One of the most challenging aspects of difficult conversations can be finding the right time to have them. To select the best time to have a courageous conversation, there are three key factors to consider:
- Your mindset
- Their ability to receive the conversation
- The timing of the interaction
When all three are favorable, you are more likely to have a positive outcome. Let’s take a deeper look at each of these factors.
You Are in the Right Mindset
To assess whether you are in the right frame of mind to have a courageous conversation, you’ll first need to check your emotions. What are you feeling about the situation? If your emotions are particularly strong, you may need to process them before approaching the other person. If you enter into the conversation with raw emotions, you’re implying that you expect the other person to handle your emotional load, which is unfair to them and to the conversation. Do your own work first.
Emotional processing can be approached in a number of ways. You might choose to talk about the situation with an uninvolved third party, such as a friend outside of work, your spouse or life partner, or an executive coach. Some people benefit from capturing their emotions in a journal, while others may prefer to think through the situation while engaging in physical activity, such as a rigorous workout or a brisk walk.
In addition to checking your emotions, evaluate your assumptions and logic. What assumptions are you making about the situation or the other person’s motivations? Have you jumped to any conclusions prematurely?
Also, consider the outcome you want from the conversation. What are you hoping to achieve? Mutual understanding? A solution to a complex issue? A forum to express your grievances? Be realistic about the outcome you’re striving for given the people involved and the current circumstances.
They Are in a Place to Receive It
The next factor to consider is the other person’s headspace. While you can’t be a mind reader, people often provide obvious clues about where they are mentally. Avoid times when they might be rushed, stressed, or distracted, and if necessary, choose a time that might be better for a challenging conversation. Make sure to consider their personality and current circumstances so you can best judge when they’re likely to be receptive to the dialogue.
If possible, choose a time when you can be face-to-face. This enables both parties to read non-verbal cues, which can help de-escalate emotions. If a face-to-face meeting isn’t feasible, a video call is the next best option. If video isn’t available, a phone call can suffice. When you are relying on voice alone, be mindful that you may need to both offer to and request from the other person more verbal reassurances during the conversation.
The Conversation is Timely
Difficult conversations are best handled as soon as possible after an incident. Once you recognize the need for a courageous conversation, don’t delay unnecessarily. Because these types of conversations are inherently challenging, many people avoid the discomfort of having them until a separate issue arises, which is the wrong way to approach them. When multiple grievances are raised at once, it can overwhelm the recipient, creating a string of unresolved problems.
The Intersection of All Three Factors
You could spend weeks getting your thoughts in order but miss the chance to address the issue promptly, or you might bring up the problem the moment you notice it but fail to realize the other person is in a hurry to catch a flight.
The best time for a courageous conversation is when you’ve had enough time to process your thoughts and emotions, considered when the other person is most able to receive the conversation, and taken the necessary action without further delay.
For more information about how to have successful courageous conversations, explore our tools and resources at CMOE.com. If you’re ready to build stronger relationships and foster open dialogue in challenging situations, discover how our Courageous Conversations™ Workshop can equip you with the essential skills for impactful communication. Start transforming the way you approach difficult conversations and create win-win outcomes today!
Guest Author
Sarah-June Carroll is a facilitator and consultant at CMOE, specializing in Leadership Development, Daring Leadership, Psychological Safety, Courageous Conversations, and Emotional Literacy. With over 12 years of experience, she is certified in the Myers-Briggs Type Indicator and holds a certification in Training and Facilitation from ATD. Sarah-June delivers workshops, keynotes, and coaching sessions that focus on building trust, communication, resilience, and team-building.
