Need to have a Tough Conversation? How Can We Get Team Members to Engage in Difficult Conversations?
Author: Julie Chance, Founder of Action Strategies by Design
Here’s How to Help Your Team Communicate Clearly When Things Get Tense.
There’s a well-worn saying that “communication is key”. It’s easy to gloss over a phrase we’ve all heard a hundred times, stuck to office posters and PowerPoint slides. But behind its overuse lies a truth too easily overlooked. Communication is the lifeblood of every high-performing team.
The quality of a team’s communication, especially how they handle difficult conversations, is the difference between a team that thrives and one that fractures. In this edition of our High-Performing Teams series, we’re zeroing in on how leaders can best manage difficult conversations and conduct them in a professional, confident manner.
Leaders Need to Be Willing To Have Difficult Conversations
You can be doing a lot of things right as a leader, but if you avoid the difficult conversations, there’s only so far you and your team can go. Ironically, the same skills we use in everyday conversations, like empathy, active listening, emotional intelligence, and perspective taking, are what we need during these conversations. The challenge is that those skills become harder to access when emotions are high. And this is because our brain perceives high-stakes conversations as a threat, forcing our brains into a fight-or-flight response.
As the authors of Crucial Conversations: Tools for Talking When Stakes Are High1 — Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler explain, when we enter the fight or flight response, we handle complex human situations with the intellectual capacity of a mouse. In this moment, the conversations that demand our best thinking are most likely to trigger our worst instincts. So we react, defend, avoid, or lash out instead of responding thoughtfully. Not exactly inspiring, is it?
So, how do you, as a leader, break free from this instinctual response(and how do we help our team members do so)? The key is to stay grounded in your prefrontal cortex, the executive part of the brain responsible for rational thought. When we can keep ourselves in that space, we help others maintain their composure, creating the conditions for a more productive conversation, no matter how difficult the issue may be.
The authors of Crucial Conversations further point out how we act out our feelings in high-stakes situations instead of talking through the problem. We default to becoming passive-aggressive or ignoring the issue entirely. Yet, these are the conversations that matter most.
When done right, difficult conversations have the power to resolve conflicts, build trust, improve performance, spark innovation, and strengthen relationships.
This isn’t just theory—it’s backed by some compelling statistics showing employees skilled at holding crucial conversations respond five times faster to financial challenges and make smarter budget decisions. They’re also two-thirds more likely to avoid injury or fatal accidents in unsafe conditions. In fact, every effective conversation can save up to $1,500 in an 8-hour workday.
What Do Difficult Conversations Look Like In Real Life?
To bring this closer to home, here are a few real-life scenarios leaders across organizations navigate regularly.
- A client gives negative feedback about an employee, and now it’s your job to address it.
- A team member resists a new process or change initiative, and you need to get them on board.
- One person’s communication style keeps creating tension, but they don’t see it.
- Two team members disagree about how to move forward with a project and they are not talking directly to each other about the issue.
- You’re struggling to get timely information from another department, and delays are affecting your team’s work.
- A colleague keeps missing deadlines, putting pressure on your team to pick up the slack.
- There’s confusion or conflict over who owns which part of a cross-functional project.
- A team member is showing up disheveled or unprofessional, and it’s time for a conversation about expectations.
8 Steps to Preparing for Difficult Conversations
Timing can greatly affect the success of a crucial conversation. As much as these conversations need to be held close to the time a situation occurs, it’s often better to allow some time for emotions to settle. Here are a few tips on preparing for difficult conversations with your team and preparing team members to have these conversations with each other:
1. Identify Your Positive Purpose
The best conversations start with the right reason. Wanting to prove a point, isn’t it! Instead, think about what you genuinely hope to achieve, like improving a working relationship or offering helpful insight. Consider what you want for yourself, the other person, and the relationship as a whole.
2. Clearly Define the Desired Outcome
Define the outcome clearly and anchor it to the positive by focusing on what you want, not what you don’t want. Saying something like “Don’t interrupt colleagues during meetings” is like telling a dog not to jump; he’ll find other ways to act out. You want to reframe your goal positively: “Allow your colleagues to finish speaking before responding.” That kind of clarity leaves less room for confusion
3. Identify Positives
What do you appreciate about the other person? What strengths do they bring to the table? Recognizing those helps shift your mindset from adversarial to collaborative, and reminds the other person that this isn’t a complaint session.
