Don’t Ruin Dinner: 5 Tips To Succeed at Having Difficult Conversations

The Inheritance Project
8 min readDec 20, 2020


by Dr. Lauren Borden, executive leadership coach

As a coach, I specialize in supporting leaders and growth-minded individuals in having a positive impact and initiating change in their organizations and industries. A large part of my work involves supporting these leaders in having challenging and uncomfortable conversations with other leaders, coworkers, and direct reports. It involves coaching them to act boldly, challenge the status quo, and to be agents of change in their organizations and industries.

In my work as a coach, I inevitably get asked the following question:

How do I apply what I’ve learned about communication and difficult conversations with my family? I can have these incredibly challenging conversations about diversity and inclusion at work, and then I go home and I’m constantly triggered. What’s up?

It’s one thing to be willing to say something bold as a leader or member of a team, it’s another thing entirely to be the person who calls Grandma out for making a racist joke over cranberry sauce and stuffing.

The truth is that there’s no ‘right’ way to navigate these conversations. The news that there is no clear or easy way to have difficult conversations with family should not be daunting. It should be freeing. It humanizes all of us. No one has it figured out. Everyone is scared of getting it wrong and triggering someone. It doesn’t make us inept, it makes us human.

From this common ground, we can start to build something else — deeper connection, understanding, and maybe even healing. What follows is not intended to be law or universal truth. What I offer you is a series of considerations and practices to help you navigate this landscape a bit more smoothly.

So, let’s take it from the top.

1. Release the expectation that you’re going to change their mind

I know. How could a self-proclaimed activist coach suggest such a thing? Someone who has dedicated her career to empowering change agents?

Let me be clear: I’m not saying that you should accept racism, bigotry, or cruelty. I’m also not saying to give up hope that your family might change their mind on important topics that you care about. Instead, my point is that people are actually more likely to change their opinions when we stop being so attached to changing them.

Psychological research makes clear that in political conversations, trying to change someone’s mind about something can actually have the opposite effect: instead of changing their perspective, people typically respond to opposition and pressure by digging more deeply into their current beliefs . They argue harder, feel misunderstood and get defensive. Not to mention, you’ll end up leaving these conversations feeling frustrated and a little bit crazy.

Now, this doesn’t mean that you should ignore racist or bigoted comments from your family — quite the opposite. It’s that instead of trying to persuade or change people, practice asking lots of questions, have discussions to understand, establish common ground, or even just express your own opinions without attachment to the outcome. When you let go of the expectation that you’ll change them, conversations open up for your own healing and self expression, and actually makes change on their end more likely.

2. Get clear on your intentions.

You may be wondering, “If my goal isn’t to change someone’s mind, what are we even doing here?”

The beautiful thing is that once you release the expectation that you’re going to persuade your family of your views, it gives you a ton of space and energy for love, connection, understanding and self expression.

With this in mind, before you enter one of these conversations, get clear on your personal commitment and intention. For example, is it to truly embody and model love? Is it to own your truth and voice? Is it to stand up for what you believe is right, regardless of the outcome? Is it to connect with your family? To better understand their thinking? Is it merely to show up in the conversation and stay grounded, present and hold space?

Before you dive into these conversations, be clear on what your intention and commitment is. That way, when you get triggered and the temptation to get sucked into a conversation that does not match your intention arises, it will be easier to redirect the conversation to what you’re actually committed to.

3. Call people up rather than calling them out

Here’s the necessary caveat to all of this: Sometimes our family members will let us down. Sometimes we go home and people say things that are hurtful, cruel, or biased. In these instances, sometimes it’s necessary to speak up and say the bold thing in order for us to maintain our personal sense of integrity.

