The Cornerplay started as a hobby, a fun creative outlet. You’d think a tech start-up is enough of that, but in reality I do more editing than building.  It’s amazing to take a step back and see how much this blog has grown over the last 1.5 months.

Now that I know this thing will run for a while, it might be time for us to get a real logo.  And so we turned to 99designs, a leader of crowd-sourced design.  In case you’re not familiar with the service, you submit a project (e.g. need a new logo) and the website’s community of designers vie with each other to provide the winning creative.

Running a contest on 99designs is fascinating.  It truly is a game; experienced contestants understand the game’s rules and use those rules to maximize their chances of winning.  Their incentives may not always align with yours.  So if you’re thinking about holding a contest there, here are a few things you should do.

Submit a good brief and headline

You’re not a designer so don’t micro-manage designers, even if that’s what they want you to do just so they can win the game.  In the contest brief, focus not on the what but on the why.  If you want to use an existing logo as a reference point, ask why you like it.  You don’t actually want Microsoft Window’s logo; what you really want is a logo that’s strong, simple, modern, yet a little different.  If you ask for the former, all you’ll get is minor variations of it.

The logo and the product should be tightly integrated.  Our brief was easier to understand because the blog already exists so it’s the logo that must fit with it.  You can tell which designers visited this blog and took the time to understand its brand, because the ones who didn’t were horribly off.

This logo doesn’t go with this website at all — the font, colors and aesthetics are off

If your product doesn’t exist yet, consider providing a mood board to act as a guideline; this is easy to do with Pinterest.

You also want a great headline so designers can notice your project out of what is presumably a sea of them.  I got the bronze package, which is the cheapest contest at $300, so the need for an eye-catching headline is even more important.  The Cornerplay is about brains and beauty, so our headline was “Smart, good looking designer needed for smart, good looking brand.”  Flattery always helps, right?

Give feedback as soon as possible and guarantee a winner

The contest received a dozen entries a few hours after posting, which was great.  We didn’t want to give feedback right away out of fear designers would become too focused on a given direction.  So we waited for more to come in…and waited…and waited.  It was just a trickle after the initial burst, and 48 hours later I thought our contest was destined for just a handful of entries.  Only then did I start giving feedback; rating each logo and leaving comments on what I liked and didn’t like.

Shortly after, we received an avalanche of new logos.  We hit over 100 entries in the next 24 hours!

There are two theories on why this happened:

1.  Contests are not guaranteed.  The contest holder can withdraw and get a refund if not happy with initial results, so designers may hold back until they see signs of commitment.  A contest holder who actively gives feedback is one such sign.  This is the theory that 99designs pushes forward, and so the website continually reminds you to give feedback.

There is an option to guarantee a winner — i.e. the contest holder waives her right to get a refund.  We didn’t exercise this option but we probably should have.

(Is Ashley even a real person?)

2.  Designers are smart creatures who want to do minimal work for maximum gain.  Creating to an opinion is hard — sometimes it’s just luck that you design something the customer happens to like.  The probability of achieving that in the beginning is low when you have no information; and far higher when the customer has already given feedback on other entries.  So you get designers who “watch” the contest and wait for a favored concept to emerge; once it does, the game is simply to out-execute the competition.

This dynamic is so strong that, when we rated a particular logo as a “great design” (just one rank lower from “leading contender”), the designer actually withdrew the logo!  We messaged the designer to ask why, and the reply was she didn’t want other designers to know we liked it so much that they would copy it.

Wow!

And so she re-submitted the logo as a new design and we left it un-rated.

To combat this copycat dynamic, actively praise a diverse set of logos so designers won’t think there’s only one way to go.  Nevertheless, assuming the contest goes well, you will get so many entries that you’d want to do some funneling anyway.

We didn’t eliminate any designs in the first round but we should have.  Also, some designers clearly don’t share our sense of aesthetic, and we should have also eliminated them from the contest to save both our time.

There was one designer we gave a lot of feedback to and she kept coming up with new designs; but alas the fit wasn’t there no matter how many iterations.  It might seem mean to terminate her — which is why we hadn’t — but in retrospect it was the right thing to do for both parties.

Who would’ve thought crowdsourcing a logo is like dating?

Bottom line, the pros of giving feedback early and often outweighs the cons.

Giving feedback early and often to designers you like is worth the effort

Don’t just select logos, select designers

There were two logos from the first round that we loved and three more logos that we liked.  We were tempted to advance the designers of those five logos to the final round (you can advance a maximum of six).

But that would have been the wrong move.

When we looked closely, we realized some of those designers were good but not great — almost as if they created a great logo by luck.  This is fine for the logos we loved, but what is the point of advancing average designers whose logos we merely liked?  Chances are they wouldn’t be able to improve their existing logos enough or design new ones to win.

So in addition to the two designers whose logos we loved, we shortlisted two other designers we thought were strong but weren’t yet on-target with their initial set of logos.  If they were skilled enough, with time and feedback, we reasoned they will come up with something great.

That hypothesis turned out to be true.  The two designers we picked on the basis of the person (vs. the logo) came up with some of the best designs in the next round.

You can usually tell which designers are objectively good, even if you may not subjectively like their logos.  However, if you don’t have the confidence to judge, you can always view their profiles.  You can see how many contests they participated in and won, as well as their winning designs.

That brings us to the end of today’s post.  We are still working with those four designers to come up with our favorite logo from each designer; and then we plan to put the four to a vote on this blog.  Probably this Friday.  Stay tuned for that!

P.S.  If you’re wondering about the cover image, I highly, highly recommend watching HBO’s Silicon Valley.  It’s a hilarious show about the tech start-up life and also does a wonderful job of representing minorities.