Like most leaders, I am in a position in which I must occasionally have conversations with people that I would much rather avoid. I had to confront someone recently. I had to address a problem that had come up. This is never an easy conversation to have and one that could easily go wrong. A conversation like this should not be rushed into quickly, but prepared for carefully.
Here are a few things I have learned over the years about how to confront carefully.
Engage the Person Respectfully.
No matter what the issue is, or how terribly they may have messed up, when you meet with the person be respectful of them as a person.

This is not a time to make them feel inadequate, but a time to be clear on what they are doing wrong and how it can be fixed. Ideally, the goal is to fix the situation even as you maintain a good relationship.
Confront Prayerfully.
One of the ways to make sure that you are being careful is to ask God to guide your conversation. Ask God into the conversation. Ask God for wisdom. Ask Him for the ability to listen and truly hear the other person to make sure you are not making assumptions as you confront. Pray about this beforehand, and during, and even after so that neither you nor the person you spoke with will misconstrue things that came up in the conversation.
Clarify the Issue.
It helps to clarify the problem. Make sure you know what it is that you are addressing. This is not about some vague feeling something is wrong, or doing something because someone else is pressuring you. If you are going to confront someone, you must be clear on what the issue is. Clarify the issue in your mind, and then be clear when you address it in your conversation. If you need to, write down a few key points, or even the main statement you want to make so you don’t waffle in the middle of the conversation and back off the issue to the point the person has no idea what you are addressing. You want to make sure you address the issue correctly.
Determine a Solution.
If you are addressing someone about a problem, it is essential that you have an idea of how to fix the problem. Simply pointing out a problem doesn’t solve the problem. Once you are clear about the issue, then become clear on one or more ways of addressing it. If the issue demands one specific response – for example, “be on time”, then be clear that is the response required. If the issue allows for a number of solutions, identify a few options that the other person may choose from. Make sure that the solution matches the problem.
Arrange the Meeting.
Where you meet will determine the atmosphere, and even the conversation. If there is a specific problem about a role at work, then meet in your office, or the board room. If there is an issue with someone you know well, and you want to be less confrontational, you might do it over a coffee, or a meal. Remember that when and where you have the meeting will play into how the confrontation will go. It might be good to give the person a heads up about what you will be addressing.
Listen as you Converse.
As you point out the problem, listen to the response from the other person. You want to make sure, first, that you are correct in your own understanding of what they did wrong, but also listen to make sure they understand what you are telling them.

Be clear and precise on the problem. Allow them an opportunity to defend their actions or clarify why they did what they did. Present the solutions as you see them, and then invite a response to see if they understand and whether they will respond as you need them to.
Know Your Next Steps Ahead of Time.
When you confront, you need to be clear on what you will do based on how they respond. If they agree with you and accept a solution to try, then you have made good progress. If they deny everything you are saying and try to blame others, you need to know if you will give them another chance or if it is time to part ways. If you are willing to move ahead together, you may want to set up follow up meeting with them soon after to see if issues have been resolved or not.
Confront carefully. You want to be clear what you the problem is and what the solution can be. You also want to be clear that you are focusing on the work the person is doing or how they are relating to the rest of the team, without putting them down personally.
Yes, we do need to confront occasionally. Hopefully we do it well. We want to honour the person and honour Christ even as we have the tough conversations.
Keep looking up,
Andy Wiebe