today’s question is: “what makes a great boss?” (it’s a long one, we know!)



i love to ask this question to potential directors when i go on interviews. i’ve worked with amazing and award winning bosses and ones that made me cry and want to quit. watching the good and bad has made me realize what kind i want to be one day.

i think a great boss gives their designers creative freedom and doesn’t micromanage them. personally, i work better when i’m given a project brief and (when time permits) run with it for a couple of hours. i will bring back sketches and inspiration and we usually pick a direction together. sometimes the direction is already set and part of the fun isn’t there, but i like that my superiors trust me to get it done on my own. the worst is when they’re standing behind your desk asking you to move that square a little to left. a little more. more. just a litttttle bit more. has that happened to you? have you seen this tumblr?

a great boss is someone who inspires you creatively and/or personally. i’ve been lucky to have had both. i work with these fabulous rock star women who are incredibly talented. i am very fortunate to train underneath them because i know that it makes me a stronger designer and person. i’ve had some negative nancys before and they would bring me down. they didn’t like their jobs, they were never excited about the work we were doing and it reflected in their work and mine.

a great boss will involve you in as much of the project as possible. i think it’s so beneficial to be part of the entire process. you learn so much more that way. and if the designer isn’t at a level for a certain aspect of it ask them to come and observe. just being included and listening will be rewarding.

a great boss gives clear feedback. i’ve had really good and really bad art directors at this. the best were always confident in what they said and responded in a timely manner. the ones that weren’t so great were always contradicting themselves from revision to revision. it wasted a lot of our time.


like katie, i have had a great boss and one really terrible one in the past. and now as i am still learning to be a good boss MYSELF, i think this topic is interesting. (there was such good feedback to this post about my struggle with it. and i feel like i learned a lot from the comments!)

we will start with my good boss. she was VERY hard-working which set a great example for me. she was enthusiastic and fun, yet very serious at the end of the day. whenever i would bring her a project, she always had notes. she always gave me something i could improve…which at the time felt like she was being hard on me, but looking back it’s what made me try that much harder. it gave me thick skin. i also started to be able to anticipate what she would circle with her red pen and fix it before i presented it to her. it definitely made me less lazy when you know someone is very detail oriented (some bosses just say “good job” and barely look over it.)

and now for the bad. some bosses have an ego and don’t actually want to help you, they just will try to hold you back. i would much rather receive feedback than someone just taking the project back and fixing it themselves with no notes on how to improve in the future. i was young, and SURE i probably wasn’t even that great. but i needed guidance at that time and was really held back. this job is what made me start this blog. so much frustration…i knew i needed to start finding my own voice in design.

now, the kind of boss i WANT to be. like i said in this post, i am hard on myself and that makes me hard on the people that work for me. i think back to the people that made me stronger and they were always pushing me to do better. be faster. be more efficient.  be less lazy. i had a teacher that would throw my work on the floor and say “there’s a chip in this paint, why wouldn’t you just start over?” i couldn’t believe he would tell me something like that. he would rather me REDO my whole project than just knock off a few points for the chip on the corner? but this runs through my mind all the time now. when i am too lazy to tag my posts, or post on every social media channel or post everyday…i think about that classroom. he inspired perfection and detail in me.

it is hard to talk about myself as a boss, so i asked my assistant about what she’s learned working with me and what she would say about my management style (no pressure there! ha.)

from alex: “i think when i first started here over a year and a half ago, neither bri nor i were sure just how this whole business would shape up. we knew we were growing and that there was a lot of opportunity, but i know that bri hadn’t had her own employee in this capacity before, and i had never started with a small business that i would be helping to build from the ground up. one of the things i like best about working for bri is that she is very communicative. if we have a misunderstanding or she’s not happy about something, i will know about it. i feel like it’s an environment where we can openly discuss things like my job performance, her expectations, how we can improve etc.

bri has actually taught me a lot of things in this regard, and one lesson that has stuck with me is that yes, it will be scary to bring certain things up sometimes, but that moment will pass very quickly once you’re in the conversation. there is no room for passive aggressiveness when you’re trying to get things done, and open communication is key to any successful relationship. bri will also lay out her expectations and make them clear. if they change she will let me know. she gives feedback about my work but instead of just expressing her approval or disapproval she takes care to give me suggestions about what could make it better next time. this has been invaluable for me and like she mentioned above, i now anticipate her reaction to what i would bring her and adjust it before presenting accordingly.

i think when you’re working with or for someone close in age (or anyone actually!) it can be a delicate balance, but somehow bri manages to allow us to have a friendship and good personal relationship while making it clear what our roles are and that a certain level of respect and professionalism is always expected. she has taught me to be confident in my opinions and to ask for help when i need it (which we’re both still learning to do!) and i always feel she is approchable and open, which for me is one of the most important aspects of creating a work environment in which an employee can learn, grow, make mistakes to learn from and ultimately flourish.”

