July 9, 2020

Hiring Your First Designer

Most of my career has been spent at early-stage start-ups. Due to the nature of small design teams, I have had to get familiar with design practices across the full spectrum of design within a company. Most companies separate design into two functions: product design and brand design. As companies scale, they might separate these functions further by creating new teams like UX Design, UX Research, Growth Design, or IxD.

I often talk to founders who are looking for guidance on making their first design hire. This might be the founding design hire, or it might be the first internal hire who is taking over for a combination of external agencies and design contractors. The design community is filled with a ton of talented creatives, so searching for the right person can feel like a daunting task. What are the skills required to support a new business finding its footing in the market? Here are a couple of learnings from my past experiences. I hope it helps answer some common questions.

Should I hire a generalist or a specialist?

This is somewhat dependent on the type of business you are building, but in my experience, I have found that there is generally (no pun intended) a good fit for most situations.

If your product is a digital product, you might look for a designer who can spike in more strategic thinking, user research, and building an MVP to find product-market fit. In your search, you might feel confident with a specialist in Product Design. On the contrary, if your business is more aligned with traditional DTC companies and can leverage out of the box digital solutions like Shopify, you might feel good hiring someone more specialized in marketing and branding. In both cases, you will be able to tackle immediate needs.

The common mistake I see when hiring specialists is a lack of understanding of how the holistic picture of design affects the big picture view of the business. Hiring someone who specializes in a certain type of design without a generalist’s understanding of design’s impact on every facet of the business can put you in a situation where you will need to hire more designers to fill that gap in understanding. (Something I wouldn’t recommend doing early on.) For example, a great product designer still needs an understanding of marketing design to help support your acquisition strategy, and a marketing designer needs to understand how product design works or else you will be sending high-quality traffic to a poorly functioning digital experience.

My advice is to hire someone who has more of a generalist approach, with a deep understanding of building a business. This type of hire is extremely important when building a design team, and can be equally important when finding someone to manage your design team as a whole.

Should I hire a senior design hire or a junior design hire?

This is mostly a question about optimizing your budget, which is understandable. Ultimately, you should be optimizing for strategic thinking, experience, and understanding. If you have strategic team members who can help drive design strategy, you might be able to get away with hiring more junior talent on the team. This is a great way to give a talented designer exposure to an experience that allows them to take on responsibility and learn through exposure to complex problems.

If you feel like you need someone to fill your gap in understanding of design practices, definitely hire senior design talent. I would suggest this for most companies if there isn’t a founder who has a background in design.

A common mistake I see here is that founders who have a passion for design (but no experience working in design and building design functions within organizations) feel that their sensibility for aesthetics will be enough to carry a junior designer to success. I would advise against this strategy. Design at this level is a function of process and thinking and not simply defined by the output. Good design can’t be defined by your objective view of what good design is, and you are much better off hiring someone who you can delegate defining that term to.

Should I work with a contractor instead of hiring?

This is a tough question. It is highly dependent on your needs as a business. A good way to determine if this is a good route is to draft your job description for your first design hire. If you need someone proficient in: motion design, 3D, product design, illustration, marketing design, leadership, prototyping, and everything in between…you are probably overreaching. If you can find this person, pay them a ton of money and hold onto them as long as you can.

Define what your core needs are and hire someone who can help you build a strategic plan to outsource things like photography and motion design. If you are passing on a great designer because they aren’t a photographer, you aren’t ready to hire a designer. Fill the gaps with contractors until you’re prepared to build design as a function within your organization.

There are a lot of other questions I get asked, but these were the top questions I felt would set folks on the right path. If you have more questions or would like to suggest additions to this list feel free to reach out!

June 24, 2020

Diversity in Orgs

When I first started managing design teams I was excited to contribute to the ongoing efforts of making tech and design more diverse. As an individual contributor, I had been on teams that were extremely diverse, and teams that were extremely homogenous. (Read: white males.) I felt a deep responsibility to ensure that our internal and external teammates reflected the diversity of our community.

