Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

Working with a Difficult Direct Report

Dear Brittney,

I have a direct report. He is very volatile, not at all a team player. Everyone gets along great in the department except him. He always tries to point out everyone’s faults but not his own. He is very difficult to talk to. How can I overcome this?

Leader of Difficult Direct Report

Dear Leader,

Nothing tests your confidence and motivation as a leader more than a difficult direct report. When I first had the opportunity to manage people, I naively thought, “Wow, I’m pretty good at this.” My small team was efficient, avoided drama, enjoyed working together, and executed well. Surely, I thought, I must be a natural leader.

A few years later, I took a new role and had the opportunity to manage a new team. This team included people with various levels of experience, dynamic personalities, and even what I categorized as a few bad attitudes. I entered the role with naïve excitement that faded quickly. Leading this team wasn’t easy and I struggled to do it well.

So, I empathize with your challenge. It only takes one difficult direct report to make your job as a leader challenging. And it sounds like in your case, this direct report is also making it miserable for others on your team. Let me share a few tips to help you navigate this situation.

Embrace This As YOUR Responsibility

Recently, I overheard one of my colleagues say, “I realize, that as the senior employee and as someone in a leadership role, it’s my responsibility to ensure I have good working relationships with my team.” This statement is both admirable and accurate. You are the leader here, so you must take the uncomfortable first steps required to improve both the relationship and results with your direct report. This isn’t something you can “overcome.” This is something you must resolve. It will take work and it will be hard, but this is what you signed up for when you accepted the role of leader.

It sounds as if your direct report is completely unaware of how his behavior is affecting you and the team. I’ll start with the assumption that you’ve yet to address it with him directly. If that is the case, your first job as his leader is to hold a Crucial Conversation.

Schedule a Face-to-Face Conversation

When sharing difficult feedback, resist the urge to do it in an email, throw it at the tail end of your next 1:1, or sandwich it between two compliments. Instead, realize that this is a conversation you need to prepare for. So, give the other person the opportunity to prepare for it as well. This can be as simple as casually asking him when he’d have time to talk about something that’s been on your mind. And then when he offers availability, put it on the calendar. When I was facing a similar conversation, I asked if I could take my teammate out to lunch to talk. It was a perfect opportunity.

Assume the Best

Since this is your first time addressing the bad behavior, you need to assume your direct report is unaware of what he’s doing or how he’s affecting others. You might be thinking, “Yeah right, there’s no way he’s that unaware.” And while that may be the case, your ability to approach the conversation as a curious mentor rather than an angry manager will ensure the conversation goes smoothly.

Talk Tentatively

Resist the urge to use labels like “volatile,” “not a team player,” and “difficult.” Begin to describe the problem by saying “I’m not sure you’re intending this…” or “I’m not sure you’re even aware…” This gives your direct report a chance to process the feedback without reacting to labels he may feel are unfair.

Share Facts Not Conclusions

Statements like “he is not a team player” and “everyone gets along great in the department except him” are conclusions. Not only are conclusions possibly wrong, but they can also lead to defensiveness. A fact might be “You rarely contribute to group discussions” or “When we reach consensus, you often come up with excuses or reasons why the decision is bad or unachievable.” By sharing factual, observable behaviors, you can quickly get to the heart of the issue, and he can account for things that have actually happened.

Share Natural Consequences

Once you’ve described some of the behaviors, you can address their impact. Assume a reasonable, rational person will be concerned about natural consequences like loss of friendship, goodwill, or reputation. Resist the urge to jump straight to disciplinary consequences like a performance improvement plan, probation, or termination. Instead, let him know that when he raises his voice, he shuts down ideas. Or when he refuses to get on board, people feel he isn’t a team player. Give him the opportunity to change his behavior based on how it might be impacting those around him and outcomes he cares about.

Ask for His Viewpoint and Listen

After you’ve presented your concern, give him a chance to respond. Ask him if he sees the problem differently and then stop talking. Simply listen to his side of the story. You’re now poised to have a healthy conversation about bad behavior.

If this conversation goes well, it’s likely your direct report will start to make small, incremental changes in his behavior. And I point that out because it’s difficult for people to change overnight. Consider any measure of improvement as a sign that his motivation and goals are in the right place. And use future 1:1 meetings to continue coaching and encouraging.

If this conversation goes poorly, or if you see no change in your direct report, it’s probably time to address the concerns with HR and start an official performance improvement plan. Likely your organization has something in place. But again, as his leader, it’s your job to do what you can to ensure this formal process does not come by surprise. He should know, because of your efforts to dialogue with him, that he has improvements to make. And I’d like to think he’ll want to make them.

Best of luck as you navigate this difficult conversation.


Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

6 thoughts on “Working with a Difficult Direct Report”

  1. John Bourke

    Thank you for your thoughts on this challenging situation. In your response piece, in the section entitled: SHARE FACTS NOT CONCLUSIONS, you offered the following:

    A fact might be “You rarely contribute to group discussions” or “When we reach consensus, you often come up with excuses or reasons why the decision is bad or unachievable.”

    I would suggest eliminating the words “rarely” and “often” in your offer of facts as these words are also conclusions vs. facts. I have witnessed conversations where the use of these words trigger defensive rebuttals wherein the other person argues that they exercise great judgment when contributing input to discussions as a show of respect for the team so as not to waste valuable team time and resources. They argue that they challenge team consensus only when they fear that the process was tainted or the consensus seems to represent a shallow understanding of the problem!

    I recommend sticking with one or two specific occasions wherein the stated behavior was observed. (“During yesterday’s Progress Meeting you offered alternative solutions after the team’s consensus position was finalized and adopted. “

    This fact may not be easy to hear although it may stir less defensiveness than when using interpretive words like “rarely” or “often”.

    Thank you for this chance to share my perspective.

    John Bourke
    President: Bourke & Associates

    1. Marji K

      Good point. Facts are friendly, opinions can lead to rabbit holes. Great addition to this good plan.

    2. Brittney Maxfield

      Yes, good point John. Thanks for adding your wisdom!

    3. Tonya F.

      Great points. Having been a nurse manager in the past and having 3 difficult direct reports, I suggest having a 1:1 direct report meeting with the presence of another manager if there is no resolution after the first meeting/meetings.

  2. jacqueline hardesty

    Thanks Brittany for all the guidance information on how to approach and resolve a difficult direct report. I work as a charge nurse occasionally and the information can help me to approaching an issue, which is always a difficult thing to do.

  3. Worth a Glance – December 23, 2021

    […] Crucial Learning, September 8, 2021. Link. It only takes one difficult direct report to make your job as a leader challenging. Brittney […]

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox