Why Most Enterprise Software is Confusing

and Why Great UX is Worth the Investment

Jeff Brydon
4 min readMar 22, 2018

With the success of Slack, AirBnB, and Apple, business leaders have seen the importance of great user experiences. CEOs agree that great design is important, even for enterprise software. So why are so many enterprise tools still confusing and difficult to use?

Designers often blame feature creep: companies keep adding new features to expand their user base, which tends to increase complexity while adding diminishing value (compared to the original core features). Eventually, the tool grows into a confusing monstrosity. While this is often true, there are other forces that lead to confusing enterprise software.

Product Teams always endeavor to build great user experiences. However, this would require spending development time on numerous little details – smooth transitions, informative empty states, useful error messages, and much more. It would require testing your product with users, and spending time to make improvements. The problem is: Scrum Teams are always strapped for time. They usually underestimate how long a feature will take to build, and they’re forced to cut scope in order to meet deadlines. The first things cut are the “polish” — the seemingly unimportant details. Without admitting it, teams end up releasing unpolished features.

Agile Development makes it difficult for Designers to push for polished features and great UX. In theory, Agile Development means that Scrum Teams can release unpolished features, get feedback, and quickly improve them. In practice, these improvements get left on the back burner. By the time a feature has been released and feedback has been collected (even if the feature is confusing to users) there’s always a new feature demanding the team’s attention. Designers may push for the team to improve unpolished features, but Product Managers will often ask, “what’s the return on investment for improving the old feature, vs. building the shiny new feature the sales team is asking for?”

With enterprise software, the Sales Team tips the balance towards speed over quality. Buyers ask for specific features, and the Sales Team pressures Product Managers to build them. During a Free Trial, one might expect a confusing user experience to be a deal-breaker. However, the buyers are not the end users, and a great user experience is not their top concern. Salespeople can handhold trial users, glossing over confusing features. Having a bunch of features ends up being more important than having fewer, higher quality features. Despite the CEO’s conviction that a great user experience is important, confusing software is born.

If this sales-driven approach helps the Sales Team land more deals, then is it an optimal approach? Is spending development time on a great user experience just not in the best interest of the business? I think not. This approach is short-sighted: too focused on landing new deals (kept in the company spotlight by vocal salespeople), while underestimating the value of happy customers. A few enterprise software companies have shown that great user experiences are extremely valuable. In The Future of Enterprise Design Is Consumer-Grade UX, Amanda Linden writes, “today, teams and employees often choose their own products. That means it’s the best product and design that wins, rather than the best sales and marketing. Slack, Sketch, Dropbox, Sunrise, Google Drive, and Asana are all examples of this trend… Adoption, in this scenario, is organic, and users will ultimately be more loyal to your product than something they’ve been ‘forced’ to use.”

It pays to prioritize a great user experience, and some enterprise software companies have seen the light. They’ve managed to keep their core experience simple, rather than muddled by tacked-on features. They’ve kept existing users in mind, even if it meant saying “no” to shiny new features new sales. And they’ve incentivized their Scrum Teams to deliver quality features, staying focused on user outcomes rather than output. For the people that have to use this software, let’s hope that more companies start to prioritize great user experiences.

Thanks for reading! Feel free to check out my portfolio at www.jeffbrydon.com

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