While individual development plans tend to stay within the boundaries of the current role or company, career conversations take a broader view. They are about understanding someone’s long-term goals, even if those goals lead beyond your team or company.
With average tenure hovering around 4 years, it’s short-sighted to tie career planning too closely to retention. Yet most leaders still avoid these conversations, either because they don’t know how to start or because they fear the honesty they might uncover.
Good frameworks exist. They only work when you ditch the agenda. No hidden motives, no plugging people into your roadmap – just genuine curiosity about their path.
I couldn’t find any practical how-tos when I started doing these talks in 2020. I built on a short chapter in Radical Candor and insights from Russ Laraway, who later expanded the idea in When They Win, You Win. I eventually shared my approach publicly in 2023 – partly because I wished I had something like it back then.
Recommended Resources
How to Hold Effective Career Conversations (~36 min read total)
My personal 4-part series for all leaders who are serious about learning about their reports and helping them achieve their career dreams. The framework is based on the popular Radical Candor book, but evolved and adjusted for practical (re)use. I also included sample briefings for the meeting invites as well as a flexible spreadsheet that serves as the source of truth.
- Part 1 – Their Life Story 📙 (5 min read)
- Part 2 – Their Dreams 💖 (12 min read)
- Part 3 – The Career Action Plan 🎯 (9 min read)
- Part 4 – Their Check-In with You 🌱 (10 min read)
Initiate the conversation by understanding your team member's background, motivations, and key life experiences that have shaped their career trajectory.
Encourage open dialogue about long-term career aspirations, creating a safe space for team members to share their ambitions beyond their current role.
Collaboratively develop a structured plan that aligns individual goals with organizational opportunities, outlining clear steps and milestones.
Establish a cadence for regular check-ins to review progress, provide support, and adjust plans as needed, ensuring ongoing alignment and development.
Career Development and Mobility: GitLab open-sourced their employee handbook which also contains a treasure trove of information on growing your career. Many mature companies mandate individual development plans which are called individual growth plans at GitLab. Employees drive their career development as managers support. This may not apply to your workplace, but the collection of infographics and videos is priceless for any manager in any organization. (10 min read - multiple hours of videos)
Career Conversations Tool: Russ Laraway created this toolkit as a supplementary resource for his “When They Win, You Win” book. I particularly appreciate all the examples and callouts on what to focus on and how the elements of each conversation are connected. It’s worth mentioning that this feels like a promotion for Coda, but you can use the content in any other tool or medium that works for you, as the toolkit is totally accessible for free. (20 min exploring in total)