What I Learned from doing 100+ Sales Demos and Webinars in Six Months

When I started at Lucid Software a year ago, I began as a Customer Success Manager. I received my own book of accounts and was tasked with ensuring users and admins maximized the value Lucidchart offers.

Shortly after starting, I decided to offer a webinar training to one of my accounts as a way of helping users get in the product and discover the many features that generally go undiscovered.

Six months later, I had conducted over 100 live webinars. Some had five attendees, and some had more than 1700. I also began to conduct many sales demos along the way.

A year has passed, and I’ve now done more than 200 live webinars, sales demos, and onsite visits. I’ve trained Fortune 500 companies and Fortune 100 companies, yet still am continually tagged as the 12 year old trainer (perhaps one day I’ll be able to grow facial hair). Product education and training have become a core piece of what we do at Lucid Software. While I believe I’ve only begun to scratch the surface of effective product training, there are some great lessons I’ve learned along the way.

1. Solutions Over Features

When I first conducted these webinars, each webinar began with all the cool tips and tricks that I thought people would be unfamiliar with. I showed how to automatically arrange sets of shapes with the click of a button or how you could easily group shapes together and create custom shape libraries. These features were sexy! At least I thought so. I would even get some “ooohs” and “ahhhs,” and it made me feel good about myself.

But I quickly found they didn’t mean anything to anyone. In the end, I was only showing features. Yes, they were sexy. But they didn’t hold any value. It was just like the “triple tap the iPhone home button and open up the magnifying glass.” Yes, sexy. But I still can’t figure out why and when I would use it.

I didn’t demonstrate the problems these features solved for individuals and teams. I was incredibly feature-focused. And as soon as I became feature-focused, I lost sight of the customer and the value disappeared.

“People have little interest in purchasing a bed. What they want is a good night’s sleep”

— Gregory Ciotti, Features Tell, but Benefits Sell

Bottom Line: Don’t expect individuals to naturally find the value and application of the features you present. You must show them and connect those dots.

The purpose of training and sales demos is to empower individuals and teams to solve the problems they’re facing. The product/service and its features are a means to an end, not the end. Thus, our training and demos must focus on providing solutions to their problems with our product or service. It requires a change of mindset.

So how we do this? The next four principles I mention discuss the framework we need to truly train and sell with a solution-over-feature mindset.

2. Know Your Content

When I was at Qualtrics, there was a sign above my desk space that had a famous quote from the CEO, Ryan Smith. It went something like this: “Those that know the product best sell the most.”

This is truth. If we are going to truly solve customer problems with our product, then we must know our product perfectly. Knowing the product will empower us to creatively solve any problems our customers are facing.

Additionally, it endows us with confidence. Instead of trying to BS our way through another training or sales call, we can approach trainings and demos with confidence that we will solve their problems with our product. Our goal is to empower individuals to solve their own problems. But we cannot do that until we’ve mastered the product.

Ironically, this is the very first thing that gets placed on the back burner. I see it over and over again. We get busy filling our pipeline or reaching out to customers to understand how they’re using our product. And learning the product gets put on the back burner. Months go by, and we say to ourselves, “Man, I need to get in the product.” Then we see someone kill it in the product, and it hits us again, “I really need to get in the product. I don’t know it at all.”

But then it never happens.

Make it happen. The first step to maximizing the value of your product is knowing it and knowing it perfectly, Not just knowing about it, but knowing it by using it, weaving it into your daily workflow, and using it in the same way you hope other people will use it.

3. Know Your Audience

A few months ago, I was training a team at a very large tech company. I was stopped in the middle of the training and was told there wasn’t enough time for me to finish. Following the training, I had an email in my inbox from the director telling me that the training had been a complete waste of time. She said, “We felt like you were treating us like a group of children who had never even used Google before. It wasn’t worth our time.”

It cut pretty deep. But I quickly realized that I hadn’t done my homework. It was completely my fault. I should have been reaching out to potential attendees, seeking to understand their initiatives, current challenges, and understanding the type of training that would help them most.

