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Nov 2022
2h 14m

Courageous Conversations

Christopher Lembke
About this episode

The only win in a conversation is conquering yourself

“Those who make conversations impossible, make escalation inevitable.” – Stefan Molyneaux

Courageous conversations are, like other interactions, all about the participants internal process relating to how they perceive their input and output. Our ability to follow through with a courageous conversation without turning it into a combative conflict is determined upon our preparation. Like Dan Sullivan in the podcast, “Exponential Wisdom” pointed out; “Crisis doesn’t bring out the best in us, rather we sink to our lowest level of preparedness”. Hence, if we haven’t resourced ourselves to deal with our own triggers, we are unlikely to be performing well in any conversation that is ladened with trigger mines without ratcheting up the conflict. 

The general foundation for the successful conduct of courageous conversations the must be mutually exercised are:

  • A desire to resolve to the mutual benefit of all parties, i.e. not having the view of needing to win.
  • A desire to connect with and understand each other deeply.
  • A certain level of empathy.
  • High levels of self-awareness and ability or reflect on oneself.
  • Holding a higher vibration.

Similarly, the following conditions would most certainly stand in the way of the successful engagement in a courageous conversation:

  • Being stuck in one’s head.
  • Deflecting responsibility for one’s own triggers.
  • Desiring to win the conversation.
  • Reacting to triggers.
  • Externalising one’s own experience.
  • Making assumptions of others.
  • Inability to raise one’s vibrational frequency. 

As with anytime we are triggered we use the technique of “observation”, we observe our own experiences from the perspective of our awareness to avoid judging and attaching to our experience. This process allows us to manage our triggers and choose our response to them. Rather than reacting from the triggered aspect of our core wounding, we can, through realising that the trigger isn’t anyone else’s fault but belongs to ourselves, express our triggered emotion with compassion and awareness. 

Whenever we are communicating, especially in courageous conversations, it is critical to express any expectations we might have on the outcome of the conversation. Rather than expecting the other party to agree with you, which is unreasonable since there is then an element of “winning” which isn’t conducive with the process, set an expectation for you to be able to convey your perspective and that the other person can have empathy for where you are coming from. Most of the time there is no need for the conversation to resolve an issue or for any type of agreement to be made. As long as anyone involved are able to authentically express themselves and their point of view being heard, that can then be progress. If we are open to any outcome of the interaction and prepared to make choices based on that, we can leave the interaction with a high vibration and having avoided toxic confrontation. 

Authenticity and knowing our boundaries are key for us to express ourselves clearly without coming across as combative. Authenticity is something that never changes, but since we are only aware of aspects of it anytime, it is, from the perspective of our awareness ever evolving. Being open to these continuous discoveries will help us pursue our optimal selves. A spiritual bypass that is often observed is when we “drop-the-mic”, i.e. we say whatever we want from the perspective of our core wounding and call it “authenticity”. Don’t use authenticity as an excuse for not managing your triggers; it brings toxicity into the conversation and is less than courageous. 

We all have blind spots, and our shadow aspect will try to worm its way in any way it can. It is each party’s responsibility to observe their own. Some key areas to keep an eye on and to manage are:

  • Escalation
  • Defensiveness 
  • Rising emotions
  • Feeling of winning
  • Unexpressed expectations
  • Judgement

Individually, seek to hold compassion, acceptance, forgiveness and gratitude in your body; it will allow you to hold a higher vibration where empathy comes natural. The Four Agreements (Don Miguel Ruiz) will help you to stay cool; don’t take anything personally, don’t make assumptions, use your words impeccably and always do your best. Your focus is how you show up, so continuously question how you show up and your own motives. The aim is to build bridges, not widen the divides. We have a tendency to make statements based on assumptions, which often only cause to trigger the person you are interacting with. Rather than making assumptions, ask questions so that you can understand and not jump to conclusions. When you do understand, not necessarily agreeing, but, understanding, express and repeat back and accept their point of view. It is critical to understand the difference between agreeing with someone’s point of view and accepting it. It is of course ok to agree with an argument if it resonates with us, but if we don’t, we must strive to accept it as the other party’s perspective as their own. Part of the process of acceptance and empathy is understanding our own boundaries. Boundaries are not about lines in the sand that you will punish others if they cross, but rather about you knowing yourself and being able to hold your ground in the knowledge that you are safe to do so (please refer to my article on “Boundaries” for a deeper dive into the topic). 

None of these tools, techniques or practices are developed within a day, they are part of a continuous process that we evolve and grow into. Being steadfast in that journey reassures us that we continually become more of the optimal versions of ourselves and can, with strength and compassion, enter into any courageous conversations safe in the knowledge that we will come out the other end quite safe having grown and evolved even further. That is our win. 



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