How to Have Difficult Conversations with Family Members in the Business

Two generations of a family running a small business on textile

Recently I was coaching one of the owners of a mid-size company who was having issues with his brother on some thorny issues around compensation, their roles in the business, and the time spent working IN the business. After spending an hour or more listening to him vent his frustrations, I moved to a concluding action step to take, which involved utilizing a tool for having a difficult conversation.


I assume you might be able to relate to feeling stuck at times – I know I feel stuck and felt challenged with family members at times – so I want you to know you have options i.e., opportunities to make a shift. And, the outcomes will differ depending on your ultimate goals.


Having with members can be challenging, but with careful planning and , you can navigate these conversations more successfully.


Here are some steps to help you have a difficult conversation with a family business member:


  1. Prepare and clarify your goals: Before initiating the conversation, take time to reflect on your objectives. Clarify what you hope to achieve from the conversation and what specific issues or concerns you want to address. This will help you stay focused and ensure a productive discussion. This is crucial if you want to avoid the “kitchen sink” scenario where one or both of you are throwing a whole lot of other issues into the conversation mix.
  2. Choose the right time and place: Select a suitable time and private setting where you can have an uninterrupted conversation. Avoid having the discussion during stressful or emotionally charged moments, as it may escalate tensions further. Find a neutral location where both parties can feel comfortable expressing their thoughts. Consider taking a walk together, meeting for lunch or dinner outside the home and business, or planning some quality alone time while traveling on a road trip, business or pleasure trip.
  3. Practice active listening: Effective communication involves active listening. Approach the conversation with an open mind and be genuinely interested in understanding the other person's perspective. Listen attentively, ask clarifying questions, and paraphrase to demonstrate your understanding. This will help create a sense of mutual respect and encourage the other person to listen to you as well.
  4. Use “I” statements: When discussing sensitive issues, focus on expressing your own thoughts and feelings using “I” statements. This approach avoids sounding accusatory or judgmental. For example, instead of saying, “You never listen to anyone's ideas,” you can say, “I feel frustrated when I think my ideas aren't being heard.” This avoids judgement, can't be argued with, and expresses your feelings from your point of view.
  5. Be specific and provide examples: Clearly articulate the issues you want to address and support your statements with specific examples. Concrete examples help illustrate your concerns and provide a basis for discussion. However, be mindful not to come across as overly critical or confrontational.
  6. Maintain emotional control: Difficult conversations can evoke strong emotions, especially when dealing with family members. Stay composed and avoid letting your emotions dictate your words and actions. If you feel overwhelmed, take a short break to regain your composure before continuing the conversation.
  7. Seek common ground and propose solutions: Look for areas of agreement or shared goals. Highlight common interests to establish a foundation for finding solutions. Propose constructive suggestions or compromises that address the issues at hand. Emphasize the importance of maintaining a healthy and successful family business.
  8. Keep the long-term perspective in mind: Remember that family relationships are typically long-lasting, and the goal is to find resolutions that preserve both the family bond and the business. Keep the bigger picture in mind and strive for compromises that benefit everyone involved. Remember to keep your eye on the prize, which is about winning collectively and family cohesion.
  9. Consider involving a neutral third party: If the conversation becomes highly contentious or you're struggling to find common ground, it may be beneficial to involve a neutral third party, such as a mediator or facilitator.


Conflict helps us grow and learn. Having difficult conversations can remove our blind spots. When lead with a servant heart, other people will follow. And the same is true in our intimate relationships with family members. Following a for these conversations provides structure and consistency, embraces communication, boosts our confidence, facilitates ongoing improvement, and enhances our effectiveness.


Criteria for Crucial Conversations

When opinions vary, stakes are high and emotions run high, it may be time to have a difficult conversation. When you have the conversation, you can improve your relationships, organization, and business.


Remember to define the outcome clearly i.e., what you want to achieve. Determine the goal, assess the current situation, and decide together where do you go from there.


Conduct the actual conversation following the . Share your facts – personal observations. Tell them your story or perspective on the situation. Ask for their story or perspective. Talk tentatively – describe it using “I think, I feel” statements. Encourage testing.


For example: “I'd like to talk about our last week's weekly team meeting. Is this a good time? You said that we messed up on serving that client, when in fact it was my client, and you never asked for my input on the client relationship. From my perspective you aren't onboard with the direction I'm giving our team and ‘threw me under the bus” there. Am I off base? What's your perspective?” Perhaps they are frustrated losing the business. Be open to hearing their side.


If you are finding that family for firm dynamics are getting in the way of productive leadership and , perhaps it's time to discuss with an outsider who is skilled in facilitating these conversations or guiding you and your teammates to a better outcome.


For a 30-minute complimentary conversation, you can click this link, and schedule your call today.