How Do I Confront My Boss?

I saw a sign that said: “Tell your boss the truth and the truth shall set you free.” It made me smile, but for a lot of staff that’s not so funny.

Have you ever wanted to confront your boss? Did you do it? How’d it go?

I wish we could have coffee and I could hear your story because I have great passion for this unique relationship between boss and employee to flourish. Yet I’m aware that similar to a marriage, it’s just not always that easy.

This might surprise you, but most of the time that I do get to hear a story about this issue in churches of all shapes and sizes, the answer to that question is “no.” The staff member never confronted their boss. Sometimes that’s a good thing. The confrontation wasn’t needed, or perhaps it was even inappropriate.

But most of the time they should have gone for it. That’s part of the foundation of a healthy and productive relationship.

Some bosses are humble and receptive, and others — well not so much. Confronting your boss can be very intimidating. You might lose your job. But the flip side is, do you want to continue in a difficult position?

If the issue that’s bugging you is not a big deal, then let it go. But if you tell yourself to let it go, then you need to let it go. If you don’t it will eat at you, and you’ll begin to dislike your boss, and your perspective will become skewed. By that I mean, you’ll see everything through dark-colored glasses and no boss can survive that. And neither will you.

The real issue always boils down to two things, why and how.

  • Why do you want to confront your boss?
  • How will you confront your boss?

These are two critical questions, and their outcomes have a significant bearing on how well you do in your job and how much you enjoy it.

2 important questions to consider:

1) Why do you want to confront your boss?

There are good reasons to confront your boss, such as:

  • You want to understand something about your working relationship that you don’t understand.
  • You have too much on your plate with no options for help.
  • You want clarity about expectations. You’ve tried, but it’s not working.

Sometimes the reasons are more subjective, but still good to pursue, such as:

  • You disagreed with a decision that you felt strongly about.
  • You feel that part of your job is unreasonable, or your boss lacks empathy for what you really do.
  • You feel the relationship lacks mutual respect.
  • You were passed over for a promotion or an opportunity that you wanted, and you don’t know why. 

5 guidelines to follow before you confront:

  1. You sincerely want to serve your boss well.
  2. You enjoy your job and want to work at the church.
  3. You are not gossiping to friends about the situation.
  4. Your motives are pure, you want your boss to succeed.
  5. You have prayed and asked God for guidance.

The best frame of reference for the reason you confront is that you want a mutually beneficial outcome.

Specifically, that both you and your boss enjoy a better working relationship. Besides, the church realizes greater productivity and a healthy model of Christian relationship.

Now, let’s tackle this issue where the rubber meets the road, that is, how you confront.

2) How will you confront your boss?

Let’s start with the hard part. You report to your boss; they don’t report to you. Hopefully, that formal authority structure doesn’t reflect the nature of your working relationship, but if it does, keep in mind, that’s not unreasonable.

Most of us prefer a warm and personal working relationship, but it’s not wrong or bad if the relationship is more formal. The principle here is that there is little point to confront what is subjective and not likely to change, especially if it’s just a matter of preference.

Decide to confront only on issues that matter, will contribute to a better working relationship, and greater productivity for the organization.

Keep in mind, the goal is not to “fix” your boss, but always feel free to speak up on an issue that matters regarding your working relationship.

5 guidelines for a smart and successful confrontation:

A) Clear your heart for a pure motive.

It is wise and honest to acknowledge that as human beings it’s impossible to have completely pure motives. We all have a selfish side. But with sincerity, clear your heart with God in prayer that you genuinely want the best for your boss, the church and yourself.

B) Show genuine respect.

There’s a reason God and others have placed your boss in a position of leadership over you. Honor that. Even if you disagree with a few things, your boss deserves your basic respect.

Begin the conversation with the positive reason for bringing this issue to the table and communicate the positive outcome you hope to achieve. If you don’t know what you hope to achieve, you are not ready for the conversation.

C) Bring the confrontation in a timely manner.

If something is bothering you, don’t hold it for months and months. That only makes things worse. The sooner you talk about it, the better.

The flip side is to give it enough time to know it’s an issue that is actually worth confronting.

Be smart about your sense of timing. Don’t ask for the conversation in a time of high stress, personal pressure or looming deadlines. It’s not that you are waiting for a perfect time, but the best time for the best result.

D) Present a well thought through solution.

It’s so important to show up, as I’ve mentioned, knowing what you want. Nothing is more frustrating than a conversation with someone who wants change but doesn’t know what that change is.

This doesn’t mean your solution is the only right solution, but it’s very common that your boss may just say yes. He may apologize saying he didn’t realize or thank you for a good idea. Or, both of you come up with an ideal solution together.

E) Listen carefully and own some responsibility.

Prepare well to communicate your point from the heart. Get to the point quickly without rushing. Do you best to be relaxed, remember you want the best for both of you and the church, that helps you relax.

When you have shared your basic thoughts with your boss, (should take only a couple minutes), then stop and listen. The following conversation may be long, but your initial impressions should be clear and concise.

When you’re in the conversation, it’s vital that you own some of the responsibility for whatever the situation might be.

These conversations are not always easy, but they are worth it.

I love this quote by Josh McDowell:

“It’s always better to resolve a conflict than to dissolve a relationship.”

Josh McDowell

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