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When we hear the term challenging conversation, what do we think about? We think about giving or receiving a message that poses the risk of at least denting if not fully damaging or breaking the relationship. Even before we have the conversation our brain goes into stress mode. This is expected as our primal brain’s function is survival. And when we were roaming in the wild, being voted off the island (or the tribe) meant death (literally!).

When I was still living at home and my mom would tell me ‘I need to talk to you’, I would immediately go into high alert. With a nonchalance I did not feel at the time I would ask ‘what about?’ and she would say ‘I will tell you when we talk.’ That was it! I would lose sleep, my stomach would be all over the place, I wanted to get it over with. Sounds familiar? I am sure many of you may be laughing now at how much energy we wasted stressing about nothing (for the most part).

And the paradox is that most of the topics that fall into the category of challenging conversations are not relationship-breaking material. On the contrary, if we can train our primal and emotional brains to stay put, the relationship will become stronger and we, as individuals, will have additional knowledge and awareness we did not previously have.

“Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values.” – Douglas Stone, Difficult Conversations: How to Discuss What Matters Most

Here are some techniques to incorporate as we navigate challenging conversations.

1) Be direct and kind

As the messenger, we want to consider the emotional state of the other person and how much ‘heat’ they can take. This includes our listening skills, words, body language, tone of voice, etc. Equally importantly, we want to allow the other person to save face, to have a small escaping route.

Also, focus on the behavior, and do not attack the person. And we want to be both direct and kind. We are all adults and sugarcoating something that needs to be said, could only confuse the message and give it less importance.

For example, a colleague made a comment you found offensive during a meeting. The dialog could go like this:

You: Hey do you have a minute?

Colleague: Sure, what’s up?

You: I wanted to talk to you about the comment you made during the meeting yesterday of how some people cannot understand simple concepts [direct]. I am sure this was not your intention [shows kindness without sugarcoating, this is the escape route and the chance for your colleague to save face] but I felt as if you were telling me, I was not smart enough.

Colleague: You are right, that was not my intention [colleague took the small escape route and is now saving face]

“You’re not learning anything unless you’re having the difficult conversations.” Gwyneth Paltrow

2) Timing is everything

When I was a teenager and I wanted my parents to respond positively to my message of attending a party, for example, I would bring it up during lunch. Everyone was usually in a good mood, had food in their stomachs and were not yet as tired as at the end of the day. That meant that my chances of going to that party were high.

Most of the time we can decide when to have the conversation with someone. As the messenger, consider the urgency and timing. Could this wait until tomorrow morning when we are all in a better place to give and receive the message? Or is this something that must be addressed now, at 5:00 pm even if we are tired and hungry?

On the flip side, sometimes having a challenging conversation at the end of the day is the best option. Many years ago, one of my co-workers was laid off. For some reason, his manager decided to tell him at 10:00 am when everyone was at the office. Unfortunately, for my colleague, there were other things going on in his life at the time and losing his job was the last straw, so his emotional expression was not the most productive one.

That manager could have waited until the end of the day, when most people would have been out of the office already. This way, my colleague’s emotional expression would have happened in front of a much smaller audience, if any at all.

“The real art of conversation is not only to say the right thing at the right place but to leave unsaid the wrong thing at the tempting moment.” – Anonymous

3) Short suffering, long peace of mind

A challenging conversation even a long one (or a seemingly long one) takes only a short period of time compared to days, weeks, months, or years.

Let us go back to the example of the colleague who said something we found offensive during a meeting. The conversation with that person would last approximately ten minutes (or maybe less), that is 0.7% of a day.

If we decide not to have the conversation because our primal and emotional brains hijack our sage brain, we will have the discomfort much longer than 10 minutes that day. Even worse, our colleague may make another offensive (to us) comment – most likely unintentionally. So now we have two comments over which our catabolic emotions are festering. It can snowball really quickly.

Next time you are dreading having a challenging conversation, take out the calculator app in your phone and do the math. I think we can all ‘suffer’ for 1%, 5%, or even 10% of discomfort in exchange of getting back to higher levels of anabolic energy or vibrations and strengthening the relationship.

“That conversation you’ve been avoiding is actually a leadership opportunity.” – Anonymous

4) Give each other space

Some challenging conversations may require us to allow the other person to process their feelings, response, and reaction. It is not necessary to fill in the silence.

I appreciate that many of us are uncomfortable with silence and/or with emotional display. Being present without trying to fix anything is part of being kind.

Depending on the situation, we could use a brief respite such as fetching a glass of water, to allow the other person to compose him/herself and for us to take a deep breath and refocus.

“We can make a reasonable argument that engaging (well) in difficult conversations is a sign of health in a relationship.” – Douglas Stone, Difficult Conversations: How to Discuss What Matters Most

Not all challenging conversations may have the immediate positive results we expect. At this point in my life and career I only regret not saying something sooner or at all.

As we grow as leaders in an organization, community, and/or family, we will find more (not less) opportunities of having challenging conversations. Most recipients will be thankful either immediately or later on.

Giving or receiving a challenging message does not mean we are a bad person or that we will be voted off the island. It means that we are all human and we cannot (yet) read each other’s minds. Sometimes we will do something that would hurt someone else even if that was not our intention. And we want to know that, so we do not repeat it again.

Investing the small percentage of time in exchange of stronger relationships is a no brainer. Everyone will benefit in the short or long term.

How do you go about having challenging conversations? Which technique would you try first? Please, let us know in the comments. You can write in English, Spanish, Portuguese, or French.

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My mission is to help women transition from mid to senior level leadership positions by creating awareness, increasing emotional intelligence, and unveiling the tools and choices available to them, so they can confidently realize and fulfill their potential.