Why Big Companies Become a Talent Wasteland

"Why Big Companies Become a Talent Wasteland" header image

It was my first day on the job and I was excited—my first high-paying corporate job, nay, career.

The office admin was showing me to my desk and helping me set up my workstation.

“What email client do you guys use?” I asked innocently.

“Ugh, [redacted],” he replied with a massive eye roll. “You’ll get used to it.”

I let this little comment bounce off me because I was riding super high on the new gig and wasn’t going to let something as trivial as learning a new email client pop my balloon.

But little frustrations in my day-to-day communications started popping up almost instantly.

Oh, I can’t receive attachments over 2MB? Seems kinda weird but OK…

Those little frustrations were compounded by company policy.

Wait, I’m not allowed to install Dropbox to work around this arbitrary file size limit because of company policy?

Over time, these frustrations killed my productivity and drove me toward an apathetic, mail-it-in attitude toward my work.

Ugh, I cannot find ANYTHING I am looking for in my inbox and have resorted to taking screenshots of important emails. This is nuts!

Looking back at my time at that company, that antiquated email client stole hours of productivity from the organization, created dozens of internal technical support tickets, and drove me absolutely crazy.

It’s likely not something most business leaders think about every day, but the technological tools you use at your organization carry a hard truth in terms of employee retention:

Smart, talented people don’t want to be stuck working for a company that uses clunky systems where they can’t do their best work.

In this post, we’ll take a closer look at how outdated technology affects employee retention and morale, and conversely, how you can use modern tools to create environments for employees to thrive.

The Link Between Tech and Employee Retention

Millennials and Gen Z (who will comprise 70% of the workforce by 2025) have extremely high expectations of their workplace technology, and it has nothing to do with entitlement or some sort of attitude problem. They were raised their whole lives around instant access to information and real-time communication tools, and have therefore developed an ‘always-on’ mentality.

Pie charts showing percentage of the workforce that millenials and Gen Zers will make up by 2025

So when they show up to their first day of work on Monday and they hear:

“The HR and IT staff will meet you on Thursday at 9AM to train you on our systems.”

It simply does not compute. They expect the tools they will be given to be intuitively designed so that by Thursday they’ve not only learned how to use the tools, they’re logging feature requests for the future and designing new workflows to get their work done better and faster.

The combination of outdated technology and bureaucracy is deadly for organizations who want to employ and retain those generations of talent.

If you’re using outdated technology at work, think about how starkly that contrasts with every consumer application your employees are using during their free time. If they’re able to manage their side projects more efficiently by integrating a multitude of applications for cloud storage, communication, and project management than they’re able to do at their ‘9-5 job’ using the tools provided, how do you think they’ll feel about their future at your organization?

It’s a rhetorical question—they’ll feel like they’re going backward in their career.

Let’s take a closer look at some of the symptoms clunky technology has on morale.

How Does Old Technology Impact Staff Morale?

44% of digital workers at "technology laggard" companies expressed frustration with their employer, compared to 7% of workers at "technology leader" organizations (Unisys).

There are a few ways that outdated tech can have a direct effect on the happiness of your employees. Take a look at a few common areas that cause a dip in employee morale.


It’s pretty well established that nobody likes waiting in lines, buffering YouTube videos, and lagging workplace tools.

Employees spend less time on annual leave than waiting for technology at their offices to work as intended - 167 hours (21 days)

Employees can spend as many as 167 hours waiting for technology at their offices to work as its intended—that’s 21 days! Legacy software programs, jammed printers, and Internet connectivity issues can all play an all-too-common role in increasing wait time at your company—this not only disrupts productivity, but it also erodes morale.

Lack of collaboration

If nobody uses the company intranet, does it really exist?

Modern projects require collaboration, feedback loops, and real-time availability—is your current project management tool providing all these features? If it’s not, you’re likely dealing with a lot of grumpy employees who are using workarounds to get their jobs done, which may also represent a security risk.

Outdated devices

According to The New Digital Workplace Divide, 45% of employees at “technology laggard” companies say that outdated versions keep them from being productive. While it may be expensive to distribute up-to-date equipment to your staff, it’s far more expensive to allow them to become frustrated—disengaged employees cost companies $483 billion to $605 billion each year (Gallup).

Do you see any of these causes of employee frustration at your workplace? Here’s what to do.

The Best Technology for Increasing Employee Retention

Here are a few technology systems that can create more productive environments for your employees.

Communication and collaboration tools

It’s not new data that more and more people crave remote work— 80 % of workers would choose a job that offered flexible working over a job that didn't (IWG). In order to pull this off from an organizational standpoint, however, you must enable employees to share, meet, and manage their time effectively.

Consider using tools like Slack, Zoom, and Asana to stay in touch via chat and video conference while also keeping tabs on the status of the projects they’re working on.

Offer virtual training

42% of employees say that learning and development were the most important benefits when choosing where to work (Udemy). If you’re able to give your employees space to level up their skills, they’re more likely to reward you with their loyalty.

A conversation between a CFO and CEO, asking what happens if employees are trained and leave, and CEO responds asking if employees are not trained and they stay

There are tons of virtual training tools that you can use to offer this perk affordably and in a manner that the modern workforce likes—virtually.

Streamline workflows

Contracts, signatures, and file storage are a part of life—paperwork is a part of life. But that doesn’t mean they have to be boring, inefficient, and outdated.

HelloSign digital signature technology is built on the belief that work can get done faster (and more securely) if the workflows are intuitive, adaptable, and fun to use.

HelloSign allows users to get their work done faster with legally-binding eSignatures. And with the HelloSign API, companies can customize their workflows for some dramatic results. Learn how AdvicePay sped up their user contract management by 50%.

HellowWorks takes this a step further with advanced document workflows that transform static PDFs into dynamic online forms that automatically map data back to the original PDF. Here’s how Instacart used HelloWorks to onboard contractors 270% faster.

Learn more about how Dropbox is working to improve document workflows for hundreds of millions of users by acquiring HelloSign.

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