Frontline Supervisors: Courageous Conversations, Feedback, and Coaching

Written by: Michael Huff

Is there a conversation you are putting off that you know you need to have? If so, how many times have you had that conversation with yourself?

We ask this during our 3-day Leadership Fundamentals course. The responses are nearly universal: Yes, I’m avoiding a conversation. And yes, I’ve had it with myself more than five times.

So why do people avoid these moments? Why do otherwise strong leaders pause when it’s time to speak up? The reasons vary, including fear of hurting someone, fear of making the situation worse, and fear of being misunderstood, but each reason points to the same truth: Courageous conversations are complex but essential. They’re how teams grow, how we build trust, how performance improves, and how authentic leadership shows up on the floor, not just in the office.

Making the Case for Courageous Conversations

When you avoid tough feedback, it may feel like you’re protecting the person or the relationship. In reality, avoidance sends a different message, not just to that individual, but to the rest of the team about what your core values look like in practice. It may be uncomfortable to admit, but avoiding tough conversations is more about protecting ourselves from discomfort. If you care about your people and they trust you, they welcome feedback.

In one of our leadership training sessions, a senior leader shared a story that brought this idea home. Early in his career, a respected leader pulled him aside and shared something hard to hear. The message was simple, but difficult: the way he was treating people was hurting his ability to lead. What felt like a painful withdrawal in the moment became one of the most meaningful deposits in his entire career. You could hear it in his voice when he told the story: “I wouldn’t be where I am today without that conversation.”

Most people, when they look back, don’t resent the leader who cared enough to help them grow. No one likes to make mistakes or feel like they aren’t good enough, but most people do want to improve. That’s where real leadership emerges, by removing barriers, providing support, and caring enough to confront uncomfortable truths. As Craig Groeschel emphasizes, we should foster a culture where employees crave feedback. “Because I trust you to give me feedback, giving feedback is something I crave, need, all the time.”

Build Trust Before You Deliver Feedback

We introduce two concepts during Double E Workplace Solution’s  Frontline Leader Training to help leaders get there: finding the good and Covey’s Emotional Bank Account. When leaders focus on finding the good and acknowledging it, employees’ perceptions change. They recognize you aren’t just trying to catch mistakes, you’re also watching for success.

Covey’s Emotional Bank Account builds off of that concept. You have a bank of trust with everyone you interact with, where every interaction is either a deposit or a withdrawal. When you make enough deposits over time, the feeling of a withdrawal that often comes with a courageous conversation doesn’t wipe out the entire trust bank. I love how Mark Batterson puts it in his book, Please, Sorry, Thanks, The Three Words That Change Everything. “When you consistently compliment what people do right, it gives you ground for confronting them when they do something wrong.”

Feedback, especially when it’s constructive, might feel like a withdrawal in the moment. But when done with care and clarity, it becomes a long-term investment in that person’s growth and your shared trust.

Set the Stage for Giving Constructive Feedback

Before jumping into strategies for delivering feedback, let’s talk about timing, the environment, and everything else to consider before the big talk. Factors such as personal energy, location, time of day, and state of mind can derail the conversation if not taken into account. For instance, is the person going to complete a high-risk task that same day? If so, it might not be the best time to have the conversation so that they can stay focused.

What Matters When Setting the Stage

• Timing – Are they rushed, stressed, or about to do something high-risk?
• Environment – Private, distraction-free, psychologically safe, and appropriate for the message.
• Emotional state – Yours and theirs. Elevated emotions limit listening.
• Clarity of purpose – Why are you having this conversation, and what needs to change?
• Delivery approach – Clear and direct, not softened to the point of confusion.
• Trust level – Have you made enough deposits for this to land?
• Expectation management – No surprises that trigger fear or defensiveness.

The idea is to put yourself and the person receiving the feedback in the best possible position to manage workplace conflict. Our participants often recommend being specific, delivering the feedback in private, remaining fact-based, and even using the compliment sandwich.

