Preparing for a Difficult Career Conversation

Career Navigation & Self-AdvocacyMid10-15 min

Introduction: What You’ll Learn

Having a conversation about your career, whether it's about salary, a new title, or changes to your role, can be tough. This simulation is here to help you prepare for those discussions by focusing on clear communication and effective self-advocacy.

You’ll practice:

  • Crafting your main points with clear examples
  • Thinking ahead about how your manager might respond
  • Speaking up for yourself confidently
  • Listening actively and addressing any concerns

Step-by-Step Simulation

Scene 1: Setting the Stage

Facilitator: "Hi everyone. Today, we’re going to prep for a career discussion. Picture yourself setting up a meeting with your manager to talk about your salary and the possibility of a new title. Start by jotting down your main points and some specific examples you can use."

Participant: "I want to highlight my leadership in a recent project that boosted conversion rates by 25% and the new process I set up that cut onboarding time by 15%. I feel these accomplishments support my request for a salary review and a title change."

Facilitator: "Great start. Let's dig into how you'll present these achievements and their impact."


Scene 2: Highlighting Achievements

Participant: "I’ll emphasize the strategic decisions I made during the project, like optimizing the user flow based on data analytics, which drove the conversion increase. For the onboarding improvement, I’ll mention how I worked with other teams to streamline processes."

Facilitator: "Those are strong examples. How will you tie these into your request for a title change and salary review?"

Participant: "I’ll point out that my contributions and leadership align with the responsibilities of the next title level, and I’ve taken on tasks typically associated with that role."

Facilitator: "Sounds good. Let’s figure out how you’ll lay out the conversation to make these points effectively."


Scene 3: Structuring the Request

Participant: "I’ll start by expressing gratitude for past opportunities and feedback. Then, I’ll share my achievements and suggest a title change with a salary review, backed by industry benchmarks if needed."

Facilitator: "Nicely done. Now, let’s get ready for how your manager might respond. What if they ask about timing or mention budget constraints?"

Participant: "I’d explain that the timing aligns with my recent achievements and increased responsibilities. If budget constraints come up, I’ll ask about other growth opportunities or timelines for future reviews."


Scene 4: Engaging with Objections

Facilitator: "Let’s roleplay a possible objection. I’ll be your manager."

Manager: "While your contributions are appreciated, we’re currently facing budget constraints."

Participant: "I understand the budget challenges and appreciate the transparency. Could we explore other ways to recognize my contributions, like professional development opportunities, or outline a clear path for future advancement?"

Facilitator: "That’s a thoughtful and constructive response. Let’s also consider how you’ll listen and adapt during the conversation."


Scene 5: Closing and Next Steps

Facilitator: "As we wrap up, summarize your main points and propose some practical next steps."

Participant: "Thank you for considering my request. I believe my contributions justify a title change and a salary review. I’m open to discussing other forms of recognition and look forward to your feedback. Could we set a follow-up meeting to go over potential next steps?"

Facilitator: "Well done. You’ve put together a solid and respectful case. Let’s recap the key takeaways."


Mini Roleplay Challenges

Challenge 1: Your manager seems non-committal about future opportunities.

  • Best Response: “Could we set a specific follow-up meeting to discuss concrete steps and timelines?”

Challenge 2: Your manager points out a skill gap as a reason for delaying the title change.

  • Best Response: “I’d appreciate your guidance on addressing this gap. Can we create a development plan together?”

Challenge 3: Your manager suggests that other team members are also due for reviews.

  • Best Response: “I understand. Could we discuss how my specific contributions align with the criteria for advancement?”

Optional Curveball Mode

Add one of these scenarios during practice:

  • Your manager is unexpectedly unavailable, and the conversation is postponed.
  • You receive feedback that conflicts with your perception of your performance.
  • Budget cuts are announced company-wide just before your meeting.

Practice handling each one with poise and flexibility.

Reflection Checklist

Preparation

  • Did I clearly articulate my achievements and contributions with specific examples?
  • Did I prepare emotionally for potential objections?

Delivery

  • Was I confident, respectful, and engaged in active listening?
  • Did I keep the conversation focused and constructive?

Follow-Up

  • Did I propose clear next steps and timelines?
  • Did I remain open to feedback and alternative solutions?

Common Mistakes to Avoid

  • Being overly defensive or aggressive
  • Lacking evidence or concrete examples to support your case
  • Not considering alternative forms of recognition
  • Failing to follow up on the conversation