The Future Favors the Curious

If you’re a designer in the market for a job right now, you probably feel behind the AI wave already, and you’re wondering if the skills you’ve honed in your career are even useful anymore. One of the benefits of being an oldster in this field is that you begin to see patterns in everything, and I’m here to tell you that this pattern has happened many times before and there is a clear way through it as a designer.

In 1995, halfway through college, I determined I was going to be a designer. At that time, 99.99% of “professional designers” had no experience designing anything for the internet. You could have tasked some of the most accomplished designers at the time — Jony Ive, Paula Scher, David Carson, Paul Rand, Massimo Vignelli — with creating a simple 468×60 banner ad and none of them would even know what you were talking about.

Over the next five years, the world would discover what banner ads and the internet were, but most experienced designers stayed put in print, television, or whatever field they were already comfortable with. The designers who would go on to help shape the internet were from two groups:

• People brand new to the industry
• People who looked forward to starting over and getting good at something new

I was somewhere between the two groups, having spent a few years in print but leaning more into a childhood love for new technology than anything else.

Within a few years, the demand for internet-native designers exploded and created the thriving job market we have enjoyed almost uninterrupted until now. Analog design still produces some of the most amazing creative work on the planet, but the growth of that part of the profession has not been the same.

Running design at Microsoft AI and having done a decent amount of hiring lately, I can tell you that the patterns emerging now are exactly as they were in 1995. There is a giant population of designers who have a bunch of really great skills. Some of those designers will decide they are content doing the same sort of design they have done for their whole careers. Others will decide to learn as much as they can about AI and prepare for an industry that will look very different in 5 to 10 years. Finally, there is another group of people who have no design experience whatsoever but are so enamored with this new technology that they will teach themselves very useful skills in a short amount of time. Do not underestimate this third group as it’s easier than ever to fake it ’til you make it right now.

If you are content in your comfort zone, that’s perfectly fine. If, however, you are looking to lean into what’s next, here are some suggestions.

You are not (far) behind

One thing I tell people who are trying to get into running is “you are always only a month away from being in decent running shape”. What I mean by that is, your first run is going to be 5 minutes long before you tap out, but if you do it every day for a month, you’ll be able to run at least a mile or two.

I see so many people trying to fake their AI experience by adding those two letters to every job they’ve had for the last 10 years. You are not fooling anyone. 99% of designers’ “AI experience” has come in the last two years. You will very occasionally find someone who was super early, but even that doesn’t mean much, as they might not be very good. It’s like saying in 1995 that you had a Commodore 64 growing up. Cool, but not exactly an endorsement of your actual design skills.

Someone may have told you to pepper your résumé with references to AI so it gets past certain filters, but we run a big operation here at Microsoft with thousands of designers and we don’t filter like this. Furthermore, when I see someone doing this, I actually take it as a sign that I should be suspicious of what else is on their résumé. When I was in college, I was a rampant gilder of my résumé, so I understand the temptation. “Salad Bar Director” did not actually get me any jobs though. Don’t do it. Just be honest. In terms of calendar years, your competition doesn’t have much more AI experience than you do. The clock is ticking though, and designers are already learning to do extraordinary things each time a new model or technique emerges. Pay attention. Learn by doing.

Know how our field is changing

For as long as design has been a profession, there has been a debate about the relative value of generalists vs. specialists. My view has been that in digital product design, you usually want generalists, but every so often, there is no substitute for a specialist. Some people are looking at AI as a specialty right now, and that may be true in some parts of engineering like model training, but for design, it’s a tool that will make generalism more common and accessible. Even pre-AI, I have always preferred hiring designers who I can give an entire project to. I want people who can frame up a user problem, explore the solution space with functional prototypes, produce high fidelity production designs/code, and also be involved in the testing and refinement of said solutions. This is a LOT to ask of most designers, but the best generalists can usually play all four quarters of the game.

With the help of AI, there are fewer barriers to designers participating in all parts of the product making process. Want to quickly research a problem you suspect exists in the world? There are now tools to help you write and analyze that survey. Want to quickly mock up a dozen high fidelity interfaces just to get a discussion going? Now you don’t have to spend days on that. Need hundreds of illustrations in a consistent style? Plenty of tools for that. And perhaps the biggest barrier for some designers over the last couple of decades: turning your ideas into functional code. That future is now here.

