Difficult Conversations

Aug 11, 2021
having a difficult conversation on a beach

It’s inevitable.  It’s time to sit down and have a difficult conversation. You know the ones I’m talking about – you’ve run through it in your head a thousand times over, but it still doesn’t go as planned, or it’s sprung on you by your partner when you’re least expecting it!

The thing with difficult conversations is that we have all had them, and they will continue to pop up in our lives, both professionally and personally. I am sure you can think of a difficult conversation that you wish you could have a “do-over”,  or one that is coming up in the near future that you would prefer to slink away from and ignore completely.

I met a couple of friends recently for coffee to discuss their upcoming overseas travels that they will be taking together. However, once they’d ordered their drinks and sat down, one friend tells the other that she and her partner have decided to “give things another go in their relationship,” and that they are going traveling together as a couple. This means the two friends will have to wait and go traveling together at a later date, if at all.

A married couple both arrive home from work, get the children settled, and begin to prepare dinner. The woman tells her partner that the marriage isn’t working.  That she is tired of feeling like a loser and that she would like to move out.  She grabs her car keys and walks out the door, leaving her partner shocked and unable to even have a conversation with her about her decision.

It’s annual compensation time and the HR manager is meeting with each staff member to discuss raises. In one particular session, the manager asks the staff member if they believe they should receive an increase in their salary this year. The staff member replies, “Yes,” and then states their reasons why. The director responds, “Well, you will be disappointed then, because you will not receive one this year – and it is not likely you will get one next year.”

These were difficult conversations.  Unended, rear-ended, derailed.. Maybe you can imagine being in one of the above situations, or one that’s similar. How would you respond? Our hardwired responses of fight, flight, or freeze often come up when having a difficult conversation, which can cloud our judgment when trying to form a response.


Upon further discussion and exploration with each of the above individuals, the following is how they responded in the moment:

The Friends Scenario: Freeze. After hearing they wouldn’t be going travelling together, the friend was overwhelmed with emotions and got so upset at her potential travel partner’s lack of consideration that they froze, could not talk or think, and overall felt numb. The friendship dissolved because of this difficult conversation.

The Partners: Flight. The woman who left felt so lost as to how to manage their emotions or even have this difficult conversation that she fled the home and retreated into their own bubble for months thereafter. This marriage ended in divorce.

The Human Resources Scenario: Fight. The staff member was so angry and upset by the HR manager’s words that he argued back in an attempt to make a point as to why they should receive a raise. They were very forthcoming, stormed out of the manager’s office, and slammed the door behind them. The staff member no longer works for this agency due to this conversation.

In an attempt to avoid the fight, flight, or freeze responses like the examples above, here are some tips that will help you find the best possible outcome for everyone involved in the difficult conversation:

  1. Be clear with yourself about why you want to have the conversation. Consider alternative ways to resolve the issue first – would having a casual chat with the person be enough to mitigate a difficult conversation or ease the tension if one is required later on? Be sure to ask yourself what outcome(s) you are after.

  2. Challenge your own assumptions about the conversation. Take a moment to consider why you need to have the difficult conversation. Is it your place to take this on, or would it be more appropriately conducted by another?

  3. Set a date, time, and place to have the conversation and ensure this will also work for the other person. This will allow the other person to feel respected and considered in the situation. Ensure the other person knows the agenda of the conversation so they are not shocked by the topic. There is nothing worse than being called into a meeting or confronted by a friend or family member with no insight to the topic. This will also allow for a more productive and thoughtful conversation to take place.

  4. Be direct and respectful throughout. Whether you are delivering bad news or attempting to solve a problem, be clear and concise.

  5. Take the time to listen to the other person’s point of view – we can always agree to disagree. Stick to the facts and be consistent with your points. Do you have enough accurate information to bring into the conversation and what is your intention behind doing so? Do you have any uncertainties going into this conversation?

  6. Be curious, withhold judgement, and apologize if you need to. Convey a genuine interest in resolving the issue and be authentic in your interaction.

  7. Focus on a win-win outcome for everyone. This will make the next difficult conversation easier to approach!

  8. So, what if you have a difficult conversation thrust upon you without a moment’s notice? First, take a deep breath – you’ve got this! Try and shift your mindset to be curious about the other’s intention in the conversation. Be sure to listen to their point of view and pause to collect your own thoughts before you respond. Be as clear as you can with your point of view, and ask to follow up with them so you can take some time to process what they are saying.

We have all had conversations where we felt the outcome was successful for all involved, but we’ve also had others that didn’t go so well. Using these steps will help us be clear about our intentions, and avoid giving in to our initial fear response.

I wish you all the best in having your next difficult conversation!

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