Podcast Summary
Help Wanted – Money News Network
Episode: "How Do I Tell My Employee I Might Fire Him? Help!"
Date: April 14, 2026

Episode Overview
In this episode, hosts Jason Feifer, Editor in Chief of Entrepreneur Magazine, and Nicole Lapin, money expert and bestselling author, tackle a sensitive issue sent in by a listener: How can a first-time manager have an honest, constructive conversation with an underperforming employee—one that might lead to termination? Through personal stories, expert advice, and actionable steps, the hosts explore how to communicate tough feedback without falling into confrontation or personal attacks, all while supporting both team morale and professional growth.

Key Discussion Points & Insights

1. The Manager’s Dilemma: When Feedback Feels like Confrontation

• The listener, a new manager, struggles with how to tell an underperforming employee they might be let go.
• Their concerns include anxiety over confrontation, how honest to be, and the structural approach of the conversation.
  • [05:35] Listener: “I have a direct report...he’s doing a pretty sucky job...if he continues like this, I’ll probably have to let him go...I hate confrontation. How can I structure this conversation?...How can I overcome my anxiety?”

2. The Bigger Picture: It's About Team Dynamics, Not Just One Employee

• Jason emphasizes the importance of recognizing that managing underperformance impacts the entire team, not just the individual.
  • [06:07] Jason: “This is not just about the person...this is about the whole team. They are coming to you. They are expecting you to do something, and if you don’t, then that is going to hurt the entire team and also the team’s expectations of you.”

3. Personal Experience: Being Fired and Learning from It

• Jason shares his own experience of being abruptly fired and what he learned about delivering tough news:
  • Clarity and calm are essential for both parties.
  • The best feedback doesn’t feel personal or like an ambush—it's direct, honest, and sets a “safe space” for discussion.
  • Employees often sense when things aren’t going well before you say a word.
  • [09:00] Jason: “Frankly...I knew that. I knew it...I would not be surprised if the person you are going to sit down and talk to knows there’s a problem too.”

4. Core Principles for Hard Conversations

• Have the conversation in person or via video, not in writing or over chat—body language and tone matter.
• Begin directly: state there is a problem that needs to be discussed.
• Bring specifics: Give concrete examples of performance issues, not generalities. This avoids defensiveness and makes the conversation productive.
• Give the employee a chance to explain their side—there may be unknown circumstances.
• [12:40] Jason: “The next thing you’re going to need is specifics, have specifics...so that it doesn’t feel like you don’t really know what the problem is...No, this thing happened and I’ve talked to everybody involved and it seems like there was a problem.”

5. Understand the ‘Why’: Don't Conflate Actions with Character

• Reference to psychological research: Critiquing actions, not personality, is key for effective feedback.

  • [16:48] Jason (quoting Jeremy Sutton, PhD): “Don’t confuse the person with their actions. Being personal will lead the recipient to shut down. They’ll be less likely to act on or learn from the points shared.”

• Consider the possibility of redeemable factors: stress, mismatched roles, lack of training, or personal challenges.

• The goal is not to attack but to collaborate towards improvement or an amicable departure.

6. Balance: Negative and Positive Feedback

• Mix critique with genuine recognition of strengths to reduce defensiveness and foster openness.
  • [19:25] Jason: “He was acknowledging that I have strengths, and that feels good...He’s just saying that those things, valuable as they are, aren’t fulfilling all the needs of the team right now.”

7. Reducing Anxiety Around Feedback Conversations

• The conversation is often less traumatic than anticipated.

• Anxiety before sending “the email” is normal—don’t let it dictate your actions. The act of initiating the meeting is the hardest part.

  • [24:00] Jason: “You will probably be at your computer...‘Hey, do you have a moment to talk?’...You’re going to start to overthink every single word...But eventually you’re going to have to decide what that note is. For what it’s worth, I think ‘Do you have a moment to talk?’ is fine.”

• Permission to feel anxious and empathetic toward yourself and the employee—everyone’s growing from the process.

8. See Feedback as a Developmental Opportunity for the Manager

• Jason encourages new managers to treat the outcome as feedback for themselves as well, “reviewing” their own performance afterward to improve in the future.
  • [27:00] Jason: “In a way what you’re doing is you are setting yourself up to then give a performance review to yourself.”

Notable Quotes & Memorable Moments

• [06:07] Jason: “This is not just about the person you’re giving a bad review to. This is about a lot of people.”
• [09:00] Jason: “I thought, he’s very good at this...because I don’t feel defensive. He doesn’t feel angry. He feels calm. He feels direct. This feels like a pretty safe space.”
• [12:40] Jason: “You’re going to need specifics...so that they can’t wriggle out of it. No, this thing happened...”
• [16:48] Jason (quoting Jeremy Sutton, PhD): “Don’t confuse the person with their actions. Being personal will lead the recipient to shut down.”
• [19:25] Jason: “He was acknowledging that I have strengths, and that feels good.”

Important Timestamps

• [04:22] Episode launches into topic: Why giving critical feedback is challenging for everyone
• [05:35] Listener question: New manager dreads the conversation with underperforming employee
• [06:07–08:50] Jason unpacks the wider impact on the team and manager
• [09:00–14:00] Jason’s personal story of being fired and how it shaped his view
• [14:00–18:50] How to structure the conversation: directness, specifics, context, empathy
• [18:53–22:00] Balancing criticism with positives, and the importance of listening
• [24:00] Normalizing pre-conversation anxiety and how to push through it
• [27:00] Using the experience as feedback for your own growth as a manager

Actionable Advice (Recap)

• Have difficult conversations in person or over video, not by text/email.
• Start with directness—be clear about purpose, bring specifics.
• Separate the person's actions from their character.
• Ask for the employee’s perspective—discover if there are outside factors.
• Offer positive feedback and recognition alongside criticism.
• Accept and process your own anxiety; growth comes through action.
• Use each hard conversation as an opportunity to improve as a leader.

Tone & Takeaway
The hosts maintain a supportive, empathetic, and practical tone throughout, emphasizing that while difficult feedback is uncomfortable for everyone, it need not be confrontational or painful. These conversations, handled well, can fuel individual and organizational growth. Even first-time managers can—and must—embrace these challenges to lead effectively.

End of Summary