24 Designers in 4 Days: An Experiment with Office Hours

Tips for new designers entering the industry

Last week, I did my best to give advice to 24 strangers in a series of 30 minute one-on-one sessions over 4 days. It was one of the most fun / unique / rewarding / stressful / exciting / weird experiences I’ve had in a long time. Some quick stats before I explain further:

• 21 were over Google Hangouts, 3 were in person at coffee shops in NYC
• Folks dialed in from: India, Netherlands, Mexico, San Francisco, San Diego, Mountain View, Denver, Baltimore, Boston, and New York
• ♂ 13 ♀ 11
• Only 1 person was a white american male. Everyone else could be considered a minority in one way or another, which was a pleasant surprise and encouraged some great discussions around diversity
• Only 3 cancelled and were unable to reschedule (not included in the 24)

I spoke primarily with two categories of designers:

1. Students (some undergrad and some grad) looking for advice on getting a job and where to look.
2. Industry professionals (e.g. marketing, consulting, business) looking to switch into design and wondering how to do it.

There were a few people who had some common thread or shared interest with me outside of just design, whether it was a love for prototyping, or having attended the same university. This makes sense; people feel more comfortable meeting new people when there’s some shared context to start the conversation.

Ok. So what the heck was I doing? What did people ask? What did I learn?Why did I do this at all? Let’s rewind a bit.

Context

I’ve been reflecting a lot on where and how to best focus my time in the new year. At the backbone of this exercise is a core motivation, best articulated in one of my favorite quotes:

Put simply: learn stuff and help people. So where to start? I’ve invested most of my time so far in learning design and design management to help build technology that enables people to live better lives. But one of the biggest challenges I’ve faced in doing this well is hiring design teams. Meanwhile, conversely it seems some of the biggest challenges designers entering the industry face is getting hired, or at least getting productive advice on where to start. So where are the gaps? Why is this so challenging for both sides?

Fortunately, Dustin Senos, a design leader in the industry, recently announced an inspiring initiative called Out of Office Hours, to help pair people looking for advice on how to enter the workforce with people who’ve been at it for a while. If you haven’t heard about it, you should read a bit about how and why it started here. He sets the context nicely.

Turns out it’s started to take off — Over 120 tech leaders have generously offered their time to help people. I wanted to take part, so I put up my schedule, with the following context to help guide the conversation:

Noah Levin leads the product design team at ClassPass and is an advisor at FramerJs. Before recently moving to New York, he spent 5 years in San Francisco designing at Google, and before that at NASA. Talk to Noah about anything from large companies vs start ups, resumes and portfolios, prototyping, or building design teams. Schedule time with him here.

And in less than 24 hours I was fully booked!

I should’ve thought ahead about bathroom breaks…

There wasn’t much communication before the meetings started, so I had no idea know what to expect or how to prepare. All I could do was gear up my work set up, put on some pants, grab some coffee, and get ready.

Frequently Asked Questions

Every conversation was different, but there were a lot of similar questions, challenges, and themes. Keep in mind all of my advice listed here is from my perspective and personal experience and may not apply for everyone or every situation. I’ve added more about these caveats later on.

1. How do I get my foot in the door and get noticed?
2. Once I get an interview, how do I land the job?
3. How do I gain confidence?

1. How do I get my foot in the door and get noticed?

The most important thing in finding a job is your portfolio, which is largely an exercise in marketing yourself. I recommend starting by reviewing great advice on portfolios here from Bryan Landers. He summarizes some great tips from Marc Hemeon’s review of portfolios. Jared Erondu also recently started a great discussion on twitter about them. Finally, consider researching the perspective of the hiring manager to put yourself in their shoes through these tips on how to review portfolios by Chad Thornton.

Here’s a few more thoughts of my own:

Find inspiration from great examples

Let’s look at who does marketing well and see if we can apply any lessons from there. Take Apple for example. They consistently pair simple and appealing imagery with succinct story telling that stands out and pulls you in to want to learn more and see what it’s about. You don’t have to read much when viewing their “portfolio” to make a decision; you can walk into an apple store and talk to a rep or ask a friend who has tried their products before you spend time and money on it.

Same goes for portfolio reviews. I don’t need to deeply understand everything you did; that’s not realistic and would be much better done with a conversation. I just want to see proof that you’ve worked on a few interesting projects, have a good work ethic, and have the chops to build simple easy to use interfaces. Ideally you can also show you’ve worked with engineers and shipped products — doesn’t have to be anything major, small side projects are great, and engineers can include classmates.

Here are 3 examples of portfolios I’ve recently enjoyed:

jeanniehuangdesigns.com

Jeannie Huang: Her portfolio shows great positioning as a problem-solver, realigning the common misconception that designers are there to just make things look pretty, with the one-two-punch of showing wonderful and appealing imagery with a wide variety of examples to pull you in.

georgeotsubo.com

George Otsubo: His case studies do a great job with stunning visuals, sharing iteration, being honest about what worked and what didn’t, and showcasing a wide range of skills from icon design to branding to photography to animation to prototyping to storytelling.

midtonedesign.com

Jonatan Castro: Immediately you notice an animated prototype, which is cut off at the bottom to attract attention with one simple focus. Sometimes I get overwhelmed with a massive grid of projects and don’t know where to start, so I appreciated the one-project-at-a-time tactic to guide me toward his favorite projects.

