Connections for Success



Six Useful Steps to Evaluating Software and Cloud Solutions
Chris Arndt

We recently had a Tip of the Day in the bi-monthly newsletter, the Granite Scoop, that suggested you should “Invest in tech to succeed.”

While that tip is, in our opinion, awesome – it perhaps leaves you wanting more. What technology should I invest in? How do I ensure I’m choosing the correct solution? Is it worth the initial time and money investment to make the transition to this new system? All the options and availability of new solutions out there can be understandably daunting.

So, we’d like to offer some useful steps in evaluating software and cloud solutions:

Outsource or Delegate the Research

We’ve mentioned this before in our post on tools for productivity, but we firmly believe in the value of outsourcing. There are plenty of competent, knowledgeable people out there that you could hire to do your initial legwork. Tell them what you’re looking for in a solution, and why you’re looking for it, along with a specific list of needs and enhancements.  Then have them come back to you with three options. If outsourcing doesn’t make sense, and you need someone who really understands the workings of your business, use an entry-level staff to compile this list of three options for you.

The Rule of Three

On that note, it’s a good habit to always narrow down your list to three options and then have a comparison or a good ol’ pros and cons list drafted. This way you can be sure you’re not stuck with someone’s favorite for one reason that may be trumped by functionality. For example, you may not want to choose a specific task manager simply because they really enjoy the user-interface and the fact that hitting tab + B repeatedly fills your screen with tabby cats. (We happen to think this is awesome, Asana, but maybe it’s not for everyone!)

Ask for References

If the tech company has been around for long enough, they should have a reasonable customer base from various industries that you could source references from. Ask for at least one from a similar industry as the one your business operates in.

Develop a Strategy

Have your designated researcher or team develop a strategy that includes cost analysis, a timeline for the investment and implementation of the new solutions. It could include:

  • The cost of the new tool in comparison to how much data entry time is spent on average using the existing software/model.
  • An estimate of the time it will save in staffing costs or other efficiencies.
  • A plan for how the new solution will be deployed to staff: all at once or in a trial group.
  • The requirements from IT support in order to roll out the new tool.
  • The contact or support team if problems do arise with the software/cloud solution.
  • The person or team responsible for tracking the new tool’s time/cost savings and how.

The strategy should also include long-term plans for upgrading or future investments. We all know that eventually that “iPhone 7” will have to be replaced by an “iPhone 9” down the line, so plan accordingly.

Have a Trial-Run with a Focus Group

If it’s feasible with the size of your company, ask for a free trial and have a few key members of your team, who would be working with this solution on a frequent basis, take it for a trial run. Make sure this team doesn’t solely consist of new staff so they are more likely to foresee any hurdles or gaps in the tech solution’s features and functionalities. Ensure this team is also taking into account the process for onboarding new teams and employees.

Know and Understand the Future of the Software

On more than one occasion we’ve witnessed a company invest an incredible amount of money into software without realizing it may be obsolete within a year due to being bought out by another company, or advancements in cloud computing.

“It is a fact: cloud services and SaaS-based business models drive innovation across all industries.” — @ThisWayUp via

Will this software sync with other solutions you currently use? If not, do they have plans to develop new integrations in the future? Don’t assume that just because a certain software solution has been the “gold standard” for years that there isn’t a new company that could offer more for less.

“It’s the “gold standard” of bookkeeping, but has your business outgrown QuickBooks?”

Read related article: All the Most Common Signs You Have Outgrown QuickBooks

So, while there’s a lot to consider when looking for new software or cloud solutions, if you approach your evaluation in a strategic way, we promise it will be a worthy investment.

For more information, contact Chris Arndt at or call him at 312.494.7014. Visit to learn more about our Cloud CFO Services. 

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