For all the excitement about these advancements, they also raise uncomfortable questions. The most obvious is: do we need fewer designers now? To that, I would say yes, we need fewer designers (and engineers, and everyone else in product development) for the same amount of output. Do we need fewer designers overall though? That remains to be seen. The growth of the economy since the beginning of time has been based on productivity increases leading to greater total output of our population. So if you think we have already maxxed out our total output of products and services in the world, I would expect a nosedive in the amount of designers and engineers needed. But if you think we are only scratching the surface of product development, you should expect a future where millions of designers and engineers continue to do great things but much more prolifically. Think of the farmer 1000 years ago who could feed a few families vs. the farmer of today who can feed an entire town.

In order to prepare for this, you should anticipate companies initially employing fewer designers (and engineers, and PMs) to do the same amount of work they were doing yesterday. Managers aren’t going completely away, but organizations will flatten somewhat as companies concentrate their budgets on people close to the metal. As my colleague Jon Friedman said the other day, “there will be people directing AI, and people directing people and AI”.

Companies will increasingly ask the question they should always be asking regardless of technology trends: what is the smallest team of people I need to create the best version of this product? The difference this time is that we now have a transformative technology that can turn an inefficient team of 3 designers, 2 researchers, 2 PMs, and 50 engineers into a one-pizza squad of 1 designer, 1 researcher, 1 PM, and 7 engineers. Furthermore, the lines between job functions are blurred such that each member of that team can do some of what another member can. Engineers can help with design, design can help with research, research can help with PM, etc. There will even be one-person startups where the same person does everything and eats the whole pizza!

Another way our field is changing is that the term “product designer” will encompass more of the humanities than it did before. Our currency used to be mostly pixels, but now it is also words, personalities, and other emerging areas of focus. Content Designers and UX Writers may argue this has been the case all along, but until now, the market for pixel-focused designers has been much stronger. The best thing you can do to prepare for this expansion of design’s role is to poke around and get comfortable with all of the new powers you have at your fingertips. Go “program” the personality of a GPT for an hour. The process requires nothing more than plain English.

Learning is free

When I got into this industry, you needed to buy books and take expensive classes in order to learn how to use tools like Adobe Illustrator. There is nothing about designing for AI that requires you to spend significant money to learn. It’s all about the time you are willing to invest.

Furthermore, learning about the general field of design requires years of getting familiar with hundreds of concepts, but AI is such a nascent technology that you can count the new essential design skills on two hands right now. Image generation, prompting, evals, generative UI… there aren’t thousands of AI-specific concepts yet, so get started now.

From an employer perspective, I also don’t want to hear that you want a job here so you can start getting into AI. Just start. The most impressive applicants I’ve seen are people who have, on their own, created personal experiments with the sole purpose of learning the technology. I don’t need to see that you have used AI to help a multi-billion dollar company increase its profits by 200%. I’m also impressed seeing a series of album covers you made for your garage band using Midjourney, or how you have used a combination of your design skills, Recraft, and Lovable Dev to build a site for your non-profit in a weekend. There is no better quality in a teammate than initiative, and by showing you’ve cleared your own trail into the world of AI, you’ve shown me you might be curious enough to be an industry great one day.

Aside from understandable demands on your free time, there is nothing structural holding you back from knowing just as much about designing with AI as your competitors in the job market. If you’re looking for a couple of good newsletters to get started with, try Heather Cooper’s Visually AI or Xinran Ma’s Design with AI.

Don’t get discouraged by the hunt

I’ve worked at some of the smallest and biggest companies in the world and let me just tell you that we all have significant problems with our interview processes. If you get rejected by a company, it might be you, but there is just as much of a chance that it’s them. We’ve said no to hundreds of incredibly qualified candidates for a number of reasons, and only a fraction of the time is it because someone screwed up in their interviews. More often it’s because we are choosing one person between many qualified candidates. Or because we had to pause our process for any number of reasons completely unrelated to the candidates. Or because we screwed up in our evaluation of someone’s strengths and weaknesses.

