Taproot Law

Taproot Law

Human-Centered Legal Advocates

With our roots in the Upper Peninsula of Michigan


Difficult Conversations during the Holidays

TLDR: Ann hasn’t quite figured it out herself, but she’s here with some helpful resources

That’s right, we are approaching another year of holidays and we know that while the season can be filled with joy, love, and festivities, stress and anxiety can also run high. It’s also a time that families and friends might come together to have some hard conversations related to loss, change, and other tough topics. 

If you’re feeling the stress, you’re not alone

In 2022, over 1,000 Americans were surveyed about relationships and setting boundaries. 64 percent of those polled reported they experience holiday stress related to finances, spending time with friends and family, seasonal depression, and not getting enough self-care. It’s clear we’re already dealing with a lot of stress during this time of year. Adding the stress of hard conversations can be even more stressful. 

In this week’s blog post, I’m sharing some tips from resources to navigate the holidays and difficult conversations, along with a worksheet developed by Erica that we hope you’ll find helpful throughout the year. Please know that I’m no expert on this and having hard conversations is an imperfect, ongoing journey for anyone, including me. I’ve simply picked up some tips along the way that make it feel easier each time and I hope what’s below will help to make things a little easier for you too.

We Stan* (and resources for having hard conversations)

We’ve shared before that much of what we listen to and read informs our work here at Taproot. Resources that we constantly refer back to are the  “We Can Do Hard Things,” podcast from Glennon Doyle, Abby Wambach, and Amanda Doyle and Priya Parker’s Art of Gathering to explore what we really mean by our “human-centered” values and how we can better serve our clients. Let’s face it, we are pretty much “stans” for these experts and the work they do to help people through hard things that we face in everyday life. And, one of the hardest things to do sometimes is the holidays. But…it’s not impossible.

* Stan: an expression of extreme support for something, or that you are a huge fan of someone (urbandictionary.com)

Start with what you need  

In their “Happyish Holidays” episode, Glennon, Abby, and Amanda remind us that, even though it may not always feel like it, it’s your holiday too. 

If you’re facing the possibility of difficult conversations this holiday season, start with what you need and do some self-reflection. You might even write your ideas down (perhaps, with Erica’s worksheet below) so you can refer to them later:

  • What do I hope to gain from this conversation? 
  • Does this conversation even need to happen during the holidays? Why or why not? 
  • What do I want others involved in this possible conversation to know?

Healthy “heat” in hard conversations

Hard conversations can sometimes get the best of us, especially when we’re emotionally invested. While it can be frustrating, we also know that we can’t always control how others are going to react. At the same time, there are ways to prepare for these conversations and create space for healthy conflict or as Priya Parker describes it, “heat.” “Heat,” Parker explains, “can be around decision-making, it can be around power, it can be around longly held and beloved rituals.”

This year, I’m working with Michigan State University students who are currently wrapping up team-based projects for the fall semester. Team-based work can be really challenging, and even if it’s going well, imposed deadlines and other constraints can create major obstacles for effective collaboration. We’re at a point in the semester where we are feeling the heat and hard conversations need to be had. Faking peace won’t save us. I shared Parker’s work with my students and asked them to reflect on and talk to each other about how they can navigate heat, based on their own conflict styles, in order to successfully move forward together for the remainder of the semester. It occurs to me that those same questions are relevant here in this space. 

What is your conflict style? How can you leverage or downplay your conflict style to “hold conflict with care”? What is it you need from others? What might others need from you?

Parker argues that, “Heat is a doorway into having conversations that are relevant and affect our lives.” And in taking on that heat in hard conversations, it’s also important to listen to others’ needs, which can help you gain insights on how you might resolve a problem or answer tough questions together. 

Be unsurprised, Be prepared: Sketch out a plan for your hard conversation 

In the Happyish Holidays episode mentioned above, the hosts conclude with this advice: be unsurprised and be prepared for what might unfold during holiday family or friend gatherings. Hard conversations aren’t necessarily about changing who your friends and family are. But it is about moving forward together as best you can. Whoever this hard conversation is with, be unsurprised that they may react in ways that feel challenging. This shouldn’t deter you from being prepared to start the hard conversation. In the spirit of being unsurprised and prepared, Erica developed a really helpful worksheet that can help you to articulate what it is you need and how to listen to what others need. Try it out and let us know how it goes! 


Whether it’s the holidays or any old day in the year, Taproot is here to help you with the hard conversations that you may need to have related to legal issues and questions. Learn more about how coaching can help you with those conversations or give us a call at 906-284-8426 to schedule an appointment today!