Being a designer at a big tech org is an odd experience. You're expected to push the boundaries of creative and technological frontiers to imagine the impossible and will something innovative into existence, all while working within the confines of an organization that operates at such a massive scale that shipping any design that's bold and "out-there" is perceived as risky when the product controls so many metrics that matter to the bottom line.
This is the whiplash I often feel when working on strategic initiatives. There are clear opportunities out there that will easily let us differentiate our experience in a way that delivers a ton of value to customers, but the catch is often that it is either too expensive to build or it modifies an existing workflow in a way that's unknown and makes it impossible to predict the outcome, almost certainly dooming it to the graveyard of failed ideas before it even had a chance to stand a fair trial.
Startups don't have this problem. A small team of 20 people working with an audience of some 1,000-2,000 customers can easily take big swings and experiment with bold ideas. If it fails, not much has been lost and outcome doesn't result in some massive diff to the balance sheets and income statements. But a big tech org that has to make payroll for 10,000 employees worldwide and needs to hit its quarterly estimates for the next earnings call is going to profusely start sweating at the thought of this.
The ironic thing about this is that you're almost certainly doomed to fail if you don't take the risks. You rarely see bold, groundbreaking products come out of massive tech orgs like Microsoft or Amazon. This is because they're in full-on optimization mode. They've found their success in their products like Windows or the Office suite and have cornered entire markets like e-commerce. At this point, all they need to do is optimize the hell out of it. Test a hundred variations of the interface, experiment with new pricing models, drive subscription growth and expand into new verticals, you get the idea. They believe they've found product-market fit and are now just making it "fit" better.
Therein lies the danger. Product-market fit is not a one-time thing that you achieve once and then just deliver the product. The market is continually changing with demographic trends, new incumbents, changing consumer behaviors, and economic shifts. What was true 2-3 years ago may not be relevant anymore. So you continually need to be revisiting product-market fit and constantly keep asking the question "Is my product still useful to people?" or "What new unmet needs have arisen that aren't being serviced by the market right now?" to really keep pace with the rapid rate of change.
If a tech org starts slipping into optimization mode where it's just operating in a mode of tweaking numbers and "keeping the lights on," it's a big red flag to me. It signals that they aren't aware of the the fact that they're barreling towards their demise and are content to just ride out the rest of the time they have. They have no ambition or desire to innovate and compete, so they slowly die a painful death. This kind of company culture with low risk-taking tolerance also is terrible for morale, where every new idea or solution gets shot down under the guise of "Well, that's just not how we do things around here."
• • •
At the start of a new company or industry, there are creators. These are the artists and technologists who break new ground in establishing a brand new market or product. Think the Sony Walkman or the iPod, Uber or Airbnb, and OpenAI with their agentic models. It's an explosive entrance that completely disrupts the way people have been accustomed to interacting with technology and opens the floodgates for an entirely new era of forming habits with tech. Then it becomes the "new normal" while the MBAs and Business Operations teams start to outnumber the R&D and Product Development teams. This is when things start going downhill. If you don't have a culture of continual innovation, you're not going anywhere.
The most painful part about all this is how obvious it all feels to me but doesn't to others. So many colleagues and peers I work with are okay with just making small tweaks to things that have existed and call it a day. I personally don't feel inspired or energized to work at a place like this, and I'd much rather be taking bigger risks. Most of my time at the large tech orgs I've worked at has been spent trying to convince people that it's worth taking a bet on something that is bigger and better than what we have today. Most of the time it doesn't work. But some rare few times — when the stars of resourcing, timing, and goals align — it works. People say yes and they take that risk. And nearly every time it's happened for me, we saw success. Things worked, and people came out the other end happy that we tried it.
Most of the designers working in big tech have developed very specific skillsets on how to do exactly this: how do you sell risky ideas in the context of the metrics and goals that their business cares about? how do you get people comfortable with taking a leap of faith? how do you showcase wins through design that may not be obvious to those without a clear eye for these details? And a lot of these times, they find themselves asking why. Why am I spending so much time doing that, and not building the actual design that I want?
As we enter the era of AI-assisted development, this paradigm is shifting for good. Designers are spending less time trying to convince people to take risks and build things and are instead just building the products themselves with AI coding tools. I've personally been doing this and it has been a game-changer for how many ideas I can explore before even uttering a word of it to anyone. A lot of them don't go anywhere and most of them end up in a dramatic reveal to me about why the product or idea won't work (which is still a good outcome). What it's personally helped me the most with is to build conviction in my ideas. The more I play with a prototype I coded and feel that it's solving the problem I set out to solve, the more convinced I am that this is the inevitable path we must take. And at the end of the day, this conviction helps me sell the idea to others, even if it means influencing others to invest in that risky direction.