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5-Steps to Having Hard Conversations

Welcome to one of my very favorite subjects in the whole wide world. Which may seem weird. Growing up as a first-born daughter, people-pleaser, & conflict-avoider, this concept should make me break out in a cold sweat. And I’ll be honest, it used to. 

(Ok, I’ll be really honest. Sometimes it still does.) 

But I LOVE this topic (cold sweats and all) because having hard conversations is easily one of the most important and simultaneously most challenging aspects of owning and operating a business with your family members. 

Being able to have hard conversations with your family members is really essential for your business. You need to be able to communicate about things that are difficult. You need to be able to disagree effectively. And you need to be able to hold both ends of the communication circuit fully & completely by not only speaking from a clear & grounded place, but also listening with openness & curiosity. 

It’s also important to understand that words move energy. When things are feeling tense, uncomfortable, or stagnant, having a really intentional conversation is an extremely effective way to get things moving. This can be a tough one to remember when we’re anticipating (and avoiding) the potential discomfort of a difficult conversation. I think sometimes we have a tendency to think “Welllll, maybe if we let some time pass, things might improve on their own.” And maybe it will… in some random way… eventually… Kind of like if you break a glass on a patio and then just wait a year or two before going out there barefoot. Over time the wind, rain, & snow may have washed away and dulled the glass enough that you don’t cut your foot. But you’ll also have to spend two years tiptoeing around and even then there are no guarantees. Whereas, coming in with a broom & dustpan and really intentionally cleaning up the space, while it takes time & effort, creates a quicker & more clear resolution. And you can move more freely as a result.

Words & conversation can be our broom & dustpan!

Now, while the “bad” news is that we indeed know that we have to have hard conversations, the GOOD news is that I have a few tools to help increase the effectiveness of this necessary (if not sometimes cold-sweat-producing) work. 

Today I’d like to share my 5-Steps to Having Hard Conversations. Now, I'm not going to sugarcoat this and just say, “So if you do these five things, you will never have a disagreement again,” or “You will always get what you want.” This is not a magic pill, but it is a structure that I have used for years and continue to use – and I can assure you that it will at least set you up in a way to get the most benefit out of the conversation with a higher likelihood of success, whatever that may need to be.  

Step 1: Connect to what is most true.

Give yourself a little space to reflect & get a clear perspective. What is actually happening here? What are we going for? And will this conversation help accomplish that? 

Friends, I would be remiss if I didn’t also take a minute here to say – This step can actually be the hardest part. As Ram Doss once said, “If you think you're enlightened, go spend a week with your family.” Sometimes things get tangley and confusing – especially when our emotions are involved and especially when our family is involved. 

This is where getting yourself some support can be very helpful. Talking things through with a trusted friend, advisor, mentor, or coach who can really hold space for the whole process & all of the feelings that come with it can be really invaluable. 

Step 2: Set a specific time to sit down & talk.

It's very tempting in a heated moment to want to have a hard conversation right then and there. Especially for those of us who like to nip things in the bud. I get it. But, when we're emotionally activated (angry, hurt, frustrated, etc.), chances are we're not going to be able to really listen and receive at the level that we need, in order to have a really meaningful exchange of ideas and come to an understanding. 

So, setting a specific time to talk when everyone is calm and not in a heightened state is really important – and so is being really clear about what you want to discuss. We all have way too much pre-conditioned anxiety around the phrase “We need to talk,” so best you let everyone know about what and why at the same time!  

Step 3: Make sure you are fully resourced. 

Nothing leads to harsh words quicker than a case of the “hangries” in my family! Make sure you’ve all eaten. Drink some water.

Is everyone well rested? And comfortable?  Not too hot or too cold? All of these basic human body things make a real difference in how receptive we are. So just getting all of that taken care of before you even begin is really important in setting up a difficult conversation for success. 

 Step 4: Ground yourself & get clear.  

This is a big one. 

The hard truth is we can't control how everyone else is going to react. Nor should we. Everyone gets to have their own experience. AND. The more you can ground yourself in your own energy & the energy of what it is you’re all going for, the more freedom it gives everyone else to have their own experience without the whole conversation (and your energy & attention) getting pulled completely off course. 

Begin by expressing and feeling what is truly important here. Maybe it’s gratitude for your family’s business and your desire to see it move forward in a more aligned way. Maybe it’s appreciation for your partner and wanting to ensure you both feel a deep and clear connection in partnership. Whatever it is, get yourself grounded and then move into…

Step 5: Practice speaking from the heart. 

Yes, yes, we’ve all heard the old adage “It’s not personal, it’s just business,” but what’s more personal than working to create something you’re truly passionate about with the people that you are most deeply connected to? 

So, let all of that corporate conditioning take a back-seat for just a minute and say what’s in your heart. And allow everyone else to do the same. This is how authentic connection & communication happens. And it takes practice. So even if it feels weird or awkward or sticky at first, please try try again!

You can trust yourself.


If you’re interested in hearing more on this subject, I invite you to check out this week’s Podcast Episode: (also available on Spotify, Amazon & Apple Podcasts!) and be sure to follow Legacy with Anne Bauer to hear about new articles & episodes released every week.

This is hard work, my friends. But it’s also vital. After all,what’s more powerful than doing the work that you care about most in the world with the people that you care about most within it?



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