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Painlessly Switch your Business Management Software

Anytime you’re considering switching the software that does a lot for your business, there’s naturally some hesitancy. There might be pain involved with making that type of change. No, there will be pain involved with that change. 

So how do you manage it? What do you need to know about making that type of transition? How do you jump ship without upending your entire business? We’ll show you how to painlessly (well, mostly painlessly) switch your business management software. 

We’ve tried this before

As a software company, we hear from potential customers frequently that “We’ve tried this before.” They realized the limitations of their software and even tried to switch to a new platform. And, in that switch, the wheels fell off. There was a long, painful process to get the latest software up and running.

They received a lot of pushback from their team. 

Certain functionality they’d become comfortable with would change or be gone altogether. 

Concerns about losing valuable jobs and customer history data surfaced. 

They never got it off the ground because it was too complicated. 

We’re going to take a deeper dive into each of these in this post. There’s a way to navigate each of these so that the transition is less rocky. Set yourself up for success by following these principles. 

Gaining buy-in

Buy-in from your team is the crucial first step that many companies who want to make this transition overlook. 

Many owners or managers keep the selection process behind closed doors. Then, when they’ve selected a software they’re happy with, they roll it out and expect everyone else to be excited about it. The truth is that this doesn’t account for the changes it’s going to make in the lives of the people who will use the software most frequently. 

Take the time to gain input from everyday users of the new software you’re considering. You don’t have to accept all of their feedback, but you should listen. 

I wish I could take credit for this idea, but I can’t. This practice came to me from the leadership of a company for which I worked several years. Here’s a personal story about how to make this transition easier for your team. 

Create space for people to feel heard

We reached a point where a software we had been using for over a decade would no longer be supported. The software company gave us an ultimatum. They said, “After X date, the product version you’re using will no longer be supported. We want you to upgrade for a high cost. You can keep using the current version, but any bugs, loss of data, etc., will not be our responsibility.” 

What choice did we have, right? We had to make a change. 

Knowing that we began to explore other options. The company’s leadership sent two representatives to a tech conference to explore possible solutions. Our IT manager and Operations manager were tasked with selecting the software. 

That was the first savvy part of the process. The Operations manager needed to use it day-to-day, but so did the Sales team. There had been a low level of friction between Operations and Sales (where isn’t there?), and they empowered Operations to make the call. It made Operations feel like they were heard and valued in the process. 

When these two managers returned from the conference, they had narrowed the options down to the top two contenders. (Another strategic decision – don’t come back with five or six options, narrow it down to two that will be a good fit.) 

And then the truly brilliant part – they put everyone in the room for demos. They brought in every user – schedulers, admins, sales leaders, marketing leaders, field users – everyone. We all sat through demos as a group. We were all empowered to ask questions of the people running the demos of the software. After the demos were over, we had a group discussion about the pros and cons of the platform we’d just discussed. Finally, there was a large group meeting to compare the options side-by-side. 

Recap: How to Get Buy-In

In case you missed it, this company took some efficient and insightful steps. 

  • They gave ownership of the selection process to a stakeholder who had been feeling a bit slighted (Operations manager)
  • Then, narrowed the options down to the best two available platforms
  • Put everyone who would be impacted by this change in the demos
  • They held a final discussion to give everyone who would have to use the new option a voice at the table

The software they decided on, in the end, wasn’t the perfect solution for everyone. But no one walked away from the process feeling as if their input and concerns had been completely ignored. They pre-empted the “pushback” by allowing everyone to have a voice. 

I realize this may not be practical at every organization. If that’s the case, put the key influencers in your organization in the room. They may or may not have a management or supervisory role, but others in the company listen to them. They’re influential. Get those people in the room alongside the truly crucial stakeholders, and the ripple through the organization will be positive. 

Doing this will truly help save you a ton of headaches and make the process far less stressful for everyone involved. This is a critical step in contributing to the “painless” switch (like the title of this blog suggests).

If you wait until you’re already implementing new software to roll this out to your team, you’ve put the cart before the horse. It’s too late, and you should expect pushback and a hit to your team’s morale. 

Loss of Functionality

Not every software does the same thing. While many have similarities (managing customer data, billing, etc.), there will always be some things that one software offers that another does not. 

Conversely, your existing software might have some functional limitations. These may be holding your company back from the growth targets you’re trying to achieve. 

