Pleasant Middelhof

#470: How to Make Your Complex Sales Simple by Exploding the View

#470: How to Make Your Complex Sales Simple by Exploding the View

Have you read The Subtle Art of Not Giving a F*ck?

I loved it. Talking about a new refreshing take on stoicism.

One of my favorite takeaways from Mark Manson’s book is that we all should aspire to manage good problems versus tackling bad ones.

But we often get overwhelmed by the bad problems that suck our energy because we wrestle with them in all of their complexity.

Today’s guest, Pleasant Middelhof, shares how to simplify complexity by exploding the view, especially in sales.

She uses the analogy of her six-year-old son, who is a huge fan of Legos, assembling a 10,296-piece Titanic set in just seven days by exploding the project to its component parts.

Pleasant explains how you can do the same thing to simplify your complex sales for both you and the buyer.


Pleasant is a small-town teacher gone rogue in the tech startup world! She believes that doing right by others, working hard AND smart, and being bold to go after new opportunities has brought her to where she is today….which is a proud wife, mom, and COO of an incredible startup, Operator.ai..

Pleasant is a perennial revenue leader in sales because of her unique ability to make complex subjects simple to understand and act upon. 

As the newly minted Chief Operating Officer of Operator.ai, her leadership style is collaborative and empowering, rooted in the belief that nurturing talent and fostering an inclusive environment leads to the best outcomes.

On a personal note, she deeply values balance, family, and personal growth, believing that a fulfilling life outside of work enhances professional success – they are not mutually exclusive!


  1. Approach complex sales by breaking them down into smaller, manageable pieces.
  2. Complexity can be reduced simply by using language to paint the picture of the exploded view of the problem you are solving.
  3. Use language that resonates with the customer and avoids internal jargon.
  4. Why simplifying complex ideas and processes is crucial for effective communication and connection with your customers.
  5. How to use the ABT (And, But, Therefore) framework as a powerful tool for simplifying complex ideas.


  • 00:00 Introduction and Background
  • 03:10 Transition from Teaching to Sales
  • 06:37 The Exploded View Approach
  • 10:26 The Influence of Strategy Games
  • 13:21 Pleasant’s Sales Career Journey
  • 15:17 Lessons from an Unprepared Sales Pitch
  • 21:49 Using Language to Simplify Complexity
  • 23:55 The Power of Simplicity
  • 26:34 Navigating Buyer Complexity
  • 28:27 Introducing operator.ai
  • 31:44 The Benefits of Simplifying
  • 41:29 Using the and but therefore Framework
  • 47:06 Upcoming Launch of operator.ai


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