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Courageous Conversations

CourageousConversationsI don’t know many people who relish uncomfortable conversations. Personally, I do not. These are the conversations that can look and feel awfully messy when we think about them. They can make the heart flutter in dreadful anticipation. Fear sometimes factors in. As a social worker, I have been part of many such conversations between people.

Difficult conversations are inevitable. Like it or not, they are necessary for delivering bad news, working toward solutions, resolving disagreement or disappointment, and correcting or negating a mistake (and we all make mistakes).

Uncomfortable conversations are a necessary part of relationships. They happen at work, with our kids, friends and significant others, and with clients. Getting good at difficult conversations takes practice rather than avoidance, even though avoidance can seem easier.

Courageous conversations may sound like a bit of a stretch, but I find it helpful for nudging these sometimes sticky exchanges forward. What makes the difference?

Is what you need to say in the best interests of the other person, the project or the business?

Are you driven by reasons rather than emotions?

Do you feel compassion or empathy for the person or situation?

If you answered ‘no’ or ‘don’t know’ to any of these questions, step back and think this through a little bit more.

  1. What, when, how and why will you say what you need to say. If you are in the throes of an emotional reaction involving resentment, anger, anxiety or frustration, it’s probably better to not say anything. Calm down and pull yourself together.
  2. Gain perspective, clarity and reason. It may help to make a list of points to help your confidence, not to play gotcha but to avoid getting derailed by the other person’s reaction (which could make matters more difficult). You may not need the list during the conversation, but it can help you stay grounded about why you are having this conversation.
  3. Avoid using ‘you’ in your talking points. This sounds more accusatory, blameful, personal and critical. Use “I” in terms of how another person’s actions affect you. Example, “I feel uncomfortable making a commitment to the client unless we know we can follow through.” Or, “It’s my job as … to talk about potential trouble spots with the project so bear with me.” Stay away from ordering, warnings and preaching too.
  4. Pick a good time. In the middle of frantic pressure of demands would not be a good time to expect someone to give you their attention and vice versa. Vacation, nights and weekends are bad too. In some cases, no time is really “a good time,” so you just have to do the best you can and make sure the first three points are covered.

With any courageous conversation, there is always risk—risk of an extreme reaction or reprisal (I have seen and experienced this a time or two). I am a big believer in prayer for guidance and wisdom in the face of these and other challenges. I also believe most people are doing the best they can in their circumstances, with the worldly and inner resources they have available.

The takeaway? Balance your head and your heart in the right place first. The rest? What will be will be, but you will feel strength from seeing through this challenge. Courageous conversations are necessary in life.

cherilynnvelandSMTake care,

Cherilynn Veland is a therapist living in Chicago. She also blogs about home, work, life and love at She is author of the book Stop Giving It Away.

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Courageous Conversations

Cherilynn Veland, LCSW, MSW

Cherilynn Veland, MSW, LCSW, is a counselor and coach based in Chicago. She has been helping individuals, couples and families for more than 20 years. She is author of Stop Giving It Away, a book about developing healthier relationships with yourself and others. The Stop Giving It Away movement aims to stop the detrimental level of self-sacrifice in which many women live and work. Winner of the 2015 National Indie Excellence Book Award in the Women's Issues category - Stop Giving It Away.

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APA Reference
, . (2016). Courageous Conversations. Psych Central. Retrieved on May 25, 2020, from


Last updated: 5 Jul 2016
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