How to Have a Courageous Conversation at Work

Most problems don’t explode overnight—they quietly compound.

Unspoken frustrations turn into assumptions. Assumptions turn into resentment. Resentment hardens into distance.  

What started as a conversation you “meant to have someday” becomes the reason trust erodes, teams disengage, and relationships stall.

The healthiest teams and families intentionally build cultures of trust and openness. People listen with care, receive feedback with humility, and feel safe bringing concerns into the light. Encouragement is offered freely and without delay.

Questions are not asked to challenge, but to understand. Clarifying conversations are essential to staying connected, aligned, and strong—because cohesion grows where curiosity replaces criticism.

Struggling teams and families waste time and energy sidestepping core issues. They see negative feedback as rejection and judgment rather than information needed to learn and grow. 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 those that, if left unaddressed, cause more problems (e.g., missed opportunities, strained relationships, financial difficulties, job loss, etc.).

You may justify your avoidance 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 questions 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, etc.))
   Example: "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: "You were late to a meeting last Monday and yesterday."
3. How have you contributed to this problem? Leave out excuses.
   Example: "I've hesitated to have these types of conversations in the past, which isn't good."
4. How do you feel about this situation?
   Example: "I feel frustrated by you being late."
5. How do you want this situation resolved? Be specific.
   Example: "Since you're a top leader here, I want you to be an example for your team."
6. What are the benefits of getting this resolved?
   Example: "I believe in you as a leader. Resolving will keep my confidence in you high."
7. What are the consequences of not getting this resolved?
   Example: "My confidence in your leadership will decrease."

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 hard 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. When you go in prepared, this takes up less than 30% of the conversation. Then ask a question to draw out their thoughts, like "What's your perspective on this? ", "How can this be resolved?"
   Example: "April, how do you see things from where you sit?"
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 answers.
   Example: "Tell me more about your childcare issues."
3. Direct the conversation to an agreement, and 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: "What I hear you say is that you would like to work some mornings from home. That can definitely happen if you join in over Zoom."
4. Decide on an agreement and determine how you will hold them accountable. Request that they summarize what's been decided.
   Example: "Just to confirm we are on the same page, what are you committing to?"

You don’t have to wait for your family or team to be healthy to make a difference. When you commit to doing your part—especially by addressing core issues—you raise the standard. One healthier person strengthens the whole team.

If this was helpful, SUBSCRIBE TODAY and get instant access to my free video and worksheet: Shatterproof Yourself — 7 Small Steps to a Giant Leap in Your Confidence.

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

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