On April 5th, we held a dinner on “How to Have Tough Conversations.” This dinner was sparked by previous attendees, who wanted to bring crucial, taboo conversations into their day to day life.
We had different definitions of tough, and what makes something tough. We began to explore the fears, expectations/assumptions, feelings, and norms that were involved. Below are some of our questions and thoughts.
As you read, notice what is useful to you — notice what you disagree with, and where that disagreement is coming from. These takeaways are not meant to support one position or another, but as raw ingredients for new thoughts and reflections!
What makes tough conversations tough?
What does tough mean for you? What do you notice about conversations that are most difficult?
What would you like to get from those conversations? What makes them necessary for you?
What do you expect from the other person? How do you anticipate them reacting?
When it’s tied to my worth as a person (ie money, equity, for work)
When there are established social or cultural norms (ie not getting married, not having kids, being gay, women being less assertive at work)
When I have to be honest about a disruptive realisation (ie not the right job for me, no longer want to make this relationship work)
When I would like to change the beliefs or behavior of someone who doesn’t desire or realise it
Fear of emotional reactions or messy aftermath
Fear of being seen as a bad person — a judgement, negative, assertive, weird, picky, etc person
Fear of being misunderstood or rejected, particularly when I would like to be open and vulnerable
How do we approach tough conversations?
What’s worked for you?
What would you like to do more often?
Problem-solving angle — I dig for problems that can be solved, focusing on the issue and facts rather than on the people it involves.
Giving disclaimers — I initiate a tough conversation by saying that it is important and difficult for me, and perhaps sharing what big picture goals we can explore. I look for times when we are relaxed and not starving.
Writing to process emotions — I write emails or blogs to express intense emotions, and never send them to the other person. I can write and then wait an hour or a day to see which feelings stick and which didn’t.
Stepping back — When I feel an intense burst of emotion, I step back, take a deep breath, and try to postpone the conversation. I use this time to reflect on what I want from speaking, where this emotion is coming from, how they other person might be feeling, etc.
Hypothetical situations — my partner and I walk through potential (negative) outcomes so that we can spot trouble areas in advance, or be prepared for something if it does happen. We will be more emotional later, so we try to take a logical approach now.
Social fatalism — I believe that people are exactly as they should be, so there is no pressure in trying to change them. This helps me be more curious and less judgement about them, because that judgement is useless.
In theory VS in practice
We have lots of great advice and approaches for having tough conversations, but we don’t always follow through with them.
How do you feel when you don’t behave as you “should” in having or reacting to a tough conversation?
What other considerations are there?
It seems like we often escape tough conversations that require reflection and thought by choosing a pop culture topic or going to our mobile devices.
I think the digital age has made us want more things, more quickly, more tangibly, so giving attention to these uncertain tough conversations is harder.
Respect, appreciation, need for full disclosure, responsibility of having conversations, etc is all different across cultures.
Seems like less people brought up being on the “receiving end” of a tough conversation.
Perhaps because it is more vulnerable to share.
Perhaps because initiating takes more courage. This makes me appreciate those who have had a tough conversation with me.
Does it get easier over time? Perhaps it is just practice?
Moving forward – cultures of openness
How do we create a culture of openness in a team or relationship so that tough conversations become the norm, and thus less tough?
Perhaps it is by setting an example of giving feedback as soon as possible, speaking from a place of really caring for the other, establishing habits for having tougher conversations often, saying “I think, I feel” rather than “you” to keep the subjective parts subjective.
How do we have more intimate and vulnerable conversations with people, earlier on? How can we invite people to be more open and curious?