11 tips for managing a team of creatives

I wrote this as part of my previous post, but it made it way too long. So here is partish-twoish:

I understand the need — or at least the want — for measurable benchmarks when managing a team of workers. I also understand that it’s probably a bit nerve wracking for a boss / manager type to write checks and send them out into the void not knowing if a worker is spending company time on Netflix.

However – my brother’s boss had the right idea. In over 12+ years of working in web development I have managed my fair share of junior designers and programmers. And it’s not rocket science.

For example, I wasn’t happy with any of the existing programs to automate some repetitive tasks at Sun Tails. So I hired some programmers to create a program that would import orders, manage inventory, update customer shipping status, etc.) We went over the jobs, they named their price and gave me an estimate of how long it would take, and I hired them. The job has taken a bit longer than we thought (jobs like this always do) but I’ve been able to see their progress all along the way. First orders began importing automagically, already saving me a huge chunk of time. Then we spent some time fixing some shipping errors. When that was working, they moved on to inventory management, then notifying the customer correctly of their shipping statuses.

All along the way I could see progress; I could tell they were doing a good job. Is it any of my business if they take a break at 2pm to eat a sandwich and watch an episode of Breaking Bad? Nope. All I care about is that the job gets done in a decent amount of time, does what it’s supposed to, and saves me time.

It wouldn’t help anything if I were phoning the programmers every morning for a status update. It would only interrupt their work and probably annoy them to the point that they might prioritize other tasks over mine. This feels so normal and natural to me, but maybe that’s because I understand how they work.


Bad bosses get things done; some of their skills obviously work for them. But when working with creatives, there can be a long term cost. High turn over and people crying in heaps on their bedroom floor is not how I want to run my company, whether it pays in dollars and cents or not.

I have this (probably) silly fear that as our company grows I’ll forget what it was like and morph into some kind of Mr. Burns or Miranda Priestly. So I’m noting my advice for myself and anyone else managing creatives lest it fade in my memory:

