Tips and Insights

from Lange’s communications thought leaders

Preparing for a Tough Conversation? 5 Strategies for a Better Outcome

Image of two coffee mugs and the hands holding them

by Jenna Lange

Looking at the headlines recently, you can quickly surmise that leaders—especially those in the tech sector—are having tough conversations right now. Managing conversations about org changes, layoffs, budget cuts, travel restrictions, and more—all the while, trying to manage a healthy relationship with their team, and keep them inspired. A tall order!

As an executive communication coach and consultant, I hear about good and bad outcomes from these high-stakes communication moments. Those leaders who have difficult conversations, provide hard-to-hear feedback, or talk through layoffs in a way that is emphatic, respectful, and poised usually use some, if not all, of these five strategies.

Tip #1: Manage your mindset

Challenging communications must begin with your mindset.

What do I mean by that? I mean we need to reset how we are thinking about this “tough” conversation. By simply having negative thoughts about the meeting before it’s even happened, we are setting ourselves up to think in a combative or defensive way. Just saying “tough” puts us in a frame of mind that might make us dread an outcome. Think about how “tough” shows up on our face, in our bodies, in our hands. When we are so focused on TOUGH, we look like we’re headed into battle, versus into a conversation!

This is an opportunity to change your perspective. Come at it with the attitude of, “I am ready to be enlightened, to learn something. I am curious and eager to have answers or a resolution. I am leading with compassion and presence.” Your thoughts are the most important switch you can flip in deciding how the conversation is going to go. 

Next, think about finding joy. No, I’m not crazy… this tactic helps shift your mood in just a few moments. It works, I promise! We start many of our workshops with this exercise, adapted from Wendy Palmer: Lift, Lighten, and Settle. 

Here’s what you do…

LIFT: Inhale – take a deep breath. 

LIGHTEN: Think of something that brings you total joy, whether it’s your favorite vacation, a hike, or your kids. Take five deep breaths and think about this person or thing or experience. For me? Fresh chocolate cookies, right out of the oven. Pure joy, every time. 

Now, it only works if you are intentional and focused. Choose something that instantly puts a smile on your face; something that makes you feel lighter.

SETTLE: Relax your shoulders, settle into your seat or stance, and be present.

This technique centers you on the long game of life, the big picture. It serves as a reminder to you that this difficult conversation is just one moment in time. It anchors you and helps you stay present and grounded.

Tip #2: Think about your audience’s perspective

Okay, now that you’re feeling more positive, it’s time to think about the other person. What is their objective? What can you deduce what they are thinking, feeling, and wanting? You may know the answers, or you may have to give it your best guess. But it’s time to put yourself in their shoes and truly come at the conversation with curiosity. 

Next, consider your perspective. What do you think, feel, and want? 

Being thoughtful about how you feel and how you perceive your audience to feel is critical to ensuring they feel heard and that you protect the relationship. 

Tip #3: Plan for how you’ll structure your conversation

Without keen preparation for this conversation, you are likely to talk too much, over-explain, or over-apologize. You might easily slip into defense mode. And, if you’re nervous, it’s going to show up in how you talk and in your body language. 

There are two structures that are very effective for difficult conversations. 

Conversation Structure #1

With this structure, you deliver the news in a concise way and you own your part in it. Then, you WAIT for their reaction. You want to make sure they feel acknowledged and know that you are listening. Wait it out until you get a response and then you acknowledge their feelings – which may include an apology. Finally, you ask if you can help in any way moving forward, or you discuss the next steps. 

To recap, the structure looks like:

  1. Concisely deliver the news “I can’t give you that promotion right now…”

  2. Wait for the response. 

  3. Acknowledge their feelings “I understand that you’re frustrated…”

  4. Ask how you can help or figure out the next steps “Let’s put together a plan and document it next week…”

Conversation Structure #2

This next structure may be even more common and effective in the workplace. I like this version for its flexibility. 

First, you talk to the other person about how you’ve observed something. For example, you may have noticed behaviors from this individual that do not sync up with company values. You let them know what you are seeing, and then you explain to them that when you observe this, you’re telling yourself a story. The story leads you to assume, to believe…what? This is what the conversation is all about. 

Then, you ask them if it’s true – are you correct in your story and your assumptions? Or, are you understanding it all wrong? 

This opens the door for them to ask questions, explain themselves, and respond – hopefully in a manner that is productive and enlightening, versus defensive. 

Finally, you can respond to their explanation. Either you two are on the same page or perhaps their behavior or explanation is still not in line with your values or your needs. This is the time to clarify in full. 

Here’s what this structure might look like:

  1. You share what you’ve observed (“I noticed that you’re not committing to a product roadmap for this coming year.”)

  2. You share what that makes you think/feel/assume (“When I see that, I assume you’re either over-committed or unsure of budget…It’s important to me that the members of my team demonstrate clear leadership in….Is this correct?”)

  3. They respond and you earnestly listen. 

  4. You acknowledge their accounting and discuss the path forward and next steps. “Thanks for sharing… I’d like a follow-up meeting next week on…”)

Tip #4: Practice your delivery

You don’t need a word-by-word script for your conversation, but make sure you practice the flow a few times. Say it out loud, record yourself, or use a mirror. You may be displaying unintended body language (facial expressions or posture) that diminishes rapport or confidence.  

Your clear and crisp delivery is important to shift the conversation away from blaming and into a mode of “explaining and understanding.” Above all else, do not get defensive. The moment you turn defensive, the entire conversation will crumble. Be prepared to listen with an open mind.

Tip #5: Manage the relationship

Don’t let the conversation pass without considering what needs to be done to protect the relationship. You may want to ask the other person, “Are we okay?” 

Or, if they are feeling sensitive or defensive, you may want to give them several days to let the conversation soak in before you send them an email, “Checking in on you, are we good? Do you want to talk?”

Follow through is so important to ensure they feel heard and cared for. Do not skip this important step! 

Become a confident communicator.

At Lange International, we frequently work with executives one-on-one, or with their entire team, to ensure they are confident and prepared for every high-stakes communication moment. We guide them on everything from stage presence and sales kick-offs to team motivation and negotiation to impactful writing and presenting. Interested in a keynote, workshop, or retreat? Contact us – we’d love to hear more.

Jenna Lange