Leadership Caffeine™—Fear the Conversations You’re Not Having

Challenging management and performance conversations regularly run off the rails. They are often muddled, mixed-up, and monumentally massacred. Nonetheless, at least people are attempting to talk about the tough topics—even if things occasionally go cattywampus (look it up!) with them. The conversations I genuinely worry about are the ones that aren’t taking place. As a leader, just thinking about what’s not getting talked about ]should scare the daylights out of you.

Don’t Let This Be Your Biggest Leadership Regret

Some years ago, reaching the end of the interviews for Practical Lessons in Leadership, I had a chance to connect with “Ron” a retired CEO. Ron had enjoyed considerable career success, and I was thrilled to gain his insights for the book project. As our interview was wrapping up, I threw in the “biggest regrets” question, and without missing a beat, Ron responded, “I wish I had learned how to have the tough conversations with teams and people. To this day, I wonder how much money and performance I left on the table by avoiding these conversations.

I’ve been processing on that statement for over a decade. Ron was/is right—you don’t want to limit your success by letting fear govern your actions or inactions when it comes to challenging conversations.

Your Brain is Fighting You—It’s Time to Fight Back

There’s science behind our tendency to avoid challenging conversations. Research suggests your boss’s statement, “I have some feedback you,” is a sure-fire trigger for your fight-or-flight sensor(s) to kick-in and overwhelm your more logical self. The same goes with the idea of leading one of those discussions. The former is a potential threat to our sense-of-self, something our brains don’t take lightly. The latter is more of a defensive reaction. Our opening or leading of a challenging conversation might go wrong in so many ways that it’s easier to avoid it.

It’s a fact of life—when it comes to challenging conversations, you’ve got biology working against you. You’ve got to fight back, or you’ll end up like Ron with some serious regrets. (Every once in a while some workshop participant points out to me that Ron was indeed a CEO, so his struggles with challenging conversations didn’t limit his success. If that’s your thinking, you missed the point! Reframe.)

While I teach approaches to manage your brain in challenging workplace situations and perform at your best when your system is pushing you in the opposite direction, there’s one part of this that can only come from you. Your recognition of the power and importance of challenging conversations must be part of your leadership DNA, and your commitment to yourself to engage must be inviolable. All the technique training in the world is useless unless you commit to making challenging conversations a core part of every day.

Strategy, Tough Calls, and Performance, Oh My!

The most difficult conversations of my career congregate around strategy (direction) choices, operational and people decisions and just about every constructive performance conversation ever.

Strategy and other direction-focused conversations are challenging on all levels. If the strategy work/process is valid, you spend time striving to rethink your entire business and approaches. Add in the varying opinions and the omnipresent human and political biases, and these are some of the most robust discussions of your work life. Many firms and management teams fail at this work, in large part because they don’t trust each other enough to talk about the real issues of their situation.

While strategy discussions are tough, the people issues keep me awake at night.

From selecting the right people and unselecting the wrong ones, these decisions create ripple effects for teams, organizations, and the individuals involved. People are the difference makers, and you need to get this more right than wrong. From choosing the candidate no one else opted for to helping (or shoving) individuals into roles they perceived they weren’t ready for, these are profoundly important moments and conversations. Imagine what happens if you don’t have them. Nothing happens, and that’s a problem.

Performance discussions are the ones most commonly referenced in articles and books about challenging conversations. And while there are a few of these I would like back, these are also the discussions where technique can be taught. However, before the training takes root, you still have to find the courage to sit across from someone and open the conversation on their performance.

Courage backed by the belief in the importance of the discussion is essential.

Beware Management Teams That Can’t Shoot Straight

Every poor performing management team I’ve observed, coached, (or have been a part of) struggled to talk. Sure, there was a lot of talking, but it typically went in circles on the big issues. Lacking process, trust, and commitment to finding success together, most discussions in these settings devolve to power-plays of varying proportions. Typically, the central issue is someone’s drive to promote change and a lot of someones who resist change because it threatens their version of the status quo.