Tips for managing creatives

  1. If at all possible, let the work speak for itself. Phone calls and meetings should be a last resort. They interrupt his/her day and destroy productivity.
  2. Use project and task management software. Something like Asana or Basecamp. Piling on new ideas, new projects, future ideas, or future projects via a phone call is utterly overwhelming, and email threads can be hard to follow if the conversation is long or changes frequently. Creative brains are consumed with the current task. We can’t multitask creativity with your ever changing task list. Write it down in a permanent cloud-hosted space and prioritize it so we have a clear task to move on to when we finish the current one.
  3. Not every task can be priority A+++. If it is, and you only have one designer / programmer / creative, you need more people on your team. You cannot give one person sixty-seven top priority tasks and expect her to finish things at a super human pace. My programmers couldn’t do every single thing I requested at once. We had to take it in chunks. I hired two because I had two important tasks: integrating orders with the shopping cart, and doing the same for ebay. One is working on the cart, the other ebay, neither one is overwhelmed.
  4. Understand that when reviewing a project (website, software, logo, design, fabric, etc.) giving the entire company the opportunity to chime in with their opinions on said project will slow the project down. This is not the fault of the creative. When a simple one page directory takes over a month and you call the creative up to holler about how much it is costing, ask yourself how YOU as the project manager / boss person can speed things up. One of those ways, I guarantee, will be to make the ‘feedback group’ much, much smaller. When Bertha in customer service, Biff from accounting, and Opal who isn’t even with the company anymore all get to tell you what they thinks of the logo, that will not only slow progress, but it will also affect the quality of the project. AHEM.
  5. Be willing to familiarize yourself with how a creative person works. Be willing to adapt to how they need to work, especially if it means more productivity for you. For example, if you go on vacation and accidentally give your designer more space than usual, she will envelope herself in work. She will forget to eat and forget to shower and she will be hand coding your responsive blog from sun-up to… probably sun-up, only collapsing into bed to dream of code. When you get home from your vacation and realize you haven’t heard from her in four weeks, do not lose your crap all over the place. Do not call her and accuse her of dropping off the face of the earth. Take some time to listen. To understand. To realize and appreciate all she has been doing while you have blessedly been otherwise occupied and not calling her every ten minutes.
  6. Throw out everything you learned at the “How to win at business by being a douche bag” conferences. Creatives are generally not hard-nosed business types schooled in fangs-out negotiation. We are generally people who were major dorks growing up, and a lot of us were bullied and teased for our introverted head-in-the-cloud mannerisms. We’ve turned things that made us weird into marketable skills, and all your fist-to-face negotiation tactics do is remind us of being shoved up against the locker room wall and having our lunch money stolen. You might cow us for a while, but if you can’t turn off your fight mentality, you’re going to lose creatives; none will want to join your company ‘family’ long term with that kind of treatment.
  7. Keep accurate notes and records for yourself (this is where task management software helps). If you set a designer or programmer to task claiming that this particular task beats all other tasks in urgency and importance and the world might implode if this task is not completed in six days, then forget and in five days start shouting at them for spending so much time on the thing you told them to spend all their time on, that’s actually your fault, not theirs. Don’t be a jerk, remember the things you say, the instructions you give, and go the extra mile: If the creative says the all important task will take at least three weeks, don’t start blowing your top in two. Save that for when the project takes four weeks, because it totally will.
  8. Don’t ignore personality differences. If you’re a red-type managing a bunch of blues, yellows, and whites, they’re going to hate your guts unless you learn how to talk to, communicate with, and understand people who function differently. If this is hard, buy some books. Hire a personality specialist. Go to non-douchebaggy conferences to learn about love languages. Maybe try to apply the empathy and sympathy you apply in other areas of your life to your work life, too.
  9. Don’t make your creative type defensive. Creatives generally love what they do, and can do a LOT for your company, but if you start getting suspicious about their time and hours, accusing them of wasting time or fighting with them about how they run their freelancing business, they’ll start to feel backed into a corner. When your creative is forced to constantly step outside her quiet comfort zone to stand up for herself, to try to explain, to even shout over your shouting on the telephone, you have a serious problem. She won’t feel safe, she won’t feel like she is trusted, and she’ll leave.
  10. Recognize your strengths and weaknesses. If you aren’t a creative type and can’t hope to understand why they don’t like to work 9 – 5 in an office environment or why your programmer delivers files at 3am, maybe hire a project manager who understands them. Hiring someone (and paying them what they are worth) who understands creatives will skyrocket your productivity, increase the happiness and well-being of your paid underlings, and should alleviate stress all around.
  11. Read Clients from hell and don’t be too stuffy or proud to see yourself in the stories. Learn from them. Improve. Laugh off differences. Make an effort to understand the needs of the people whose skills your company needs. Appreciate them. Reward them rather than yelling at them, and you just might find yourself with a team that feels loyal to you and your company and doesn’t cringe when you call them ‘family’ during your now once in a blue moon staff meetings.

Geek productivity

My programmer brother sent this to me during an extremely stressful period in my life, and we laughed and laughed over it on instant messenger.


It is the truest comic ever.

At the time, I had a full work load for a client who very much wanted to pound my freelancer square peg into his cubicled employee round hole. And I was resisting.


My client, I am quite sure, would have expected my work day to look like that red dashed line. At my desk at 9, clocking out at 6, and nice, measurable chunks of productivity in between.




Knowing that my client probably functioned like this himself, or at least expected me to, I tried very hard to keep regular hours, so that when he called to check in, I was available. But my productivity during the year plus I worked for them? The solid blue line. To a T.

That midnight spike of brilliance? Yup. The spike wherein you wake up at 4am with a full brain and you stumble to the computer to get all your ideas out before they flee. TOTALLY. (The 4am spike can also come from trying to shut it down at 1am and sleep like a normal person, but you can’t because ALL OF THE IDEAS are running through your head and you finally give in and get up and work.)

My absolute favorite is the bit of the chart showing the recovery period after an interruption or a meeting.