Initially, my understanding was that the diversity problems in tech and design stemmed from bad hiring practices. There are plenty of talented BIPOC designers in the world, and by and large internal design teams don’t reflect the diversity of the design community. By hiring more of these people on internal teams, we can fix the diversity problem in tech.

I’ve come to find that this is a flawed way of thinking about the problem. While we should always prioritize fair and equitable hiring practices in the workplace, it’s treating a symptom of the issue and not the cause. What this way of thinking fails to recognize is that once people are hired into a work environment they have to interact with the complex cultural systems of that organization. Often times, these systems are built to limit the influence of BIPOC employees and elevate white members of the organization.

Organizations often exhibit the following white supremacy characteristics: perfectionism, a sense of urgency, defensiveness, a focus on quantity over quality, worship of the written word, paternalism, either/or thinking, power hoarding, fear of open conflict, individualism, defining progress as growth, objectivity, and a right to comfort. (You can read more about these characteristics and how to combat them here.)

Because of these characteristics, BIPOC voices are seen as detracting voices that get in the way of progress.” While organizations might focus on diversity as a hiring goal, their systems of white supremacy form a racist immune system that protects those with power and reject those that pose a threat to that power. BIPOC are often pushed out of organizations or exposed to toxicity until they leave on their own accord.

If we want to see progress in our industry, we need to focus on dismantling these systems and combating these characteristics of white supremacy within our organizations. Real change has to happen at the top and needs to be reflected as a cultural shift in our organizations. Until this change happens, we won’t see progress.

April 26, 2020

Sky Ting

Sky Ting

Been doing some yoga from home with Sky Ting. Really enjoying the experience. For whatever reason, I’ve never been able to jive with apps like Glo and Asana Rebel. Sky Ting feels like less of a commitment and more focused on delivering good content vs. features. Give it a try. 😎

April 23, 2020

Sustainability at Buffy

Sustainability at Buffy

I’m excited to launch our sustainability commitment at Buffy! Not only was it a huge accomplishment to share our values with the public, it was a huge step forward for our design and product org. This marks our first major milestone in transitioning to a React environment.

A lot is going on under the hood that has established new norms with how we design and build digital experiences. With this came a lot of updates to our design system, both on the brand and product design side.

Sustainability Stickers

We took time revisiting some of our core styles and viewed our brand and product through a lens of emotional expression and usability/accessibility. During that process we made some key changes to our color system and typography to increase legibility and optimize our website to be more accessible. (We are now using Inter by Rasmus Andersson!)

We introduced some new brand elements. My favorite being our stickers that were inspired by the intersection of commerce and activism that was popularized in the 70’s by way of merchandise like bumper stickers, t-shirts, and hats.

Mission Page

All of this came together with our new Mission page that features all of this fun stuff in action.

I’m excited to share more about our baseline grid (named Lattice) and our design system (named Quilt) in the coming months.

This has been a group effort for Buffy, but I wanted to give a special shout out to my close collaborators on this project: Blair Pfander, Landon Fears, and Erin Kelly. ✌️

April 22, 2020

Decision Making vs. Execution

I was recently listening to Shane Parrish describe the relationship between decision making and execution. He speaks briefly in this podcast about how the distance between decision making and outcomes put people in a position where they evaluate outcomes based on execution. In situations where there is minimal space between decision making and outcomes (in his example, putting your hand on a hot stove) it is more clear to us that our decisions directly relate to the outcome.

This bounced around in my head for a bit. It reminded me of past work I executed on, work that I knew to be executed at a high level, which led to poor outcomes. In retrospect, it is clear to me that the work was not responsible for the poor outcome, but it was strategically flawed from the start. Perhaps, those projects might have also suffered from sunk cost fallacies and flawed analysis at key milestones.

In some of those situations, time was wasted for weeks or even months trying to fix” execution in hopes it would shift the outcome. This was not going to happen as the execution wasn’t responsible for the negative outcome in the first place.

