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Navigating Tough Talks

Written by Chuck Olson

September 2014 – The tension in his voice was undeniable. His halting words spoke volumes. Brian’s working relationship with his boss was broken. Badly. A candid conversation was overdue, but he wasn’t sure where to start.

Been there?

Whether it’s with your direct report or your boss, tough talks are part of the terrain every leader must travel.

One of the hats I wear day-to-day is leadership coach, and in that role one of the most predictable themes that I address with clients is how to navigate difficult conversations. Both the WHY and the HOW.

Of all that could be said on this crucial topic, I’d like to call out four of my own MVLs –most valuable learnings—for your consideration.

Check the heart. When a tough talk is stamped PAST DUE, the temptation is to focus on yourself and ‘get it off your chest’. Not a good idea. Every successful conversation of this nature starts with a rehearsal of your motivation. Have I owned my part in the broken partnership? Are my reasons for initiating this conversation motivated by my commitment to the person’s best interests?

Create the context. Tough talks should never feel like a blindside. Preset the encounter: “Jerry, I’m glad that we can meet tomorrow. Beyond the normal things for us to catch up on, I have some important thoughts for us to discuss.” Once in the meeting, create a mental mindset of being seated side-by-side (a partnership posture) instead of being seated across from each other (a confrontational posture). William Ury in his practical book Getting Past No captures this well when he says “…turn face-to-face confrontation into side-by-side problem-solving.” In the presence and under the guidance of God Himself, you are working TOGETHER to figure out a shared concern.

Frame the conversation. Just like a painting is enhanced by its frame, so a tough talk is positioned for success by how it is set up. The optimum way to do this is to move yourself from a posture of certainty to a posture of curiosity. It is risky to presume that you have a full perspective on the matter at hand. Start with questions, not pronouncements. Invite the person into the conversation. “I think we have different understandings about how to bring out the best in our team. I’d like to hear your thoughts on this.” Mutual understanding is the foundation upon which shared solutions are built.

Recap the conversation. When it comes to tough talks, the practice of utilizing a post-meeting recap email is the leader’s best friend. It allows you to create both a memorial and a momentum to the time. Something like this. “Steve, thanks for our time yesterday. Really appreciated both your openness and resourcefulness to our discussion. I was able to gain a greater understanding about how you approach the development of your team members, and I appreciated the chance to share my perspectives. From our conversation, we agreed that going forward you would start your weekly meetings with your direct reports with some specific items of affirmation—to build on their successes. I believe this will make a big difference in both their morale and contribution to this important project. I look forward to hearing how this goes when we meet next.”

Ultimately, taking on tough talks is a matter of courage. Courage to do the right thing. And to do it in the right way.


What has been one of your key learnings in navigating tough talks?

Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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