Difficult conversations can be transformational experiences that can change the course of events, shift the outcome of a situation and alter the very DNA of a relationship. We have all experienced the consequences of not initiating these conversations in a timely manner, resulting in ugly terminations, uncomfortable relationships and challenging workplace dynamics. We also know the benefits and metamorphoses that can happen when these conversations take place sooner rather than later, including complete turnarounds in behavior, new motivations and unhappy employees leaving the company.

Consider difficult conversations as a show of respect, compassion, and love toward the recipient. You are demonstrating that you care enough to muster up the unusual amount of courage, tenderness and compassion required to lead this exchange in a sensitive and caring manner.

Related: Karen Joy: Recalling My Best Sale Ever

My experience on the receiving end of poor communication as well as my own lack of courage to initiate difficult conversations in a timely manner has been so painful that it drove me to figure out how to transform my own experience on both sides of this communication. Being able to transcend and move beyond feelings of shock, shame, fear, rage, and humiliation was my motivation to learn the skills that help me navigate these situations successfully. In sales, business and life, these interactions have transformed into rewarding, satisfying and fulfilling experiences full of caring and compassion. 

Here are the foundational strategies I have learned along the way:

  1. 1. Help diminish your fear and discomfort by letting go of your story and your judgments. Separate what happened (someone was late for the meeting) from your story of what happened (someone doesn’t value my time or anyone else’s, someone doesn’t care about keeping us waiting, etc.)
  2. 2. Use Step No. 1 to insure that you are not bringing baggage into the conversation that could come out as accusation or defensiveness. You need to be able to experience this person without preconceived notions or assumptions about their behavior and motivations. Ideally, you will enter these conversations without anger.
  3. 3. Take responsibility for time and place. If you are proactive and have the conversation when you know you need to instead of waiting, most of the time you will have the option of choosing the time and place of the conversation. You will be able to bring a level of sensitivity and compassion that may not convey the same way if the conversation is a reaction rather than an action.
  4. 4. Acknowledge what you’re feeling, and account for the other person’s feelings. You could start a difficult conversation by saying, “Sally, I asked to meet with you because we need to have a difficult conversation, and I'm feeling uncomfortable about it.” Or you could start with, “Bob, my goal is to talk through some challenging issues with you and see if we can find some ways to resolve them. I want to bring these up now, because they are minor, and I don’t want them to become something more significant that impacts either our relationship or our roles and responsibilities.”

If you start with these strategies, you’ll diminish the amount of cleanup you are faced with, and you’ll begin to clear a path to have more potent and transformational conversations in sales and in life. On the other side of these challenges is the joy you will feel when you connect with someone who deeply appreciates your communication and thanks you for your honesty. 

Next time, we will focus on the advanced strategies of difficult conversations.


Karen Joy is a strategic growth consultant to companies in the fitness, health and wellness sector. Her team provides cutting-edge, mindful sales and marketing strategies and training programs to growing companies, both virtual and physical. Email her at karen@fit4mom.com or call 858-248-1553.