The Missing Conversations are the Most Expensive

Be very afraid of the conversations on the tough topics of performance, improvement, and innovation that aren’t taking place on your team or in your organization.

The Missing Conversations are the stuff of a leader’s nightmares—or at least they should be. They reflect the problems not solved, innovations not realized, and performance never improved. And yet, there’s a fix. It’s simple—but not simplistic, if only you dare to tackle it head-on.

A Leader’s Nightmares—Opportunities Foregone

My coaching clients and workshop participants are to be excused if they roll their eyes when they hear me utter for at least the hundredth time, “Everything important takes place in one or more challenging conversations.”

Think about it.

The most important conversations are when we openly share and respectfully debate perspectives to pursue a way forward in a tough situation. Or when we strive to improve performance by engaging in discussions about how our or their behaviors might change to produce better outcomes.

Be very afraid of the conversations on the tough topics of performance, improvement, and innovation that aren’t taking place on your team or in your organization. Share on X

In many cases, the challenging conversations—the exchanges that determine the fate of strategies, initiatives, and even organizations are the ones where moral courage is a pre-requisite, and the environment must invite, not penalize honest, frank sharing.

The Essential Need for Perspective-Taking

Tough conversations include the need to listen and invest in perspective-taking, where we jump out of our minds and strive to climb into and understand the viewpoint of others as part of problem-solving or idea-making.

Unfortunately, too many challenging conversations never occur because leaders fail to find ways to cut through the b.s. that dominates most organization-speak. We fail to create environments where psychological safety is present (they’re rare), and we leave what might be the seeds of great ideas and novel solutions stuck in the minds of our people.

That’s the stuff that should dominate a leader’s nightmares.

Fixing the Culture Starts with the Leader

Every year, a few hundred people go through my Feedback Skills and Challenging Conversations programs. I love when good people are motivated to get better at a challenging task. Yet, the solution for your organization doesn’t start with training—that’s a follow-on. Fix your culture first and then help people master the skills essential for engaging in challenging conversations.

Fix your culture first and then help people master the skills essential for engaging in challenging conversations. Share on X

Start by Fixing Your Feedback Culture

Let’s focus on feedback and how to make the expectation and practice of sharing quality, behavioral feedback in all directions (up, down, and sideways) part of your team’s DNA.

In an article I wrote for SmartBrief on Leadership, I offer: One of the reasons feedback is in short supply, or just poor quality in most environments is the failure of leaders to ensure the need and obligation to give and receive quality feedback as a price of admission.

I want you to bake the expectation for conducting, receiving, and engaging thoughtfully, conscientiously, and immediately in challenging feedback conversations into your firm’s or team’s values. And then model the behaviors. 

Coach, Train, Evaluate, Reinforce

Coach individuals on how to do this and how to strengthen and improve. Train them and expose them to the fundamentals. Evaluate their performance and constantly reinforce when and what people get right and how it helps drive success. 

And then move on to establish the same expectations for all challenging conversations. 

Build safety into the environment. Reward perspective-taking, and ultimately, coach and teach on decision-making. The pursuit of strengthening a culture for challenging conversations isn’t the pursuit of consensus; it’s advancing the best ideas for the situation. 

The Bottom Line for Now:

Ask yourself these questions:

How comfortable are your team members pointing out when your behaviors push them into coping, not creating? Do your teams descend on tough issues and tackle them passionately while never veering away from mutual respect? Are you hearing ideas from those less comfortable standing in the spotlight? How creative are the solutions emanating from those around you? And, when was the last time someone said your approach was hurting performance or morale, and you did something about it? 

They’re all challenging conversations by definition. You need to help bring them to life.

Art's Signature