They say the best kind of problems are the ones you can watch your neighbors having. Learning from someone else’s problems is something akin to finding free money. It’s with this in mind that I’ve approached a series of entrepreneurs and freelance designers about their biggest struggles in attempting to smoothly run a design project. So that their benefit might be your stepping stone.

We’ve got pure gold from the trenches, so you can learn and avoid those mistakes yourself. Here it goes:

Struggle #1: Will they deliver what they promise?

Design projects can be really generic, at first: Design a new logotype. Build a website. To make the process more manageable, break it down into three-to-four stages which make sense for you, and define “deliverables” for each part. Get creative when defining each milestone, and stick to them no matter what. For instance, when getting a new logo, you can have:

  • Concept: Designer and entrepreneur can work together to create three mood boards, with possible creative concepts for each. Give them names or themes, that inspire you: Conservative, Cutting edge, From the streets, Fashionista, etc.
  • Sketch: Once you can envision a few possible concepts, building off of the central idea, pick one and commit to exploring it further. Start sketching possible solutions. At this point, simpler really is better: your sketches can be hand-drawn, with an everlasting pen and paper technology, or a quick outline from shapes on the computer.
  • Artwork: With a mature idea of the work that needs to be done, computers can be really handy for producing vibrant and professional-looking artwork. A finalized version with colors and definitive fonts should be produced, ready for use both in high and low resolutions.

It’s clear: working in smaller stages, you can avoid that big “Eureka!” moment, when designer and entrepreneur talk quickly (and vaguely) about their needs, go back to their caves, and only see each other after two months for Groundhog’s day. Which is, of course, how all the worst disasters happen. For Lisa Penson, a business coach and trainer from Australia, trust is the biggest struggle. “Will a freelancer delivery what they promise?” She recommends trialing people and paying on delivery of milestones. Co-create and work in stages, and you’ll save time and money in corrections and revisions.

Struggle #2: Is the freelancer a good match for my project?

As with any relationship, the work between designer and entrepreneur should be permeated by shared values and vision. If that’s bordering on too much common sense, why don’t we break that down into something a little more practical?

Designer freelancer, Joli Campbell, gives valuable tips for vetting your designer:

  • “Are you drawn to their style?” Make a decision, based on your first impressions of the designer’s portfolio. What attracts you to their work? Which elements stand out as unique to you? Conversely, if you’ve found their work isn’t exactly in line with your expectations, could they be flexible with their skills, according to your specific instructions? There are many ways to approach any project, if everyone involved is flexible.
  • “Are they over or underpriced?” The idea of that “you get what you paid for” might seem overly untrusting to some people, but it’s a very real part of the hiring process. Still, there may be other reasons for a low or overly high price. If the designer isn’t charging very much for their services, they may not be pricing themselves appropriately, or have taken on a schedule of too many minor jobs. If they are overcharging, they may be honestly estimating according to their experience, or even simply trying to “catch a whale”. There’s a reason behind every quote. For Joli, “the right price for your budget does not always make the best bang for your buck when it comes to a designer. Quality counts here.”
  • “List out all of your expected needs from a designer” With this information dictated and ready, take your goals out into the job market and specifically find a freelancer that can help you fulfill as many of the points on your list as possible. Joli suggests it is not simple enough to just say the entrepreneur needs a logo – it matters to the designer to know all the places that logo will be used (website, business cards, etc), because they need to plan how it will look across different applications, and price the project accordingly.

Struggle #3: How can I keep the project on track?

Communication (or, especially, the lack of it) can make or break a design project. So establish a routine, weekly or bi-weekly, wherein you and your collaborator chat about the project, how it’s progressing, and any delays you’ve run into. Try to keep it simple: can be something that works for both parties, like a fifteen-minute call, or rather a succinct email with updates? It may sound like micro-management, as first, but as long as you both strike a balance for the ideal interval, this can work wonders to keep the project on track.

Marketing Manager at Enqos, a startup boutique based in India, Aiswarya Jaishankar emphasizes fixing an hourly rate and then mailing statuses back and forth between yourself and your designer in order to keep the lines of communication clear. “I think finding a good designer is a good first step to avoiding problems or challenges.”

Struggle #4: Knowing in advance if the designer can deliver what they promise.

The importance of human connection can’t be overstated. Knowing how your freelancer worked with previous clients can be an invaluable source of insight into whether you should hire a particular designer, or continue in the pursuit of another professional. Asking for two or three references can be good practice in understanding what worked well in the past – and what didn’t. Brendan Hufford, from Photo MBA, a blog about the business of photography, suggests: “Ask for the details of people that they’ve worked for that you can speak to. if they decline, it’s a no-go.”

[Extract from the book Growth by Design]