Instead, I treated them exactly the same as another group I trained for an equally large company — a group that could, in reality, barely turn on their computer.

After you’ve mastered the product, you must know your audience. This is frequently forgotten or pushed aside. It’s easy to get caught in the rut of believing product knowledge can compensate for lack of understanding of our audience. As soon as this happens, we’ve lost the customer completely. We can no longer provide value for them. We can’t help them solve their problems. And then we lose their interest and, ultimately, their business.

Before we jump on that demo or conduct a training for a team, we must know them. We must understand the current problems they’re facing and why they’re interested in our product. In the end, it’s not about figuring out how they are a good fit for your product. It’s strategically seeking to understand how the product is a good fit for them and their challenges. It’s a simple change, but it makes all the difference in how we work with our prospects and customers. This must happen before every training and every demo.

Take a look at this conversation as an example:

Trainer/Salesperson: Why are you interested in Lucidchart?

Customer/Prospect: Well, we have a current initiative to diagram processes on our team. It’s an initiative that’s coming from the executive team. They’ve been hitting it hard for a while now.

Trainer/Salesperson: Great. Thanks for sharing that. We can definitely dial in on diagramming processes in our next training.

It’s easy to believe the why has been answered in this scenario. But this isn’t deep enough. All we know is they need to be diagramming. But we still don’t know why. Here’s an alternative:

Trainer/Salesperson: Why are you interested in Lucidchart?

Customer/Prospect: Well, we have a current initiative diagram processes on our team. It’s coming from the executive team. They’ve been hitting it hard for a while now.

Trainer/Salesperson: Great. Thanks for sharing that. Please elaborate on that a bit more. Why is diagramming processes such a big focus for the executive team?

Customer/Prospect: Well, the executive team has noticed how much money is being lost when any change takes place. All the processes exist as tribal knowledge, and nothing’s centralized. If processes are recorded, they’re all over the place.

Trainer/Salesperson: That makes a lot of sense. It sounds like the big pain point is time and money that’s being lost in documenting processes and having them available for new employees, other departments, etc.

Customer/Prospect: Yup, exactly.

That’s the why. The why is not diagramming. It’s deeper than that. The why, in this case, is time and money. And now that you have that central concern from stakeholders and attendees, you can address that directly in the training and demos. With that knowledge, you can now focus on their challenges and show real solutions through your product and its features. Your task now is to show how your product and its features will, indeed, save them time and money, and in turn solve their problems.

4. Staking

Have you ever done all your homework, prepared well, knew your audience, and then when it starts, it goes right out the window? I feel your pain. Even while you’re talking, you’re thinking: “What am I saying right now? This is the same thing I’ve said 100 times, and I don’t even know what it means.”

There are a few ways to avoid this inclination. First, open with questions to better understand your audience. If there are new individuals attending with whom you haven’t interacted, ask them open-ended questions:

  • Why did you attend today?
  • What challenges are you currently facing?
  • What will make work better for you?

If you’ve already asked these questions previously to many of those attending, don’t hesitate to restate the given answers to those questions, and an overview of the solutions you’re going to provide.

As you conduct the training/demo, consistently tie your features and material back to the central problems they are facing.

I’ve come to call this “staking.” Think of a large pole tent you would use at a big corporate event or wedding. I know, it sounds weird. But it works. The tent provides the overarching, solution-based context — a solution that’s solving a problem your audience faces. You may present several features, but each one of the features should act as a pole that supports that solution-based context. You must stake those features in the ground, and immediately use them as a support to the solution.

In How to Give a Perfect Sales Demo, Hubspot’s Senior Marketing Manager, Niti Shah, recommends using tie down questions (no pun intended) to “spark agreement and invite the prospect to better define the value of a given tool or solution for their business.”

For example, a common problem organizations face is a lack of collaboration. So, I might discuss sharing the document over the cloud, generating access links, in-editor commenting, tagging, and in-editor chatting. Even though I’m listing 5–6 features, I tie each one of those back to the central challenge: collaboration.

