Episode 26:

Brett Gilliland is Founder and CEO of Elite Entrepreneurs, a company that specializes in giving $1M+ business owners the knowledge, processes, and tools to grow to $10M and beyond. Brett is an expert in organization development, leadership, and strategy and spent 10 years helping Infusionsoft grow from $7M in revenue to over $100M. Brett was involved in the foundational work of Purpose, Values, and Mission at Infusionsoft and facilitated the strategic planning process for many years.

One of Brett’s favorite professional accomplishments is co-creating Infusionsoft’s Elite Forum along with Clate Mask and building the Elite business inside of Infusionsoft. As the leader of the Elite business, Brett has helped hundreds of struggling seven-figure business owners overcome their biggest challenges and achieve new levels of success. He also played a central role in the development of Infusionsoft’s Leadership Model and was serving as the VP of Leadership Development when the decision was made to spin the Elite business out of Infusionsoft. As the new owner of Elite Entrepreneurs, Brett can’t think of anything else he’d rather be doing professionally. When Brett isn’t busy helping $1M+ businesses succeed, he is a family man who enjoys spending time with his beautiful wife, Sharon, and their 8 children.

What the podcast will teach you:

  • What sorts of issues in the workplace can result in difficult conversations with your team members
  • Why you might feel hesitant to have difficult conversations and how to get past these fears and concerns
  • How to prepare yourself to have a difficult conversation, and why it is important to remember that people behave logically to the world as it appears to them
  • Why “bad apples” are few and far between, and why most people want to do well and succeed in their roles
  • Why it can be easy for a business leader to become an “accomplice” to poor performance or inappropriate business behavior
  • Why the time you spend on employees who aren’t meeting expectations is being taken from the time you could be better spending elsewhere
  • Why it is important to remember that your perspective may differ from the perspective of the person you’re speaking with
  • How to know when it is appropriate to have a difficult conversation, and why performance numbers are key
  • Why avoiding tough conversations impacts not just you but the entire team and everyone else around you


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