If you’re not getting calls back from your applications, it could be because your portfolio needs work, or it could be because your approach needs work. More on each of those below. If you aren’t getting selected after interviewing, it could be because you truly didn’t interview well, but more likely it is because one person interviewed better than you did. That’s all it takes. Even at a giant company like Microsoft, it’s usually one person chosen per position. In other words, we are rarely able to hire every finalist who was qualified.

Get your book in order

These days, hiring managers will often pass judgement on your portfolio in less than 30 seconds. When you have 50 portfolios to go through in an afternoon, there are all sorts of things that will put candidates in the “No” pile quickly. If I can’t figure out how to navigate your site? No. If you have basic errors which show a lack of attention to detail? No. If I need to type in a password that you haven’t provided? No. The best portfolios show off a small handful of projects (3-5) straightforwardly, but deeply. Tell me:

1. What problem were you trying to solve?
2. Why did you think it was a problem? Research? Gut?
3. How did you explore the problem and solution space?
4. What did you end up with as a solution?
5. How did you measure if you were correct?

Importantly, remember to show a taste of #4 first for those of us with very short attention spans or a ton of stuff to get through. Wow me with the end result first and then show me how you got there.

Getting in the door is the same as it ever was

When I was in school, I remember being determined not to get jobs because of who I knew. I only wanted to get hired based on my portfolio. Only a couple of years into my career, however, I realized that that simply isn’t how the world works, and there is very little you can do to change that. There is no substitute for a trusted reference vouching for how valuable of a teammate you are. Do the social archeology to figure out the shortest line between you and someone close to the hiring manager. The reason this is so important is that what’s in your portfolio is only half your story. What you are like to work with is the other half, and to determine that, there is no better source than others who have worked with you.

To show you how important networking is: I’ve been lucky enough in my career to never be unintentionally unemployed. Every time I’ve left a job, it’s been on my own volition, and every time I’ve re-entered the job market, I’ve lucked out with multiple options. After I left my last job in 2022, I took a few months off before peeking my head up again. Within a few weeks, I ended up getting to offer stage with 5 companies, including Microsoft. I happened to be on LinkedIn one night and randomly saw a Head of Design post for Major League Baseball’s digital division in my feed. There was a one-click “Apply” button, so I hit it, just for kicks. 24 hours later I got a canned rejection notice. This whole paragraph contains enough cringey braggadocio already, but having specifically designed for ESPN, MLB, NBA, NFL, NHL, the Mariners, Twitter, NBC, and even having a current offer in hand from Disney/ESPN, you’d think I would have at least gotten a call back! Nope.

The point is: no matter how perfectly matched your qualifications might be, applying to a position cold is like buying a lottery ticket. You might get lucky, but the chances are incredibly small.

Creating opportunities for your future self starts many years before you need your next job. Build relationships inside the industry, especially with recruiters. I always shake my head when I see people in tech speaking ill of recruiters. Sure there are some bad ones, but in design, the best recruiters are often in charge of filling the best positions. Treating them badly is not only unkind, but it’s also specifically bad for your future self. Whether you are an early career individual contributor or a longtime design executive, make an effort to know the very best design recruiters in the world.

If you think that you, a member of the creative class 🤡, are somehow above the world’s best talent matchmakers 💍, think again. They have furthered the careers of thousands of people who are better than both you and me… and the best ones are some of the nicest, most interesting people on the planet.

These are the fun times

When it comes down to it, your future in design is the sum of all of your actions that got you here in the first place. The skills you’ve built, the artifacts demonstrated in your portfolio, your helpfulness as a teammate, your reputation as a person, and now more than ever, your curiosity to shed your skin and jump into an undiscovered ocean teeming with new life, hazards, and opportunity. Someone will invent the next CSS, the next Responsive Design, the next sIFR, the next TypeKit, the next IE6 clearfix, and the next Masonry for the AI era. That someone might as well be you.

These periods of technological turnover are the most exciting times to be a designer. They are when we get to flap around chaotically and create the interaction patterns for the next couple of decades. Dive in while you can, because in a few years, we’ll all be back to making the same things again.

For now, the future favors the curious.