How to Have a Difficult or Potentially Awkward Conversation with Your Spouse, Child, or Co-Worker


I don’t think I became a good communicator until our son was 6 years old. At that point, I had been married for about 10 years, I was fluent in avoidance and passive aggression.

Our son’s inability to read facial expressions, social cues, and voice inflection taught me to narrate my feelings constantly. In turn, difficult and uncomfortable conversations at home and in my professional life became easier.

Here’s how…

Before I have a tough conversation, I identify if this is my issue, his/her issue, or a God issue (no one can control). If it is my issue, knowing what I really want out of this situation (corrected behavior, desired outcome, etc.) is critical. However, I also have to be willing to accept that my expectation may not be realistic.

I intentionally set aside time and safe place to have the conversation. The amount of time, thought, and energy the issue has taken from me just feels more and more insurmountable the longer I put off a crucial conversation. I cannot afford to put these conversations off but I also don’t just barge in and have them. I will put these conversations off though until everyone involved is calm.

Listen, engage, respond. Sometimes I have to apologize for my role or expectations in hurting. I don’t get the luxury of going silent. I must participate fully. Actively listen. Put the phone down, close the computer, move closer to the individual (without penetrating their personal bubble). Breathe. Listen. Listen without emotion and then listen some more. Then breathe again and respond—even if it is, “I hear you, but need a minute to process.”

Lay out a clear plan.
I’m a fixer so I have to fight my natural instinct to fix the problem myself. Doing this is a lot like avoiding the problem, I’ll have to deal with it again, and probably sooner rather than later. Both parties need to be involved in the plan and have ownership over it. Take your time, however, don’t over-complicate this part of the process.

Here are a couple of my most memorable crucial conversation scenarios with some fill-in-the blanks for practice:

A conversation with my spouse:

When my husband’s work hours wrecked havoc on our home and family life for months on end (and even when he was home, he was working) I was so completely overwhelmed with adulting and parenting alone. With no change in sight, and knowing our relationship needed help too, I took ownership that my belief of our perfect family life expectation vs. reality held some of the blame. Realistically, he wasn’t going to leave the job he loved and that provided for our family, so the perfect life 8-5 Monday-Friday wasn’t really going to exist–ever, but I needed support at home, a girls night out, and a date night. One night after the kids were in bed, and my husband finally got home, I calmly asked him to come into our bedroom and sit down. I straddled his lap (very sexy and this kept his attention), then I took his face tenderly into my hands and begin, “When you ________ (put work before us), I feel _______ (inconsequential and taken for granted).”

This moment was intimate, vulnerable, and a relief to us both. I was putting myself out there and trusting him to engage with me and lean into the discomfort of accepting his role in our lives and  letting go of the passive aggressive manner we’d been throwing at one another. We both knew that we were safe and invested together in resolving the issue.

In a matter of minutes, we formulated a plan that helped us both—hiring a standing Wednesday night sitter, and a cleaning and lawn crew so that family time and date night (while still acknowledging it would be minimal) was truly meaningful and a priority. And we lived happily ever after…okay maybe not the fairy tale ending you read in books, but that was more than 10 years ago and we’ve learned a few ways to either avoid getting to that point  by avoiding the problem, and communicating effectively with one another. 

A conversation with our teenage son:

Before the holidays last year, we sat down with our son and had a tough conversation about being “present” (not on our cell phones) so instead of holding on to my expectation of him impressing all of our relatives with his charm and ability to engage in thoughtful dialogue vs. reality—“Dylan! Put your phone down and visit with your grandfather!” (insert teenage eyeball and parental authoritative hushed shout about respect thus causing everyone to be uncomfortable)—we worked together beforehand so that we all knew what was expected at these gatherings. To begin, we planted the seeds of curiosity. “Dylan, did you know that my dad use to be Santa Claus for company parties?!?” Then we would shift quickly to, “You should ask him about that…oh and lets talk about being ‘present’ this year…”

We always ask him for his thoughts because most people will support what they help create, but this also allows him to give us his thoughts—maybe he thinks it is boring or no one talks to him, etc. Then we can make accommodations as needed (packing a board game, or desired activity that isn’t the phone). I do have to say, after enduring the holidays alone this year, Dylan is ecstatic about family gatherings in the future, so this may no longer be relevant.

A conversation at work:

These are the conversations that keep me up at night. With my husband and son, I feel safe, loved, and valued. At work, we don’t always get to feel this way so it can make tough conversations more stressful. Still, the best way to approach an obstacle is usually through not around. I don’t always have access to an intimate setting, however, I prefer face to face or phone interactions for these conversations. I identify what I want or need, and then acknowledge my own expectation—whether it is realistic or not, then schedule the meeting or call. Since I don’t like surprises, I assume others don’t as well, and will set the agenda or announce why I’m asking for the meeting. Presume good intent here and not that this gives them an opportunity to gather all their stones. (If the meeting occurs with multiple people, I try to sit next to the person I need to have this conversation with and NOT across from him/her—even if it means I move from behind my desk.) Since many of these discussions stem from miscommunication, asking for clarification or definitions helps tremendously. (i.e. Question, “What is your definition of ________ (success)?” Answer, “____________ (not burning the building down. hitting our sales projections. lowering turnover. decreasing expenses?)”

You would be surprised how varied this definition can be—especially between department heads. Once a shared understanding of the situation is identified, we can move to resolution and planning together. Be creative in how implementation might occur and again, you will support what you help create so the other person’s perceptive is invaluable too.

Obviously, no one is perfect, least of all me, and stumbling through these conversations happens. Avoiding them gives us less opportunity to get better at them, and allows problems and sometimes life-threatening situations to occur. A couple of books that have inspired me to not run from these situations are Malcolm Gladwell’s book Outliers, (Chapter 7, Culture and Ethnic Theory on Plane Crashes) and Crucial Conversations: Tools for Talking when Stakes are High


Please enter your comment!
Please enter your name here