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9 Ways to Avoid Software Rollout Mistakes

office, workplace technology
The Robin Team
Published on

Implementing new enterprise-level software across your organization involves several layers of planning. There’s no be all end all method to an implementation but when done well, the process for an IT admin can feel seamless. To better understand the do’s and dont’s, we're launching a series outlining best practices and tips for a successful company-wide shift. First up: common implementation mistakes.


Avoid these common mistakes

Global enterprise software spending is expected to reach about $387 billion this year. That’s a 9.4 percent growth from last year. Organizations around the world are investing more money than ever into the growing selection of enterprise software for IT execs to choose from. That list only continues to grow.

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Implementing new enterprise software across an organization is a daunting task. Core questions you should ask yourself and your stakeholders before diving in are:

  • What problem do we need this to solve?
  • Who should use this?
  • What’s the best way to train end users?
  • How will we measure success?
Worldwide IT spending forcast chart

Deployment mistakes have costly consequences. The amount of resources and time you put into set up and onboarding makes all the difference.

1. Not including real users in the decision-making process

At least until the robots take control, software has to help real live humans do something important. A little research goes a long way. What separates your power users from your casual end users? What’s their most common complaint today?  Where do people expect to find this software? Do they want a separate app on their desktop? A browser plugin? A mobile app? The software should fit seamlessly into how someone is already working. Make sure to ask both basic and advanced users -- lower usage folks generally avoid commitments like mobile apps in favor of set-and-forget plugins.

“When implementing an [ERP] system, many organizations focus their time and effort on gaining approval from leadership executives, when they should be engaging key employees who will be using the system the most," - Kevin Beasley, CIO of VAI.

2. Ignoring the opposers

As Joseph P. Kennedy once said, “When the going gets tough, the tough get going.” It’d be a miracle if your first pitch received 100% buy-in and zero reservation. Start with an advocacy group of real users. These power users know their pain points better than anyone else and they’ll be able to address potential deficiencies. It’s best to attack potential issues before they exist.

If end users advocate against a proposed solution, understand why. If you understand exactly why employees need a new piece of software, this should be easy. Keep these notes close when you look into more vendors.If your advocacy group needs to be able to manage object level permissions, they’ll probably shake their heads at a reporting and analytics software that lacks row/column level security, for example.


3. Inaccurate budgeting

There are several layers of investment to consider when deploying new software across your organization. Budget should align with how critical the job is for your business. You’ll find low and high-end options for just about everything. Find options in both before you lock in budgets. This leaves flexibility  if needed, and it’s often easier to scale back if you find a great option under-budget.

If this isn’t mission critical, you can get it done with pocket change. Ready-made products like MS Office, which is targeted to a wide range of users and often uncustomizable, will be significantly cheaper than custom or bespoke software that allows you to customize it specifically to your company’s needs.

“We often see leaders underestimate the expenses involved with an implementation, which include maintenance and the level of talent needed to get the project off the ground successfully."  -Tim Webb,  practice director of enterprise technology services at Robert Half Technology.

The more specificity your looking for, the more expensive the software becomes. If you’re looking to provide end users with custom software like CRM, you’ll pay more for something that works exactly how you need it to.

4. Ignoring change management

Rolling out across an entire organization cannot be done with a simple 'set it and forget it' mentality. Change is hard, but you can help. Change management means you're thinking through how each individual will interact with the product throughout the entire process to make sure they are supported and changes are communicated efficiently.The business environment is always changing. With new software, your workplace processes will transform. You must adjust to those changes as a team.

Kotter's theory

5. Not using an implementation strategy

Choosing the right solution for your enterprise is only part of the battle. How IT implements the software is a make or break for most companies. Start with a pilot group and focus on the end-user. Calendar out the entire process. Discuss with stakeholders what the best way to roll out changes is.

How will you communicate changes? Company-wide email? An internal wiki?  Will you do large or small group training? Keep in mind that training doesn’t end with current employees. Consider how your enterprise will grow over the next few months or years and map an implementation strategy for those users as well. Will your new software training be a part of employee onboarding as your company expands?

6. Not communicating info across departments to get buy-in

Let others own authority over new software they’ll be using most by including them in all steps of the process. If several departments will use it, communicate all relevant updates in real-time. Identify your stakeholders. Adoption is a lot easier when those people are bought in and excited about the software. Otherwise, you lose the battle before you even implement.

Who are your stakholders graph

7. Not having a maintenance plan

If the software was down for 10 minutes, would anyone notice? If so, you’ll need monitoring tools.What is the plan to have employees communicate issues or request help?  Will there be automatic updates to admins when certain things go awry? An upcoming update in Robin will proactively email admins anytime a device goes offline. Tools like that one prevent an influx of IT support tickets and identify the issue immediately.

Screenshot of Robin app

With Robin, your maintenance plan can be as easy as a click of a button.[/caption]

8. Not pressing vendors for thorough demonstrations and information

Companies sometimes choose whatever is cheapest or instinctively feels right instead of fully investigating the options. This happens for several reasons:

  • The company’s on a time crunch.
  • The company’s on a budget crunch.
  • Vendor documentation and expertise is overlooked.
  • End users are not involved in the decision-making process.

While time consuming, that's where RFPs can come in handy, especially if your priorities are set before you look into the options. When done correctly, a vendor will provide you with clear documentation or technical expertise that will help you become a pro yourself. Some companies hire out consulting firms or temporary contractors in order to help project management RFP processes or big implementations.

Reasons for consultants graphc

9. Rushing the process

Don’t speed through an enterprise software implementation. A “hurry up get it done” attitude may be satisfying at first but down the line, the steps you skipped over will come back in the form of the office Grim Reaper.

"If a company rushes to install an enterprise system without first having a clear understanding of the business implications, the dream of integration can quickly turn into a nightmare.” -HBR

That’s why having a thorough implementation strategy with change management in mind is crucial to the system’s success. While you may not have control over how many software choices are out there, you do have control over how you implement the one you choose. Avoid these mistakes and you’re golden.


Now that you know what NOT to do, let your software journey begin. Check out our other posts of the series:

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Does your office collaboration need a reboot?

Find out if your workplace strategy is a hit or a miss.

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