Be sure to read part 1, part 2 and part 3 for some background on my researching, developing and hiring of this role. This entry dives into takeaways and post-hiring thoughts, as well as an update on the state of the program. It's possible that there will be future entries, but at this time part 4 concludes the series.
<aside> 🔗 Click here to jump to the "Key Takeaways" from this entire experience and skip the specifics of onboarding, our first project and the work/life balance breakdowns.
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The first thing I did after fully committing to a single designer was schedule a meeting for questions. I fielded obvious ones like, "Why me?" and "When do we start?" We also discussed the first project — I just happened to land a perfect "first assignment" a few days before hiring — and looked at an independent contractor agreement together.
<aside> 👩⚖️ For the billionth time: get yourself a business attorney.
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The apprenticeship contract is practically identical to the freelancer agreement I use, the only addition being the following paragraph under the section that covers compensation:
As additional consideration, HIDEOUT may, subject to CONTRACTOR’s interest and availability, offer educational opportunities in the practice of owning and operating a design studio.
We reviewed the contract together, going over each paragraph and settling on a fixed rate for this first project. In addition to pausing for questions about the agreement and discussing the review process, we went over the tools we would be using together.
I set up a Slack group for my business. I opted for the free plan, which covers my basic needs as a messaging application. Once I got us both access, I connected a few other programs I use — Dropbox, Notion and Playbook.
Speaking of Playbook, I've begun integrating it into my workflow for every project I accept. It acts as a hub for collecting inspiration, moodboarding with clients and collecting their feedback, as well as a one-stop for sharing final assets. At its simplest, Playbook is a less-cluttered Pinterest board for my Dropbox account, but I count on it for way more. I definitely recommend signing up for access (I joined during Beta, so I'm uncertain what their current status is).
The biggest learning curve was with Notion itself. Teaching someone new project management software is always time-consuming, but with Notion's extreme range, it was a little overwhelming. I had to segment specific tasks onto their own timelines, and while this is a little redundant (I basically duplicated existing pages) the templates within Notion saved me some time. It's also nice to share specific pages with someone, and I enjoy having the option to keep some things private. I ended up purchasing a yearly subscription for this reason (well worth the $4/month).
<aside> 😅 I wanted to say that since our initial onboarding, Notion has become a favorite and now my new designer says they'll be using it for other things besides work. I'm glad I could convert someone else! It's a game-changer!
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I'll have more to share soon (if I ever find time to write another case study), but I wanted to quickly describe our first project together and how I set that up for us both.
I built a brief based on a modest (yet fun/important/meaningful) branding assignment for a former coworker whose substack needed an avatar. I created a checklist, timeline and template for notes/updates (all in Notion), as well as a library of helpful links and references. It was awesome being able to manage and share the entire process in a single application!
Here's a screenshot of the brief. Each bar on the timeline is a page to house progress shots. Every piece of this project lived right here.
I asked my new designer to come up with a 2-3 sketchbook pages worth of ideas (sketches) and I did the same. We shared progress after a week and picked two unique directions with the intent to combine them into a single brand family. It was important to me that whatever we designed together ultimately felt like it was something that made sense within The Hideout's body of work. I was extremely interested to figure out how we combined our styles and general approach to branding without everything feeling awkwardly glued together.
<aside> 🤝 By giving specific feedback and focusing on things we could each control within our own workflow — colors, stroke weight, typography, etc — we were able to look at each other's work collectively and share feedback via Notion and Slack. I know sure there are other tools for real-time collaboration (Figma, for example) that would make sense too, but for my own methods, enabling each of us to focus on elements of the project without fear of messing the other up was excellent. I love it when a plan comes together.
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After sketches, we each tackled a method for producing finals. I focused on drawing things by hand and bringing them into Illustrator (live-tracing some raster images) while the newby tried using the pen tool to vectorize everything and build a cleaner version of the same concepts. We both liked this approach and I think segmenting specific pieces resulted in a much more united concept in the end.
I'm really happy with the result and will share our finals asap. Peep them in use here.