TCF550: Contractor Q&A – “Best Way to Deal with a Stubborn Old-School Salesman”

Tom and Dan talk about the importance of having a polarized approach while selling and address questions about dealing with old-school salespeople who are stuck in their ways, concerns about overselling and not being able to do the work, and accepting the fact that not every client could be yours.

In this episode, we talk about…  

  • Speaking the language your prospects and audience understand
  • Having a polarized approach when selling
  • You have to stand out at whatever level you are


Question1: What is the best way to deal with an old-school salesman stuck in his ways? 

  • Roleplay with the guy — prove the point that you can’t be backed into a corner
  • Be the example and the proof of concept to teach them new tricks


Question2: As someone with a small crew who has been booked for over a million dollars project, I have to keep selling to reach my goal, but I’m concerned that I will be unable to do the work.

  • Keep selling because you can always find crews to produce
  • To scale your business, you must sell and recruit
  • Know your numbers and job costs, and then work on finding your ideal clients and raising your prices


Question3: How do you get over the fact that not every phone conversation is my customer?

  • You’re marketing to the wrong customer



Submit your questions to with the subject “Podcast” and Tom and Dan will try to answer them on an upcoming show.

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