To gain the greatest value from these questions you should role play and imagine you are the client. Imagine the coach working with you to clarify and brainstorm over each issue as it is raised. And finally, imagine the clarity and confidence you would have in your understanding that investment after you are done with coaching. 

Just think, avoiding just one bad investment, misstep, or error in analysis could pay for years of coaching. Imagine what that would be worth to you if it occurred on a regular basis? 

What is the game you are playing with this investment?

• Is it a game you love?

• What is it about this game that you enjoy?

• How did you choose this game over other competing games?

• What is it about this deal that makes it more appealing to you than any of the other deals or investments available to you?

What is your strategy?

•  What do you want from this investment?

•  How does this investment fit into the bigger picture of your overall portfolio?

What is your competitive edge in this deal?

How are you applying the principle of leverage in this deal?

What is your risk management plan?

• What is the low risk idea here?

• What are the risks in the deal?

• How could you lose money?

• What could go wrong with your plan?

• Now let’s take each of the identified risks and ask the question “how are you planning on managing that risk?” 

•  What is your exit strategy if everything goes well and according to plan?

• How will you know if things aren’t going according to plan? How will you exit then?

• How else could you offset risk besides exiting if things don’t work out?

What does your risk/reward analysis look like?

• Give me an optimistic, worst case, and expected scenario for this investment.

• How could you improve the risk/reward picture?

If you had the opportunity to do 100 deals that looked
     just like  this one, would you do it?

What else would you need to know to completely
     understand this deal?

• What questions remain unanswered?

• What further analysis or due diligence could you do to complete the picture?

• What do you need to know to make a final decision to move forward or not?

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