A successful conversation “doesn’t just reshuffle the cards: it creates new cards.”

Whether at work or at home, we all have moments where we need to talk through something difficult with someone. And often what we need to say might be confronting and challenging, for them to hear and for us to say. In times like these, it is common to avoid the topic, shy away from talking or stumble about in an insecure manner without really getting to the point. All of which leads to feeling unfulfilled, frustrated and resentful. On both parts.

Speaking in a courageous way is a skill that takes a little practice, but when done right clears the air without offending someone or leaving you feeling over compromised.

To start with, in general, a courageous conversation is where you need to manage emotions and information in a sensitive way in order to:

  • Address poor performance or conduct at work
  • Deal with personal problems, be honest about behavior or give bad news.
  • Investigate complaints/deal with grievances and disputes.
  • Comfort or reassure someone – for example, if they are to be made redundant or with romantic break ups
  • Tackle personality clashes.

Conversations that fall in these 5 categories often need to navigate through emotional and psychological hurdles. There are differing opinions, perceptions, and needs/wants that can create problems and often, unknown emotional minefields, as we express what we want to say to another person. Feelings and emotions can run strong and distract from positive outcomes. At times, the consequences or stakes in ‘winning’ an argument or conversation with someone can become more significant than finding a resolution. With all the unknowns, it is no surprise we avoid telling the truth and addressing how someone’s behavior or actions have affected us.

Handling a courageous conversation requires skill and empathy, but ultimately, it requires the courage to go ahead and do it. Much like any new strategy, the more you get into the habit of facing issues, the more adept you will become at it. Being honest and authentic to yourself and to others is one of the skills that leads to a happier and smoother life. It isn’t easy to speak your mind in a way that won’t offend, but it is doable.

If you’re unsure of how to best approach a courageous conversation, here are some tips to guide you:

  • Be clear about the issue: To prepare for the conversation, you need to ask yourself two important questions: “What exactly is the behavior that is causing the problem?” and “What is the impact that the behavior is having on you, (or if at work, the team or the organisation)?” Clarity will allow you to articulate the problem in two or three succinct statements. If not, you risk going off on a tangent and confusing the listener. The lack of focus on the central issue will derail the conversation and sabotage your intentions.


  • Know your objective: What do you want to accomplish with the conversation? What is the desired outcome? What are the non-negotiables? As English philosopher Theodore Zeldin put it: A successful conversation “doesn’t just reshuffle the cards: it creates new cards.” What are the new cards that you want to have in your hands by the end of the conversation? Once you have determined this, plan how you will close the conversation. Don’t end without clearly expressed action items. What is the person agreeing to do? What support are you committed to provide? How do you want them to feel at the end of the conversation? How do you want to feel? What obstacles might prevent these remedial actions from taking place? What do you both agree to do to overcome potential obstacles? Do you think and are you prepared to follow up to evaluate progress on the problem? Are you prepared to let the issue go?


  • Adopt a mindset of inquiry: Spend a little time to reflect on your attitude toward the situation and the person involved. What are your preconceived notions about it? Your thinking will predetermine your reaction and interpretations of the other person’s responses, so it pays to approach such a conversation with the right mindset—which in this context is one of inquiry. A good doctor diagnoses a situation before reaching for his prescription pad. This applies equally to courageous conversations. Be open to hearing what the other person has to say before reacting and deciding your response. Even if the evidence is so clear that there is no reason to beat around the bush, we still owe it to the person to let them tell their story. A courageous conversation means you need to remain open and curious about what is being said.


  • Manage the emotions: We all can get anxious, upset or even angry when faced with difficult discussions. Sometimes the hurt and disappointment blinds us to problem solving or hearing a challenging opinion. Check in on your emotions. Rate your feelings from1 to 10 and if those emotions are getting too elevated, take some time out, regroup and start again. Be aware of the other person’s feelings too. If things are getting too heated or they look overwhelmed. Stop. Slow down and think about your approach again.