Do not hesitate to be explicit as you’re doing this. I might address that challenge by saying something like this:

“You mentioned a critical problem you’re facing is collaboration. Many applications force individuals to collaborate outside the actual product, creating more dissonance and communication silos between individuals. It’s a big loss of time and money. And it creates a lot of confusion.

“In Lucidchart, you can do all the communication within the product. Real-time chatting allows you to talk back and forth without having to leave the product. Additionally, you can use the commenting tool to tag individuals. This way, you can continue to collaborate as documents and processes span across multiple departments or teams. And you have all that collaboration tracked on the actual document. You don’t need to worry about documenting or accessing that somewhere else. With Lucidchart, you can stay in the product throughout the whole collaboration process so your team members can stay focused and track the collaboration taking place.”

Each feature is explained as a solution to the problem they’re facing. Tie it back every time. When you’re doing this, it may feel like you’re beating a dead horse or repeating yourself. That’s okay. You beat that dead horse. Beat it over and over again until it looks like canned horse meat from the 1880s. It maximizes the value of your product every time you do.

If you find that you’re struggling to do this effectively, go through every feature of your product, list its functionality, the problem it addresses, and the solution it offers. If you’re able to do that in just a sentence or two, you’ll be able to infinitely multiply the perceived value. And, if you’re in sales, you’ll be able to sell through value propositions rather than just offering price reductions and discounts every time.

5. Seeing Beyond the Question

During my first week at Lucid Software, Ryan Butters, the VP of Customer Success, said something I’ll never forget. He said, “We have to get to the point where we can look beyond customers’ questions, see what they’re truly asking, and then answer that.”

I’ll be honest. I had no idea what he meant at that time. I just nodded my head and was like, “Totally. Absolutely. For sure.”

It wasn’t until I had done these 100 webinars in 6 months that his advice started to make sense.

As you’re doing these trainings and demos, you will, without a doubt, get questions. The way we answer questions can be one of our biggest mistakes. Often, we will get a question we know the answer to. I remember feeling super excited when somebody would ask a question that I could answer with our product. I felt like I was adding value, and I felt that, if I could answer all their questions, I would be set to go.

However, I often found that users wouldn’t get into the product or prospects wouldn’t buy even though I had answered all their questions.

Take a look:

Prospect/Customer: Hey, is there a way I can change the fill color of a shape to be transparent?

Trainer/Salesperson: Yes, you can! You just go to the properties bar, and select opacity from the colors option.

We get so trigger happy when we know the answer of the question that we forget to understand why they’re asking the question. Here’s an alternative:

Prospect/Customer: Hey, is there a way I can change the fill color of a shape to be transparent?

Trainer/Salesperson: Yes, there is. Absolutely. Tell me a bit more about what you’re trying to accomplish.

Prospect/Customer: Well, I’ve created a swim lane diagram, and I’d like to color coordinate it by coloring the shapes.

Trainer/Salesperson: Ah, yes. That’s a great idea. However, did you know that instead of using shapes to build out your swim lanes, you can use our dynamic swim lane containers? You can customize the amount of swim lanes you need and color coordinate them. It will be much faster and more effective to use those instead of shapes.

Trainer/Salesperson: I didn’t even know those existed. That’s going to save me a ton of time. Thanks.

When we take time to understand the underlying problem, and not just the question, we can continually add unanticipated value. But it requires us to dig deeper and not get trigger happy.

The Bottom Line

Sales demos are tough. Training is tough. Especially at the beginning. But it’s not something that some people are just naturally good or not good at. It’s a skill that can be learned and mastered. Getting our priorities mixed up, however, can make it harder than it needs to be. When you’re starting to sell or train on a new product, do everything you can to know your product and its domain. Study the customer personas, the use-cases, the features, the market, and become an expert. Once you’ve become an expert in your product and your audience, the other pieces will fall into place. I promise.

About Taylor Dolbin

Taylor Dolbin is the Lucidchart Product Pro and Training Lead at Lucid Software. He loves empowering people to solve challenges they are facing every day. But, most of all, he loves spending time with his wife and his dirt bike.