How To Break into UX Design, Part 1: Environments for Growth

A couple of weeks ago, I was introduced to a young designer named Lauren. Her graphic design work is incredibly stunning, though largely print focused. She wanted to get some words of advice on how to break into a career in user experience design. Speaking with her, it gave me empathy for how daunting those first steps in our ever-changing discipline are, and how intimidating the variety of paths can be without a little guidance.

Many UX Designers don’t go to UX School

Full disclosure: when I started undergraduate studies in ‘96, I didn’t know what user experience was. I was at an Ivy League university (University of Pennsylvania) studying psychology. My grades were good, the subject matter was interesting, but I just didn’t see psychology as my future career. I was very interested in the interaction of creativity and technology, and took both computer science and design classes. At the time, design classes at Penn were focused on traditional graphic design — form, color, typography, and digital tools. I wanted to make things that were both digital and interactive, dynamic and creative.

So I dropped out of an Ivy.

Well, not exactly (though that’s what it felt like to my parents). I deferred for a year and moved to San Francisco, just before the first dotcom crash, and witnessed firsthand the infectious energy in the Bay Area at the time. A company called Google was in Beta. You could buy books and a bunch of other things on a website called Amazon. Microsoft was making dialup-enabled televisions.

I ended up transferring to a state school in Silicon Valley to pursue a mix of raw skills in computer science, graphic design and industrial design. New York University’s Interactive Telecommunications Program helped me connect the dots to think like an entrepreneur, prototype an idea, and validate it with customers.

Since then, many more university-level programs offer curricula for aspiring UX designers, and a number of schools provide intensive programs for those looking to switch careers. Still, the hard reality for designers new to the industry seeking employment is that you are not a product designer until you’ve designed products.

Your First Job is where you learn UX

My first title was “Product Designer II” at Microsoft. That meant I knew something about product design, academically speaking, and produced some interesting conceptual projects. But I had no idea how to lead a process, work with teams, deal with heavy amounts of ambiguity.

That first job gave me some of the most important things for a new designer in any type of environment:

  1. Great senior mentors. People who have been through what you’re going through in their own journey. They not only know the craft of design, but understand the process of getting better at it.
  2. Talented peers. People who are sharing the experience of the humbling ups and downs of learning something new, with strengths of their own to learn from.
  3. A failure-safe environment. The type of place where mistakes are not only forgiven but embraced as opportunities for learning.
  4. The space to think. An environment that provides the resources, time and processes to design well, paired with enough restraints to teach the discipline of working under pressure and trade-offs.

Finding Your Superpower

Every UX designer comes to it from a different path. Chances are, there’s something about your background, even coming into your first job, that makes you unique.

In my case, it was research. As a potential psychology major at an Ivy, I was working with the president of the American Psychology Association on understanding ways to improve inner city education in West Philadelphia. This is a man who was renowned for checking himself into a mental care facility incognito based on his hypothesis that those facilities were actually making patients worse, not better. These types of bold, immersive research practices were very similar to some of the practices I ended up using at Microsoft to try to get into the heads of different cultures and audiences of the products we were designing for. To this day, the relationship between research and design practice is one of my biggest passions.

Finding the Right Environment to Grow

Your first few jobs as a product designer will offer you the ability to grow the breadth of your skill set. These include the hard skills of customer research, architecture and interaction design, visual design, and prototyping, as well as the soft skills of cross-team collaboration, strategic design thinking, and advocating for the customer.


A big company can be a great environment to begin the designer’s journey for a few reasons. Unlike a startup, your mistakes will likely not result in the company’s demise, and the ability to feel comfortable failing will give you the courage to think bigger down the line. You will likely have a team of designers that will provide you with both peer mentorship as well as senior leadership (who will help with the aforementioned soft skills of product design leadership).

You are also likely going to work on products that already have an audience, and you will see and react to potentially millions of customers using your product. You will be closer to this customer data than you would in an agency. And the sometimes slower speed of the corporation, which may be a frustration to you at times, may be a blessing as well, as you and your team have the runway to be a part of big-budget research or build products with massive impact.

