Five Rounds – Round Three


It’s Round 3 of 5 Rounds where we examine agency, freelancing, and in-house life by chatting with three experts:

Deanna Dionne, Creative Contractor
Jim Masie, Senior Graphic Designer at AmTrust Financial Services, Inc.
Chris Haas, Art Director at Flourish Agency

This week we’re talking about the people. If you missed them, here are Round 1 (the office) and Round 2 (the work).


DD: Just me!

JM: 1,300 people are assigned to our building. I work on the 21st floor, which has around 80 people. Our department has 5 employees on site.

CH: 17


DD: Every way you can imagine. Email, texting, Facebook messaging, Instagram messaging, phone calls, video conferencing, in-person… It depends on my clients’ preference. It used to bother me when clients first began texting me or using social media, but I’ve since become more lax about my “personal space.” I can always turn my devices off. As long as I keep my notes organized I don’t mind the variety of communication sources.

It depends on the project. I enjoy when I can invite a collaborator to work in my studio and we can get real-time feedback to integrate each other’s strengths as we move along in a project. Other times a relay-race style handoff may be more appropriate. As far as clients go, I often view myself as doing a service for them and keeping them apprised during touchpoints here and there rather than inviting them to be highly involved in the process. Not all freelancers share that mindset, and that’s okay, this is just how I work. The busy businesses I work with seem to appreciate that I’m independent– and I always give them homework, too.

Definitely. Clients become friends and friends become clients. Friends are collaborators and a support system.

JM: My preference is email, to use a point-of-reference and communication log. I also use the phone (office and cell) and face-to-face.

Collaboration is handled by specific roles. Marketing Managers act as a bridge between subject matter experts (SMEs) and production assets (copywriters, graphic designers, vendors). The production assets work together to ensure content and visuals meet the Marketing Managers’ project specifications. Communication is handled mostly via email, but we do conduct meetings (in-person and/or teleconference). On occasion, we will have brainstorming sessions to discuss ideas.

Yes, but very limited. The majority of our social interaction is through company-sponsored events (ex. holiday lunch, conferences, vendor meetings).

CH: We typically don’t have a kickoff meeting or creative brainstorms. We work very fast and each creative is responsible for developing their project. The collaboration happens with feedback for completed or close to completed work during critiques. If a creative wants feedback, they just shout out to whomever they would like to collaborate with.

Not one bit. I completely disconnect from design when I leave work or am not doing freelance.


DD: I’m usually the only one involved in a project. Sometimes I may subcontract help such as photographers, videographers, back-end coders, copywriters, or other designers.

JM: At least 4. Marketing Manager, Copywriter, Graphic Designer, Vendor (fulfillment). On occasion, I will work on projects for executive level and mid-management.

CH: Normally about 3-4 people. Typically an Account Executive handles communication and day-to-day needs of the client, an Art Director or Creative Director that oversees the work or possibly does the work, and one or two designers that handle the creative work.


DD: I may spell out that I’m using a subcontractor in the invoice, or I may not, depending on the project. Sometimes I’ll have my subcontractor work directly with the client, or sometimes the client is unaware that I had help at all.

JM: We receive an annual performance review (employee appraisal). In the appraisal, our supervisor(s) will share significant contributions they think you’ve made. Usually, the end-result is a merit increase and/or bonus.

CH: High-fives

By Kassey Sikora
Published November 10, 2017