Making Onboarding Fun: Why Empathy, Simplicity, and Play Matter in Sales

This past summer, I found myself feeling lost in my entrepreneurial direction. I spent months applying for high-ticket sales positions, looking for an opportunity that aligned with my passion for helping businesses thrive. One opportunity stood out—a multi-million dollar company specializing in streamlining the digital sales process for entrepreneurs. It felt like the perfect fit.

As part of the application, I watched over 5 hours of their top salespeople on calls. But instead of being inspired, I was extremely disappointed. What I saw was a lack of empathy and genuine care for each client, paired with big, confusing sales jargon that left buyers overwhelmed. It felt more like a pitch than a conversation.

I knew there had to be a better way. So, I took notes on how we could improve the process—not just for the company, but for the client. I focused on ways to add value, create a smoother experience, and make the buyer feel understood. When I shared my ideas with the company owner, hoping for collaboration and growth, I was met with dismissal and disinterest. It was disheartening, but also clarifying.

Here’s what I learned and what I believe can truly enhance the onboarding process, especially for small business owners:

💡 Bring the Client Back to Their Dream Vision

Always start by reminding the client of their big picture. What’s their dream? Begin with the end in mind, and let them feel that you’re on that journey with them.

💡 Simplify the Process with a Ladder of Believability

Break down their goals into achievable steps. Show them how your service will actually help them reach those milestones, without the overwhelm.

💡 Showcase Organic Marketing Strategies for Those Not Interested in Ads

Not every entrepreneur wants to rely on paid ads. By offering creative strategies like maximizing CLV (Customer Lifetime Value) or using organic marketing, you provide solutions that truly fit their needs.

💡 Hand-Holding & Reassurance

Stress less. Grow more. By emphasizing a hands-on, collaborative approach, you give clients the confidence to focus on high-value tasks and trust that the details are taken care of.

💡 Incorporate Fun & Play Back Into Their Business

Business doesn’t have to be boring! Reintroduce elements of fun and creativity into the process, making it enjoyable for both the client and the closer.

💡 A Simple, Interactive Timeline for the Sales Call

We can keep things engaging and stress-free by implementing a structured call:

The goal is to keep it interactive, easy to follow, and clear.