Working with a Difficult Direct Report

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 categorised 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.

It only takes one difficult direct report to make your job as a leader challenging. Let me share a few tips to help 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.

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.

Assume The Best

If it is your first time addressing the bad behaviour, 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 behaviours, 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 behaviours, 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 behaviour 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 behaviour.

If this conversation goes well, it’s likely your direct report will start to make small, incremental changes in his behaviour. 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.

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