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Fun is Fundamental to Sales w/ Bridget Gleason [Episode 638]

Bridget Gleason is VP of Sales for Logz.io and my regular partner on Front Line Fridays.


  • Black Panther is compelling and well-done!
  • Andy would like to see more conversations about the fun of sales — meeting people, building relationships, humorous situations, etc. Bridget says that more and more, sales today lacks face-to-face interaction.
  • Hitting a number is fun. Having a goal and achieving it is fun. Team dynamics are fun.
  • Andy looks back at his sales time. Over 90% of his sales interactions were by phone, supplemented with meeting an international customer once or twice a year. Getting a customer to a good decision for them was fun.
  • For Bridget, most deals were done face-to-face. Today, that is not true for her team, even though there are face-to-face meetings along with phone, email, text, and Zoom videos. The composition of deals has changed.
  • Bridget agrees that fun is really important at work. Sales can be very, very stressful.
  • Andy wrote in his newsletter that we take sales too seriously (compared to other things in this world). Having fun correlates with better outcomes and success.
  • Jerry Seinfeld on a late-night show talked about his father’s career in sales. His father would play a game he called “Break that Face,” where he got the customer to laugh, even if there wasn’t a likely sale.
  • Andy and Bridget also tried to get people to break out of their hard, difficult personas in their interactions. The attitude that we bring every day to the office matters. It affects our success.
  • Sales is not typically a matter of life and death. If you project a sense of enjoyment in your work, it’s contagious and it can help you overcome some buyer hurdles. Creating human connections can lead to business.
  • Bridget talks about a hiring interview she had with someone who maintained a flat, emotionless appearance. She was determined to have some fun with that person. Who do you want to be around? Make things interesting.
  • Be authentic; be yourself. Don’t mirror a dull expression. The worst that can happen is that they won’t connect with you. At least you can have fun trying. Enjoy yourself. Others will be more inspired.