4. Objectively Outline the Facts
Stick to the facts. Avoid sweeping statements like “You’re always late” and stick to specific, recent examples: “You arrived late to our last two meetings.” Use neutral, non-judgmental language. It keeps the focus on observable behaviors rather than subjective conclusions or assumptions.
5. Change Perspectives
Step outside your view for a minute. What might the other person be thinking or feeling? What outcome are they hoping for? You can even imagine how a neutral third party might see the situation.
6. Determine What You Need to Say
Consider role-playing the conversation as part of your preparation. A helpful technique is to have a colleague play your role while you take on the perspective of the person you’ll be speaking with. Also, remember that personality styles significantly influence how messages are perceived. You might need to adjust your approach depending on who you’re talking to. Tools like the Everything DiSC model can help you tailor your communication style to different personalities.
8. Do a Mindset Check
Finally, take a moment to check your mindset. Are you calm? Focused on the positive purpose? Ready to listen as much as talk? A grounded mindset helps you navigate any unexpected turns with grace.
Navigating the Difficult Conversation
Let’s assume you’re clear on your positive purpose and have done all of the work to mentally and emotionally prepare for the difficult conversation (good for you!). Now we move on to the conversation itself.
Deliver the Message in Person
Ideally, deliver your message in person and as close to the event as possible. If you can’t be in the same room, a video call is second-best, followed by a phone call. Text and email are not an option!. With sensitive conversations, there’s too much room for things to go sideways when you rely on written words alone.
Set the Context and Ask Permission
Start by setting the stage and asking if it’s okay to have the conversation. It can be as simple as, “There’s something I’d like to discuss with you. Is now a good time?” This small step invites the other person into the conversation instead of springing it on them. If you know what motivates them, tie your feedback to their goals. For example, “Sue, you’ve mentioned wanting to move into a leadership role.”
Describe What You Saw and Why It Mattered
Keep your feedback focused on a specific behavior or action, and speak from your perspective. What did you observe? What was the impact on the situation then, and how is it affecting things now? Be prepared to discuss the consequences of their behavior vs. intent. If you’re playing catch and throw a wild pitch that breaks a window, you didn’t mean to break it (intent). But the window is still broken(impact). It still needs to be fixed.
Ask for Their Perspective
It’s important to give the other person space to share how they see things. Conversations go better when people feel heard. They may provide insights you hadn’t considered, which can help refine your approach to resolving the issue.
Own Your Piece
If expectations weren’t met, start by reflecting on whether you communicated them clearly. For example, saying “I understand that I may not have been as clear as I needed to be regarding my expectations. From my perspective, I was expecting your team to take on a bigger piece of the implementation” shows ownership and opens the door for productive dialogue.
Collaborate on a Solution and Follow Up
From there, work together on what moving forward looks like. What needs to change? What support is required? Involve them in designing solutions rather than imposing fixes unilaterally. This brings about ownership of change and increases commitment to implementing improvements.
Offer Support and Celebrate Success
Provide ongoing support as they work toward behavioral changes or solutions. Additionally, acknowledge progress when a team member succeeds in making adjustments or contributing positively. An effective strategy used by basketball coach Phil Jackson is offering five positive comments for every critical one over time. Research supports this approach, showing that teams with a 5:1 ratio of positive interactions perform better overall.
Want your team to get better at having difficult conversations?
Getting better starts with you. Leaders need to be skilled at navigating them, because that’s how team members learn: by watching, being coached, and by experiencing it done well.
The Work Smart Module for Managers is built for this. If your organization or team leaders need support in handling and helping team members handle crucial workplace conversations, this is a great place to start.
To assist you further, we have also included a free tool (Planning Worksheet) to help you approach a difficult conversation. Download it here. You can also check out our Guide to Having Difficult Conversations whitepaper.
1. https://trans4mind.com/download-pdfs/Crucial%20Conversations.pdf