for moving it there.

      I have had their insurance for 26 years. Two weeks ago, I bought my first car in 13 1/2 years, and I used both USAA’s car buying service (paid less than invoice) and loan service (borrowed half the price and my rate on a 3-year loan is 0.89%).

      I have always gotten the best products and the best service from USAA.

    • Veronique :

      Subscribing for comments

    • Wildkitten :

      Wealth management companies usually charge higher fees and don’t perform any better than the market.

    • I’m in the process of rolling over a 401k equivalent to an IRA at USAA. Both my old and new retirement accounts are at Fidelity, but I’ve had nothing but good experiences with USAA and figure it will be easier to keep track of everything there- I also have a Roth IRA, credit card, checking, savings, and insurance with USAA. USAA also had clear instructions on how to do this on their web page, while all Fidelity’s web page would tell me is that I had to call them to find out my options and I didn’t want to have to deal with someone trying to hard sell me on funds I wasn’t interested in. I’m still waiting for Fidelity to get me the check that I then mail to USAA, but it seems like it’s going smoothly so far…

  8. Read every managerial post at

    She covers things like this all the time! And her advice is spot on.

  9. ‘Ok not to be liked’

    I’ve been a senior manager ie. a manager of managers for many years at places which undertake 360-degree annual reviews and have observed, with a high degree of consistency over many cohorts and functions, that supervisees are the toughest graders of their own boss. Supervisors and peers are much more generous. A good supervisor usually gets a better evaluation than a poor one, of course, but is still likely to have been graded better by their peers and boss. My first evaluating manager told me the same thing the first time I flipped out over my own poor ratings as a young manager, and the HR folks I know confirm it as well.

    It comes down to the supervisee-supervisor dynamics. For most supervisors, supervising is only one of their many responsibilities and each supervisee is only one of their team. So they try to do their best by all their competing responsibilities and will fail, sometimes, in small ways. Whereas for a supervisee, their evaluating manager usually looms all-powerful in decisions regarding pay, promotion and opportunities, and very possibly their day-to-day workload and well-being. Their supervisor’s small occasional failings at supervisory duties as it pertains to them have high impact and are therefore graded much more harshly.

    Kat’s advice on communicating expectations is spot-on though.