Keep it simple. Save the novel for the phone call

Unfortunately I don’t have time to read long narratives. I look at hundreds of portfolios a month, so I just need to quickly see if there’s a hook that catches my interest enough to make a phone call.

Think of your portfolio like a movie trailer. It doesn’t need to share everything, it just needs to show enough to get your audience curious enough to want to ask questions and get excited about watching the movie.

Simplify your text, and lead with the punch. Strong animated simple imagery helps guide attention, and is easier to follow than larger complex flow-diagrams. Some portfolios had me scrolling all the way to the bottom of a case study to see the finished product. Lead with a strong image of the before/after if the project was a redesign, then share some iterations along the way. Consider using a simple framework to help explain your narrative like: Problem > Hypothesis > Solution > Findings.

Light on the process, heavy on the learnings and results

I believe one of the biggest misalignments in what I was taught vs what I actually practice, is the idea of a clear repeatable design process:

The squiggle: The reality of a real world design process.

In college I was taught process is everything. I learned fancy methods like contextual inquiries and modeling, affinity diagrams, and heuristic analysis. These might be popular in some companies like agencies whose product is often the process itself, but in the product world we don’t always have the luxury of an extensive research process. We have to ship things and iterate on tight timelines and limited resources.

Design can be messy, but it’s not completely without structure; we have a range of methods in our toolbox. It’s just about applying the right method to the right problem given a set of constraints.

I personally love the Google Ventures Design Sprint, which focuses on a short 1-week process to maximize on learning from real customers quickly using prototypes, but that doesn’t mean we use it for every problem.

I see a lot of portfolios flooded with pictures of a bunch of people in a room with sticky notes. Unfortunately this doesn’t tell me much about your creativity and problem solving skills; I don’t know those people and I can’t read those sticky notes.

Consider going a bit lighter on visually showing your personas, sketches, and wireframes, and instead having your narrative prepared to talk about on the phone or in person. A prototype or motion video of the finished product will be easier and more compelling for me to interact with and understand.

Reach out to those who’ve built things you love

Once you have a good portfolio, the beauty of the internet and our industry is that it is starting to matter less what you’re background or education might be (often a privilege in our society), and more about the quality of your work (merit). A great portfolio outshines a long and impressive looking resume for me any day.

Certainly we have a lot more work to do on better understanding unconscious bias and diversity in hiring (for another article), but for what it’s worth some of the best designers I’ve worked with came from non-traditional backgrounds. For example, my manager at Google was an acting major; one of the best hires I’ve ever made dropped out of college; one of the best researchers I’ve worked with was a landscape architect with only a few years of experience who outperformed some with extensive experience at Google, Yahoo, Twitter, and Facebook. I truly believe it’s not just about years of experience with known brands or universities; they certainly help get your foot in the door, but talent, potential and work ethic go a long way.

So once you have something you’re proud of, send it out to folks you’d like to work with through twitter messages, emails you can find on job pages, or networking through friends and family.

2. Once I get an interview, how do I land the job?

Some designers I spoke with had no issues getting their foot in the door, but had a hard time landing any offers. In this case, it may come down to how well you’re able to speak to your past projects, and your social demeanor. If you made it on site, it’s likely they’ve already evaluated and enjoyed your work, they just want to see if you’d be a good fit.

Clear storytelling requires knowing your audience

A lot of what you’re doing in portfolio presentations is telling a story about your work. Remember that the people you’re speaking with have very little context of the complexities that went into your project. Start from the beginning and clearly describe what problem you were trying to solve, and fill them in assuming they have never heard of the product you worked on — in most cases, they haven’t. If you’re using a slideshow to share your work (which is often helpful as it forces focus) make sure to not show too much on the screen; you don’t want them reading, you want them listening.

Practice with peers, friends, or family

For many newcomers in the industry, presenting your work is not something you’ve needed to do often so it may feel unfamiliar. Turns out interviewing is a lot about practice, so don’t be shy to practice with whomever will listen, or even in the mirror. Think of it like user testing your product, sometimes it takes a few iterations and trying it with real people to get right.

Do some research and come prepared

It often helps to research the company and think about what you’d improve so you can ask insightful questions. Two articles in particular you may find helpful from the perspective of the interviewer are Irene Au’s ux recruiting toolkit, and Braden Kowitz’s how to conduct a design exercise.

If you found your dream job, consider going all-in

I like how Joel Califa outlined his process for getting his job at Digital Ocean. You can tell how passionate he was in working there. I remember when I first graduated college, I would send out my portfolio at the time (which ironically goes against a lot of the advice I’m mentioning here now that I’ve been in the industry), while occasionally making custom letters or even web sites to show my genuine interest or passion in the company. I actually found the cover letter I had sent to Google, which I hope in some way helped me land the job. Another great example is from Abi Jones with her clever visual resume, which is super easy to parse and engaging, and still holds up well 6 years later!

