How to Have a Courageous Conversation

The healthiest workplace teams and families create cultures where members give and accept frequent feedback. Members feel safe enough to have conversations in order to address concerns. When they see an opportunity to encourage someone, they do so with little delay.

They also often ask clarifying questions to gain understand. They view these questions as essential to staying cohesive, not as interrogation or criticism.

Struggling team and families waste time and energy sidestepping core issues. They see negative feedback as rejection and judgement rather than information needed to learn and growth. They view positive feedback with skepticism.

On a low trust team, members often want to address core issues, but avoid them because of potential negative repercussions. Core issues are ones that, if not addressed, cause more problems (e.g., missed opportunities, hurt relationships, financial problems, job loss, etc.). 

Your may justify your aviodance through excuses (e.g., “I’m not good with conflict), perfectionism (e.g., “I’m not ready yet”), and negativity (e.g., “It won’t make a difference anyway”). This avoidance causes stress and anxiety, and it’s completely avoidable. 

Assertive conversations, handled appropriately, build trust. Answering these question will give you the clarity and confidence needed to have courageous conversations.

Questions to Ask Yourself

1. What’s the issue you want to address? (e.g., challenge, concern, opportunity, recurring problem, etc.) Example: “Dave, I want to discuss your delinquency in paying rent?” Example 2: “April, I would like to have a conversation about punctuality.”
2. What are the facts of the situation? Leave out your opinions or assumptions. Example 1: “Dave, you owe me $4,000 in rent.” Example 2: “You were late to a meeting last Monday and yesterday without reason.”
3. How have you contributed to this problem? Leave out excuses. Example 1: “I regret not addressing this 2 months ago which would have kept it from festering.” Example 2: “I’ve hesitated to have these types of conversations in the past which isn’t fair to you.”
4. How do you feel about this situation? Example 1: “I feel frustrated that I’ve not been paid rent and that I’m needing to have this conversation.” Example 2: “I feel discouraged by this tardiness.”
5. How do you want this situation resolved? Be specific. Example 1: “I want you to pay all your past due rent by the end of next week.” Example 2: “Since you’re a leader at our company, I want you to be an example of punctuality for your team.”
6. What are the benefits of getting this resolved? Example 1: “So we can go back to having a good landlord/tenant relationships.” Example 2: ” So I can count on you the way I have in the past.”
7. What are the consequences of not getting this resolved? Example 1: “I won’t be able to trust you as a tenant and will move towards legal action.” Example 2: “You won’t be able to keep this leadership position.”

Ambiguity increases anxiety (e.g., lack of clarity). Decrease the ambiguity and anxiety decreases. Taking the time to answer the above 7 questions, before having a tough conversation, will decrease your anxiety.

Having the Conversation

1. Ask them to visit to discuss a concern you have. Conversationally share your answers to the questions avove. When you go in prepared, this takes up less than 30% of the conversation. Then ask the question of “How can this be resolved?”. Example 1: “Dave, how are you going to resolve this?” Example 2: “How can we get this fixed April.”
2. Listen carefully to their thoughts and ideas. Don’t defend yourself or get drawn into their distractions (e.g., excuses, bringing up other issues, defensiveness, etc.), stay on topic, paraphrase, and ask more clarifying questions based on their answer. Example: “What do you mean by creating a payment plan?” Example 2: “Tell me more about your childcare issues.”
3. Direct the conversation to an agreement, determine how you’ll move forward. Clarify your thoughts by stating “it seems to me ____________”. Be willing to negotiate based on what you learn. Example: “It seems to me you think paying it by next week is unreasonable. I can accept your payment plan if you sign this contract.”
4. Decide on an agreement and determine how you will hold them accountable. Request they summarize what’s been decided. Example: “So what have we decided here?”

If your family or team is unhealthy, you can still do your part to help make positive change. Your commitment to doing your best to address core issues is one huge way you can help. On a team, one person getting healthier, always positively impacts everyone else.

Question: What’s the most helpful piece of information you learned from this article?

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Side Note: The book Fierce Conversations by Susan Scott has been useful in formulating my thoughts on the topic.

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