Giving tough feedback
Today’s edition of Sticky Situations is the stickiest of situations as a manager - managing a direct report who is underperforming.
Read on to get some tips on giving feedback and handling tough conversations.
The Situation
I suck at giving feedback to my team. I struggle with softening the feedback to the point that it doesn’t come across serious enough. I have one direct who is underperforming. In hindsight I could have been more direct with my feedback, because now it’s impacting their performance. Now I have to have a tougher conversation with some consequences. How can I give better feedback?
My Take
Ah, the unglamorous realities of being a manager.
At some point you’ll have to give tough feedback…and it sucks. But avoiding it only makes things worse. The short-term awkwardness of being direct is nothing compared to the long-term pain of unclear expectations, frustrated teams, or performance issues that snowball.
So, how do you do it well? How do you give feedback that’s clear, kind, and actually helps someone improve—without ruining every shirt you own from your sweat stains?
Let’s break it down into three parts:
• Have a game plan
• PREP for the convo
• Use AI to help
Have a game plan
You can’t wing a high-stakes feedback conversation — that’s how things get softened, muddled, or just straight up avoided.
Here’s how to set it all up before you even say anything:
Schedule time 1:1
This might be a no-brainer but let’s just say it out loud in case. Put aside time to deliver feedback in a 1:1 setting. Don’t do it in the meeting or ad hoc in the hallway. Allow yourself time to prepare and that person to be in the right mindset. Keep it timely though — if you notice the issue today, don’t wait ‘til 3 weeks from now to chat.
Start, middle, and end with a question
Prepping these gives you a deliberate read on their awareness and makes it more of a convo and less a lecture.
Start: Sometimes this is all you need to kick start the convo, because after all, who is your biggest critic? You! Your direct may already be well aware of what they suck at and ready to admit it when given the chance. A simple, “How do you think that went?” to start could do it.
Middle: Prepare 1-2 probing questions, like “What’s going through your head when deadlines slip?”
End: “What do you think?” or “Is any of that unclear?” after you deliver the feedback allows for some discussion or questions.
Match your tone to the message
If it’s serious, your tone should reflect that. If it’s minor, keep it light. Prep some explicit lines to match your message. Do NOT skip this in your prep. It is very hard to convey this on the fly, and it’s why a lot of feedback is not clear enough.
Minor: “This is not a huge deal but is a small thing that would take your effectiveness to the next level.”
Major: “This is not meeting the expectations for this role.” or “If you don’t improve on this, it will negatively impact your performance.”
Prepare multiple examples
Prep more than one. As an employee, I want some concrete, objective examples so I can understand clearly what the issue is. And I want more than one to prove it’s not just a one-off.
Send an email recap afterward
HR may tell you do this to document it, but in the best interest of your direct, do this for alignment and clarity. It may be hard to receive and digest the feedback in the moment, so having it in another format is helpful. It also provides another way to ensure understanding and is something you can both reference.
PREP for the convo
Now that you’ve got your mindset and examples ready, structure the actual feedback with PREP:
P — Positive Intent + Point
Starting with your positive intent (but legit, genuine positive intent, not BS) can show that you want the same goal as the employee. It will help set the tone, but it shouldn’t soften the blow or sandwich constructive feedback. Then state the issue clearly.
“I want you to shine and get the credit you deserve in leadership reviews. So I think you can work on answering more of the questions yourself and not defer to others.”
R — Reason
Connect the issue to impact.
“When you do this, the perception is that you don’t have an answer or a POV on the situation. Though I know you do and your POV is a value-add.”
E — Evidence
Share specific examples — no vague generalities.
“In yesterday’s review, when they asked about XYZ, you knew the answer but waited for ABC to chime in. You are the expert, no one in that room knows more than you. What was going through your head?”
P — Path Forward
Based on their answer, you can tailor the path forward. Give them a clear plan and expectations.
“I expect you to be able to answer questions and represent your area of ownership in meetings. So here’s some things you can try to feel more confident answering. If you know the answer but want to buy time to collect your thoughts, you can say ‘Good question’ to acknowledge that you will answer and then take a second to collect your thoughts. Sometimes it helps me to jot down a few thoughts that come to me when someone asks a question so I don’t forget when I’m answering. Before next month’s review, we can do a prep session to practice answering ad hoc questions. What do you think?”
Using PREP keeps you grounded—it’s still direct, but a little more human, and the structure will help the recipient digest it better.
Use AI to Help
AI is a great place to practice before talking to your actual employee. You can rehearse tone, clarity, structure, and even potential worst case responses to better prepare you.
Try This PREP Practice Prompt
“Act as my direct report who is underperforming. I want to practice giving feedback using the PREP model (Positive Intent + Point → Reason → Evidence → Path Forward). Push back a little so I can practice staying clear and firm. The issue is: [insert issue]. After we role-play, critique my tone and rewrite a stronger version.”
This gives you:
• A realistic practice session
• Immediate feedback
• A stronger script to model
• A chance to adjust tone and emphasis before the real thing
Final thought
You may mess up the delivery, they may have an emotional reaction, things may not go perfectly. But softened feedback is not the answer. It creates confusion and bigger problems later.
Having a plan, prepping with intention, and practicing with AI gives you the confidence to deliver feedback more effectively and helps (you and) your people grow. The more you prep, the easier it will be.