How the Compliment Sandwich Dilutes Feedback

If you aren’t familiar with this strategy, it goes like this. You start with a positive, something the individual is doing well. Next, you jump into the meat, or the main reason for the conversation.  The meat section contains what needs to be addressed or fixed. Once everything has been covered, you close with a positive. Unfortunately, there can be a risk when you use the sandwich method.

Sometimes, the effort to soften the blow can confuse the recipient, but two out of three isn’t bad, right? Instead, aim for clarity. You’ve already put this conversation off long enough; the last thing you want to do is have it again, especially if you can avoid this pitfall. This is one you want to get right the first time.

The SARA Cycle and Feedback

Setting the stage also helps mitigate the SARA cycle. Surprise, Anger, Rationalization, and Acceptance are common emotional responses to unexpected or poorly timed feedback. Defenses can go up, and active listening may shut down when people are caught off guard. They may be wondering, ‘Am I in trouble?’ or ‘Am I being fired?’ and totally miss the message. When trust is already in place and the environment is right, people are far more likely to actually hear the feedback rather than fight it.

Being intentional about timing, environment, and approach doesn’t eliminate emotion, but it reduces unnecessary friction. It gives the other person a better chance to hear what you’re saying instead of reacting to how it feels. And that’s critical before we ever get into how to deliver feedback effectively.

How to Deliver Feedback That Leads to Change

A simple structure helps. In our training, we use the GROW model because it keeps feedback grounded, collaborative, and action-oriented. The GROW model was introduced by Sir John Whitmore in his book, Coaching for Performance.

Use the GROW Model for Coaching Conversations at Work

Think of GROW as guardrails for the conversation, not a script.

• What is the GOAL of the conversation? Start by clarifying what good looks like. What does success look like in this role, on this task, or in this situation?
• What is the REALITY of the situation? Here, you are seeking to understand through focused questions and empathetic listening. Discuss what’s happening right now. Stay fact-based and specific. This is where clarity matters most.
• What OPTIONS are available to you? Empowers the employee to reflect and evaluate options and other considerations. Identify options for doing it differently. Ask questions. Invite ideas. You should see ownership begin to shift.
• What is the WAY forward? Agree on what will happen next. What will change, by when, and how will progress be checked?

In our training, leaders don’t just learn this framework. They practice it. We provide them with a generic scenario to work through and then have them work through the courageous conversation they have been putting off. Participants write out their feedback using GROW, then deliver it to a peer in a low-risk environment. Afterward, they debrief. What landed? What felt awkward? Where did clarity slip?

Used well, the GROW model keeps the focus on growth rather than blame. It also signals that feedback is collaborative. It’s something we work through together.

This practice matters. It builds muscle memory, clarity, and confidence. By the time leaders step into real conversations, they’re no longer guessing; they’re ready. Sounds great in theory, right? The real test is what happens when leaders take it back to the floor. Here’s what participants shared after applying the GROW model to give constructive feedback in their workplaces.

• “It helped guide me in the conversation. It helped me to see improvement and align expectations and have the recipient own some accountability.”
• “The GROW model helped me get through a safety conversation with an employee.”
• “We just had our year-end reviews. Our manager adopted the GROW model for these conversations.”
• “Framing it with the GROW guidelines was definitely helpful. It was well received and didn’t get combative.”
• “I used the GROW model to clarify the impact of a mistake, and the employee—who’s usually defensive—was receptive. It drove accountability for him and improved performance across the team.”
• “It has helped us plan and prepare for conversations, primarily the Goal portion for alignment and understanding.”
• “I built confidence. I can have hard conversations now. I don’t feel stuck anymore.”

Courageous conversations will never be effortless, but they don’t have to feel reckless. When leaders prepare well, use a clear structure, and follow through, feedback stops being something to avoid and becomes one of the most effective tools they have to help people grow.

Equip your leaders to build a culture of accountability with clarity and confidence.

At Double E Workplace Solutions, we partner with organizations to develop leaders who coach effectively, communicate clearly, and follow through to strengthen trust and performance. Contact us today to learn more about our in-person or virtual leadership training options.