How to Wisely Navigate a Difficult Conversation with Your Boss

Have you ever felt the need to have a difficult conversation with your boss?
Did you do it?
How’d it go?

I wish we could grab a coffee right now so I could hear your story. I have great passion for seeing this unique relationship between a boss and a staff member truly flourish. There is so much potential for meaningful, enjoyable work, when you are aligned. Yet, I’m fully aware that just like a good a marriage, it takes work – it isn’t always easy.

It takes two to tango, right?

Conflict is rarely a one-sided situation. Even with two good and reasonable people there are:

• Communication breakdowns
• Pressures unknown to the other
• Misunderstandings
• Unclear expectations

If the issue that’s bugging you about your boss is not a big deal, let it go. Give them grace and stay focused on doing a good job.

But if you tell yourself to let it go, you need to let it go. If you don’t it will eat at you, and you may begin to dislike your boss, causing your perspective to become skewed. By that I mean, you’ll see the situation through dark-colored glasses and no boss can survive that. (And neither will you.)

There are times, however, when it’s reasonable to have that tough, maybe intimidating conversation.

Candidly, it usually goes better than you expect if you handle it with wisdom and good intention – which is the intent of this post.

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

There are two essential questions to consider, and their outcomes have a significant bearing on how well you do in your job and how much you enjoy it.

2 essential questions:

1) WHY do you want to have this tough conversation?

There are good reasons to have an honest conversation with your boss, such as:

• You want to understand something about your working relationship that doesn’t seem reasonable.
• 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 major decision that you felt strongly about.
• You feel that part of your job is unreasonable, or your boss lacks empathy for what you do.
• You feel the relationship lacks mutual respect.
• You were passed over for a promotion or an opportunity that you wanted and genuinely would like to understand why.

5 guidelines to follow before the conversation:

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 your reason to have a tough conversation with your boss is that you want a mutually beneficial outcome.

Specifically, that both you and your boss enjoy a better working relationship, and others see a healthy model of Christian workplace relationships.

It’s usually wise to refrain from having a tough conversation based on a one-off situation. Everyone can have a bad day. It’s better to initiate a conversation like this based on a pattern of some kind.

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

2) HOW will you navigate this tough conversation?

Let’s start with the hard part. You report to your boss; they don’t report to you. Hopefully, that formal authority structure does not 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.

Deciding to deal only with issues that matter will contribute to a better working relationship, and greater productivity for the organization.

5 guidelines for a healthy and productive conversation:

A) Clear your heart for a pure motive

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

B) Lead with genuine respect and positive intent

There is a reason God and others have placed your boss in a position of leadership. Honor that. Even if you disagree on certain things, your manager deserves your basic respect. 

Begin the conversation by stating the positive reason you are bringing this issue to the table and clearly communicate the constructive outcome you hope to achieve. If you don’t know what you hope to achieve yet, you aren’t quite ready for the conversation.

C) Choose a wise and timely manner

If something is bothering you, don’t hold it for months — that only allows the tension to build. Usually, the sooner you talk about it, the better.

The flip side, however, is giving yourself enough time to ensure that the issue is actually worth addressing.

Be thoughtful about your sense of timing. Avoid requesting this meeting in a time of high stress, personal pressure or soon-approaching ministry deadlines. You aren’t waiting for a “perfect” time, but rather the best time for a healthy result.

D) Present a well-considered solution

As mentioned, it’s important to show up knowing what you want. Few things are more frustrating for a leader than a conversation with someone who wants change but doesn’t know what that change should look like.

This doesn’t mean your solution is the only good option. And, you might be surprised by how often a boss will simply say yes, thank you for a great idea, or even apologize for a blind spot. One of my favorite remedies is when you build an ideal solution together!

E) Listen actively and share the responsibility.

Prepare well so you can communicate your heart clearly. Get straight to the point quickly without rushing. Stay relaxed and remembering you want the best for the church and your supervisor helps you remain at ease.

Once you have shared your initial thoughts (which should only take a couple of minutes), stop and listen. The dialogue that follows may be long, but your opening framing should be concise. As the conversation unfolds, look for ways to own your part in the situation. Healthy partnerships require shared responsibility.

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

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

Josh McDowell