4 Business-Tested Ways To Help Software Training Stick

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A software demo will always show the product in its most flattering light, but once your employees get logged into the new system, usability issues are bound to pop up.

If a software user does not know how to use a new system, they may enter customer data in the wrong fields, skip important workflow steps, or worse—expose sensitive business data.

Avoid these kinds of mistakes and get the most value out of new software with thoughtful training. After reaching out to business leaders and tech experts to identify ways to make software training “stick,” we’ve found the following four tips:

  1. Champion the value of software
  2. Leverage your subject matter experts
  3. Establish a grace period
  4. Motivate to make training “stick”

1. Champion the value of software

Most people want justification for any big change at work, and many will hesitate to embrace new software without knowing the value it will bring.

Business leaders owe it to their employees to explain this value in clear terms that align with the key challenge they want to solve. An incredibly effective move here is an appeal to emotion that addresses individual concerns—for example, show how a new project management system can save workers a couple hours of especially tedious work each day by automating workflows.

Kevin Tash, CEO of Tack Media

Kevin Tash, CEO of digital agency Tack Media, has experience implementing Slack, Infusionsoft, and other project management systems and integrations. However impactful the training materials are, Tash says employees still need to understand the value software brings before they truly embrace the change. “It’s important to understand why you are adding a new tool and that the team has proper time to transition,” he says. “It’s important when adding new software that you understand that it will help the company grow and that the team understands the value.”

Demonstrate how a new CRM will make it easier for the sales team to find opportunities to close more deals or how a project management tool will prevent frustrating bottlenecks when completing tasks.

Don’t expect employees to buy in without a nudge of some kind. When they’re being asked to do things outside of their daily duties, frustration can set in. Show workers how their efforts will benefit them in the end.

2. Leverage your subject matter experts

Every business has their MVPs. These are the employees who know a particular process like the back of their hand, the ones typically assigned to help new workers ramp up, and the ones you should include in configuring and testing new software before, during, and after launch.

Shayne Sherman, CEO of TechLoris

Shayne Sherman, CEO of TechLoris, a PC problem-solving resource, describes how the company contracted a third-party developer to work on the software, but says the developer was unaware of the nuances of their specific industry and business. As a result, the first version of the software didn’t hit the mark.

It took the knowledge of internal subject matter experts (SMEs) to configure a data transfer tool that helped save the implementation from failure. “Our data entry operators had knowledge of these caveats; the contractors did not,” he says. “Had our end users been involved in, at least, the compiling of the requirements, we could have saved a lot of time and a fair amount of money.”

Sherman knew he had to find people who knew this data intimately and found some SMEs to use the software from the perspective of a knowledgeable insider.

“When we were working on our system, our lead data entry noticed that the fields available in the forms did not encompass all of the data types that we could expect in the files,” he says. “This is an example of something that someone who has spent a lot of time pouring over those files will notice and could raise early on.”

The takeaway? If you want your employees to use new software effectively, include them early on in the configuration process, and take their suggestions and concerns to heart.

3. Establish a grace period

New drivers tend to make little mistakes—a clipped mirror here, running over a curb there. Users of new software will do the same, which is why it helps to give employees a defined grace period where they feel comfortable asking questions and exploring the new technology with low stakes.

Following a formal training introduction from the vendor, it’s up to management to arrange for a time when users can try out the software and jot down questions.

“Once they write down their questions, they can have a Q&A with the internal or external training manager,” Tash says. “At that point, it’s good to give them a grace period to transition to minimize stress and an abundance of mistakes.”

Make the grace period at least one week. It may be necessary to extend that timeframe, depending on the industry, your go-live date, and the time it typically takes for a business to run into a variety of software-related situations that may need attention.

Jesse Silkoff, co-founder and president of MyRoofingPal

Even high-performing workers need practice time. Jesse Silkoff, co-founder and president of MyRoofingPal, a resource to find professional roofing services, suggests making it a collaborative process between managers and their direct reports.

“[Scheduled training] shows your employees that learning this software is a priority and that they’ll have help throughout the process,” he says. “If you just throw them into the deep end, you run the risk of some employees never learning what they need to know.”

Silkoff also suggests scheduling some additional time with vendor experts who can respond to questions following the grace period and demonstrate how to perform specific tasks.

4. Motivate to make training “stick”

Employees tend to maintain software training when they are actually invested and committed to learning, but people need motivation that makes sense for them. Showing the value, as mentioned above, is powerful. But there are several “motivational levers” you can pull that help show workers why taking the training seriously benefits them personally.

Motivational levers How it works
Assess their learning Most people like the feeling of checking off tasks or reaching milestones. This is easy to achieve by breaking software training into smaller courses and giving workers access to check their progress.
Offer a variety of learning opportunities Videos, games, quizzes, and simulations make for more interactive and engaging training. Plus, this helps individual employees learn in the most effective way (with visuals, competitions, text, demonstrations, etc.).
Incentivize Gift cards, free lunch, or coffee are simple, inexpensive rewards for employees who reach milestones first or perform well in the grace period. Be sure to also reward your SMEs for helping with onboarding.
Make training collaborative As social creatures, people usually want to work as a team to solve problems. It’s also not uncommon for employees who work together to ideate clever new methods of working in the system that they can then share companywide.

Training shouldn’t end immediately after the go-live date. In fact, it should occur for new and existing employees at least annually, in addition to when major software updates are released that impact workflows. Each time training occurs, use a method to motivate trainees with rewards or other incentives.

“It’s just a fun little thing that lets the employees know I appreciate their hard work and the time they’re having to take out of their normal duties to learn something new,” Silkoff says.

How will you train your employees?

Companies can put these best practices into action now to create an inclusive, effective training plan for new software. This process can be done manually, but for ongoing training with new hires, training software is highly recommended.

You may ask yourself, “New software to help train employees on new software?”

Yes! This software allows users to create training courses, then easily administer to employees and track their progress. And once you’re done training current employees, use the software to store the courses, and roll them out when new hires are getting started. Best of all, most employees don’t need to learn how to use it.

Our training software buyers guide offers more detail about benefits, features, and costs, as well as links to similar software guides for learning management (LMS), course authoring, and learning experience platforms.

Looking for Training software? Check out Capterra's list of the best Training software solutions.

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About the Author

Taylor Short

Taylor Short

Taylor Short is a Senior Content Analyst at Capterra, covering technology and changing trends in the hotel industry, property, and maintenance management. He conducts primary research with both consumers and business owners to publish market reports and video content. His work has been cited in dozens of notable publications, including The Washington Post, Lodging Magazine, Facility Management Magazine, and Facility Executive Magazine. After earning a bachelor's degree in Journalism from the University of North Texas, he worked as a reporter covering city governments, businesses, schools, and police for newspapers in Dallas, Austin, and other regional markets. Taylor has also freelanced for Reuters News Agency and tutored students in English and writing at Austin Community College.


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