Using Positive Framing to Re-Engage Pre-Retirement Employees

Do you remember Johnny Paycheck’s hit “Take This Job and Shove It”? That song of workplace frustration might feel a little too familiar when working with employees who are nearing retirement. Some may quietly shift into “coasting mode” — less interested in growing, improving, or taking on new challenges. So how do you re-engage someone who seems to be mentally packing up before their final day? Disengagement near retirement isn’t inevitable — it’s often a leadership opportunity.

In this week’s Monday Kickstarters group, we applied positive framing and generative questions to tackle this workplace communication challenge. Positive framing is about consciously flipping the story we’re telling ourselves. Generative questions help you and the employee move towards the frame.

Positive Framing: Shifting the Narrative

Name It:
Managers don’t know how to engage employees who are close to retirement in improving and growing.

Flip It:
Managers do know how to engage these employees in improving and growing.

Elevate It With a Positive Frame:
Energized and engaged employees thrive in a culture of learning — at every career stage.

Generative Questions to Help Move Towards the Frame

Generative Questions for Yourself

Leadership begins with self-awareness. Before you meet with the employee, reflect:

• What does “energized and engaged” look like to me?
• How am I modeling growth and curiosity?
• What assumptions might I be making?
• What could I be doing differently?

Generative Questions for the Employee

Instead of telling employees what they should be doing, invite them into reflection:

• What is most meaningful to you at work right now?
• When was the last time you felt energized and engaged at work? What was happening?
• Imagine it’s a year from now and an article is written about your final year here. What does it say?
• What gives you joy about learning something new?
• What would you like your legacy to be as you move into retirement?
• You have so much wisdom to share. How would you like to pass that on?
• What personal or professional goal would you still like to work toward? What’s one small next step?
• What topics or skills still spark your curiosity?

Conversations Worth Having Cool Tip

When we shift the frame, we shift the energy — and energy is contagious.

This topic came from Conversations Worth Having's Winter 2026 Monday Kickstarters series. Monday Kickstarters are interactive sessions to apply the Conversations Worth Having practices in real-life scenarios—a tough situation, challenge, or problem with leadership or performance. If you have a tough situation you’d like to reframe or want to join us to continue your CWH practice, register here.

Shared by: Sylvette Wake, a certified Conversations Worth Having and Strategic Conversations Guru. Reframe your thoughts, reshape your world.

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