How to Have Difficult Conversations with Your Family


Oh, the holiday season. It brings good cheer, great food, and, of course, interactions with our family members. 

Every year, people ask me questions like, “Seena, how do I finally say something to my uncle who keeps using racist language?” So this year, I’ve decided to take the advice that I give in my coaching sessions and in our online community and share it with the world. 

In order to have a difficult conversation, preparation is mandatory. Here are a few questions that you might ask yourself in advance of your interaction. 

Framing the conversation

These questions will help you better understand your why and your purpose. That framing is critical to developing a level of self-awareness around what you’re about to do.

  1. What is the purpose of the conversation? 
  2. Who is the audience? 
  3. What assumptions are you making about this person’s intentions? 
  4. What “buttons” of yours might be pushed? 
  5. How is your attitude toward the conversation influencing your perception of it?

Preparing for the conversation

After you know the purpose of the conversation and your audience, and have examined your assumptions and biases, you should:  

    1. Opt-in. I’ve found one of the most important steps is really committing to the doing part. It’s one thing to rehearse conversations in advance, but actually declaring to yourself, and maybe an accountability partner, that you are. Going. To. Have. The. Conversation. The declaration will put you in the mindset of moving to action.
    2. Identify fellow accomplices who can help. Maybe it’s your cousin, Jean, or your aunt, Sally. There is usually someone who agrees with you, though also may be too afraid to take a stand. Talk with them, let them know your commitment. Even if they’re still afraid, they might be willing to have your back or help facilitate a dialogue. If you don’t have anyone in your family who’s on your side, have a “phone a friend” ready as a way to vent, strategize, and reflect.
    3. Determine your threshold. The reality is that you’re not going to convince anyone of your perspective in one conversation. This will be an ongoing thing (yet the first time is definitely the hardest). So, decide how far you’re willing to go and what you’re willing to take at this particular moment. 
    4. Address any physical or emotional needs that you might have. When we engage in what can feel confrontational or difficult, we have to take care of our needs, too. Part of the work of an accomplice is being able to do it sustainably and consistently. If you need to meditate or get your mind right with some music beforehand-- do it. If you need to have a hard cry at the end, know a place to retreat to and do so. If you need to throw a rock at something hard to let out your frustrations, identify a location away from your family to address the need. Those needs are real and catering to them, versus ignoring them, will help you help yourself. 
    5. Think about how to chip away and commit to continuing to do so. Because you’re not going to have a full conversion in one conversation, focus your efforts on one or two topics or one or two points. By chipping away versus throwing everything at the other person, you maintain your sanity and you keep the dialogue contained. 

Having the Conversation

Transitioning from opting in to actually having the conversation isn’t easy. It’s like going from rehearsal to showtime. You might be nervous, but here are a few guiding principles.

  1. Don’t make it about them, make it about the ideas. As much as you can, detach your comments from them, as people. No one wants to feel like an asshole and if they start feeling like you’re attacking them, the attempted conversation will be for naught. So name the offense specifically, like, “When you make generalizations and disparaging comments about immigrants, it doesn’t reflect the true accounts from migrants that I’ve read.”
  2. Have data ready. While anecdotes and primary sources are often the most compelling, data rises above that when you’re trying to make a point. Data disproves gaslighting comments like, “That’s just one case.” or “If they just complied…”  
  3. Address counter-arguments directly. Don’t let your ideological perspective get in the way of a good ol’ fashioned debate. The truth is, the person you’re engaging with already thinks your ideologies are wrong, so you have to find new ways to state your point. And addressing the counter-arguments carefully and directly will provide a deeper level of dialogue than stating your points over and over again (even when those points are right, my friend).
  4. Ask clarifying questions. Often, when we’re engaging with different perspectives, we focus on getting in the last word or making our point. Asking questions that might help bring the other person to your point, rather than telling them your point, is a really useful tool. It diffuses the situation and questions engage our brains differently. The other person will be more likely to feel heard and respected if you clearly want to know what they think. 
  5. Remember your why and hold your agenda. Remember your purpose for having the conversation and hold it close. You might be tempted to go off on another path or tangent, but don’t. Remain focused. If you feel yourself or the conversation veer off course, allow yourself to step back and reassess. This is not about “winning” in this exact moment, it’s about engaging as openly and respectfully as you can.
  6. Set a specific time to continue the conversation (if necessary). We all know that change doesn’t necessarily happen in one interaction. Knowing that, be prepared to continue the conversation. If it helps, set a time and date for a phone call or a zoom meeting to keep engaging.

This is not an exhaustive list, but it’s a place to start. Remember that this is an opportunity to broaden your perspective as well--you can learn new skills as well as what fuels other people’s ideas that differ from your own. As difficult as it may seem to be open to what feels narrow or “wrong,” we have a lot of work to do to find our way forward in this country. And it will require engaging with differences, of all kinds. So, don’t take anything personally, trust yourself, and know that by deciding to have the conversation at all you’re making progress.  

Have a wonderful holiday season and a great conversation. And let me know how it goes.