Critical Questions to Ask When Purchasing
a Learning Management System (LMS)


Enterprise learning has evolved significantly over the past decade, driven by advances in technology, changing workforce demographics and the need for continuous skill development. Many organizations now take a more strategic approach to corporate training, seeing it as a way to build competitive advantage rather than just a cost center. While technology is reshaping training, the human element remains vital. Successful enterprise learning strategies consider both business goals and individual learner needs. The focus is on building a true culture of continuous learning and growth.


The challenge lies in creating a versatile learning technology stack that adapts within the dynamic HR landscape. Understanding which technologies you need and how to be sure the technology you are purchasing will meet those needs is more confusing than ever. Market confusion is driven by the swift evolution of new features, mixed platform types, unclear terminology and M&A activities.


As you set out to make any LMS purchasing decision, consider the following list of critical questions. They are organized based on three key aspects of the decision. This is not meant to be an exhaustive list but a starting point. Add as many questions as you can think to add under each section. Not all of these will apply to every purchase decision either. Feel free to edit out what doesn’t apply.

Strategy and Scope

These are the starting point, before even beginning to talk to vendors, consider the big picture of the solution you need and the problem you are focused on solving.

The value of an LMS solution provider as a business partner consistently rises to the top of priorities for survey respondents. Use these questions to help you evaluate the partnership effectiveness of any provider you are talking to.

  • Are we clear on what we need the system to do for us?
  • What are the use cases we need this system to meet?
  • Do we have a clearly documented set of requirements for data, security, capability and integration?
  • Have I involved the right internal partners in preparation for making this decision?

Provider as Partner

The value of an LMS solution provider as a business partner consistently rises to the top of priorities for survey respondents. Use these questions to help you evaluate the partnership effectiveness of any provider you are talking to.

  • Has the provider clearly laid out all the costs associated with this purchase?
  • How confident are we in the ability of this provider to operate as a true business partner to our organization?
  • Has the provider given us references from their existing customers or have we talked with other customers to evaluate their experience?

Technical Capabilities

These questions will be most relevant to your technical use cases and in the demo/proposal phase of your selection process. More than the other two groups, there will likely be questions that do not apply to your situation. Ignore any that don’t fit your specific scenario.

  • Have we seen a clear example, in demonstration, for each of our critical use cases?
  • Is the implementation plan clear?
  • Can the tool support or integrate with our Talent Management solutions?
  • Can the tool support or integrate with our Talent Acquisition solutions?
  • Does this tool offer the capability for social and collaborative interaction?
  • Will this tool support a skills cloud if needed?
  • Does this tool support assessment tools if needed?
  • Does this tool support integration with our learning data solution?
  • Does this tool help our learning operations team be more effective?
  • Does this tool produce data that can be used in our analytics strategy?
  • Will this tool support gamification if needed?
  • Does this tool allow for eCommerce?
  • How will this tool interact with our curated learning content?
  • How will this tool interact with our content authoring tools?
  • Can this tool support our coaching/ mentoring program needs?
  • Does this tool support assessment creation?

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1. Be clear about what you need the system to do.

What seems abundantly clear from our research is that buyers are looking for LMS providers to be partners first. For any technology provider to be a good partner for you, you must first be clear on what you need their technology to do for you, how you need to use it and how it fits into your overall business plan. Applying some simple Design Thinking processes before you start meeting with potential providers can save you money and heartache in the long haul.

Have clearly defined use cases that link to practical and actual business needs for the LMS. Understand what kind of data you need. And be clear about what may be missing from your current tool (if you have one) and what capability you need the technology to have. Proper preparation for this kind of selection can take several weeks, but it is time well spent as it makes evaluating potential solutions and moving to decision-making much faster. If you don’t invest the time upfront, you will spend it in the decision-making process and likely delay any purchase and implementation planning.

2. Involve IT and HR to make sure all possible integration needs and data requirements are captured before implementation.

One surefire way to understand your data requirements and integration needs is to involve key business partners from IT and HR as soon as you begin thinking about needing to select a new LMS vendor. In most large organizations, IT sometimes drives the selection process for new vendors anyway. IT support will help map out data output requirements for any larger Business Intelligence work, key system integrations that will need to be in place and any security requirements specific to your company’s environment. HR partners will ensure that employee data needs are met and any special considerations for larger employee-impacting work are factored in. Involve them from the beginning; they can help shape your use case definitions and include them on any decision-making team as active participants. This will make the implementation and longer-term adoption of the new LMS much quicker.

3. If you aren’t sure, ask the question. Always.

You are the buyer. It is critical that you understand what you are buying. The size investment your organization will be making is not easily undone if a problem arises after implementation. It is easy to make assumptions that issues or concerns can be “worked out” later. That is a serious miscalculation. You must make sure that you are calling out and asking any and every question anyone on the team may have as you go through the process. Create mechanisms to ensure question feedback is captured and encouraged, and set an early ground rule that anyone who is unclear about anything, curious about any aspect, or not satisfied with any answer, must speak up.


Preparation is the key to ensuring a smooth and seamless LMS purchasing decision. Be clear on what you need. Involve the right internal partners to round out the perspective and preparation. Have a clear plan and set of requirements and questions to be addressed by the provider. All of that front-end work will help the decision-making process when the time comes.

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Matt Pittman



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Matt Pittman

Matt Pittman brings nearly 30 years of experience developing people and teams in a variety of settings and organizations. As an HR Practitioner, he has sat in nearly every seat including Learning and Leadership Development, Talent Management and Succession Planning, Talent Acquisition and as a Human Resources Business Partner. A significant part of those roles involved building out functions in organizations and driving large scale change efforts. As a Principal Analyst, Matt leverages this in-depth experience and expertise to provide clients and providers with breakthrough insights and ideas to drive their business forward.