Since the introduction of the mainframe, industries from banking to healthcare to logistics have been run by software. But back when the Baby Boomers were playing Pong, the notion of user experience didn’t even exist yet. Today, the legacy systems still employed by big business are dreadfully behind.

I spent the first decade of my career working in big business. During a six-year stint in the motorsports industry, I got to work on a proprietary ticketing system that enabled online, box office, and call center sales for NASCAR races all over the country. The system served the business well—it was one solution for a variety of use cases—but it didn’t serve the needs of the users as effectively as it could. In my tenure at that publicly traded organization, which I look back upon fondly, I helped reduce friction with a variety of software: three content management systems, a SharePoint-powered intranet, support issue tracking and, of course, the revenue-driving ticketing system. Although we improved upon them, most of those systems still left a lot to be desired in terms of their user experience. Polishing a turd, as it were.

That’s why Khoi Vinh’s groundbreaking post about the flaws in enterprise software caught my attention way back in 2007. Jason Fried’s follow-up on Why Enterprise Software Sucks and innumerable others have continued the gripe-sesh about the sad state of software that is supposed to drive business and help employees work—efficiently.

Employees are consumers too; and they are hooked on technology. Design is a competitive advantage in today’s marketplace which is being influenced by trends like BYOD (Bring Your Own Device) and cloud computing. Here is some advice on how to bring a bit of design culture to your next enterprise software project.

UX is UX. And Yours Sucks.

If you’re reading this post, you’re probably acutely aware that software is eating the world. Companies in every industry have become reliant on software to attract and acquire customers, train employees, and run their back-office. According to the Nielsen Norman Group, “User experience encompasses all aspects of the end-user’s interaction with the company, its services, and its products.” Whether your business is a flooring supplies distributorship or a SaaS startup, the “enterprise UX” of the software used by your workforce is no different than the “consumer UX” that marketing and design teams are championing for your customers.

But when I look around… I still see so much shitty software.

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Case in point, next time you’re wrapping up a transaction to… let’s say… get an oil change. Notice the software your vendor is utilizing. I went to my car’s dealership recently and was shocked when they printed out my receipt on a dot matrix printer! I wince every time I check-in at a hotel, or need to ship a package. With the success of disruptive companies, such as, Uber and Airbnb, it’s unreal to me that so many big companies haven’t taken a hard look at the the systems that run their businesses.

The state of enterprise software isn’t completely bleak. is one example of a company that “gets it.” To be fair, during its humble beginnings, as notes, “…the company did not have any of its own technology.’s development team had to build everything within its application from the ground up, in terms of features, functionality and development tools.” The trouble with so many established companies is that their software is old, inherited and dependent on a variety of other systems. Starting from the ground-up affords a company a great opportunity to be intuitively creative with their enterprise software choices.

There’s also smaller companies, such as ZenDesk, that offer software-as-a-service (SaaS) that’s pretty dang user-friendly, too. ZenDesk has created an elegant system for dealing with inbound support requests from any channel—email, web, social, phone, or chat—as well as a customer self-service system that provides users a simple way to help themselves, quickly find what they need, and minimize their frustration.  

Why is enterprise software so rife with friction?

The answer, as many of our landmark whistleblowers have opined, is that the buyers of enterprise software simply aren’t the users (Karl Marx would be rolling his eyes right now). Putting traditional enterprise systems in place is expensive, time consuming, and requires massive customization. Once it’s deployed, it gets relied on by other software, workflows and processes. Over time, it becomes mission critical and a load bearing wall. Companies are entrenched in their systems and don’t dare touch it, if it’s ‘working’ (think: Windows XP).

How to Approach Design in a Corporate Environment

Over the past decade or so I’ve worked with large corporations in a variety of industries. Along the way, I’ve learned a few lessons. Here are some tips for boosting the performance of your team when working with an enterprise product.


Whatever your design process is, be flexible. Our design philosophy, Objective-Based Design, embraces change. Our process centers around meeting business objectives by reducing friction in the user experience. We work backwards to determine strategies that will accomplish our most important goal. At the end of the day, keep the focus on your product’s end-users and making their experience better. In many cases, the end-user is low-ranking, non-managerial employees who need an advocate at every stage of the product design process.

Objective-Based Design: A creative approach to solving any business challenge

They’re the ones who will be more productive once their frustration with dated software is resolved, right? Like we said, commonly end-users don’t have purchase power regarding the software they use daily. Conduct interviews or put together an advisory committee—find some way to let their voice be heard.


The benefits of good design can be quantified. Productivity means more money; employee satisfaction reduces churn. Products employed in-house, that are easy-to-use, can lead to a variety of monetizable benefits. For instance, if you’re updating the way potential applicants apply for jobs on their website, improved design could very-well lead to better applicants. The opportunities for quantifying the benefits of better design are endless.

According to Gerald Storch, vice chairman at Target, their “cheap-chic” strategy was in direct response to rising competition from stores like Wal-Mart. A differentiated shopping experience and high-profile partnerships enabled Tar-zhay to become a market-leader.


Empathy is a key trait of any great designer. Empathy can be demonstrated in the form of shared language. Every corporation I have ever worked with, or for, has had a unique lexicon of words that they use internally to speak to one another. It’s their corporation’s lingo. Once you learn it, start sprinkling it throughout your presentations and notice what happens. This small change to your language will almost certainly help you gain a deeper level of trust with your executive board or steering committee—you’ll soon become a part of their tribe!


In the same way that you may need to learn the executive jargon, and what drives revenue, your stakeholders may need some education about how the design process works. When presenting solutions, be sure to explain the problem at hand, and why certain decisions were made. Modify your language so that it can be understood by even the most left-brained constituent. Most everyone involved in the project won’t be interested in design trends, or specific interactions, but they will have an opinion on how screens are segmented and ordered. Look for opportunities to cite insights from user interviews or observed behavior, or even connect decisions to the physical environment in the workplace.

The best products are constantly under development. This is another opportunity to educate (or perhaps remind) your stakeholders that the product your team is charged with reinventing is going to need iterations. Here’s an example that worked well for me recently: Would you rather drive a Ford Model T, or a Tesla Model S? Without iteration, any innovation you dream up will eventually be outpaced by the competition, or otherwise become obsolete.

I Love Designing Enterprise Software

Some people cringe when I talk about how much I love working with legacy systems. Sure, new products are fun but you never know if they’re going to take off. Incumbent software with a huge user bases affords a great opportunity to engage users and test ideas throughout the product design process. Also, those dedicated support teams can serve as amazing subject matter experts (SMEs) to answer tough questions about why certain features exist, or how they could be made better. They’re probably just as sick of addressing help tickets as the employees are of turning them in!

Big corporations have a vested interest in improving their products, they just don’t know it yet. It’s just a matter of finding the right stakeholders to champion the project. Getting buy-in, navigating the labyrinth of bureaucracy with it’s focus on deadlines and the bottom line, and the outdated tech stacks: those are the real challenges. But finding support from employees, that should be simple. Once you update or improve these aging systems, you have guaranteed adoption. And guaranteed sighs of relief.

All projects are tough; it’s just a matter of perspective. And I’d rather take on the challenge of refactoring a successful product than pouring my heart and soul into creating something “disruptive” that may never see the light of day.

Working within an enterprise may be a challenge, but there is no greater opportunity to directly improve someone’s life than with the applications they use day-in and day-out to file expenses, book travel or even apply for a job. With a built-in user base and a corporate desire to quantify productivity, designers should be chomping at the bit to get their hands on back office software.

What do you think about working on complex systems?