16 Ways To Make Working With A Designer Easier

Chelsea O'Brien
NYC Design
Published in
8 min readJun 20, 2018

I’ve been working as a professional designer for 16 years now. With the help of my team, I design, build and launch an average of 45 sites a year (3–4 per month) along with designing branding collateral, apps, product labels and landing pages.

To get to this point, I’ve seen a lot in regards to web design: the ugly pages that convert really well, the long form sales pages that take a half hour to read, flashy photo galleries and distracting trendy effects, the predictable + stale look from using a bunch of cliche stock photos.

I’ve also learned a lot from working with clients: where they get stuck, what troubles they run into when working with designers and developers, the expenses and time that can sink a once-great idea.

One thing I’ve noticed is that there are certain things about outsourcing design that nobody talks about.

From quick + cheap jobs to in-depth, long-term relationships, I want to share what I’ve learned over the years so you can save yourself some of the frustration and emotional turbulence that come with working with a designer.

Keep reading if you are thinking of hiring a designer sometime soon — or if you’ve worked with one before and you want to see what others have gone through.

Outsourcing Mistakes To Avoid When Hiring a Designer

Until you’ve worked with a range of designers and invested in premium design services, you don’t know exactly what could be missing. It’s the difference between mediocre results with unnecessary expense and time and kick-ass results you want to show the world.

1. Lack of consistency
Say you run a contest to get a logo on 99Designs, get a website designed by someone on Upwork.com and get your business cards + stationery created from a person on Fiverr. Unless you have a clear and thorough style guide to give them to work from, you’re going to have a cluster of deliverables that don’t look like they’re from the same place.

Looking disconnected looks sloppy and amateurish; take the time to establish a set of brand guidelines that say what a brand is, what tone and personality it has and how it communicates to customers. With that clarity, you can confirm the colors, typefaces, style of images and message of your brand.

With a detailed style guide, you can increase the chances that your final results will look connected and congruent.

2. Overcomplicating your designs
A tendency of less experienced designers (or the company hiring them) is to fill up space in a design with more and more information to maximize the space. It doesn’t need to be complicated to look good! In many cases, adding more elements, colors, text, etc. dilutes the overall impact the design. If you look at high-end fashion brands, for example, many times their labels, websites, logos and ads are full of space. Less is more: having less to focus on gives power to the things that remain.

Make sure you’re working with a designer that understands the reasoning behind including each element of your design.

3. Copying others
It’s one thing to research and find examples of brand elements of companies you respect. That helps you understand the tone you’d like to capture in your own designs. But if you imitate their design or messaging too closely, you’ll blend in instead of standing out for your own unique attributes.

You can’t build a serious long-term income or business if you’re constantly piggy-backing on the work of others.

4. Going cheap
It seems to make sense to look for the cheapest price when it comes to outsourcing…and, therefore, get as many designs for as little money as possible. But going cheap can cost you more in the long run.

First, you risk having unscrupulous designers rip off the work of others, creating copied designs to get you a result cheaply and quickly.

Secondly, you may find that what initially sounded good in the designer’s marketing spiel ends up being different from what’s delivered. For example, some designers on low-cost platforms like Fiverr will advertise $5 for a design — but require an additional fee to release the final, full quality vector (or editable files).

5. Focusing on price instead of designs
When you’re shopping for a designer, rather than comparing prices, compare portfolio examples and look for the style of design that looks something like what you want for your own project. If you find a designer you love, you’ll want to develop an on-going relationship with him or her. You can negotiate on price later. When you’re getting started with someone new and want to get a result you love, go with seeing what you like already created in their portfolio.

6. A badly written design brief
Getting high-quality designs and creating a design brief that will get what you want is a skill unto itself. Many folks have a hard time explaining what they want. They figure they’ll “know it when they see it.” If this is you, and you outsource to a designer hoping he or she will hit on it one way or another, you could be left spending twice the time at twice the cost (either from multiple revisions or having to fire a designer and find another).

Designers (especially those in countries other than your own) are not going to be familiar with the terms, references and meanings behind the ideas you send their way. So be as explicit as you can — and provide them with reference information and something to provide context if at all possible. For example, send a crude sketch, a written description, a few reference images or website,

7. Not taking responsibility
It’s your business, so it’s your responsibility. If a designer rips off someone else’s design, that’s on you to make it right. If they misspell a word, or use an unreadable font, it’s on you to notice it and request it to be fixed.