This is where you need to dig into the nitty-gritty and ask yourself and your stakeholders some hard questions. Here are some that I recommend asking.

What functionality is absolutely necessary?

Which functions are crucial for you to run your business? What information do you need your software to provide? Essentially, what functions must be performed for your business to keep thriving? These things might include: 

  • Managing customer contact information (name, address, phone, email, etc.)
  • Invoicing
  • Scheduling/routing
  • Reporting
  • A way to reach support with issues

There may be more (or different) fields for your business, but you need to ask yourself what is an absolute minimum. Once you’ve established “table stakes” for new software, you can move on to the next question.

What functions do we want?

A “want” in software is different from a “need.” As I said, not all software options will have the same functionality. (That makes sense, doesn’t it? No two businesses are run the same way because they all have different founders, different stakeholders who have helped make critical decisions in the company’s history, etc. Software companies are no exception.)

Look for things you’d like your current software to do but that it currently does not offer. What functionality would make your life easier? Is there functionality that will save you time? Maybe there are options that a new platform provides that your current one lacks, and they’re not critical, but they would save frustration. 

Here are just a few things to consider on the “want” list: 

  • More robust reporting (offers you more ways to look at your metrics than your current software)
  • Better workflow automation (moving closed deals automatically to scheduling queue, for example)
  • Customer communication directly in-app (send emails or text to customers)
  • Accepting payments (your customers can also pay their bill in the software)
  • Excellent customer support (perhaps a live person?) when you have an issue

Take a hard look at the options you are considering switching to for your new software. Do any of them line up with your “wish list” for a new business management software? 

If we lose some functionality, what are we gaining instead?

There will probably be some sort of tradeoff between what you’re losing on your old platform and what you’re gaining from switching. 

It may be as simple as creating a “pros and cons” list based on your input from your team. Perhaps you create a simple Venn diagram to help you visualize the options. The point is that you perform some sort of exercise that allows you to think through what you’re gaining from the change. 

There’s naturally going to be some things you lose. But if you’ve correctly gained buy-in from your team and you’ve done an honest evaluation of what you’re going to gain from the change, the transition will be much smoother. 

Loss of customer or job data

Per Intelligent HQ, “Simply put, data migration refers to the movement of data from one application to another.” When we talk about “migrating” data, this is what we’re discussing.

Loss of data is a legitimate concern and one that any software you’re considering should address. Here’s are some areas you should concentrate on to help address this issue. 

How much data (if any) are we losing?

The first question you’ll need to ask is, “Are we losing any data?” You may not lose any significant amount of information, depending on the platform you’re moving from and where you’re moving that information to. 

If you will lose any data, you’ll need to do another cost/benefit analysis here. Will the loss of this “legacy data” (that’s a software-industry term) impact your ability to deliver the type of service to which your customers have become accustomed? If so, will the benefits you gain from the added functionality and reporting in your new software outweigh the loss of this data? 

How will this loss of data impact your business from a high level?

From a “10,000 foot view,” will this loss impact your bottom line? If your business is incredibly dependent on job histories, then losing this information could be a real hindrance to your growth. 

If you are more reliant on customer contact information than the specifics of a particular job, the switch won’t be that dramatic. I worked in a business where we made a switch and lost the histories but kept the customer contact information. 

(In full disclosure, we had access to the job history [i.e., they had a mulching job five years ago], but not the job specifics [i.e., yards of mulch, man-hours worked, etc.] in another place.) 

How will data loss impact the day-to-day operations of your business?

From operations, sales, and customer service perspectives, will the loss of this data impact your day-to-day operations? 

It’s most likely that this will impact your sales and customer service departments. Customers may call the office or contact their sales representative directly with questions or requests based on previous jobs. If that information is lost, but you decide the benefit is worth switching, you will want to have some way to empower your front-line employees to help customers with this transition. Offering a discount for incredibly disgruntled customers, without having to ask permission, is a great way to help them smooth ruffled feathers. 

Does the software we’re considering help transfer any data from my previous system?

Some software companies will help with this transition, while others will not. Ask the platform you’re considering if they have a Legacy Data Specialist of Legacy Data Team that will help you move the information from your old system to theirs. 

If a company puts this burden on you, that’s not necessarily a deal-breaker. You have to decide if it’s worth the investment of your office staff’s time to make the migration manually. 