All of these thoughts were thoughts I had had before, but after sitting with these ideas for a bit, I started to think about how we can prevent these types of problems in future projects. Two ideas came to mind with a similar theme: closing the gap between decision making and execution.

  1. Time

Limit the amount of time between decision making and execution. Working in a more iterative and hypothesis-driven fashion will allow you the opportunity to make more decisions and understand the impact of those decisions more quickly.

  1. Distance

Limit the distance between those who make decisions and those who execute. Empower teams to make their own decisions and execute those decisions accordingly.

These sound like simple practices, but I have been in a few organizations that have achieved this type of work style. There are a lot of complex factors that can inhibit this style of work: org size, org structure, skill levels, etc. But if we start building teams and organizations with this in mind, we might build organizations that make better decisions.

April 21, 2020

Working with Me

I have seen the concept of personal user manuals” before, and have always found them interesting. While working remotely, I’ve found it more important than ever to have a deeper understanding of people’s preferred work styles. Here’s my first pass at my user manual.”

Management Style

Servant Leadership

I am a believer in servant leadership. This style of leadership starts with my natural need to serve others, and pairs with my aspirations to lead. It is good to note that leadership is secondary to serving in this style, and while I truly believe in this style of leadership it can also be problematic if I am put in a situation where my service creates tension with my leadership.

Mentorship, Coaching, and Transparency

I love teaching and coaching. The most fulfilling part of my work is watching members of the team break through into new stages of their career. I use transparency as my main tool for teaching and try to involve my direct reports in every team-level decision I make. This gives them the opportunity to be open with me about decisions I make, and also gives them the opportunity to observe how I make decisions. I also value this type of transparency with leadership because it helps me think strategically, and allows me the opportunity to get exposure to new types of business problems I might not have access to otherwise.

Process and Structure

I am a creature of habit, and try to build as much structure as possible into how I work. By being structured with how I get work done, I can clearly understand where progress is being made, and where things are getting stuck. I believe in continuous improvement and look for structures and frameworks that empower my team (and myself) to continuously improve.

Communication Style

Written Communication

I am a big fan of a well crafted memo. In most cases, I feel that written communication forces us to gather our thoughts before sharing them and forces us to edit things down to the essentials. (I am not the best editor, but strive to be.)

Meeting and Collaborating

I believe that meetings have their place in team culture and should be used for: making a decision, gathering input, collaborating, discussing a problem, or sharing information. I prefer meetings that have clear agendas and end with action items.

I also enjoy collaborating one-on-one when there is a clear problem we need to solve together. In these cases, things can (and probably should!) be more free-form.

Instant Communication

I am a deep worker. When I am locked-in on solving a problem I find it hard to shift gears into another task. For this reason, digital communication can be hard for me to manage. If I get a ping, I will most likely shift my attention to respond to it (servant mode) but I will be viewing it as a quick to-do that I need to relieve myself of before returning to deep work.

If there is something that requires deeper collaboration or shifting my attention to a task that will require me to context shift, I would prefer handling it after tending to deep work vs. during deep work.

Strengths and Quirks

Strategic Thinking

I would consider strategic thinking to be a strength of mine. It is really energizing for me to tackle complex strategic problems. Where this can become tricky is when I don’t feel like I have the context to tackle a problem strategically. In order for me to feel confident in the work I’m doing, I need to understand the why behind what I’m doing.

Systems Thinking

I am a big systems thinker. I love building complex systems and as a designer I am very energized by the types of problems that allow me to work within a system. I am challenged when I encounter problems and solutions that don’t fit into the larger whole.

Emotional Connection

I am an emotional person and I like to build deep emotional connections with those I work with. I believe it helps me understand my team at a more human level and allows us all to bring our full selves to work. I can speak emotionally, but it’s generally me working through a problem in real time and is signal that I feel very comfortable being vulnerable around you.

Let me know if you have used a user manual successfully before, or if you have any tips/tricks you would like to offer!