• Jenny Kosek

5 Steps to a Successful Software Rollout

Updated: Feb 7



The year was 2007. I was serving as Communications and Studio Manager for a music retail chain. Not only was I responsible for all internal and external communications functions for the business, I was managing a music lesson program across five store locations that comprised about 100 instructors and over 1,000 students. We were about to transition from a paper-based lessons management system to a digital one.


In 2007, that was a big deal. Several of our instructors did not even own a home computer. Fewer still were using mobile technology. Our younger instructors were excited about the new system, but there was a lot of hesitation and reluctance from other instructors to abandon paper. They were used to our paper processes and, simply, were afraid of the change. As communications manager and project manager for this rollout, it was my job to make them comfortable.


We launched a robust campaign to empower our staff to embrace the new system. Frequent communication across platforms (via print letters and emails) kept everyone up to speed on the rollout and ensured everyone knew the timeline and steps. Training materials were developed, and attending training sessions was mandatory. To ensure all staff could (and would) attend, we offered sessions during the day, in the evening, and even on weekends to make it easy for them to fit the training in at a time that worked for them (I can still picture myself in my pajamas doing an early Saturday morning training at my old desktop! This was pre-Zoom, so the narration was all via phone). Computers were made available at each store for instructors who did not have access at home, and an easy-to-navigate print book of FAQs was placed at each station for quick reference.


It helped that the software we implemented was a concise, efficient platform that didn’t overwhelm users with unnecessary features. With all of that in place, our rollout went smoothly, with over 98% adoption by staff in the first month.


I have led many software rollouts since then and while there are always variables, there are also steps organizations can consistently take to support successful adoption of new technologies. They are:


1. Make Sure Your Software’s the Right Fit

This sounds silly, right? Of course we’ve gone through careful vetting of the software to make sure it meets our needs…right? Unfortunately, I’ve been a part of software rollouts that have gone downhill because the software proves to be too complex, with too many features, or not the right features, for practical application by users. Early on, make sure that front-line staff, not just managers, are part of the conversation in selecting your software. What an IT team identifies as “easy to use” may not be what a part-time administrative assistant finds easy to use, so make sure users have a voice in the selection process at some point. The platform with the most features might be too overwhelming and unnecessary for your team. The least expensive platform may cut corners when it comes to training. What works for Municipality A may not work for Municipality B. Make sure the right people are in the room when selecting your solution and be thoughtful about how the use cases in your specific organization align with what the program offers.

2. Overcommunicate

If you think you’re communicating enough to staff about a software change, you’re not. Provide detailed, relevant, and changing information. A big mistake organizations make is vague “Get ready, new software is coming” announcements that don’t answer the questions staff have about the system. How hard will it be to learn? What training will be provided? What’s the timeline? Have other organizations used it in the way we’ll be using it? And the big one: How does this affect me and what do I need to do right now? Your messaging should evolve and provide more and more detail the closer you get to your go-live date. Understand from the beginning that staff fear change, and your job is to alleviate their fear – never dismiss it.

Use every tool in your communications arsenal to reach staff, and avoid burying communication about this launch in general newsletters or combined messaging – keep this separate to emphasize its importance. Never assume that top-down communication is happening, because as most staff at the bottom will tell you, it ain’t. Include every impacted staff member in regular, thoughtful, actionable outreach to make sure they’re feeling included and empowered to embrace their role in the implementation. Offer clear expectations and if concerns from staff make their way back to you, address them promptly and respectfully.

3. Create Your Own Training Plan

Most software providers will provide some hands-on training, and in my experience, most will completely underestimate the amount of training staff need to feel comfortable with the new software. You know your staff best, so it’s up to your project managers to craft a customized training strategy that will work for your team. In my 2007 rollout, we knew our staff of teachers were very busy during the day and into the evening because they were in the studio, teaching students. If we had offered training only during those times, they would not have come. That’s why we offered opportunities for (paid) training outside of our implementation staff’s usual schedules to accommodate them. You may have to do the same. Make it easy for staff to train and provide more opportunities than you think you need for them to do so. Formal “classes,” one-on-ones, drop-in hours, or a required webinar series may work better for your team than whatever your software provider offers. Do what works best for your staff.

And remember, training doesn’t stop on your go-live date. Training opportunities should continue for weeks or months afterwards (depending on complexity of operations) and will need to be incorporated in to onboarding or annual performance review programs to ensure new staff learn the software and veteran staff keep their skills sharp. 4. Build Your Own Manual

Most of us who have learned a new software have been directed to the provider’s Help Center, Support Pages, or other training archive to answer questions. Some of these queues are better than others, but it can be very frustrating to search through thousands of training articles to find what you think should be a quick answer. Save your staff the time and build your own training manual for them.

Most software programs offer thousands of customizable tools and features, but most users only use a fraction of them in their day-to-day. Identify the core functions your staff will use regularly, and either pull the articles specific to those functions from the software provider’s training materials, or build your own if you can make a document that’s faster and easier for staff to navigate. The one-size-fits-all-approach to training documentation that technical writers create for software companies may not fit how your team is leveraging the software or how your team learns best.


In addition, make your training materials easy for your team to find and access. Place them prominently on your intranet or provide a direct link to a shared folder that staff can easily bookmark.

5. Build Trust, Build Buy In

Staff have to trust that the new software will be a good thing in order to positively embrace the rollout process. Identify ambassadors early on and gather testimonials, short videos, or case studies to show how avid adopters in your organization are using the software. One of the biggest barriers to adoption in a software rollout is staff not knowing who to go to with questions or being vaguely directed to an online help archive to comb through articles for answers. People need handholding in a software transition – period. Use your ambassadors as go-to trainers so staff feel comfortable reaching out for help. A colleague who can gently guide them to become more confident with the software will do more than any help article, training webinar, or lengthy FAQ can. A software rollout is a big undertaking and needs a big strategy to support its success. These projects are expensive and time consuming but taking the time to do them right will make a huge impact in increasing efficiency and performance down the line. Customize your rollout to work for your team, and eliminate the “software scaries” from your organization.