The truest true that ever trued, y’all. You see, a creative geek-type gets in the zone. And it takes a while to get in the zone. You have to warm up, sketch, stretch your mind fibers. Click around the internet, look at others’ solutions before your brain clicks into gear. But once it does? It’s go time. And a five minute phone call or, heaven forbid, a meeting, will destroy it ALL.

Here’s another comic my brother sent me which illustrates this perfectly. It’s about programming, but you could replace code with any type of thinking and puzzling that preludes creative work.



I would be in the trenches, you know? The total zone. Sorting out, I don’t know, how I was going to hand paint detail on some fabric designs, or coming up with a theme for holiday promotions that would broadcast out to social media. The phone would ring.


And it wasn’t just a check in, it was a twenty minute (sometimes longer) phone call where I’d get dozens of new tasks piled on. The current project not only went poof, it was eviscerated. Once I hung up, I had piles of hastily scribbled notes in my hand, an incomplete project on the screen, and what felt like four hundred threads in front of me. I could pick up any one of them, follow it to a given task, but what to do with the others? They’d get tangled up and lost without a little care.


It would take me so much time to organize the scribbled notes, enter them into some kind of online task tracking software (I sometimes used Asana and tried to get the others at the company to use it as well, but to no avail), prioritize all the new tasks against the existing task list from the last phone call, and sort out which project needed my redirected attention first.


It was tough. Especially with a manager who didn’t seem to have the slightest idea how a creative person tended to work, or the kind of environment they needed to be the most productive. I resisted working on site in an office because I knew the interruptions would skyrocket. I don’t think working in a cubicle is bad for everyone, I just knew it would be bad for me.

I’m amazed every day at how different managing Sun Tails feels. My work load has probably quadrupled several times over, but I’m happier and calmer, and much, much more productive. I know it’s because I’m in an environment where my skills are recognized and utilized in the best way possible, and I’m exploring ways to ensure that anyone I hire feels the same way.

As our company grows, I too will be in the tough position of managing employees and trying not to utterly piss them off. My brother once said that his most wonderful boss was once a programmer — a guy who understood how programmers often worked – in erratic, irregular, unplottable fits and starts, and that the only way to ensure a programmer (or other creative) is doing a good job is to look at the end result. Very true. Super true, in fact.

I know ending a blog post with a question feels like a cheap shot for interaction, but I’m really curious: What kind of attributes do you appreciate in a boss / manager type? What things drive you mad?

Stunned. Amazed. A bit nauseated, actually.


Nausea is my response to everything. Excitement, joy, happiness, stress, anxiety, too much sleep, too little sleep, a little too cold, a little too hot. It’s like my body’s all-purpose response system. “Hey! Hey! Something is happening! Let’s throw up!”

Tuesday evening I was feeling kind of glum about the Kickstarter.  It had taken so much time and effort (it was like a full time job on top of a full time job!) and we were only 40% funded with just 10 days to go.  We’d been featured in Swim Swam earlier that day which was awesome (founder @GoldMedalMel has been really supportive and all around great), but I just wasn’t sure if we were going to make it.

I went to bed deciding I’d curtail most of my Kickstarter-based efforts the next day; turn my attention more fully to the already busy online store and ebay sales. I thought maybe my last-ditch crowdfunding effort would be to add our new realistic scale designs to the campaign as rewards, and if that failed to get us to the finish line, I’d just chalk it up as one of those character-building learning experiences.  (Such fun, those are, no?) 

Mosquitoes build character

Wednesday morning I worked on finishing up the tail design graphics and was in the middle of structuring the new reward tiers when boom, boom, boom.  Three new wholesale backers came in.  Well! After my short pity party the night before that was encouraging — it brought us up to around 60% funded.

I continued my work, and before I’d gotten the new tail designs up and announced, KABLAM.  One of my previous wholesale level backers increased his pledge a substantial amount.  Enough to get us to the 97% funded milestone.

His reason?  He believed in our product, thought we just hadn’t gotten enough press and wanted to see us succeed. 

