My Top 10 Money Insights as a Coach #5 – “Maybe” is a Gold Mine

Over the past five years of being a coach, I’ve had a number of insights into how I think and talk about money that have made it easier for me to create what I love (money) while doing what I love (coaching).

Recently I began listing them out for my apprentices and this list quickly turned into ten separate articles.

I am sharing them here in case you too love money and want to make more of it. If so, I hope that thinking and talking about money in these ways will help you like they have helped me.

Maybe I’m just a wimp, but I’ve never really been able to require someone to be a ‘Hell Yes’ or ‘Hell No’ to working with me.

Not a problem though, as I found an approach that works well for me.

When someone is a ‘maybe’ for coaching, I now get excited that we have uncovered a new place for us to do some exploring.

I actually tell people that I’m OK with them being a ‘maybe’. I also tell them that indecision is a great place to dive in and explore what might be going on beneath the surface.

To begin exploring the maybe, I ask questions like…

  • What would you need to know to make a decision?
  • What would make you a YES?
  • What would make you a NO?
  • What might you need from me before deciding?
  • What might you be worried about?
  • What will you create as a return on your investment?

These questions always open up further dialogue. It’s the best kind of dialogue too, because it takes place at the fulcrum of our relationship. There is lots of heat in that place, so it’s a great opportunity for deep alchemy.

If we do end up working together, having such an open and honest conversation makes the foundation of our relationship so much stronger because EVERYTHING was brought out at the start. No secrets. No expectations. Just vulnerable conversation and clear understanding.

Through exploring the maybe, I find people eventually settle into a clear YES or clear NO all on their own. If they aren’t, then I assume I’m missing something. There is still some gold in the mine we haven’t found yet.  In these cases I just keep diving in and exploring the maybe until we find it.


  • What ‘maybe gold mine’ could I be exploring right now?
  • How might exploring that mines serve the person who is a ‘maybe’?
  • How might exploring that mine grow me as a coach?


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