(illustration by katie evans. read more freelance advice posts are over here!)



Add your own

    I love these ADVICE posts. They are great. It’s so nice to be able to get some insight from other designers with a more experience than myself.

    A good boss can make all the difference in the world!

    alicia says:

    Great advice post, as always. I’m not going to talk about previous or current bosses, but more so about art school teachers. In a sense they are your art director while you are in school.
    We had this one teacher that was sooo strict. If you handed your work in at 8.02 when it was due at 8 he would either dock marks (a lot of them) or fail you for that project. (we got into a habit of arriving in class an hour early just to make sure we weren’t going to be late or stuck in traffic)
    We had to make brochures and print them and bind them ourselves. We were just figuring out how to use double sided tape and all our booklets looked pretty messy. He would review them and tear at them to see if the tape would hold. He was strict and harsh and taught us perfectionism and the importance of details. Just like Bri said it’s something I learned from him and it stuck with me.
    Another great skill I learned from this teacher the importance of conceptual work. As designers we weren’t expected to just “make things look pretty”. All our work had to have a strong and solid concept behind it and all the imagery, type, layout and details had to support your concepts. So many times I had to run 4 or 5 concepts by him before he approved one good enough.
    Luckily we had a few classes with this teacher and towards the end he became less scary and more approachable, but still strict and further pushing us and our ideas. Thanks to him I have developed a strong skin, can handle criticism, know how to give constructive criticism, pay high attention to detail and perfectionism and try to do more then “just make things look pretty”.

    kendall says:

    VERY insightful,
    having just had my annual review with my boss this post puts into perspective how great I have it.

    I work with all men, which can be challenging, but they support me, my blog and my creativity, I like the point about circled notes in red – I always feel discouraged when I believe I’ve done something great and it comes back bleeding red … and yet, it’s a good point, these are always points of how to improve the piece for the client – it is never really about what I’ve done.

    thanks guys!

    Jasmine says:

    As someone presently working underneath a not so great boss (and this is just my casual job!) I feel frustrated that bosses like her can’t read posts like this. I think though that bad bosses don’t think they are and thus don’t bother trying to improve themselves, and it’s the good bosses that worry about these sorts of things and constantly try to improve.

    So I think you’re already on the right path! People like space to do what they are good at but also like to know that there is someone there to help if they need it. It’s just striking that balance. And let people know that you do trust them. If they work for you, it must be because you’re confident in their abilities. If they don’t feel like you trust them then things just don’t work. Good luck!

    shayna says:

    this is so GREAT! It’s really gotten me thinking and analyzing my own behavior with my employees. I always try to be a good boss, give them space, while also maintain my level of perfectionism and standards. It’s a fine balancing act; being both understanding AND upholding standards. This has given me new perspectives to think about and improve my own performance.

    Eden bell says:

    This post is brilliant! I am currently struggling at a job with a not so great boss and often find myself going crazy trying to figure out why I feel the way I do. Sometimes all the little things add up and you don’t even realise why you are so frusterated all the time, or you start doubting your own abilities and think its you. This advice post helped put things into perspective for me and made me realise that clear communication is key. Just like a relationship, you need to have the right chemistry with your boss and sometimes it’s just not the right fit.

    KAIT says:

    i have another question for you ladies – how do you organize all of your photos? from personal photos to textures to stock photos, I’m curious how and where you organize/back up all of that information. Any advice is much appreciated! Thanks 😉

    leann says:

    hi katie, bri and alex – thank you all for taking the time to write this post. i figure it must take a lot of time to think about an answer, put it in writing and make sure it all flows! not only is this information extremely profound, it is also very well written. kudos to all 🙂

    Danielle says:

    Thank you! This was a fantastic post! I have been doing a lot of thinking in trying to figure out my voice this past year too. Working for myself has been awesome because I’ve had the time to evaluate my past jobs and working with different personalities… My first boss was great! She ran her own studio and was such a positive influence on me! I still carry the lessons she taught me. Unfortunately, I also worked in a negative environment which (as Katie put it) can have a negative effect on your work and mental state lol. You have to reject that way of working in order to get back to your happy self 🙂 Cheers to the great bosses out there!

    Moi says:

    Very great post.
    And I felt that it applied to the traditional office job I hold as well, except for the art teacher part of course. 😉 But checking my Excel sheets before handing them in to my boss to see if there are any parts he might want corrected has made the final run-through a lot smoother.

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