In these instances, something to keep in mind is to call people up, rather than calling them out. Most of us are accustomed to calling people out. We call people on their bullshit, tell them when they’re being unfair, or tell them they’re wrong. In my experience, a much more effective way of doing this is to call someone up or call them forward into their leadership and integrity. Rather than speaking to someone’s darkest and most unhealed parts, speak to their greatness and to what they’re committed to in the world. Recognize their kindness, love and commitment to doing good in the world and then highlight how their comment or action is inconsistent with those qualities. Doing so allows you to speak your truth and hold others accountable while also recognizing their inherent goodness and call them towards it.

4. Give yourself lots of grace

One of my most impactful mentors, a woman who is incredibly committed to diversity, equity and inclusion (DEI), shared an incredibly powerful insight — if you’re going to try to change the world, quit trying to start with your family. Her intent wasn’t to discourage me. It wasn’t to censor me or tell me not to speak my mind. It was an acknowledgment that conversations with your family about politics, race, and sexual orientation are by far the most triggering and challenging.

Buckle up buttercup, because you just started the game on expert level.

Our family is the birthplace of most of our childhood triggers and wounds. Even those of us with happy childhoods, for the most part, did not make it out without some sort of trauma or wounding, and conversations about charged topics are inevitably going to be drive those wounds to the surface — wounds of not feeling heard or understood, of ways in which our families may not have done right by us or others in the past, even with the best of intentions.

Given all this, if you’re just starting to practice conversations about sensitive topics, consider letting yourself practice in other places where these wounds and triggers are less deeply-rooted — with friends, at work, in volunteer organizations.

If you do choose to speak up during the holidays with your family, however, accept that this is a triggering context in which to practice. Acknowledge that you’re playing on expert level, and give yourself a bit of grace if you’re less than graceful. This might mean committing to more self care over the holidays, practicing strong boundaries about what you will or will not discuss or who you’ll engage with, or simply practicing lots and lots of deep breathing when things get tense.

5. Practice makes progress

Going into a conversation about race, sexual orientation, or our personal biases can feel terrifying. It can feel like there are a million different ways that we can get these conversations wrong, offend someone, or say the wrong thing.

If you take nothing else away from this article, I hope you take the following: there is no perfect way to have these conversations. There is no formula. Those most skilled at navigating challenging conversations about charged topics did not learn by perfecting the art of articulation. They learned through practice. They learned by taking each conversation as an opportunity to learn and understand their own and others’ triggers and biases.

Triggers can be revelatory opportunities to examine our own personal biases and traumas and shed light on the places inside of ourselves still in need of healing. Commit yourself to being in process, rather than being perfect. Do your best to learn about different perspectives on culture and DEI but, most importantly, commit to your own growth. When you inevitably say something that upsets someone or exposes an area where you’re still learning, own it, clean it up, and do what you need to do to grow and move forward. In sum, quit trying to get it right or say it the perfect way and just go practice.

About Lauren

As a coach and doctorate in Industrial/Organizational Psychology with over ten years of experience in leadership development, Dr. Lauren Borden, MA, PhD, supports her clients in leveraging their gifts to step into their unique leadership style, create diverse and inclusive corporate cultures, develop their individual voice, expand their impact, and lead with more heart, purpose, and passion.

In addition to her private practice, Lauren is a co-founder of JBL Consulting, a company dedicated to promoting corporate DEI and ally-ship. Lauren is also a mindfulness and meditation teacher. She specializes in teaching meditation as a leadership, personal growth, and stress management tool, and supporting others in creating sustainable mindfulness practices that are fully integrated into their everyday lives.

Lauren has had the privilege of coaching and training professionals within Fortune 50 companies across technology, retail, medical, and finance industries to help them use organizational psychology to develop strategy and strengthen their workforce. Additionally, she has authored numerous publications and conference presentations exploring leadership development, mindfulness and meditation, feedback, and training, including articles and chapters in The Journal of Business Psychology, Teaching Psychology, The Oxford Handbook of Justice in the Workplace, and The Handbook of industrial, Work and Organizational Psychology. Additionally, she is a leader and trainer in the Accomplishment Coaching, an International Coaching Federation accredited coach training program.

If you are curious about coaching or connecting with Lauren, feel free to contact her by email at