The Career Progression Conversation Structure
The Insight:
Career conversations often fail because managers avoid them (fearing unrealistic expectations) or make vague promises about promotions they can't guarantee.
Effective career conversations aren't about predicting the future - they're about understanding aspirations, identifying skill gaps, creating development opportunities, and being honest about what you can and cannot influence.
When done well, these build loyalty even when immediate advancement isn't possible, because people feel seen and supported in their development.
The Tool: Growth Navigator
4 steps to try now
01.
Understand Their Aspirations
Probe
Start by genuinely understanding what they want.
Ask: "What kind of work energises you most?"
Probe beyond titles: "What does that role mean to you? What would you be doing day-to-day?"
Understanding real motivation helps you support them effectively even if formal promotion isn't immediately available.
02.
Assess the Gap Between Current and Desired State
Collaborate
Work together to identify what skills, experiences, or behaviors separate where they are from where they want to be.
Ask: "What do you think you'd need to develop?" and share your perspective.
Be specific about strengths and growth areas. Honest feedback serves better than false encouragement.
If significant gaps exist, acknowledge them while framing them as achievable.
03.
Co-Create Development Actions Within Your Control
Plan
Focus on what you can actually influence: skill-building opportunities, stretch assignments, exposure to senior leadership.
Be explicit about what's within your power: "I can give you ownership of the client relationship rebuild. I can't promise a promotion timeline."
Create specific development actions: "Over the next quarter, present to the executive team, and shadow strategic planning meetings."
04.
Schedule Regular Progress Reviews and Reality Checks
Review
Career development isn't a one-time conversation - schedule quarterly check-ins focused on growth.
Review progress, provide honest feedback on readiness: "You're making strong progress on strategic thinking. Managing conflict directly still needs development."
Be transparent about changing realities: "The restructure means that role won't open this year."
This maintains trust even when circumstances change.
Why it works
Honest, specific career conversations build trust and loyalty by showing you're invested in their growth even when you can't control promotion timelines. People stay engaged when they feel genuinely supported in their development, not just managed.
Use it when
Someone asks about advancement opportunities, annual review season approaches, you notice someone seems disengaged or frustrated, or a team member has been in their role 18+ months without clear next steps.
Bonus tip
If someone's aspirations exceed what's realistic in your organisation, help them anyway. Say: "That path might not exist here, but let me help you build the skills that would make you competitive for it elsewhere." This generosity often creates more loyalty than false hope.
