You shared feedback. It didn’t go well. Now what?
Observation 🧐
Your conversation didn’t land.
You gave tough feedback. You laid out clear expectations. But instead of appreciation or reflection, you were met with defensiveness.
Now you feel frustrated. Maybe even a little disrespected.
This is where leadership gets real.
Leadership isn't about being right. It's about being responsible.
Anyone can deliver feedback. But not everyone circles back to ensure it landed the way it was intended.
What most managers get wrong
When a tough conversation goes sideways, many managers fall into these traps:
Avoid the person for a few days
Wait for the rep to “come around”
Vent to their peers, but don’t follow up directly
Assume “they’re not coachable” and write them off
But here’s the thing: your job isn’t to win the argument. It’s to lead.
A real life example
One of my clients recently had a tough performance conversation with her AE.
Her feedback was fair and well intentioned. But the AE pushed back hard. He got defensive. She left the conversation confused, how could he be so surprised by something we’ve talked about before?
When I asked what she planned to do next, she said: "I delivered the feedback clearly. It's his job to figure it out."
Technically, she wasn’t wrong.
But leadership isn't about being technically right. It's about getting results.
With power comes responsibility
When we're in positions of authority, we have inherent advantages:
We control the narrative
We have access to more information
We set the tone and direction
We have more practice with difficult conversations
Just like parents don't wait for their children to initiate difficult conversations, leaders can't wait for their team members to come back and engage. We have to go first. We have to be the bigger person. We have to swallow our pride and focus on the outcome we actually want.
The Follow-Up Framework: Four Steps to Re-engage
When a difficult conversation doesn't land the way you hoped, here's your playbook:
1. Give It Time (But Not Too Much Time)
Wait 2-3 days for minor feedback, up to a week for major performance conversations. Emotions need time to settle, but momentum dies if you wait too long.
2. Acknowledge the Disconnect
Don't pretend the conversation went smoothly. You can lead with: "It seemed like..." or "It felt like..." or "I sensed that..."
“It felt like I caught you off guard last week and wanted to check in with you.”
“I sensed that I did not communicate things as clearly as I could have. Can we revisit it together?”
3. Normalize the Discomfort
When you name it, you both show up better:
“This might be a bit uncomfortable, but it’s important.”
“I want to talk through something that I think will help us both work better together.”
“Can I share an observation I’ve had, even though you may not agree with it?”
4. Create Space for Their Perspective
Use phrases like:
"Now that you've had time to think about it..."
"I'd love to hear your thoughts on..."
"What questions came up for you?"
"How are you processing what we discussed?"
5. Focus Forward
End with an invitation to move ahead together:
"What would be helpful to discuss next?"
"How can I support you as you work on this?"
"What does success look like from your perspective?"
The turning point.
My client gave the AE the weekend, and then sent him this slack message:
“I wanted to check in on the conversation we had last week. It felt like you were surprised and caught off guard. Now that you’ve had some time to process it, I’d love to hear how you're thinking about it.”
That message did three things:
Acknowledged the tension without assigning blame
Opened the door for a more productive dialogue
Signalled care, not control
The AE’s response? Positive. Measured. Far more open. That follow-up conversation became the turning point in the AE’s performance.
The bottom line:
Great leaders don’t just deliver the hard message. They follow up to make sure it sticks.
When you choose to re-engage, you send a powerful signal:
You want a two-way dialogue
You’re committed to the relationship
That’s leadership. And it makes all the difference.
Thought Starter 🤔
Love 🥰
Communication isn’t easy, let alone difficult conversations. Jefferson Fisher is a lawyer who is known for his straightforward advice, tips and tricks on how to communicate better. I discovered him on this episode of the Mel Robbins Podcast where he discussed why miscommunication happens and how to use strategic communication to get what you want. Catch his bite size reels on Instagram at @jefferson_fisher