Start with Heart: Why Emotional Safety is the First Step to Sustainable Family Leadership

By Bryn Mars Monahan

We’ve all been there - a conversation with someone we love starts off fine, but quickly spirals into frustration and silence. In families, especially those who share assets or make decisions together, the stakes can feel high. It can be easy to focus on outcomes or strategy. Before you do, start with something more foundational: your heart. 

At the heart of it (see what I did there?), the ability to communicate with others, especially when the situation is tense or you are in disagreement, rests in the ability to “share your heart.” Or in other words, how adept you are at communicating the “why” behind what you are hoping to achieve with your conversation. 

In the third edition of the book Crucial Conversations: Tools for Talking When Stakes are High, the authors walk through eightskills that, when used properly, can help keep virtually any conversation from escalating into an argument. One of the first of these crucial steps is “Start With Heart.” To ‘start with heart’ means pausing long enough to truly understand your intent for the conversation. It’s about showing up not with an argument, but with awareness of what really matters.  

When Emotions Take Over

Stop for a moment and think back to a recent difficult conversation you had with a family member. Did it escalate to a point where someone was yelling, or someone shut down? Or did you avoid the conversation completely because you were afraid of an “inevitable” escalation? 

If you are anything like me, it is relatively easy to let your emotions get the best of you when having a difficult conversation – especially with family members, and particularly when the topic feels personally significant. 

Families who share assets, whether it’s a business, investment strategy, or foundation, are often in the position of needing to have difficult conversations. It is often because of the closeness with our family that these discussions can become emotional. We assume our love for and closeness to one another can overcome our lack of care for our words, and that’s how conversations can deteriorate into arguments. 

Why it Matters

Why does this matter at all? Why not just avoid difficult conversations altogether or let them escalate the way they “always have?” The simple answer is this – avoiding conflicts means the family isn’t addressing underlying tensions. Left unattended, tensions often grow over time, rippling across generations and resulting in missed opportunities for the family system to manage relationships better. 

On the other hand, allowing tensions to result in arguments every time they arise may literally tear a family apart. The cumulative effect of either avoidance or escalation can be devastating. But there’s another way. As an individual family member, you can start to change the culture and take an active role in shaping the future of the family by learning a better way to have difficult conversations. 

Three Questions to Guide You

So, how do you use both your heart and your head to engage in these crucial conversations? Ask yourself a few important questions: 

1. What outcome am I hoping for in this conversation?
   It’s important that the hoped-for goal does not require a behavior change from your conversation partner. For example, the outcome you desire cannot simply be “I want my parents to take me more seriously.” It can be, “I want my parents to hear that when they ask everyone in the family but me for input on business decisions, I interpret that as them not viewing me as a capable adult.” If you share your desired outcome at the start of the conversation and ask the same (and really listen to the answer) from the other person, you may be surprised to find that you have similar goals. 

2. What outcome do I want to avoid?
   Given that we are talking about family members, you likely have a sense of how things can go downhill. What, specifically, can you ensure you avoid by choosing your words wisely? If things do take a turn for the worse, how can you regain control of yourself to avoid negative outcomes? How can you better listen and respond to help avoid saying anything harmful? Sometimes taking a pause in the conversation can help. Ask for a moment to regain composure, and when you are ready, share your desired outcome once more.

3. What do I want from the relationship as a result of this conversation?
   Do you want it to stay the same? Are you hoping for improvement? Walk in knowing what your heart wants and reiterate that to your conversation partner. 

Of course, everything is easier in theory than in practice - so start simple. The next time you walk into a conversation with a family member, think ahead about these outcomes. Start with heart, and you may just find that what begins as a hard conversation becomes a doorway to deeper trust.