Ever walked away from a conversation with your boss thinking, “That did not go the way I expected”? In this episode of Don't Let the Smile Fool You, I share one of my biggest scars as a leader: the unintentions that can wreck a conversation, especially when it comes to salary increases and pay raises.

Let me take you back to a moment years ago. A member of my team asked for a salary increase, citing personal circumstances. As a manager, I thought I was being helpful and coaching them on how to present their case, but my feedback landed in a completely different way. What started out as a pay discussion quickly escalated into a lesson on empathy, misunderstandings, and the facts-driven nature of compensation in organizations.

The truth is, asking for a raise is rarely as simple as it sounds. Emotions run high, but the business side is all about data, performance, and value. A successful salary negotiation requires a different approach—one that is not about how you feel but about what you’ve delivered.

In this episode, I unpack the key takeaways for both employees and leaders on navigating pay conversations. I talk through the importance of courage, empathy, and the pitfalls of unintentional miscommunication. And I lay out a practical, honest path for anyone preparing for the “can I have a raise?” conversation.

Here’s what you’ll get:

What really happens during salary discussions between employees and managers

How emotions can muddy the waters and derail good intentions

Why evidence and performance matter more than personal circumstances

A story of misunderstanding, escalation, and the fallout from unintentions

How leaders can show empathy without compromising fairness or clarity

Actionable advice for preparing to negotiate your salary and handling rejection

Ways to ensure every conversation leaves both sides respected, valued, and clear on next steps

Whether you’re climbing the leadership ladder or just building the courage to ask for better compensation, this episode is packed with honest insight and practical advice. No matter how heavy the conversation gets, keep smiling.

Key moments and chapters:

00:00 Welcome to Don't Let the Smile Fool You: The story behind salary negotiations

00:41 The most difficult conversations as a manager: pay raises and emotions at play

01:44 Perspectives on salary discussions: employee emotions vs business facts

03:07 How to approach a pay raise request: Coaching feedback and misunderstandings

04:10 Miscommunication: What “let’s talk later” really means

04:56 Emotional fallout and escalation: When intentions get lost in translation

06:27 The aftermath: Scarred but learning, clearing up unintentions

08:27 Preparation is everything: Facts vs emotions in salary negotiations

10:50 Empathy in leadership: Treating the conversation with respect

11:53 Making sure the result—raise or not—feels fair and constructive

12:55 Key takeaways for both employees and leaders

13:52 Closing remarks: Sharing your own experiences and keeping that smile

Subscribe and share your stories in the comments. How did your salary negotiation go? What have you learned about good intentions and tough conversations in the workplace? Let’s talk about what’s really beneath the smile.

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