Selling Yourself: Why Sales Is Not As Scary As You Think

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In the Transform Sales Podcast: Life Series #83, Amir Reiter welcomed Chris Bogue, founder of Bogue isn’t your everyday sales trainer; he shines with a history as a seasoned sketch comedian. This evolution from comedy to sales underscores his incredible adaptability and resilience. Chris mentions the similarities between his comedic roots and sales, emphasizing how comedy nurtured his skills to connect with audiences and perform memorably. Such skills have proven invaluable in the competitive arena of sales. Moreover, Bogue’s journey underscores how proficiency in sales can serve as a launchpad to entrepreneurship. It’s a pathway that might not be evident to many but is teeming with opportunities for success.

Chris’s conversation with Amir touched on many facets of sales, with Bogue consistently highlighting the transformative potential of sales acumen. He believes that the art of selling can reshape not just one’s professional path but also influence personal relationships and one’s general perspective on life. In addressing the common misconceptions surrounding sales, Chris equated it to other powerful forms of advocacy, from marketing to charity initiatives and even political campaigns. He also delved deep into the role of videos in the sales process. Bogue emphasized tailoring videos to the prospect, ensuring they’re concise, and integrating subtitles for clarity. Advocating for genuine business dialogues, he described his approach of sharing financial aspirations transparently on platforms like LinkedIn. Concluding their insightful exchange, Bogue assured listeners that sales is an art everyone can learn, given the right guidance and persistence.

In case you missed it…. these are the highlights

Who are you? What is a cool fact about you that no one would know?

I am Chris Bogue, the founder of I am a sales trainer and coach, but an interesting fact about me that many might not know is that I’m also a sketch comedian. I did sketch comedy at Chicago’s Second City for 15 years, and that’s where I learned how to work with others. People often see my comedy sketches on LinkedIn, but what they don’t realize is that for a long time, I was not on stage. I was writing the shows and directing casts of actors. I like to think that I have a knack for helping other people get a good performance out of them, and that’s because I spent years playing for various audiences in Chicago. This experience has greatly influenced my approach to sales and coaching, allowing me to bring a unique perspective to the field.

How Did You Get Into Sales?

I started my career doing comedy shows in Chicago, but soon found myself working in sales because of the city’s growing tech scene. Comedy taught me a lot about connecting with people, which turned out to be super useful in sales. When the COVID-19 pandemic hit, I was selling tech products to schools. Everything changed, and I had to find new ways to reach out to customers. That’s when I started using video more, and it worked really well because of my background in performing.

This change from being a comedian to working in sales showed me something important:

“…sales isn’t just about selling stuff. It’s about telling a story and building real connections with people. It’s about understanding what people want and helping them find it…”

How Did Sales Change Your Life?

Sales has been a transformative journey for me. My initial background in comedy provided a foundation for understanding human connection, but it was the world of sales that truly deepened my appreciation for the intricacies of human interactions. Every conversation, every pitch, and every negotiation became more than just a transaction; they were opportunities to learn, grow, and make a meaningful impact on others.

As I navigated the complex landscape of sales, I encountered numerous challenges, especially during the tumultuous times of the COVID-19 pandemic. These challenges, however, were not roadblocks but catalysts that pushed me to innovate, adapt, and think outside the box. I learned the importance of resilience, adaptability, and the power of genuine relationships.

But beyond the strategies, techniques, and numbers, sales imparted invaluable life lessons. It taught me the profound significance of truly listening, understanding people’s aspirations, and offering solutions that genuinely benefit them. It’s not just about closing a deal or meeting a quota; it’s about creating lasting relationships, changing lives for the better, and leaving a positive mark in the world.

“Through sales, I’ve come to understand that our true legacy is defined not by the deals we close, but by the positive impact we have on the lives of those we interact with.”

What’s your best advice to those considering a career in Sales?

My best advice to somebody who is considering a career in sales is: Sales is a skill, just like any other, and it’s something you can learn and master. If you’re starting out, you might begin at an entry-level, but the key is to observe and learn from those who are excelling in the field. Be curious. Pay attention to top performers and notice the details: the kind of emails they send, the questions they ask during presentations, even the tone of their voice during calls. All this information is available for you to absorb. I’ve always believed in learning by doing. While sales playbooks can be helpful, there’s immense value in watching someone who’s at the top of their game in sales. Those who consistently meet their quotas have a system in place, and they stick to it. Success in sales isn’t about reinventing the wheel every time; it’s about finding a strategy that works and being consistent with it. Remember, the key is to listen, learn, and adapt from those around you.