
I have been a part of more sales calls/demos than I can remember. Nineteen years in this industry basically means two things: I’m old and I have heard it all. It seems like yesterday when I first heard of this new concept of managing learning programs online, using a tool that is hosted on a website. “That will never work”, I said…boy was I wrong.
I’ll tell you where I’m right, and that’s how to sell this thing called a Learning Management System (LMS). Here’s why: I have been watching the interactions of sales reps and customers over the countless sales cycles and taking careful notes about what is working and what is not.
The very first call/meeting…

I have sat in rooms where sales reps have completely managed the discussion, yet it felt like the customer was in control. It takes time and experience to get to this level, but one thing I know, they asked just enough to get the prospect talking.
I’ve also sat in rooms where the sales rep asked a bunch of questions, either because they did not do their “pre-meeting” homework beforehand, or they just wanted to fill the 1-hour schedule timeframe to show their boss they were “prospecting”. This post will focus on the first…whew.
Questions to ask…and when to ask them.
We have all heard about how to listen when prospects are talking, and to not interrupt them. There is a great post about that here by Craig Weiss, CEO of the Weiss Group. He actually spends more time on sales 101 than LMS specific selling, but it’s important enough for me to reference. One of the most effective ways LMS sales reps are successful in this first meeting is by making the prospect convince the CUSTOMER that they really need an LMS. “You’re kidding right”? Nope. Buyers can sometimes be quite green in the area of LMS purchasing. They simply googled it or asked around. But do they really know what they are asking for? It’s your job as a sales rep to find that out. This will save everyone both time and energy during this sales inquiry. Remember, the average sales cycle of an LMS is 12-18 months. Do you have that kind of time chasing bad leads?
Let’s get into some basics around this concept. Having the prospect establish that they mean business on a purchase looks something like this:
(After all the intros and welcomes of course)
Rep: I’d like to start off by asking a few questions around your current training program and how it’s managed today.
Always make them talk about today’s program, followed by their struggles with it. Get them to share why they THINK they need an LMS and how it will help them.
Rep: Ok, so I can see why you are frustrated with the existing program, but how do you think an LMS purchase will help you solve these issues?
WOW…you just did it. Make them sell you on the purchase. You are actually gaining incredible knowledge about their current training program, but also how much they REALLY know about LMSs. This is a key factor in how you will position the sale down the road and already gives you an advantage over your competition.
Rep: Great, thanks for explaining that in more detail, as it helps me better understand your current situation and how we can help you.
You are now building a business relationship with them, and they might not even know it. Make it personal by saying you want to help them, but you just want to make sure you have what they need. Of course, you can help, but we want to ensure we are not wasting both our times…
Get into the details and position yourself for the win…

Many experts will call this “leading questions”…meaning you are asking the first one to get to the second one, and now you can position your solution without having them realize it. Great. Talented sales reps always position questions in a way to make their LMS look good. The best reps know their solution’s weaknesses and steer clear of them during this detailed questioning process. Dangle that carrot in front of them…but do it honestly and respectfully.
Common questions to ask:
(PS – Assume your competitors have also asked these questions…you’ll know if they answer the questions right away or they need to think about it…)
In any order you need, based upon your beginning conversations:
1) How are you measuring success? Number of completions? Scoring results? Trainings delivered in the year?
2) Tell me about the audience you intend to train? Internal/External?
3) What results need to be captured, complete/incomplete? Pass/Fail? Grades? Scores?
4) What delivery modalities will you be using? Asynchronous/Synchronous? Classroom? Virtual recordings?
5) Will your organization require smaller, sub-set training sites for their own training needs (sub-domains)?
6) Do you build your own content or do you use a 3rd party for content development? Do those 3rd party vendors allow for integrations with an LMS?
7) Speaking of integrations, what system will be your system of record for all user data? CRM? HRIS? We will want to talk to IT about how we integrate with those platforms.
8) How interactive is your learning community? Meaning, will social learning be of interest to you? Does your current leaner group interact with each other independently of training classes?
9) Gamification might be a buzz word, but motivating adults to learn is almost a necessity at this point. How would you envision your learners responding to this type of engagement? Friendly competition between co-workers on who finishes courses first? Who got the most points in a certain month? Sounds corny? Maybe, but it has been proven to motivate adults to take training.
10) Do all of your learners use laptops or are we a mobile-ready organization? (make sure your solution has a fantastic mobile delivery if you go down this road).
Now, there are a vast amount of other Q’s you could ask, specific to making your LMS stand out as a front-runner, and that where your research comes in…learn your system like an engineer would. You will be better for it. This list will get you started.
In conclusion…
Let’s be honest, most adults hate to take training. Whenever I am speaking in from of an audience (every month) I will ask this question: “How many of you woke up this am and were excited about taking some training?” – A: NO ONE….
That’s the battle we as sales reps are all facing in LMS land. So, let’s make this process as simple as possible, by positioning our LMS as a way to solve a current training program problem rather than selling them software licenses.