A Practical Guide for Having a Great Career Conversation for Employees, L&D Teams, and Leaders

Have you ever walked into a career conversation and felt a little…unsure? Unsure what to say. Unsure what to ask. Unsure how to help someone move forward.

You’re not alone. Whether you’re an employee preparing for your next career step, a line manager supporting your team, or an L&D professional championing growth, career conversations can feel daunting.

Over the years, I’ve worked with hundreds of organisations around the world – from the NHS to International Organisations- helping them foster meaningful career development. And one thing has become abundantly clear: great career conversations don’t just happen. They’re created, deliberately and thoughtfully.

In this blog and video, I’d love to share with you the eight stages of a truly empowering career conversation with tips and example questions you can use to boost engagement and unlock potential. And I’ll weave in a few real-world examples (anonymised, of course!) from clients who’ve seen the power of this approach firsthand and had really great career conversations as a result.

Stage 1: Take Time to Prepare

Imagine you’re heading into a meeting. The person you’re about to speak to feels uncertain. They’re trusting you with their hopes, dreams, and fears.

Preparation matters.

Before the conversation, ask for their CV or LinkedIn profile. Give them a few guiding questions to reflect on. Frame it clearly: “This conversation is for you. It’s confidential. I’m here to support, not to judge.”

Tip: Have a few powerful questions ready to start the conversation. For example, “Is there anything specific you’d like to get out of our meeting that I can prepare for?”

Client story: In a tech company I worked with, one manager shared that by simply sending a few reflective questions in advance, their career conversations shifted from “awkward small talk” to conversations which were a lot more reflective and meaningful.

Stage 2: Set Up the Conversation

First impressions matter even in internal career discussions.

Choose a comfortable setting. Ensure privacy. Open with warmth and clarity. Reassure them that they own their career. You’re there to help, not to steer.

Tip: Prepare an opening statement that builds rapport quickly. For example: “What’s going well in your current role? What would you not want to change?”

Real-world insight: A senior HR leader told me how starting conversations by focusing on “what’s working” immediately put employees at ease; far better than jumping straight into “what next?”

Stage 3: Establish Trust

Trust isn’t built in a moment. It’s earned.

Sometimes you’ll have a long-standing relationship; sometimes you’re meeting someone new. Either way, share a little of your own career journey to create a safe space.

Tip: Reflect on lessons you’ve learned in your own career. Showing your own vulnerability invites openness from the other person.

Example questions: “What are you most proud of achieving? What was it about that experience that felt so rewarding?”

Stage 4: Agree on Desired Outcomes

What’s success for this conversation as well as their career?

Maybe it’s clarity about next steps. Maybe it’s a decision to explore options. Maybe it’s simply starting a career dialogue.

Tip: Express appreciation for their work before diving into goals.

Example question: “Suppose you could wave a magic wand and design your ideal career journey, what would you be doing day-to-day?”

Client example: At a pharmaceutical client, one manager used the ‘magic wand’ question and discovered a hidden ambition in a team member to move into public health outreach, opening up a whole new career pathway.

Stage 5: Explore Their Perspective

Career conversations aren’t interrogations. They’re explorations.

Invite the other person to reflect on their interests, values, aspirations, and strengths. Help them connect the dots between their talents and opportunities.

Tip: Use open-ended questions like: “What useful experiences have helped you get where you are today?”

Real-world story: In one organisation, an employee realised through this reflection that what energised them most wasn’t management (their current path) but subject matter expertise. A crucial insight!

Stage 6: Share Information

Employees often need help connecting their ambitions with opportunities. Share insights about your organisation’s strategy, future skills, and potential projects.

And don’t be afraid to signpost other people they can talk to.

Tip: Have a few success stories ready. Hearing about colleagues who have navigated transitions can be inspiring and reassuring.

Example questions: “What knowledge and skills do you need to develop? What relationships might support your growth?”

Stage 7: Agree on Actions

A great conversation doesn’t end with “thanks, that was nice.” It ends with action.

Agree on practical next steps. Maybe it’s shadowing someone. Maybe it’s researching a course. Maybe it’s simply reflecting more deeply on strengths.

Tip: Encourage ownership. Small actions build momentum.

Example question: “How might you make your current role even more satisfying and enjoyable?”

Stage 8: Close the Conversation

Leave enough time to summarise, agree on next steps, and, importantly, schedule a follow-up. After all, growth is a journey, not a one-time chat.

Tip: Encourage employees to track achievements and reflections between conversations. It’ll make the next dialogue even richer.

Example question: “What are three small steps you can take over the next three months toward your goal?”

Why It Matters

Meaningful career conversations change lives.

They’re not just “nice chats.” They fuel motivation. They deepen engagement. They boost retention.

And for employees, they offer a powerful reminder: your career is yours to shape, but you don’t have to do it alone.

Whether you’re an employee reflecting on your next step, an L&D team designing support programmes, or a leader investing in your people, these eight stages can help you have conversations that matter.

If you’d like even more tools, models, and practical questions to empower these career conversations, download a free chapter of my book, Confident Career Conversations, today.