Most skiers know they aren’t ready to tackle the hardest black diamond runs on a mountain without developing the necessary skills. Families faced with hard and often complex conversations around money, wealth, and estate planning benefit from similar wisdom.
Just like skiing, communication is a skill-based sport. Developing the skills to navigate challenging family topics requires practice. Fortunately, there are many life moments when families can start with easier “bunny slope” topics, like talking through allowances, college spending money, buying a car, or gifting to buy a house.
Through time, your family can develop the skills to have the harder “black diamond conversations” about topics like fairness, entitlement, integrating children’s spouses into the family, or the complexities of elder care or wealth transitions.
To help you practice as a family, here’s a quick overview of 10 conversation skills we teach at the Fidelity Center for Family Engagement.
1. Monitor tone of voice
Tone of voice influences how people interpret what you are saying, regardless of the words you choose. It is an important way to communicate that it is safe for others to join you in conversation. I often have family members practice by restating a simple question such as “Where are you going?" in 4 tones to hear the different meanings. Try saying it with aggression, empathy, suspicion, and interest. When there are unexpressed feelings that differ from what is being said, the real sentiments tend to come through in our tone of voice.
2. Explore with key word questions
We’ve all experienced conversations where opinions were just volleyed back and forth. No one asked questions to understand another perspective. To break that pattern, listen for an emotional or meaningful word—a key word—and ask a follow-up question using that same word. This skill helps us connect more intimately as we explore a person’s feelings and thinking.
If someone says, “I am really disappointed about this,” you can ask, “What are you disappointed about?” In response to hearing, “This is very important to me,” try asking, “What's important to you about it?” Even if someone says something inconsiderate, such as “That’s a ridiculous suggestion,” you can still explore their thinking by asking, “What’s ridiculous about it from your perspective?”
3. Be mindful of reactivity
A "check engine" light means that something inside a car needs to be investigated. Our Center calls an outsized reaction in an exchange a “conversational 'check engine' light.” It indicates something is going on inside you that needs to be explored.
When reactive, we often project blame onto someone else. Instead, when “the light is flashing,” pause and check in with yourself. Ask reflective questions: “What just happened in me?” or “What did I react to?” Reflection is the flip side of projection. This awareness gives you a new behavioral choice that will help you slow down and keep reactivity from escalating or becoming highly personal.
4. Choose not to personalize
Taking something personally is a choice. It can be hard, but even if a comment may have been meant as an attack—“You’re a spendthrift”—you still have a choice not to personalize or escalate the conversation.
When we personalize something, it’s usually because there is a truth in it that’s tied to our family history or past relationships. For example, your mother may have made comments about your father’s spending. And you may know that your spending can sometimes be excessive. So choose to reflect on your history and spending. Maybe even ask the person, “What do you see in my spending?”
5. Cultivate positive attributions
Attributions are highly organized beliefs about other people—characterizations that dictate how we treat another person. The challenge is that we tend to think of them as truths about a person that are beyond our control. And when our attributions are negative, it is not fair to lock a person into that characterization.
But we can change or reframe our negative attributions into kinder, gentler beliefs. For instance, consider an attribution that someone is “controlling.” Imagine shifting your thinking to “They are just trying to care for me.” That more positive reframing can open the door to a conversation about how you sometimes experience their behavior as controlling, rather than judging or dismissing them without talking.
6. Create space with doubt
When sharing a perspective, family members sometimes default to using absolute words or phrases like “always,” “never,” “hopeless,” “forget it,” “I’m out of here,” or “don’t talk to me.” This type of language tends to generate a cycle of unhealthy behavior and can ultimately end a conversation.
Instead, we can offer people respect and invite them to engage with us by putting some “doubt” into our language—openness to other opinions and options. Practice using phrases like, “What would you think about …” or “I'm not sure this is right, but maybe we could …” or “I wonder if there's value in thinking about it this way …" And, as often as possible, use words like “can,” “might,” “often,” “may,” and “maybe.”
7. Process out loud
Process Out Loud is the skill of saying what you are feeling and thinking in a way that helps others understand your experience of the situation. It creates a level of congruence and safety so people know how to engage with you.
The skill is to identify an emotion, label it with a feeling word, and follow up with a related thought to start the conversation. Here’s an example of what it would sound like from an adult child inviting their parent to talk about their later-in-life planning: “I’m feeling concerned and out of the loop on your planning around your finances and health. I’m hoping we can talk about your wishes for the future, so I know how to help and support you.”
8. Reprocess bad process
What is bad process? It’s shouting, reactivity, put-downs, walking out, shutting down, or any mode that hinders healthy communication and relationship building. Reprocess Bad Process is a skill for reflecting on your actions that goes beyond saying “I’m sorry.” It is a way to acknowledge the impact of your actions and offer an insight about what happened. And it sets you up to talk things through and reconnect after a conversation doesn’t go well.
Here are a few examples that all end with “Can we try again?”:
- "I realize I derailed the conversation with my anger."
- "I was feeling disrespected and unheard, which triggered me."
- "I was caught up in thinking about how this situation impacts me and didn't listen closely enough to what you were saying."
9. Check in through process questions
In a conversation, especially around a sensitive topic, it’s important to monitor how other people are engaging and check in with them about their experience. You can do this by asking process questions that focus on “how” people are talking, as opposed to content questions that explore “what” people are talking about.
Here’s what process questions sound like: “How are you feeling about our conversation?”; “Am I pushing too hard?”; “Am I asking enough questions?”; or “Have you been able to share your views?”.
Process questions are particularly important when there is a natural hierarchy in a group, like parent-child, expert-novice, or manager-associate. You can ask if people feel like there is a true back and forth or if the hierarchy is constraining the conversation.
10. Offer forgiveness and compassion
One conversational challenge for families is exploring options for the future in a way that feels safe for everyone. It can be useful to try “What if?” thought experiments. You can imagine possibilities without getting bogged down in decision-making. And they provide you with the freedom to explore each other’s thoughts and feelings about different planning options.
Parents who are assessing their living options for retirement could explore “What if?” with their adult children: “What if we moved to Arizona?”; “What if we lived near you?”; “What if we bought a shared home with an in-law suite?”; or “What if we bought a lake house to share in the summer?” We can imagine a wide range of conversations around those few examples.
About the author
Dr. Timothy Habbershon is currently a managing director of Fidelity Investments. For more than 25 years, Dr. Habbershon has been an advisor, consultant, and coach to ownership and management teams of large family-controlled firms and family offices worldwide. Prior to joining Fidelity Investments, Dr. Habbershon founded three applied research and practice institutes for enterprising families at the School of Business at the University of South Dakota, The Wharton School of the University of Pennsylvania, and Babson College, where he also founded a global applied research initiative, the STEP Project, and is currently an adjunct faculty member in family enterprising. Dr. Habbershon received a bachelor of arts degree in psychology from Grove City College, a master of divinity degree from Gordon-Conwell Theological Seminary, and an MBA and a doctorate degree in adult education from the University of South Dakota. The opinions expressed are those of the author and do not necessarily reflect those of Fidelity Investments.