  • Be comfortable with silence: There will be moments in the conversation where a silence occurs. Don’t rush to fill it with words. Just as the pause between musical notes helps us appreciate the music, so the periodic silence in the conversation allows us to hear what was said and lets the message sink in. A pause also has a calming effect and can help us connect better. For example, if you are an extrovert, you’re likely uncomfortable with silence, as you’re used to thinking while you’re speaking. This can be perceived as steamrolling or overbearing, especially if the other person is an introvert. Introverts want to think before they speak. Stop talking and allow them their moment—it can lead to a better outcome.


  • Preserve the relationship: People with high emotional intelligence are always mindful to limit any collateral damage to a relationship. It takes years to build bridges with people and only minutes to blow them up. Think about how the conversation can fix the situation, without erecting an irreparable wall between you and the person. The aim is to make a point about an issue not destroy the friendship, working relationship, or a person’s self-esteem.


  • Be consistent: Ensure that your objective is fair and that you are using a consistent approach. If the person sees or believes you have one set of rules for one individual and a different set for another, you’ll be perceived as showing favoritism and bias. Nothing erodes a relationship faster than perceived inequality. Friends, lovers and employees have long-term memories of how you have handled situations in the past with others. Aim for consistency in your approach in courageous conversations. We trust someone who is consistent because we don’t have to second-guess where they stand on important issues such as friendship, culture, corporate values and acceptable behaviors.


  • Develop your conflict resolution skills: Conflict is a natural part of human interaction. Managing conflict effectively is one of the vital skills of working with others and being in relationships in general. Have a few, proven phrases that can come in handy in crucial spots. Aim to dial down the conflict rather than turn up the volume.


  • Choose the right place to have the conversation: Starting a courageous conversation in the middle of a restaurant, on a train or in front of others isn’t a smart approach to reaching a solution. Neither is calling people into your office sometimes. Sitting in your own turf, behind your desk, shifts the balance of power too much on your side. Even simple body language, such as leaning forward toward the person rather than leaning back on your chair, can carry a subtle message of your positive intentions; i.e., “We’re in this together. Let’s problem solve so that we have a better workplace.” Consider holding the meeting in a neutral place such as a meeting room where you can sit adjacent to each other without the desk as a barrier.  With friends and in relationships, make time that suits you both. Chose a private place that limits being overheard. Over a kitchen bench, going for a walk or if you prefer not to be alone, select a coffee shop with some level of privacy. People can react to the fear of being overheard or public embarrassment so, be mindful of where and when you start the conversation.


  • Know how to begin: Some people put off having a courageous conversation because they don’t know how to start. The best way to start is with a direct approach. “John, I would like to talk with you about what happened at the meeting this morning when Bob asked about the missed deadline. Let’s grab a cup of coffee tomorrow morning to chat.” Or: “Linda, I want to talk about our relationship and would love to sit down when you’re ready, so I can explain where I’m coming from. Being straight forward is the authentic and respectful way to tell someone a difficult message. You don’t want to ambush people by surprising them about the nature of the “chat.” Make sure your tone of voice signals discussion and not inquisition, exploration and not punishment. Compassion not critique.


  • Be compassionate: It’s best to come at sensitive topics from a place of empathy. Be considerate; be compassionate. Although often uncomfortable we can all deliver a difficult conversation with truth, fairness and bravery. Avoid seeking compassion from the person listening to you. You are not there to emote and seek sympathy. You are doing this to get clarity and reduce friction, frustration or unhappiness. This is about you, but not about how you feel having the courageous conversations, so steer away from starting the discussion with how hard it is for you to say what you are about to say. It won’t ring true and will sound patronising.


  • Breathe: The calmer and more centered you are, the better you will be at handling courageous conversations. It’s not a bad idea to practice some mindful breathing and calming techniques. This can help you remain clear about your objectives and focused on the purpose for having the courageous conversation in the first place. Using a few centering strategies can give you a method of defense if things get too personal and you find you are under attack.


Courageous conversation can be uncomfortable for both parties involved. Take your time. Think about your objectives. Have a clear idea of the outcome you want and monitor your emotions. Don’t forget, if it isn’t working out, excuse yourself, take a walk, get a drink of water and collect your thoughts. Then try again. Success gets closer with every attempt.



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