Little Mermaid Sebastian Jaw Dropping

By the end of the day several new backers had joined us and many existing backers had increased their pledges to take advantage of the new reward tiers. We were over 100% funded. I was stunned. Truthfully, I’m still reeling from the shock.

Mermaid monofins can be funded on kickstarter!

Shock or no, it’s really pretty awesome. I’m excited for the campaign to wrap up so we can put all my hard work into action. I can’t wait to have the mermaid tails I’ve designed made and in my hands; fabric design is my jam, y’all. I love it!*


Aren’t they pretty? I’m super stoked about the gender neutral fantasy line, I’ve got more of those in the works and the feedback on them has been phenomenal!


The teen/adult sized fin engineering is 99% done and my mold manufacturer is just working on getting a base for the larger mold that is big enough to handle it. I’m so excited to see thousands of them in a full array of colors. Which one would you (or your kiddos) choose?

Rainbow monofin colors

Next up? My Kickstarter to fund a magical pill with a chocolate coating that cures adrenaline based nausea. It’s going to be huge.

Temp Hiring

Hey! Anyone have some free time this weekend and want to earn some pennies? It’s spreadsheet / data entry type boringness; pay is not that spectacular or anything, but better than a kick in the shorts. E-mail me for more info if you’re interested.

Update: I’ve got the help I need for now, and some extra to help with upcoming tasks. Thanks all!

Work and making my brain take a break


I got the Kickstarter launched and a few days later, got the store open. Timing felt crucial because we wanted to be able to be up and running / shipping before the summer crush.

I didn’t have all of our product set up at the fulfillment center yet (the warehouse that would be shipping out our products for us) but thought I could handle shipping for a few days.



I can’t believe I don’t have any pictures! They’d mostly be of me lying in a puddle of cardboard and poly-mailers rocking back and forth and muttering whilst tearing out clumps of hair.

From the 20th to the 30th shipping took over my life.

I tried to be healthy about it. I threw the kids into the car on Saturday the 21st and we found a new hang out. It was so lovely. No cell service so I couldn’t work. We skipped rocks, explored, and got some fresh air.


We went back Sunday afternoon too.

I try really, really hard not to even think about work on Sundays. It’s a religious edict, yes, but for someone like me who can completely lose themselves in work, it’s also just plain healthy. I can work straight through a night until the sun comes up and not even know what day it is by the middle of the week, so making sure one day at least is set aside to rest my brain is a really good idea.

That doesn’t mean it’s easy though. Sun Tails stuff streams through my head on a never ending marquee, and even when I sleep I dream about work. So getting the heck out of dodge, even just for the afternoon / evening on Sunday was really helpful — and the kids loved it too.


On Tuesday I took the two smallest to Utah with me (the big boys had a scout camp) and I’m still here.

In the middle of all the craziness, I went up to Bear Lake to hang out with some of my very best friends before Jennifer moves to Connecticut. (sob) There was lot of delicious food cooked my Kat, and Tracy didn’t pass out once. I’m actually sore from all our dance parties.


Again, it was super good for me to get away and decompress. I admit I tried to work the 28th (Saturday), but the wifi connection was bad so all I accomplished is a press release that still needs some polishing. Hooray for crappy wifi, because I’m really glad I got to hang out with these ladies. (We’ll say nothing of the size of my head. Note to self: find friends with bigger skulls.)


I went back to Salt Lake and was still going crazy trying to ship all the orders out (Miss K. was a huge help), but finally got all our inventory installed at the fulfillment center yesterday, and today they take over shipping! HOORAY!!!



This is pretty huge for us. We are old hands at shipping product, but since E. has a full time job and we no longer have our big shop, AND since I have a lot of other things I need to be doing for the business, it’s really great to have shipping outsourced. Plus, Integracore has been great. I’m really happy with my team, they seem like they really care about our company. I know it’s their job to care about us, but it feels personal and that’s really nice.

I’m headed out to pick up some sewing samples, and head back to Wyoming. I miss my big boys and I have more meetings this week in Colorado.

Lots more later, skaters,