The Flip Side of Foolish: Reverse the Dialogue

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In a recent coaching session, I gave Sammy, a financial adviser with more than 30 years of experience, a little homework to do before our next session. She had been concerned about prospects not seeing the value in getting her opinion on their portfolios and she wanted to know how to convince them that they should.

We had just mapped out a process that I refer to as Reversing the Dialogue, which works back from the conclusion you’d ultimately like your prospect to come to and the questions to ask to most get them to realize that conclusion most effectively. In Sammy’s situation the desired conclusion was that getting an opinion from her was in their best interest.

“I will work on it and let you know how it goes,” she said with excitement in her voice.

“Actually, why don’t you type it out and email it to me then in our next session we can role play with it,” I replied.

One of two things typically happen when I mention role play to a coaching client: either they look forward to practicing and can’t wait to start, or they have anxiety and can’t wait to explain why they don’t want to do it.

“I hate role play,” she admitted. “I’d rather just go out and practice this on prospects and tell you how it went.”

“Why?” I inquired, curiously.

“Well, it’s because I don’t want to sound foolish in front of you,” she replied cautiously.

“Ah-ha, you need to understand the flip side of foolish then,” I responded with a laugh.

After a significant pause on her end, I continued on with my explanation. Feeling foolish is like looking at only one side of the proverbial coin, I told her. There is the negative side, which for her was feeling embarrassed or inadequate; however on the flip side there are multiple positive reasons why role playing was a smart best practice.

“When it comes to role play, the flip side of feeling foolish is the fact that you WILL learn from practicing with me,” I’d told her confidently. “You WILL get better at asking questions, moving people down the pipeline and accomplishing your goals. Aren’t all of those outcomes worth a few minutes of feeling foolish?”

“When you state it that way, I’d much rather feel foolish and learn how to do it right BEFORE meeting with clients/prospects,” she said sheepishly.

In our next session I reassured her that there were no incorrect questions and that role play was merely a method that she would learn from. After two or three role play conversations she became more comfortable and relaxed with the technique of applying (and adjusting) the questions she had mapped out.

Nice job! You took me down a path of questions to help me understand why I should get an opinion from you. I absolutely felt connected and engaged while you were doing it,” I told her. I could feel her smile over the phone as she replied, “I didn’t feel foolish doing the role play with you at all. I’d like to do it more often!”

Often in order to grow our business, we have to be open to leaving our comfort zone to strengthen our weaknesses. Being willing to stretch beyond what you already know and feel comfortable with allows for you to find what your “flip side of foolish” might be.

If you read this article and find yourself wanting to learn more about how to incorporate role play into your best practices, email me at for a complimentary consultation. I can help you get comfortable with being uncomfortable.

Dan FinleyDaniel C. Finley
Advisor Solutions
St. Paul, Minn.

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