April 27, 2017 Clay Scroggins

3 Key Ways to Approach Hard Conversations with Your Boss

With the right approach, you can handle hard conversations successfully. With the wrong approach, it doesn’t matter if you’re right or wrong; it won’t work.

Working for a great leader has many benefits. My favorite aspect of working for Andy Stanley is that I feel like I’m getting a graduate-level leadership degree just by observation and osmosis. Every leader has their greatest hits of leadership maxims, those phrases and sayings that come up time and time again. As for Andy, what I have learned from him about approach is definitely on my “Best of” list for him.

Everyone has had a conversation derailed because they had a poor approach. We have all been in conversations where we were right, but we ended up apologizing because we had the wrong approach. The way you approach or lead into a conversation can often trump the content of the conversation.

With the right approach, you can say just about anything. With the wrong approach, it doesn’t matter if you’re right or wrong; it won’t work.

When I was first married, my desire to be right would cause me to bring more energy and passion to conversations. I remember being at a restaurant with my wife. There was something wrong with the food and I was clearly right. But the tone I used in speaking with the server about the issue really bothered my wife. I was right in sending the food back, but before I could be on the same page with my wife, I needed to apologize to the server because of how I approached the situation.

Approach is everything. With the right approach, you can say just about anything. With the wrong approach, it doesn’t matter if you’re right or wrong; it won’t work. This applies in your communication with your boss as well. Recognizing the importance of a correct approach can drastically change your workplace and allow you to be heard. Here are 3 key components of a good approach:

Adjust your approach to fit the person.

In order to know what approach to take, you need to be deeply acquainted with your boss’s wiring, temperament, and personality. In the same way great spouses study each other to have great marriages, you need to study your boss. There’s a lot you can do to get to know your boss’s style without taking it too far. Our kids crack up every time at that line in Planes: Fire and Rescue when Lil’ Dipper whispers to Dusty, “I like watching you sleep.” I wouldn’t suggest stalking your boss, but landing somewhere just short of that is a great idea.

What is your boss’s personality type?

Is your boss more concrete or abstract?

What level of detail does your boss need?

How does your boss like to receive information?

Do you need to send an email ahead of time with all the details or should you follow up with an email after the conversation?

These are all questions you can ask your boss when emotions are low. But later on, during challenging conversations, having done your homework will pay off. The bottom line is that you do some homework and learn the approach that best fits your boss.

Declare your intentions before you challenge.

Every great wedding gives the bride and groom a chance to declare their intentions. This is where they publicly say what this is all about, and I really appreciate that. You don’t spend that much money, invite all those people, and waste our time by not making it clear why we are all there. And the same is true when you need to have a difficult conversation. Declare your intentions up-front. It’s like clipping a carabiner to a harness. If something goes awry, your declared intentions provide a safety net for you in a free-falling conversation. Here are a few examples:

  • “I really believe in you and I love working for you. I have something I want to bring up that could really help us grow. Maybe I’m missing something, but I think this might be a better solution for all of us.”
  • “I think I’ve identified something that is holding us back and if I were in your shoes, I would want to know what it is. And I think I have an idea for how to solve it. Would you mind if I shared that with you?”
  • “I want your advice on something. I have an idea that I think is going to make us better, but I want to know what you think about it. I’ve thought a lot about it. It might initially create some complications, but in the end, I think we’ll be glad we made the change because of the results it could produce.”


How you start out and what you say here is so crucial. Before you get up in anyone’s space, trying to throw around your brilliant ideas that have the potential to wreck someone else’s world, lead with a clear statement of your intentions. You’ll either be glad you did or regret you didn’t.

Ask questions of curiosity and mean it.

One of the consistent pieces of feedback I receive about my leadership is that I have a tendency to move too quickly. When that happens, I jump to conclusions that may or may not be true. When I misjudge someone, it negatively affects the relationship. No one likes feeling judged even when it’s spot on. Being incorrectly judged is difficult to deal with on multiple levels.

Disciplining myself to lead with questions helps me avoid the trap of rash judgments. Curious questions cause humility. Lately, I’ve started beginning every important conversation similar to this: “I’ve got a lot of thoughts about this situation, but I know you do as well. Tell me how you’re processing it.” This is crucial for me. Incorrect assumptions create walls and cause humiliation. If you would choose to lead with questions during the challenging conversations, it will teach you something, it will build trust, and it will save you some embarrassment.

This excerpt was taken from How to Lead When You’re Not in Charge by Clay Scroggins.


One of the greatest myths of leadership is that you must be in charge in order to lead. Great leaders don’t buy it. Great leaders lead with or without the authority to lead. Join Clay as he interviews some of today’s most effective leaders in this free, one-time, two-hour event that will help you unleash your influence, no matter what seat you’re in. Register now.

Print Friendly, PDF & Email
, , ,

Clay Scroggins

As lead pastor of North Point Community Church, Clay Scroggins provides visionary and directional leadership for the local church staff and congregation. Clay holds a degree in industrial engineering from Georgia Tech as well as a master’s degree and a doctorate with an emphasis in online church from Dallas Theological Seminary. He lives in Forsyth County, Georgia, with his wife, Jenny, and their four children.
Loading Disqus Comments ...
Loading Facebook Comments ...

No Trackbacks.