Selecting a learning management system (LMS) is a big decision. Whether you’re launching consolidating systems or replatforming to keep up with demand, the LMS you choose will directly shape how you educate customers, partners, and employees.
Most teams understand the importance of features like course creation, reporting, and integrations. But during the request for proposal (RFP) process, even the most experienced buyers overlook critical questions that reveal how well an LMS will actually work for them.
Which might result in choosing an LMS that feels like a win—until 18 months later, when you’re back to square one. Ouch.
In this post, we’ll explore what clients often forget to ask—and why these blind spots can cost you in the long run. We’ll also link to our free RFP template to make sure you’re covered from every angle.
Before You Begin: Start with the End in Mind
Before diving into features and functions, take a step back and clarify the problems you’re trying to solve. The most successful LMS implementations begin with a clear understanding of business goals, not just system requirements. Are you trying to reduce time-to-productivity for new hires? Lower support costs through better product education? Increase ARR with a scalable certification program? When you lead with outcomes, not checklists, vendors can tailor their recommendations around the features and best practices that will actually move the needle for your organization. Let your RFP reflect that clarity by framing each requirement in terms of what it helps you achieve.
What Clients Forget to Ask—And Why It Matters
Even the most detailed RFPs can miss critical questions—especially the ones that uncover how well a platform will really work for your team. Below, we’ve outlined key categories to focus on, along with questions that go beyond surface-level features to help you evaluate true fit and future readiness.
Implementation & Onboarding
Implementation isn’t just technical—it’s behavioral. You need to know:
- Is a dedicated onboarding manager included?
- What’s the typical implementation timeline for a customer like us?
- What’s the vendor’s approach to project management and change enablement?
- How will we be supported post-implementation?
- What is the customer support experience like?
A rocky start sets the tone for your entire program. Smooth onboarding can accelerate time-to-value by months.
Historical Data Migration
If you’re moving off a legacy LMS, ask:
- Will your team assist with historical data import?
- What formats or export types are supported?
- What if we need help cleaning or mapping data?
Without a clean LMS migration, you lose valuable learner history and momentum.
Admin Experience and Usability
Beyond the learner view, consider:
- Can admins be grouped by business unit or audience?
- Is it easy to assign permissions by role?
- Can non-technical users build learning experiences without relying on IT?
If managing the LMS requires a specialist, it won’t scale across departments.
Scalability
The question you’re trying to answer here is: “Can the LMS grow as we do?”
Dig into:
- What’s the largest customer you support? In what ways are their needs similar to ours?
- Can the system handle spikes in usage (e.g., launches, events)?
- How do you ensure platform performance and availability as usage scales across regions and user types?
- What tools or controls are available to help us manage content, users, and permissions at scale?
Today’s solution can quickly become tomorrow’s limitation. Plan beyond your current program.
Product Roadmap
In the same vein, how is the LMS evolving to support where your business is headed?
Here are some questions to ask:
- Does the provider have a thoughtful roadmap?
- What drives the roadmap?
- What experience does the provider have to support and develop the roadmap?
Asking about the roadmap gives you a window into how the provider thinks, how they prioritize customer needs, and whether they’ll be a true partner in your long-term success.
Data Ownership & Access
Here are questions to ask:
- Can we schedule automatic exports of learner data?
- Does the platform have robust reporting built in that can meet complex needs and conditions?
- Is there a robust and well-documented API that we can access to serve our own custom needs?
- What happens to our data if we churn?
Your data is valuable—don’t get locked out of it.
Product Transparency & Communication
Ever been hit by changes you were unaware of? It happens all too often.
Ask these questions to get an understanding of what you can expect:
- Is there a public changelog or roadmap?
- How are customers notified about updates?
You’re not just buying software; you’re entering a partnership.
Multi-Audience Management
What you want to understand here is: “Can we educate more than one audience from the same system?”
If you support customers, employees, and partners, ask:
- Can learning environments be personalized by user type?
- Can one learner belong to multiple audiences or groups?
- Can we track learning outcomes by audience?
Consolidating your learning programs into a single LMS avoids tool sprawl and boosts ROI.
Accessibility & Security
Don’t forget to ask questions about inclusivity and compliance:
- Is your LMS WCAG 2.1 compliant?
- Does it support screen readers and keyboard navigation?
- Do you hold security certifications (e.g., SOC 2, ISO 27001)?
Accessibility and compliance are table stakes—not nice-to-haves.
The Risks of Forgetting to Ask
Neglecting these deeper questions often leads to:
- Replatforming within a year or two, which is time-consuming and expensive.
- Stakeholder misalignment, where different departments have different tools or outcomes.
- Missed business goals, like reducing churn, enabling product adoption, or scaling revenue.
How to Write a Smarter LMS RFP
Writing a strategic RFP doesn’t have to be hard. Here’s how to do it right:
- Start with your business goals.
What are you trying to enable? The most successful education programs have initiatives clearly aligned with business outcomes and corresponding metrics to demonstrate how the learning program supports those outcomes.
- Gather input from every stakeholder.
Sales, Customer Success, Enablement, and Marketing all have unique problems they’re trying to solve through learning—whether it’s reducing ramp time, increasing adoption, or driving retention. When you engage each team early and ask why they need an LMS (not just what it should do), you’ll uncover the outcomes that matter most.
This clarity empowers vendors to steer you toward the features and best practices within their platform that are most aligned with your goals, leading to better recommendations and a stronger path to success.
- Think in questions.
For every must-have, write a corresponding question to validate vendor fit. Keep in mind the ultimate goal of each type of functionality—there might be a way to meet your need that differs from the feature you were thinking about.
(Need help? We’ve compiled 200+ questions to help you fully evaluate your options—with space for scoring and comparison.)
Ask Like a Strategist
The best LMS isn’t just the one with the most bells and whistles. It’s the one that enables your entire program to scale, evolve, and deliver measurable business outcomes.
So go beyond the obvious. Ask the hard questions. Because your next LMS isn’t just a platform—it’s a growth partner.
