What Bob Ross Taught Me About Sales Leadership

 

Sales can be challenging, to say the least, with days that bring relentless rejection, self-doubt, and destructive self-talk. Your responsibility as a leader is to ensure your salespeople feel secure, not stressed. Your ultimate role is to help them find joy in the journey. Happy salespeople perform better. Anxious salespeople perform worse.

What Would Bob Ross Do?

In the late 1990s, the phrase “What would Jesus do?” (WWJD) was everywhere. WWJD was on bumper stickers, T-shirts, bracelets, and anything you could print it on. The idea behind WWJD was that people should ask themselves that question when faced with a situation and then model the behavior that Jesus would display. I certainly understand the thought process, and it seems like this would be a good principle to follow, regardless of your religious preferences.

I choose to follow a different mantra based on the perceived behavior of what a particular person would do. And much like Jesus, the person whose behavior I choose to model was kind, loved all beings, and had a dedicated following of disciples. The phrase I use is WWBRD: “What would Bob Ross do?” I can sense you smiling brightly right now! He may be my favorite human being ever to walk the planet. Every day, both in my life and in my business, when faced with a tough situation or a difficult decision, I ask myself: What would Bob Ross do?

What Bob accomplished during his all-too-short 53 years with us was nothing short of miraculous. Bob Ross is credited with teaching more than 10 million people how to paint. Even crazier is the fact that almost everyone he taught how to paint had no interest in painting before they discovered Bob!

Teaching a System

Did all 10 million people who learned how to paint from Bob Ross have God-given artistic ability? No! Of course not. So, if they had no clue how to paint, how could he teach millions of people how to create beautiful landscapes? The answer: he taught them a system. 

Sales leaders (and all leaders, for that matter), please pay attention here. Let’s say you have a salesperson (much like one of Bob’s students) who has no talent, no skills, and no ability. Let’s say you teach them a system to follow, you work with them closely, you support them, you allow them to make mistakes (Happy Accidents), and most importantly, you make it enjoyable. What do you think happens to their performance?

Bob Ross’s philosophy aligns perfectly with the Process Component® in EOS®, where documenting and following processes ensures everyone is on the same page and can execute consistently. Just as Bob Ross provided a clear and simple process for painting, providing your sales team with a clear and simple sales process can significantly enhance their performance.

Now, let’s take another type of salesperson. They have talent, skills, and abilities, and you teach them a system to follow to maximize their capabilities and get the most out of their skill sets. What do you think happens to their performance? These are your top performers. Imagine that! Teaching people a sales process while making it enjoyable helps them sell more—no matter where they are currently.

The Joy of Selling

The single best thing about my borderline obsession with Bob Ross is seeing how many lives he impacted positively. After watching one of the Bob Ross documentaries, I decided to read all the comments people posted online. I swear to you, I spent 45 minutes reading hundreds of comments from people about Bob and how much he impacted their lives. One comment stuck out for me, and I never forgot it—it struck me like a bolt of lightning.

The commenter wrote, “If teachers were all like Ross, no one would fail, no one would feel ashamed to show their work, no one would dread coming to art class. He didn’t paint to show how good of a painter he was. He painted to show how good of a painter you could be.”

If you have kids or grandkids in school right now, how would you feel if you knew this is how their teachers taught them? More importantly, how would your kids or grandkids feel about going to school every day if they were taught like this? Is this how we’re taught business? Heck no. Is this how salespeople are taught how to sell? Heck no. 

Bob’s show was called The Joy of Painting. It wasn’t called The Anxiety of Painting, The Fear of Painting, or The Stress of Painting. Salespeople who are anxious, fearful, or stressed don’t sell more. If you teach them that sales can be fun, joyful, and rewarding, their performance will be transcendent.

You need to create a culture where your sales team feels psychologically safe. If they have a problem, they should feel safe coming to you, not worried you’re going to yell at them for not “fixing it” themselves. They need to feel that it’s safe to fail. It’s safe to be themselves. It’s safe to make a mistake. You must celebrate the small wins and laugh off the losses. Creating psychological safety is akin to the People Component® in EOS, ensuring that you have the right people in the right seats and fostering a healthy, open environment.

Make sales fun, and your team will run through brick walls for you. And they’ll have a blast doing it!

That’s the art of sales leadership.

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