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The uncomfortable lesson I’m learning about being careful in team conversations

Lisa Gill
2 min readMar 16, 2022

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Throughout my career, I’ve believed that being careful in conversations is crucial.

I’ve been careful not to offend anyone, to keep my feelings and opinions close to my chest, to only share something if I’m 100% positive it contributes to the team I’m part of.

What I’ve learned is that this has kept me ‘small’, and it’s also robbed the groups I’m in of full aliveness and connection.

Being careful has a cost.

This quote from the book Fierce Conversations really woke me up:

“A careful conversation is a failed conversation. When we enter the conversation with a goal of being poised, clever, instructive, we are inhibited, and all possibilities of intimacy are held at bay.”

Here are some things that have helped me choose (sometimes) to be brave:

#1. Being self-compassionate.

All of us have developed behaviours in response to traumas (big or small) we have experienced, usually in our childhoods. My being careful once kept me safe, so I can appreciate the ways in which it served me, as well as recognising that nowadays it’s not so helpful.

#2. Getting present to what could be possible (in me, in the group) if I dare to be brave.

#3. Letting go of needing to look good.

(Often what holds me back is needing to be sure that what I’m going to say is smart, ‘right’, interesting etc.)

I really believe that amazing things are possible when we are able to choose, when appropriate, to give up being careful, and dare to be ‘consciously carefree.’

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Lisa Gill

Founder of Reimaginaire, trainer and coach with Tuff Leadership Training, host of Leadermorphosis podcast.