The 10 Most Puzzling Office Apps in the US, According to Analysis

The decades-long digital transformation of the American workplace has significantly accelerated in the last few years. Yet, despite the ongoing tectonic shift, it seems one thing will never change: the tools and technology we use to do our jobs cause no shortage of curiosity, confusion, and frustration.

Thanks to data analysis from, we can now see which tools cause this confusion the most. They analyzed internet search data for nearly 10,000 search terms to reveal which office and productivity applications raise the most questions among US workers.

The 10 Most Puzzling Office Apps in the US

1. Dropbox

The cloud storage and file-sharing platform Dropbox draws nearly 22,000 help and support-related searches per month. The platform is available for both business and personal use, possibly contributing to the large volume of online searches for it.

Dropbox is one of two services of its type among the most puzzling apps for US workers. The other is Microsoft OneDrive. Major competitors, including Google Drive, Apple iCloud, Box, and iDrive, are all absent.

2. WordPress

WordPress has long been a mainstay of DIY website creation and development. Despite the rise of competitors like Wix, Squarespace, and Shopify, WordPress remains by far the most popular content management system (CMS) available, with over 40% market share.

WordPress makes web development more accessible by breaking down complex tasks into more straightforward functionality. The platform supports online creators, IT professionals, and small business owners, many of whom do not come from a web development background.

As much as the platform endeavors to create a straightforward user experience, the space in which it operates makes some user confusion inevitable. No matter how much you streamline it, web development still has more than its share of complexity and challenges.

3. Zoom

Zoom, the video conferencing app that kept much of the world running through the remote work revolution of the early 2020s, has become one of the most question-inducing apps on the web.

While zoom doesn’t necessarily struggle with the same level of user-facing complexity that some apps on this list do, it does have one obstacle that most don’t. Stable, easy-to-use audio-video technology has always been a challenge for users and developers alike. 

Minor differences in hardware like cameras and microphones, as well as any instability in internet connection, can quickly cause trouble, often driving users to search online for how to resolve these issues.

4. Microsoft Teams

Microsoft Teams, a common choice for internal corporate communications, comes in alongside video conferencing rival Zoom for overall help-related search volume.

Teams and its predecessors in the lineup of Microsoft messaging and communication tools have long been staples of the American corporate workplace. 

With its widespread adoption among small and large businesses, it makes sense for a tool like this to raise a few question marks.

5. Microsoft OneDrive

OneDrive, another Microsoft product, is the cloud storage solution that integrates file sharing into the existing suite of Microsoft workplace tools and productivity apps. OneDrive raises approximately 26,000 monthly user questions, more than any of its competitors.

Microsoft holds the rare distinction of being the only company to have three different products appear on this list. However, it remains unclear whether that is a result of user experience that hasn’t kept up with the times or simply a reflection of the software behemoth’s sheer ubiquity in the office tools space.

6. Square

Payment processing service Square earns nearly 35,000 monthly searches, making it one of two point-of-sale (POS) solutions on this list. Square offers a variety of software and hardware tools to help businesses of all sizes manage inventory, payments, scheduling, and more.

Similarly to the video conferencing apps discussed above, the integration of various software and hardware configurations likely contributes to Square’s number of pain points.

7. Salesforce

As the longstanding #1 customer relationship management (CRM) platform available, it is no mystery that Salesforce is one of the top five most puzzling office apps in the US. 

Salesforce offers a deep and highly customizable set of tools for managing business relationships, sales data, customer service, and more. However, with powerful and versatile tools often comes a steep learning curve and a high capacity for confused workers. 

8. Shopify

Shopify joins WordPress as the only other major CMS on this list. Shopify specializes in e-commerce and offers a variety of tools to empower small businesses. 

The integration of retail POS systems, the inherent complexity of an effective CMS, and the importance of safely transferring money between customers and businesses are likely all contributing factors to Shopify’s nearly 45,000 monthly help-related searches.

9. Microsoft Excel

Microsoft Excel, the application that has long been synonymous with spreadsheets and data tracking, is the runner-up for the most puzzling office app in the US.

To Excel’s credit, the volume of online questions it garners is likely a direct result of its far-reaching capabilities. Like many products on this list, Excel is far more than a simple utility. It is a complex and powerful toolset. Expertise in Excel is a valuable professional skill in many industries. There’s even a world championship where power users compete to demonstrate their abilities.

In that light, it is little wonder why Excel is the source of more questions than almost any other office application on the market.

10. Quickbooks

Intuit Quickbooks is the overall most puzzling office app for American workers, earning nearly 68,000 searches every month. The go-to accounting software choice for businesses of all shapes and sizes, Quickbooks endeavors to make accounting available to everyone.

In the same way that CMS platforms like Shopify and WordPress offer web development tools to an audience of ranging technical expertise, Quickbooks enables accounting for everyone from career accountants to brand new small business owners.

Bridging the gap between small-scale entrepreneurs and job functions that would otherwise require specialized employees or departments is no small feat. Quickbooks sets about this goal admirably but is bound to stir some confusion in its users along the way.

New Tools, New Capabilities, Old Challenges

Even as the office environment undergoes revolutionary change, it retains some bastions of familiarity. The day-to-day friction of interfacing with the technology necessary to do our jobs is nothing new. Likewise, it doesn’t appear to be going anywhere anytime soon.

However, at least one thing is worthy of our gratitude: the internet is here to help us navigate these challenges. The apps we’ve discussed collectively gather approximately 358,700 help-related searches per month. One can safely infer that many of those searchers find what they were looking for and can return to what they do best.

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Hey, I’m Sam. I created Smarter and Harder to explore big ideas, both old and new, about building a better life. My mission is to evolve the conversation about personal growth and have fun doing it.

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