3. How do I gain confidence?

This came up a lot, particularly for folks who felt exhausted with the reality of rejection in the job application process. I wish there was an easy answer to this question, as we all struggle with it.

Remember that you are not alone.

One feeling many people suffer from as they enter the workforce is imposters syndrome, and it’s something people are finally starting to talk more about. If you’re interested in digging deeper, Julie Zhou writes about it, Jeff Smith talks about it, and I spoke about it.

Exercise and eat healthy

I know. Everyone says it, but it’s true. There are lots of studies on the positive relationship between exercise and psychological health. Shameless plug but if you’re looking for something new, consider ClassPass. The mental commitment of joining, having fixed appointments, accountability of knowing an instructor and group of people will be there, and friends who come with me, have kept me active and feeling good.

Don’t overthink it or let it stop you from applying

I’ve seen too many cases where people don’t apply to a job because they don’t think they are good enough or don’t have enough experience. Don’t assume that! What’s the harm in applying if you’re excited about the possibility? Worst case scenario is they don’t respond or they reject. The opportunity cost of not applying is maybe 10 minutes of doing anything else, or worse, missing out on an opportunity that could change your life.

Caveats

There are two important caveats I offered before each conversation to ensure people took feedback with the appropriate grain of salt:

1. I can only speak to my personal experience
   I’ve spent most of my working career at a large company, and the last year at a mid-sized startup. I’ve been on hiring committees, and hired and managed designers in both places, but I can’t speak to what other design hiring managers look for, or about places I haven’t worked — I can only speak to my experience. With that in mind, you may occasionally receive conflicting advice from people because there’s a wide range of capabilities of designers, and different companies sometimes need different skills to solve their unique problems. There’s also varying opinions of what makes a great designer (e.g. popular debates like should designers code), which leads me to:
2. UX Design is still a relatively new and quickly evolving industry
   There are only a few schools offering sufficient education for it. We don’t even have consistent names for what we do (designer, web designer, software designer, UX, UI, IA, Research, Visual, Product, etc), so we are still clearly figuring some things out. Efforts like this encourage conversation, which add maturity to it, but still create ambiguity.

Always makes for a fun thanksgiving conversation

Tips for volunteers running office hours

I’ll definitely do this again, and hope to avoid repeating the same mistakes of things that could’ve gone better. Some suggested areas of improvement:

1. Plan breaks
   To collect thoughts, take notes, go to the bathroom, etc,.
2. Better coordination
   Almost every session did not start on time, and planning for unforeseen circumstances was hard over email. A faster mode of communication, like a temporary slack setup or twitter messaging, would’ve been better. A dedicated hangout link in the cal invite would’ve helped too. Finally, I’ll limit the interviews to online only; meeting in person did not add enough value for the cost of coordination.
3. Do less, better
   I was exhausted at the end of the week — 12 total hours of talking in a short time frame is a lot. Next time I’ll pace myself and just open up a few a week rather than sprinting all at once.
4. Don’t promise a follow up
   It’s not realistic to be able to continue helping people over time. This isn’t a continual mentorship program; that wouldn’t scale as well. I need to do the best I can to provide actionable feedback in 30 minutes.

Tips for newcomers signing up to chat

First, good for you for realizing this is something that could benefit you. I hope it does. Here’s some quick tips to get the most out of your session:

1. Come prepared
   The most productive conversations I had were with people who had questions ready. Even better when they weren’t super general like “any advice for me?”, but specific to their situation: “I need help positioning this class project to be more compelling to employers, what could I be doing better?”. Coming in with some idea of what you want help with makes you get the most out of your 30 minutes.
2. Don’t see this as strictly “networking”
   I‘ve had conversations in the past where it was immediately clear the person only wanted to network. No one wants to be seen as just a small transaction along the way to building a career; we’re people, so be kind and respectful of each others time and come curious and eager to learn.
3. Consider a brief follow-up
   I really appreciated those who sent me thank you notes — it meant a lot to me to hear that it was helpful. Some people asked if there was anything they could do to help in return, to which I said:

The best way to thank us would be to work hard and achieve what you’re looking for in the next step in your career, and to pay it forward. And let me know where you land — I’d be happy to hear from you.

Thanks!

One of my favorite parts of this experience was the anonymity and the transience; I did not know any of these designers, and I may never speak to them again. Hearing about their challenges reminded me how similar we all are, even with our differences on the surface. It also reminded me that I was in their shoes not so long ago, and how much I appreciated when people took me under their wing and gave me advice. It felt great to give back, and I look forward to doing it again.

Give office hours a shot!

Thanks so much to Dustin for starting this, to all of the folks who’ve generously offered their time to help others, and for everyone brave enough to sign up for slots and share their stories. And thanks to ClassPass for supporting me and allowing me to take time away from my projects to help with this initiative.

Be sure to check out other great retrospectives of the Office Hours experiment by Noah Stokes here, and Harold Emsheimer’s here!