What I’m Thinking About
Uncomfortable conversations. Did reading those two words cause you to tense up just a bit? Me too. These are never easy, but they’re critical. Over the past month or two, I found myself engaged in a number of uncomfortable conversations – with boards, with leaders, with colleagues, with clients. I’m certainly not looking for them, yet neither am I trying to avoid them. As a consultant, I notice that I’m often the one broaching the challenges or tensions that lead to such uncomfortable conversations.
Some uncomfortable conversations are monumental – leadership changes, shuttering a program or service, reduction in force, and loss of major funding. Some are less so – how a team member is showing up negatively, when someone is not the right fit for a promotion, and why the board has become (or remains) less engaged, to name a few. So, what do we do when uncomfortable conversations are necessary? Let me offer three strategies I’ve learned over the years from leaders wiser than me.
First, don’t rush into an uncomfortable conversation. In almost all instances it can wait at least twenty-four hours for you to think through what you desire to accomplish with this conversation. Second, don’t squeeze it into a busy schedule – for you and for everyone else involved. Be intentional about creating an opportunity to be fully engaged. Don’t make it a by the way moment in a weekly check-in meeting or ask someone to remain on the virtual call for a minute when the meeting is over. Be present emotionally, physically, and mentally. Third, be open, honest, and vulnerable. Be clear about the need for the conversation and seek compromise when doing so provides a win for all. Work together to get to the desired result, whether that result is crystal clear or not. Bring compassion to the conversation. There’s a lot more to engaging in uncomfortable conversations than the three strategies I’ve suggested, but I believe starting with these provides for a productive framework.
I’d also like to share three complementary resources that you might find helpful working through all three phases of uncomfortable conversations: the before, the during, and the after. This first book is not specific to handling conversations but is tremendously valuable in dealing with a real aspect of uncomfortable conversations: stress. Dr. Jenny Taitz’s Stress Resets: How to Soothe Your Body and Mind in Minutes (Workman, 2024) is a practical guide for managing stress during intense times and for building resiliency. Its structure allows the reader to consider when, how, and why for each of the seventy-five ways offered to improve how you respond to stress. The second book, Culture Matters: A Framework for Helping Your Team Grow, Thrive, and Be Unstoppable by Jenni Catron (Maxwell Leadership, 2025), focuses on what Catron calls one of the greatest responsibilities of a leader: stewarding people. Stewarding people requires leaders to intentionally build healthy cultures. Of course, you cannot build a healthy culture without having some uncomfortable conversations along the way. Which leads to the third recommended book: Crucial Conversations: Tools for Talking When Stakes Are High (third edition, McGraw Hill, 2023) by Joseph Grenny, et al. I love how this book is presented in three parts: 1) What to do before you open your mouth, 2) How to open your mouth, and 3) How to finish. This is a very practical book with lots of vignettes that drive home the authors’ guidance. Together, these three books don’t offer a how-to guide for uncomfortable conversations. They do much more – they provide leaders the skills, awareness, and understanding that uncomfortable conversations are inevitable and can lead to some amazing outcomes. Even when the outcomes are undesirable, perhaps messy, the conversations will be had with integrity, intentionality, and compassion.