Strategically Managing Your Career During a Reorg

career-navigationMid10–15 min
How to Use This: Run this roleplay with 2–3 people, or try it solo by voicing each role. Add curveballs to test adaptability. Reflect afterward to see what went well—and what didn’t.

Roleplay Scenario

Scenario Overview

Your company is going through a reorganization, and you're curious about how it will affect your role and future opportunities. You want to make sure you're set up for success in the new structure, so you need to have a thoughtful conversation with your manager.

Roles & Setup

Role A – Employee (You)
You're concerned about how the reorg will affect your position and career growth.
Your goal: Get clarity about your role, share your career aspirations, and find ways to align them with the company's new direction.

Role B – Manager
You're aware of the reorg and are supporting your team through the transition.
Your goal: Provide reassurance, help align team members' goals with new organizational directions, and identify growth opportunities.

Suggested Openers

Employee:

  • “Can we chat about how the reorg might change my role and what opportunities might open up?”
  • “I'd like to talk about how I can align my career goals with the company's new direction.”

Manager:

  • “Of course, let’s talk about it. I’m here to help you navigate these changes.”
  • “Absolutely, we can explore how your career path fits into the new company direction.”

Sample Roleplay in Action

Employee:
“Thanks for meeting with me. With the reorg happening, I wanted to understand how it might impact my role and if there are any new opportunities I could explore.”

Manager:
“Sure thing. The reorg is meant to help us better meet market demands, but I get that it can feel a bit uncertain. How are you feeling about things?”

Employee:
“I'm a bit unsure, but I'm also interested in seeing what new roles or projects might be available. I want to make sure I keep growing and contributing.”

Manager:
“That’s a great perspective. We’re expanding [specific department], which might be a good fit for your skills. Let’s figure out where you can add the most value.”

Employee:
“I'm particularly interested in roles that use my skills in [specific area] and offer leadership opportunities. How can I prepare for these changes?”

Manager:
“We can focus on building up your expertise in [specific area] and finding ways to demonstrate leadership in your current projects. I'll keep an eye out for roles that match your career goals.”

Employee:
“Thanks for your support. I’ll start by documenting my achievements and seeing how they align with the company's new goals.”

Manager:
“Sounds great. Let’s plan regular check-ins to make sure we’re on track with your career development in this new setup.”

Post-Scenario Tools

Curveball Mode (Optional)

Introduce one of these mid-roleplay to test adaptability:

  • Manager hints at possible downsizing in your department.
  • A new role is announced that’s a perfect fit but requires additional skills or relocation.
  • The employee struggles to articulate their strengths or aspirations effectively.

Reflection Checklist

As the Employee:

  • Did you express your concerns and aspirations clearly and positively?
  • Did you show openness to new possibilities and changes?
  • Did you align your career goals with the company’s direction effectively?

As the Manager:

  • Did you offer realistic support and insights about the reorg?
  • Did you help the employee see potential opportunities?
  • Did you encourage ongoing dialogue to support career progress?

Common Mistakes to Avoid

  • Focusing solely on job security instead of growth opportunities
  • Avoiding the conversation due to fear of uncertainty
  • Sounding overly anxious or self-centered
  • Ignoring the company’s broader strategic goals

Pro Tip

Approach reorgs as opportunities to redefine your career path. Being proactive, adaptable, and aligned with the company’s goals will help you navigate changes successfully and seize new opportunities.