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Six Tips for Handling Tough Conversations With Direct Reports

A Thought Leader Post by Justine Strand de Oliveira

Justine Strand de Oliveira
by Justine Strand de Oliveira in Leadership, Thought Leader Post
December 27, 2016

No one likes feedback about problems, and it’s uncomfortable to sit down with a direct report to talk about something that needs to change. When I do, the responses can be different than I hoped. Sometimes it feels like it’s just easier to let it slide and hope things will improve. Do any of these resonate?

They just don’t get it!  The conversation occurs, and hey, it didn’t go so badly. But then nothing changes. Why? Denial is certainly a possibility, but it’s helpful to look at how clear I was with the message. Attempting to avoid the negative, did I start and end the conversation by kind of cheerleading about positives? “You’re doing a great job, so glad you’re part of the team . . . there’s this one small concern [fill in the blank] . . . so glad we had a chance to sit down and talk! Keep up the great work!” I exaggerate to make a point, but I’ve been there.

They get so defensive!  From my viewpoint, I broached a problem in a neutral fashion—but she took the conversation way beyond the issue I wanted to discuss, and it spiraled downward into negativity. Mentally preparing for the talk, did I list in my mind the reasons the direct report was wrong? Was I justifying the conversation to myself? Could I have been defensive going in?

Let’s make a new rule for everyone.  Instead of talking with the individual whose performance or behavior is an issue, I’ll announce a new policy that covers everyone and addresses the issue.  This is often a way of avoiding a difficult conversation.  The result?  The individual you were concerned about doesn’t think the rule applies to him, and the other members of the team are offended.

They get off on a tangent about how hard they work and how unappreciated they are.  That is definitely a good way to derail a conversation. And there is something called the responsibility bias, a self-serving bias, where individuals are convinced they do all the work while everyone else sits around relaxing. But how often have your heard the phrase, “If you want to get something done, ask a busy person?” That idea is just “code” for exploiting our high performing team members. As a manager, am I being even and fair with work assignments? Am I avoiding performance conversations with lower productivity team members? How fair is the workload?

They can’t even appreciate positive feedback.  It’s important to acknowledge great contributions to the team’s work. But when I do that, is it genuine and sincere? Have I tainted positive feedback by using it to frame a conversation about a performance issue? Would I believe my positive feedback if it was said to me?


Like so many of us, I was thrown into the deep end of the pool and had to learn to swim as a manager and a leader. Two decades of on-the-ground experience lead me to propose the following specific tips for handling those tough conversations:

Approach it from a learning perspective.  Appreciative inquiry is a framework for engaging others. I have been amazed by how often what I thought was the problem turned out to be something different when I really listen to direct reports after a problem occurs. Instead of saying “why didn’t you do this,” or “why did you do that” I ask, “help me understand what happened with XX.:” [Side note: my 27 year old son, who has a business degree and works in tech, says “Mom, I’d learn to be very afraid if you said ‘help me understand’” . . . so maybe a good idea to vary your verbiage!]

Avoid the feedback sandwich.  It was never a good idea, but so many of us were taught to do it. And we keep doing it because being straightforward is so uncomfortable. It muddies the message about the problem, and taints positive feedback going forward.  Check out Adam Grant’s take on it. 

Catch them doing something right.  The iconic management guru Ken Blanchard gets it right—recognize team members doing great things in the here and now. It’s immediate, and it’s sincere. And it’s motivating. How great do I feel when a team member or the person I report to says YAY about what I’m contributing to our effort?

Don’t make up stories.  If the person is being moved to another team because of organizational changes and priorities, don’t pretend there is some other reason. No one is fooled by elaborate narratives about things that aren’t real.

Check in with yourself before engaging in the conversation.  I need to take a moment to reflect on how comfortable I am, stop my internal conversation about why I am justified, and focus on the positives about the individual I’m about to engage with.  Psychologist Carl Rogers called this unconditional positive regard. I believe this is possible in the workplace. We can hold the person, who we regard positively, in our minds at the same time we engage in a dialogue about the issue at hand.

My brilliant mother in law, a retired sous chef, says: “Cooking has a beginning, but it has no end.” She’s right, and not just about cooking. As leaders, we, too, are always learning. I offer these ideas not as the “be-all and end-all,” but as lessons learned, sometimes painfully, along the road we travel together.

Photo by Rob Bye on Unsplash

Justine Strand de Oliveira
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Justine Strand de Oliveira

Justine Strand de Oliveira is a practicing physician assistant with more than two decades of leadership experience in health professions education and public health. She is passionate about creating environments where communication is open and honest, team members feel recognized and appreciated, work-life fit is optimal - and work is meaningful and rewarding.
Justine Strand de Oliveira
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