One CEO lamented to me, “The management team is collegial, but they won’t face the big issues. As a result, I’m going to have to change out the team, or we will jeopardize the future of our organization.”
Whether you’re leading from the top or leading teams somewhere in the middle, it’s imperative you break through the barriers that keep these groups from talking about their warts and blemishes.

Permission to Muddle and Massacre for the Right Reasons

While writing this sentence requires immense effort on my part, give yourself permission to muddle and massacre a few challenging conversations. I would rather you struggle and bumble than avoid the big issues.

Yeah, the Association for Effective Challenging Conversations (fake news…there isn’t one, but there should be) will likely revoke my platinum level membership, but so be it. I want you talking, not thinking about talking. As Peter Drucker suggested, “Actions in the present are the only way to create the future.”

Resolve to quit postponing or ignoring the conversations that stand in the way of resolution or forward progress. Remember, you don’t want Ron’s regrets.

4 Tips to Help Jump-Start Your Challenging Conversations

1. Lead with Empathy

Empathy is at the heart of every successful challenging conversation. I don’t care how well-baked and logical your business case or strategy is, if you are asking people to change something, this is an emotional discussion, not a logical one.

Your ability to attempt to see issues through the eyes of your audience may be the greatest superpower you will develop during your career (and life). As Dr. Mark Goulston suggests, make people “feel felt.” You do this by listening, asking questions, and showing the individual you are striving to understand how this issue affects them.

2. Create Discussions Not Monologues

I listened in on a role play in a workshop where an experience manager did just about everything right with feedback. She delivered it empathetically, focused on an observed behavior and linked the behavior to the individual’s and team’s performance. Brilliant, but it was missing something. It wasn’t a discussion. She started and ended and solved the problem for the other person. Except, she didn’t really solve anything. The other person heard the message but didn’t participate except as a passive receiver. That’s not how to communicate for results.

Every challenging conversation is navigated through open and free discussion. The best ones resolve with both parties working to design a way forward together. You don’t design solutions without dialog!

3. Ask This Question to Regain Traction

I love De Bono’s Six Thinking Hats approach, and I use variations of it regularly in my work. One of my favorite questions focuses on “positive framing” (yellow hat). When a conversation begins to slip and slide downhill in the mud, I like to reframe it with some variation of, “This is a challenging issue for sure. What will it be like for you when it’s resolved?”

It’s incredible how this shifts the negative talk toward the positive and how easily people begin sharing more about their interests (not positions) in the situation. As Keith Ferrazzi suggests, “If talking to someone is like talking to a brick wall, you’ve got to find the loose brick.” This question might help you identify that loose brick!

4. Give Control to Reduce Resistance to Challenging Topics

There’s a fair amount of psychology and research behind the idea that people naturally resist losing control and alternatively, gravitate to situations and solutions where they can control their fate. So, from the diary of Captain Obvious, give them power! Just do it strategically.

A few of my favorite approaches for ceding control include

  • Listing options and letting the other party add to the list.
  • Let the other party list all of the options for resolving the issue. (Remember, your focus is the issue. Ask yourself whether it’s really that important to dictate the outcome.)
  • Presenting three choices. (Two is too binary, one is a take-it-or-leave-it, and three opens possibilities.)
  • Asking the question, “Under what circumstances would you consider… ?

While there are many other techniques, remember, your goal is to keep the conversation moving forward toward a mutually agreeable resolution. If you’re following the first suggestion on empathy, your willingness to cede control reinforces your commitment to the individual and their concerns.

The Bottom-Line for Now:

Everything important in your organization and ultimately your career (and life) takes place via one or more challenging conversations. However, when you shy away from those conversations, you fail to bring to life the solutions and outcomes needed to succeed. They’re called challenging for a reason. Just don’t let fear slow you down. Instead, fear the conversations that aren’t happening. Those are the value killers!

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About the Author:

Art Petty is a coach, speaker and workshop presenter focusing on helping professionals and organizations learn to survive and thrive in an era of change. When he is not speaking, Art serves senior executives, business owners and high potential professionals as a coach and strategy advisor. Additionally, Art’s books are widely used in leadership development programs. To learn more or discuss a challenge, contact Art.

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