By Tess Singer, Senior Consultant
As leaders, one of our greatest responsibilities is helping people see a future for themselves within the organization.
Yet, many managers hesitate to initiate “career conversations,” unsure of where to start, what to ask, or how to balance organizational needs with employee aspirations.
Effective career conversations are not one-off check-ins or performance reviews; they are intentional dialogues that build engagement, trust, and long-term retention.
When done well, they can transform the employee experience, support succession planning, and strengthen an organization’s talent.
What are Career Conversations?
Career conversations are structured, intentional discussions between leaders and employees that explore aspirations, development needs, and alignment with organizational opportunities.
Unlike traditional performance discussions, these dialogues are forward-looking and collaborative.
At their best, they help employees envision their growth while giving leaders the insight they need to support that journey.
Why Career Conversations Matter
Career conversations create clarity for both the employee and the manager.
They help employees understand what’s possible, while signalling that their development is a priority.
For organizations, these discussions enhance engagement, increase retention, build deeper trust between employees and leaders/organizations, and fuel succession planning.
When employees feel seen, supported, and encouraged to grow, they are more likely to stay and thrive.
The Manager’s Role: Adopting a Coach Approach
Leading a great career conversation isn’t about having all the answers. It’s about listening deeply, asking thoughtful questions, and co-creating next steps.
Before the conversation, prepare reflection prompts to help guide the discussion.
During the meeting, take a coaching stance, being curious, supportive, and open.
Afterward, summarize commitments and follow up to show that the dialogue was more than a one-time exercise.
Key coaching techniques include:
- Preparing in advance with open-ended reflection questions
- Creating a neutral, comfortable setting for discussion
- Using structured questions to explore possibilities
- Staying present and avoiding a pre-determined agenda
- Holding career conversations outside of performance feedback sessions
This coach-based approach invites employees to take ownership of their development while ensuring managers act as true partners in growth.
Handling Sensitive Career Conversations and Turning Difficult Moments into Growth Opportunities
Career discussions can sometimes surface sensitive topics, including uncertainty, disappointment, or frustration.
Managers may feel pressure to provide answers or solutions they don’t have.
As an example, an employee shares that they’re frustrated about being passed over for a promotion.
- Acknowledge their perspective: “I can hear that is disappointing, thank you for being open about it.”
- Shift to a curious coach approach: “Can you tell me more about what you were hoping for in that next role?”
- Try to offer support in finding a solution or offering access to resources: “What skills or experiences do you think would help you prepare for future opportunities, and what role can I play in helping you get there?”
The key is to stay grounded in empathy and curiosity. Acknowledge the emotion, explore what’s driving it, and focus on what can be influenced.
Even when an immediate opportunity isn’t available, willingness to engage openly strengthens trust.
The Outcome: Building a Culture of Growth Through Reflection and Integration
Integrating career conversations into team culture isn’t just a development exercise; it’s a leadership practice that reinforces a sense of belonging and purpose.
Ultimately, career conversations are a cornerstone of effective leadership, creating pathways for growth, trust, and long-term success.
Build a Culture of Growth and Bring Career Conversations to Your Leaders
At Feldman Daxon, we offer Career Conversations as a leadership development workshop designed to help managers confidently lead these discussions through practical frameworks, sample questions, and real-time reflection.
The program equips leaders with tools to foster engagement, strengthen relationships, and build a culture of growth.
To learn more or schedule a workshop for your leadership team, contact us today.