Make sure you’re looking at companies that have the right product development processes in place so you’re building good habits from the get-go:

  1. Agile Product Teams. Agile is the idea of continuously deploying software in functional parts around a bigger goal or vision. You are very close to the customer and can react quickly, not investing too much time down the wrong path. In agile teams, good Product Managers and/or Design Leads can help you focus on refining your craft by providing the necessary input and feedback to keep your first design work on course. One warning: a popular and effective way of organizing agile teams is by breaking up designers, engineers, and PMs into “pods” or “squads” —giving each squad relatively independent ownership over their respective product focus areas. In this type of organization (which I happen to be a fan of), make sure you have a culture where designers can still provide feedback to one another, even if they sit on different teams within the organization.
  2. Waterfall Organizations. Pass. Waterfall is an older method of product development where much more time is spent up front planning and fine tuning requirements, perfecting detailed design, specification, testing and releasing in bulk. While organizations that use waterfall are a dying breed, there are some companies that on the surface attempt to be agile but in reality are waterfall. Not only does this type of environment train you against the industry trend, it also assumes high level of confidence in delivering the right answer to customers in one shot vs. continuous building, testing and iterating, which is exactly the part of the design brain you need to be training.


The attraction of startups to a designer is obvious. You’re making something new, exciting, ground-breaking. You’re tearing down paradigms and making behavior-changing products that are evolving how we live, play, eat, and communicate.

That said, the wrong startup can be a dangerous place to get your first footing as a product designer. No two startups are alike, but the stage of a company can sometimes be a helpful gauge for your chances of giving yourself a productive education.

Finding the right stage of startup for is critical for both your sake and your employer’s sake:

  1. Seed Stage Startups: The company has just a small amount of cash in the bank and needs to prove product-market fit. They need someone who knows what they’re doing to help them get there. If that sounds like a lot of pressure, pass. Except for rare situations, I advise designers from joining seed startups with less than 2-3 years of experience under their belt.
  2. Series A/B: The company may or may not have found product-market fit, but has convinced its investors that it’s built a great team and has proven that it may be onto something bigger. Some companies at this stage already have product design practices in place, with a few talented leads or even a director-level design that can help you grow. If they’ve made it this far without product design talent and you’d be designer number 1 or 2, be careful — you may be picking up some bad habits without peer support. On the positive side, your mistakes may not sink the business.
  3. Series C and beyond: For companies at this size, you’re likely to get the best of both worlds between startup and corporation. The company has a product people love (and hopefully, revenue), and it’s you and your team’s job to make it better. Most companies have not made it this far without giving design a seat at the table and you’re likely to work with top talent. As a new organization, it’s also likely adopting the industry’s newest and best processes and tools with an eye towards self-improvement. One risk at the most rapidly growing companies of this size are the growing pains that sometimes come with scaling too quickly. Make sure you have an advocate that’s able to navigate the “design ops” and process conversations — you’ll learn a bit of leadership from watching how they achieve organizational alignment and you can focus on your raw design skills.


Agencies are an extremely exciting prospect for the curious. One month you can work on electric vehicle interfaces for a luxury automobile brand, the next, a futuristic wearable device for a sexy athletic gear brand.

Clients hire agencies because they are looking for experts and specialists, which means if you’re lucky, you will have the ability to participate in an idealized process and refine your craft alongside some wildly talented people. Clients are also paying a premium for this service and rightfully expect a lot of your work. This means that at the right agency, directors will ensure that you are accountable for a level of perfection that will make you as detail oriented and thoughtful as the designers you admire (even if it means staying at the office until late into the evening).

The down side: When you are done with a project, at most agencies, you’re done with the client relationship. You hand off your deliverable, offer a firm handshake, and hope your baby survives. If you’ve only had the experience of coming up with the first stab at a product, and have never been a part of building and iterating upon that product, you only have half the story.

One skill that agency work teaches extremely well is communication. By learning how to sell your ideas through visual communication and the powers of persuasion, you have developed some powerful tools at your disposal as you move towards becoming a design leader.

Different sized agencies offer different amounts of support to learn and flexibility of roles:

  1. Big agencies: Similar to large corporations, in that you have a bit more slack. The multiple levels of internal critique mean, while you may be going back to the drawing board a lot, you will be learning a lot as well. Look for cultures that really foster growth and mentorship. Avoid places that ask you about your ability to “crank out wireframes”.
  2. Boutique agencies: Like a startup, the smaller the agency, the more impact and ownership each designer has on a given project. Be honest about your background and abilities, and understand where you’d fit in with the existing team. If you’ve already identified your afore-mentioned “superpower”, this is a great chance to get your foot in the door with that special skill, in exchange for strengthening your areas of growth.

There is no singular “best path” for product design. Look at what you already know and where you want to go, and listen to your heart for what feels right. There are many ways to learn and grow, and if you’re doing it right, the learning never stops — stay humble, stay curious and you’ll do just fine.

I love talking about product design and building healthy and productive product cultures. Drop me a line to chat by emailing