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Having a life worth living involves discovering your purpose, and it is only through knowing ourselves that we can find the thing we were always meant to do. The question then becomes: ‘How can I find out who I am?’ The answer: By asking big questions! Today’s show contains some of the most valuable content ever featured on the podcast because we are lucky enough to be joined by one of Chris’ biggest mentors, Dick Dillingham. Dick has a storied career in real estate through his involvement with and contributions to Keller Williams. However, Dick sees his main role in life as that of the teacher and facilitator, and you’ll discover a few of the countless coaching and personal development programs he has been a part of today. As we trace Dick’s trajectory through different roles and mentorship initiatives, we keep circling back to one central theme: what does it mean to live a life worth living. Many of the programs that Dick has taught, from masterminds on effective presenting to modules on real estate investing, are driven by the central motive of helping participants grow into the best version of themselves. So in this episode of the show, we hear the many incredible perspectives Dick brings to the table on the subject of personal growth and the attainment of meaning. Tune in and hear Dick’s thoughts on how to truly connect with others, the difference between normal questions and big questions, and how to not just think big but take action on those dreams and turn them into a reality.


Key Points From This Episode:

– The culture of constructive feedback Dick nurtured at his ‘Train the Presenter’ course.

– Remembering that constructive feedback is a gift and that taking it as such makes it more effective.

– How Dick helps people reframe presentations as conversations and the use of this.

– The value of being intentional about what we say in conversations regarding connecting with others.

– Techniques for connecting with others and how this might be done in a remote context.

– Dick’s take on how coaching has overtaken training in the corporate world and the differences between the two.

– The role of asking great questions in growth and why the world is generally bad at doing this.

– Dick’s thoughts on why he loves teaching and how he uses it to help people live their best lives.

– Aiming to be a person others want to be around and what this looks like for Dick.

– The connection between culture and leadership: how to win respect as a leader by living your values.

– The strength of the culture at Keller Williams and what they do to nourish it.

– The philosophy behind the learning methods at KW University and the types of students they  aim to teach.

– How to set goals through scheduling and turn small thinking into big thinking.

– Themes of personal growth and asking big questions in the story of Dick’s career pivots.

– The breadth of presentation experience Dick has and the huge amount of students he reaches.

– Dick’s experiences with insecurities in his journey as a teacher and how he has managed them.

– What Dick would say to a hypothetical group of potential clients he only had two minutes with.

– The one piece of advice Dick would give to people who want to live a fulfilled life. 



“You can say it any old way or you can say it the best way, the most effective way.” — Dick Dillingham [0:08:33]

“It is important to connect with people, and to connect with people, you have to be intentional or purposeful about it.” — Dick Dillingham [0:09:18]

“I love teaching and the part I love about it is I look at teaching as an opportunity to encourage other people to be their best self.” — Dick Dillingham [0:20:59]

“Get clarity on who you are and what you want to be. What I am talking about is a mission statement.” — Dick Dillingham [1:05:29]


Links Mentioned in Today’s Episode:

Dick Dillingham

Dick Dillingham on Facebook

Keller Williams Realty

Quantum Leap

Keller Williams University

Everyone Communicates, Few Connect

Episode 54 with Pat Mancuso

Andy Andrews episode with Eric Brooker

Failing Forward

The Four-Hour Workweek

The Twelve Week Year

The Traveler’s Gift

The Noticer

Goodman Coaching

Chris Goodman

Work with Chris Here

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