Leadership Through Crucial Conversations

Leadership Through Crucial Conversations

Leadership Through Crucial Conversations

Think of a time where you had a difficult conversation with someone, the kind where emotions are strong, and the stakes are high. It could be on a variety of topics: negotiating a raise at work, having to fire an employee, or even how to tell your spouse that you don’t want your in-laws coming for the holidays. Without an appropriate strategy on how to handle such situations, you might find yourself with a coming out of the conversation with less than desirable results, which can negatively impact your relationship with that individual. Unfortunately, the more important the conversation is, the worse it will be handled.

Thinking Strategically
Going in, know that you probably won’t win everything, at least not during the initial conversation. Knowing this, try think long term, especially for relationships that you are wanting to maintain moving forward.

Make a list of all your desired outcomes from the conversation and then prioritize the list. As you prepare to initiate the conversation keep your topic objectives in mind and ensure that you achieve them. The person with whom you will be having the conversation will have their own objectives that they want met, and so be aware of that. Compromise is important and is in an option in most situations; however, it is not always achievable and that is something to be aware of.

The Corner
There are times during these crucial conversations where you might find yourself “backed into a corner.” These are situations where you are given the opportunity to be honest and offend the individual(s) that you are talking with or you can back off and maintain the relationship. If you are honest then you’ll find yourself with a damaged relationship, which would take significant amounts of time to repair, or worse a burned bridge. If you choose to back off, then the issue at hand will never be addressed which would prevent the organization from moving forward. It prevents the issue from being addressed and may lead to an individual being backed into the corner again.

Refusing the Corner Through Honesty and Respect
The best way to refuse the corner, and to be successful in all crucial conversations, is to balance honesty and respect. As you begin the conversation state clearly what you would like from the conversation and state clearly what you don’t want. The honesty in being transparent will serve well as you move forward during the conversation.

As you continue through imagine a scale on one side being honesty and the other respect. As you address the main points of your critical conversation try and keep the keep the scale balanced. If you use too much honestly then the person may not feel appreciated for the efforts that they have made, and may disregard what you are saying as a person attack. If you use too much respect, then the main purpose of the conversation may not be achieved, and you may have to go through the experience of it again. The perfect balance of the two is the secret ingredient to success.


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Alan Olsen, CPA

Alan Olsen, is the Host of the American Dreams Show and the Managing Partner of GROCO.com.  GROCO is a premier family office and tax advisory firm located in the San Francisco Bay area serving clients all over the world.

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GROCO.com is a proud sponsor of The American Dreams Show.



The American Dreams show was the brainchild of Alan Olsen, CPA, MBA. It was originally created to fill a specific need; often inexperienced entrepreneurs lacked basic information about raising capital and how to successfully start a business.

Alan sincerely wanted to respond to the many requests from aspiring entrepreneurs asking for the information and introductions they needed. But he had to find a way to help in which his venture capital clients and friends would not mind.

The American Dreams show became the solution, first as a radio show and now with YouTube videos as well. Always respectful of interview guest’s time, he’s able to give access to individuals information and inspiration previously inaccessible to the first-time entrepreneurs who need it most.

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