We tried switching software once and couldn’t get it up and running

Software companies run into this issue frequently. Often a business will decide to pick up new software, and the process of onboarding the new platform is kind of a train-wreck. So, the business decides that “new software is too hard to use,” and they go back to cobbling together a process around the old, less-functional platform they’ve been using. 

There is a great deal of control that you, as the business, own over whether or not this process is successful. Here are a couple of ways you can ensure this process goes smoothly.

Designate a Project Champion in your company

One way to ensure successful onboarding of your new software is to designate an internal “Project Champion.” They become the “internal expert” and train all the stakeholders at your company on how to use the software. 

Again, a personal story about how this can work. At the company I worked for where we made this change, the Operations Manager (mentioned above) was the Project Champion. He was NOT a tech-savvy guy. (For context, I often had to help him figure out how to post things to his LinkedIn when he wanted to post something.) But he leaned into it entirely. 

Within a month of the rollout to the entire company, he was helping lead training for the Sales team on how to use the new software – how to leverage the upgrades in functionality we’d gained, best practices for data entry – you name it! 

Giving someone in your company the time, space, and designation of being the Project Champion can make all the difference in adoption by the rest of your company. When they have an internal expert they can go to with questions (easier than calling a support phone number, no matter how good the support team is), they’re more likely to begin to use it. 

Pro-tip: Make sure the person who is the Project Champion is someone who is excited about using the new software. Don’t try to recruit one of the detractors and make them love the software by forcing them to use something they didn’t want.

The added benefit is that the excited, eager Project Champion helps others get excited about the functions and features of the new product.

Ask about the implementation process

Another way you can really improve your results in this process is to ask what the implementation looks like. (Note: “Implementation” is software-speak for “onboarding.”)

Some questions you can ask are: 

Is there an implementation “road map?”

What you’re asking of the company you’re considering using is this: “Can you send me something that shows all the steps in the process, and that I can reference as we move through this process?” 

Most good software companies that want this to succeed will have thought this through and be able to provide you some sort of road map or “compass” to tell you which direction you’re heading in and the stops along the way. 

How long will it take to onboard?

I would ask how long the average new customer takes them to onboard. I would also clarify – is that how long it just takes for them to get things set up? Is there a difference between that timeframe and how long it takes a new customer to be proficient in the software? 

Pro-tip: You also need to know what roadblocks prevent the quoted time frame from being fulfilled. Basically – where are the bottlenecks in this process? Where do other customers of theirs get tripped up? 

For example, if they need a ton of time from the person on your end who handles IT internally, you will need to rearrange that person’s schedule so they have time dedicated to onboarding this new software. Otherwise, that timeframe they gave you until you’re up and running will get bogged down. 

How is onboarding handled at your company?

What you’re looking for here is information about how they bring on new customers. 

  • Is it a self-guided process? 
  • If so, can I get live, US-based support when I get stuck somewhere in the process? 
  • How do I contact support when I have an issue? (i.e. Is there a phone number? Do I have to email? Is there a support portal I have to message? Should I Tweet them? You laugh at that last one, but I know a software that only offers support via Twitter.)

Perhaps they have staff dedicated to helping new customers implement the software. 

  • If so, how do I reach my onboarding specialist? 
  • Do we have regularly scheduled meetings? 
  • If so, do you guide the conversation in those meetings, or can I bring questions that I have as I’ve begun to use the software? 

Is there a Resource Center available?

This one wouldn’t necessarily be a “deal-breaker” for me personally, but there is a lot of benefit to having a Resource Center. 

This means that the company has created assets (walkthroughs, videos, etc.) around common questions they get from their customers. The reason is that some people prefer to look up the answer and figure out the solution themselves. This helps some people learn, so asking about it is important. This is especially true if your Project Champion is someone who learns best this way. 


So, to successfully implement a new business management software, here are some practical, actionable steps you can take to help make this process pretty painless.

  • Get buy-in early
  • Make a list of “must-haves” and “wants” around functionality
  • Ask lots of questions about data migration
  • Get clarity on the implementation process before you sign anything.

These steps will help you avoid some massive headaches with your new software and will make the process a positive, painless experience for everyone involved. 

If you’re worried about the best time to make that switch, check out this blog.

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