The most expensive, costly conversations in any workplace are the ones never spoken. These are the conversations about the significant issues blocking progress or, the behavioral issues detracting from high performance. The words left unsaid are genuinely the seeds of failure for individuals and organizations. Sadly, these conversations are missed, mostly because of a surplus of fear and a deficit of self-confidence. It’s time to solve this conundrum.

The two—fear and self-confidence—are inextricably linked when it comes to challenging conversations.

Complex, controversial, and potentially emotionally charged situations trigger a natural fear reaction because they create openings for conflict to enter the picture. Few of us willingly invite conflict into our lives and days, preferring to sidestep issues and individuals and keep the peace. A tenuous peace is preferable to open conflict in our minds.

The peace is tenuous and stressful because we recognize the inherent flaw in our logic. Avoiding the difficult issues keeps stress at bay. However, it also perpetuates a disagreeable status quo. I’ve lost track of the number of managers I’ve spoken with who are agonizing over and stalling on dealing with a visibly toxic and poor performer on their team. They’re stalling mostly because they are fearful.

Peel back the layers of this challenging conversation onion beyond fear, and you’ll find the self-confidence issue at the core. Specifically, you’ll find a lack of self-confidence as the issue. Fear is an outcome, like sweat from physical exertion.

The Wrong Way to Fix the Self-Confidence Issue:

Having overcome this conundrum with considerable pain in my management career, it might be easy for me to merely encourage you with cheerleading and motivational platitudes.

“Win one for the Gipper!”

“Get in there and just do it!”

“No pain, no gain!”

Yes, pushing you is easy, and there’s a ring of truth in the notion that you must engage to master this skill. And after all, I waded into these waters without much help and came out with most of my extremities intact. If I can do it, surely you can as well.

“It’s time for you to walk on hot coals!”


This approach is disingenuous and disrespectful.

There’s no cheering or imploring worth a darn in this case. Rather, the best counsel is to help you begin the process of building the skills and approaches essential for vanquishing fear and growing your self-confidence for challenging conversations.

One thing’s for sure, and it’s not a platitude: this is hard work. Here are four big ideas that will get you started on the right path. Dig deeper into each of them and most importantly, practice with them in live-fire settings.

4 Ideas to Help You Overcome Fear and Grow Self-Confidence with Challenging Conversations:

1.Frame Your Challenging Conversations Differently in Your Mind

Earlier in my career when I was deep into stalling on a particularly challenging conversation, a wise person who recognized this asked me a few questions:

  • Who is impacted by your not dealing with this situation?
  • What’s the best outcome you can expect for all stakeholders if you never deal with it?
  • How will others view you as a leader if you fail to deal with it?

The fact that 400 families would potentially be adversely affected by my inability to navigate this challenging conversation coupled with the reality that there was no upside from avoiding it spurred me to action. The reality that I care(d) deeply about the leadership example, I am setting for others through my actions hit me deeply as well.

If you’re in stall mode as I was, try reframing the situation with a bigger picture view.

2. Revisit the Fundamentals of Quality Feedback

Many of the challenging conversations we are avoiding or soft-shoeing our way through involve delivering constructive (the negative type) feedback. There are a host of reasons—none of them good—that we resist or water-down our constructive feedback efforts. Fear in one of its many forms is at the center of all of them. Revisiting and building the basics back into your conversations will help take much of the fear out of these discussions.

The short-course on feedback:

Internalize: feedback is used to promote those behaviors that contribute to high performance or eliminate or change those behaviors that detract from high performance.

Translation: you are operating on the side of goodness when it comes to feedback.

Every discussion must include at least two critical ingredients: behavior and business-focus.

99% of the time when feedback discussions go wrong, they are missing one or both of those elements. Review the purpose of feedback statement, and then make sure you are identifying an observed, specific behavior impacting (positively or negatively) performance.

And then tie this behavior to a business-issue.

There’s a lot more to developing, delivering, and managing feedback discussions (see my feedback series of articles), and there are other great techniques, especially feed-forward. However, get the behavior and business focus right and draw upon the unarguable purpose and intent of feedback and you are miles ahead of many managers.

Plan your opening sentence for the discussion around these items, and then promote a dialog on changing the behavior and you’ll be shoving fear into a dark, cold, lonely corner.

3. Use Message Mapping to Plan for Challenging Conversations:

Nothing beats the discipline of preparation. Of course, we’ve all heard the Mike Tyson quote, “Everyone has a plan until they’re punched in the face.” I offer guidance for the “punch” below. For now, focus on the plan.

Message mapping is analogous to mind-mapping, albeit with considerably more discipline involved. (See my article: The Career Enhancing Benefits of Message Mapping)

The short-form of this technique is to focus on building a communication map starting with a core message at the center, key supporting points/drivers at the next layer out from the center, and material evidence for each of those points at the outermost ring.

Once crafted, a high-quality message map allows you to plan for and navigate most issues and questions. A practiced communicator will always strive to find a way to bring the issue back to a point on the map—either at the outer evidence layer or inner core and move in or out from there.

Message mapping is a universal tool—a veritable Swiss Army Knife—for planning for challenging conversations. Building the map forces you to think through and clarify your messaging and supporting content. It offers a visual you can use to practice or to reference in a live setting. It’s a simple but not simplistic approach you can apply immediately.

Of course, when you are surprised by Tyson’s metaphorical punch in the face in your challenging conversation, you need something beyond the map.

4. Cultivate the Tools to Respond to Sudden Confrontations:

Many managers freeze in the face of confrontation. They move into a full-scale amygdala hijack as chemicals flood the body and fight or flight reflexes kick-in. My favorite technique for navigating this is to run through a mental reboot (See my article: How to Win When You are Under Attack in a Meeting). Part of this process involves using questions to buy time for your system to calm down and allow your brain to earn its keep.

If you invest the time to both develop a deliberate response to challenging confrontations, and you have some go-to questions to help the process, you are ready for nearly any situation.

Two of my favorite time-buying survival questions or prompters include:

“I can see this is important to you. Help me understand your situation a bit better.”

“I can imagine the challenges that have place you in this position. How can I help you navigate them?”

Neither of those prompters addresses the specific issue. Both are intended to show empathy for the individual and then broaden the discussion.

Many of us avoid challenging conversations because we are fearful of the unexpected. Armed with a well-practiced mental reboot process and some generic prompters to help gain context and buy time, once again, fear is marginalized.

The Bottom-Line for Now:

We are all apprentice communicators. It takes time and practice and ample failures  to learn to effectively navigate challenging conversations.  The fear you feel about dealing with that difficult employee is real to you, and no words of encouragement are strong enough to quell that fear. However, you can choose to study the discipline of communication and develop a toolbox of approaches and abilities. You have a great living laboratory to try the ideas out and tune them over time. Just remember, no one gets better at challenging conversations avoiding them. It’s time to engage!

Art's Signature