The process of evaluating software can be a time-consuming and exhausting process. The average length of a product search is 20 weeks. You might go through multiple demos for each option, make presentations to stakeholders and decision makers, and iron out the nuances of contracts and pricing.

Starting an evaluation process can be daunting, especially if its your first time. Below, we’ll go through a few tips that will get you ready to have successful meetings with vendors, will help you assess your needs as an organization, and will streamline your internal decision-making conversations.

1. Know your stakeholders

Knowing who will be using and/or affected by your software is the first step in knowing what you need it to do. Do your internal clients need different support from you? Does your leadership need an easier approval process? Will multiple teams in your legal department be using the software?

Part of knowing your stakeholders is knowing who needs to be involved in the actual review and decision-making process. You’ll find that some team members will want to let you know how a software solutions will make their life easier and bow out of the process. Other, more passionate people, might be better served by being brought into the fold.

One of my review processes was held up by a series of passionate team members who, as we moved through the selection process, realized they would be impacted by whatever tool was selected. My leadership requested each time that I onboard the new person into the selection process and re-review the tools to ensure everyone’s needs were being met. This was a frustrating process, and our selection time tripled because the requirements and stakeholders kept changing. Identifying these stakeholders and setting a time frame or process by which they join your selection team will keep you from re-doing evaluation work.

2. Know your requirements

Now that you know who the voices are that will be speaking into your needs, you will need to set your requirements. The easiest way to do this is to determine the problems that need to be solved. Maintaining a focus on problems that require solutions will keep you on track in your evaluations and will keep you from bending toward the desires of passionate people if the “want” isn’t really a “need.”

Come up with a short list of problems that, should you find a solution, will directly impact your bottom line, your client satisfaction, or your productivity. A few examples of this are:

  • Lack of visibility into process makes OOO coverage, staff transitions, or remote work challenging/nearly impossible
  • Contract obligations vary based on the staff member writing them and creates difficulty in tracking and meeting terms of various contracts
  • Staff time is being lost to searching for documents in emails, etc., because of a lack of access to/use of a central repository
  • Staff time is being lost to managing deadlines, manually managing renewals/expiration dates
  • Internal clients are not able to see where their requests are in the process, send requests through to the wrong people, or are frustrated with the amount of lead-time needed to get things from the legal team

Use these problems to generate a list of requirements. Rank them into categories of “Must-Have” and “Nice-to-Have.”

You can include any suggestions that your selection team or stakeholders have that don’t solve your problems in the Nice-to-Have bucket, and this way you can know how vendors stack up against both your needs and your wants. And, your team will feel like they had a voice, even if your final selection is missing a desired feature.

You should also consider what existing systems you would like your system to integrate with. Consider what you would like these integrations to accomplish so you can confirm that the actions you need are possible within the integration, not just that it can integrate. You should also ask whether each user that interacts with the integration requires a full license in both systems. Some integrations can reduce your user count and save you money.

At the end of the day, your software is an investment, just like an employee. It should have a job and should be capable of doing that job. It should solve problems, not create them. Give your software a job description, and when you do your evaluations, make sure that your software meets the essential functions of that job.

3. Have a demo and trial strategy

You’ve done a lot of work to prepare for speaking with vendors. You know what job your software needs to do, you know who needs to be involved, and now you need to select your candidates and meet with the vendors.

A vendor website should have adequate information on it that lets you know what the system is capable of, a basic overview of costs, and how you can learn more. Ideally, you should be able to see an example of the system somewhere on the website as well. The more transparent a website is regarding their process, the more transparent you’ll typically find the sales process. This isn’t necessarily a bad thing when reviewing software, but for systems that offer limited visibility on their websites, you should be prepared to be more diligent in asking questions about feature functionality (make sure you see it in action) and pricing.

During your demo, present your salesperson with the problems that need to be solved in your organization. They should be able to pivot their presentation to cover how their system can meet your needs and display their functionality. Letting them know the problems you have allows them to cover features that might not be on your list, but that cover your needs in a similar way. If they don’t resolve your problem, ask about the specific features you outlined. Take notes on how they will resolve your problems. Ask about whether that is set up for you by their implementation team or if you’re responsible for laying out the processes. And when it comes to costs: Question, Question, Question!

Some software has a lot of functionality, but the features are separated into modules that each add new costs to your monthly or annual pricing. Diligently ask about which features are included in user costs and what incurs additional costs.

If you choose to take advantage of a trial period, you should have at least 30 minutes to devote to using it. Trials can be useful to get a feel of the user experience in the system, but for any custom-built program, the trial will not necessarily offer a view into how your organization will use it. If you’re looking to get a feel for what the system looks like and how you move around it, a trial will be useful. Otherwise, your time might be better spent going through a second demo and talking through what customizations are possible to meet your needs.

4. Consider your qualitative and quantitative data to make a selection

A simple point system doesn’t offer enough of a view to make a decision based solely off of whether the system has the features you were looking for. Price, customer support, implementation, and more go into determining which system is right for you. Here are a few tips for your decision-making process:

  • Compare apples to apples: Be sure you’re comparing total cost to total cost. Don’t fall into the trap of looking at per user price only. User prices may be lower in some systems that charge for every additional feature.
    • Look at the start-up cost – how much does implementation, training, and integration cost?
    • Look at the ongoing costs – what are the annual charges you’ll pay? Users, modules, additional features, etc.
  • Consider customer support: Is it outsourced? Online only? Do you pay an additional cost? What is included?
  • Implementation process: Is there a fee? What does that include? How long will it take? Who manages the implementation? Are you guided through the development or do you have to determine everything yourself? Is training included?
  • Fit: Finally, and most importantly, the software has to be the best fit for the job you’ve given it. If you are well supported, the price is within your budget, and you feel confident that it can meet the essential functions of its job, you have found your software solution.

Clarity doesn’t always come easily from the data you’ve collected. Consider taking your top scorers and writing an argument for each one. Include why it meets your needs, where it’s lacking, and what accommodations are needed to make it work. This can shift the way you’re thinking about each product, as well as prepare you to sell your selection internally.

Need more help? We’ve developed a checklist and outlined a feature grid and pricing grid to help you get started in your evaluation process. Just reach out


Brycellyn LaBorde

Brycellyn LaBorde

Operations Manager, Bigfork Technologies