Courageous Communications, Part 4: Holding Tough Conversations

Updated: May 8

This post continues our series on courageous conversations. In Part 3, we discussed how to prepare for one. Now, let’s talk about the talk itself.


A long time ago, in a galaxy far, far away (Yeah, gratuitous Star Wars reference), I worked with two leaders at roughly the same time. They worked for different organizations, but I was struck with how similar they were.


Both had a great sense of the strengths, weaknesses and potential of their respective organizations. Both had a great feel for their groups’ strategy and relative position in the marketplace. Both understood financial issues. Both had earned a great deal of respect from their peers, managers, direct reports for their intellect, knowledge and understanding of the business.


They differed in several ways, but one critical aspect really distinguished them: their willingness and ability to carry out courageous conversations.


“Samantha” would initiate the courageous conversation whenever when she saw something that needed to be addressed. She had no problem confronting anyone when it was necessary – boss, peer or direct report. In every conversation, she made sure they understood her point of view. And, (again, when appropriate) she actively sought out their point of view on the conflict rather than dictating her point of view. More on this idea later.


“Dave” took the opposite approach. He was just as perceptive as Samantha, so he knew when he needed to address a problem face-to-face. But he couldn’t bring himself to do it. Worse, in his frustration, he would occasionally discuss the lingering problem – but with another colleague, not the person who needed the feedback. He simply lacked the courage to confront others directly.


I probably don’t have to tell you that Samantha’s career has continued to progress. Dave’s career plateaued.


This is not an isolated case. We have seen dozens of otherwise talented leaders hit the proverbial career wall because they lack confidence and/or capabilities to gracefully manage the courageous conversations.


How can you be more like Samantha?


Frameworks not Scripts

First, we don’t believe in scripts. Memorizing a few key phrases – whether you’re greeting guests in a restaurant or holding a tough conversation with a peer — isn’t genuine or effective. Courageous conversations are interactive. They require deep listening to what your conversation partner is saying and feeling and really “hearing” the message behind their words. If you’re working from a “script” and the other person is not – and they won’t be – the conversation will be off-script from the start. You’ll either not hear or process what your partner is saying, or you’ll be following your script, but ignoring him or her. That’s a monologue, not a conversation.


We prefer frameworks…outlines of the key principles that apply. Having a solid framework allows you to fully engage in the rich dialogue that tough conversations require.

So, let’s talk about a framework for holding effective courageous communications.


Master the First 30 Seconds

You must get to the point quickly. You’re having the conversation because you want one or two specific things to change, and you know how you think they need to change. So say that. Define the problem. Think of the problem as a gap between what is actually happening and what needs to happen. Describe that gap, and clearly explain what you believe your coworker needs to change. Then, usually, listen to your conversation partner’s point-of-view.

If you stammer, fumble, muddle your words, or are not clear in any way, you leave much room for confusion and misinterpretation. Which can make the situation worse, not better. To master those first 30 seconds, you may need to practice what you’re going to say. And, sometimes, it makes sense to practice with a practice partner who can give you the feedback you need to make sure your message is completely clear.

What if you have more than one or two specific things that need to change? If that’s the case:

  • That’s a pretty good sign that you’ve waited too long to hold this conversation and

  • You probably need to have more than one conversation.

If you bring up a laundry list of issues, your coworker is likely to feel like you’re piling on and will respond defensively. Pick one or two issues – perhaps the most critical problem, or maybe start with a problem that’s relatively simple to solve so you both can get a “win” under your belts before addressing the next issue – and table the rest.


Don’t sugarcoat or turn the conversation into a compliment sandwich

A lot of us have been taught the script of “say something positive, give people the critical feedback and then close the conversation with something else positive.” That script is a recipe for communication disasters.


Because of the way we filter the information we’re exposed to, most people hear the positive items at the front and back end of the script, and get confused by, or totally miss, the important stuff in the middle of the compliment sandwich.


You’re having the conversation because you need to address something important. Starting with language that pretends this isn’t serious, or isn’t on point, just confuses the person who needs to receive your feedback. Besides, the other person very likely knows you’re there to discuss an important problem. If you start the conversation with a compliment, she’s just waiting for the shoe to drop.


Engage in Dialogue…most of the time. Adapt accordingly.

If this is the first time you’re addressing the issue, you want to check your own thinking and engage in joint problem solving. Why is there a gap? Does the other person perceive the situation the same way you do? If not, why not? And how will you mutually resolve the situation?


If this is the third time you’re discussing the same issue, you probably don’t want to spend much time listening to what your coworker has to say. At this point, it’s probably time to tell them what has to be done and explain the consequences to the organization and to the person if it doesn’t happen.


Manage the Conversation within the Conversation

Tough conversations often involve a significant level of emotion for both you and the other person (or people) involved. Pretty clearly, you need to keep your emotions in control. And, as importantly, be prepared for a wide range of emotions from the other(s) involved. Managing the conversation within the conversation means:

  • Deciding if you need to confront any issues or emotional reactions that come up

  • Deciding what you’re going to confront

  • Mastering the opening of that conversation (“Your reaction (anger, yelling, clamming up, etc.) is getting in the way of us having a productive conversation.”)

  • Resolving that issue (if possible within the conversation)

  • And, then, getting back on track with the initial conversation. (Or, making the decision to break off the conversation to let the emotions subside and then getting back together at some clearly defined point in the very near future.)

Close clearly

Make sure there’s no confusion about the issue, why it’s important, what both you and your coworker are committing to change, and what your time frame is to make the change. When will you talk again?


What do you think?

How well have you handled the tough conversations you’ve had to have with others? Which of the items in this framework do you handle well? Where could you use some improvement? Is there anything that you would add to this outline? Let us know what you think in the comment section below.



Intrigued by what you’re reading? Download our white paper on converting strategy into execution and learn more about us by visiting our website. WhiteWater International Consulting, Inc. helps organizations understand the challenges they face and helps enterprises achieve and sustain outstanding performance through unleashing the passion and capabilities of its people. Because an organization is only as good at the people who power it.

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