8. Not building in time for potential problems
You need systems in place to catch all of the little hiccups and problems that come with a new project. Guaranteed you will have problems. It takes time to get into a rhythm of working with others, and there’s going to be a lot of back-and-forth — especially in the early days. Prepare ahead of time by giving yourself time to request a revision (or multiple), brainstorm a new idea or incorporate additional features.

9. Overestimating cost savings
Similar to the mistake of going cheap, outsourcing never saves as much time and money as you hope. To start with, managing the relationship and the project itself takes time: measuring performance, offering feedback, answering questions, overseeing unexpected developments, etc. It adds up in the form of extra days, weeks and service expenses.

10. Getting in too deep too quickly
You find someone to outsource to, you like the initial results, you’re pumped! The tendency is to want to turn over a greater amount of responsibility in the early stages of working together — the honeymoon period. The designer may be awesome, but go step by step into the relationship.

11. Not getting involved enough
In the opposite direction of getting too deep too quickly, swinging the other way can make a project painful for both parties. Outsourcing works when there are clear guidelines, procedures and rules. The challenge is that it takes time to create guidelines, procedures and rules. Don’t mistakenly assume that some things will be automatically understood or interpreted correctly. Put everything in writing. That way, if there’s any issues down the road, you can refer back and avoid disputes.

12. Putting all your eggs in one basket
If you become heavily dependent on one person for all your design across all products and mediums, what happens if they suddenly go out of business or have a personal emergency? What if you increase your workload and they can’t handle the additional requirements? If you start with a clear style guide for consistent results, you can get support from several vendors. For example, you could have one designer for print collateral, one for your website design and another for infographics for your social media.

13. Ignoring communication frustrations
When you start working with someone and are excited by what he or she initially produces, you may overlook the fact that you won’t hear anything from her for a week at a time. Or that he’s always 5–10 minutes late for calls. Or that she’s not receptive to feedback. Watch for frustrations early on, before you get too deep into your project and start resenting the quality of service.

14. Missing the opportunity to negotiate on price
Most designers want to find on-going, reliable work. If you can offer or deliver this, then you can negotiate on price. But it’s important to figure out what a “good” price would be for you, based on what you expect to make from the designs. You may not be able to determine this until you’ve worked with the designer some initially. Once you know it’s a good match, propose some options for a price that is a win/win for both of you.

15. Not getting feedback on the designs
If your designer creates something you like but your target audience isn’t drawn to, then is it worth the investment? Make sure you get outside opinions on the design during the process–ideally from existing clients or people that represent your target customer. That extra step could save you from making a pricey mistake that gives you nothing in return.

16. Not looking at your design in the “wild”
Where is your final design going to be seen? On a product label, sitting on a shelf next to competitor products? On your website, viewed from a smartphone? On an image in a social media feed among the hundreds of other images in the feed? As the cover of a book on a bookshelf, with only the spine showing?

Wherever your final design will live, it’s important to view the design as closely as you can to that context. Print out your label, take it to a store and hold it next to the other products. Print your book cover and wrap it around a book tucked between two others. Display your site mockup on your phone and notebook devices, considering the other websites your target customer would likely be visiting on a regular basis. You only have a few seconds to make an impression with your design. Knowing what you’re competing with will help you make better decisions about what to keep and what to drop.

To sum it all up…

Your design immediately sets the tone for your brand, your messaging and the personality of your marketing. Because first impressions are hard to change, it’s crucial to take steps to get a great result with your designer. It usually gets easier as you go. Once you create something that works, additional designs can be made from those guidelines.

Thanks for reading. If you liked this piece, please hold down the “clap” button below so others can find and read it. You can also follow me to be the first to see my stories. Comments are always welcome.

About me:

Web, Ux & UI Designer, digital product strategist, entrepreneur. I’m a designer that knows front-end development and marketing, so I enjoy working with teams in both areas to bring a new idea into its place.

If you think I can help you, feel free to get in touch with me from my website.

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Check out my videos with design tips on YouTube.

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Chelsea O'Brien
NYC Design

Designer + brand strategist helping connect people, ideas and audiences https://techdivamedia.com