A Career Conversations framework for managers

Caring about the team’s growth and development can have a huge impact on their motivation.

Mayank Prabhakar
3 min readNov 7, 2020
Career development conversations

Helping your direct reports in their growth and development is one of the key responsibilities of any manager. When done well, research shows, that it has an enormous impact on employee motivation, engagement, and ownership behavior. And yet, very few managers do a good job of having career conversations with their direct reports. As a result, most employees end up feeling like just a pawn in the chessboard.

To have meaningful career conversations with direct reports that can truly motivate them and help build stronger teams, it takes authentic caring, and sincere effort over a period of time.

Here is an approach which might help:

Meeting 1: Know the Journey and the dream

The 1st meeting should have 3 broad agenda:

  1. Knowing each other: Trust is key to having open and effective communication. Neuroscience tells us that people trust familiar things. Start by sharing your background, journey, family, interests, and hobbies. Ask them about their journey so far — from kindergarten to school, college, jobs, and so on. Spend some time discussing things you have in common. Focus on the changes and choices they had made, and try to understand why they made those choices. It is in these moments of change, the core values and motivations of a person are revealed. The objective should be to know the individual a little better and understanding what they care about.
  2. Knowing the dream: Next, you should be understanding their aspirations and dreams. Usually, managers ask about “long term goals”, “career aspirations” or “five-year plan”, but sometimes these phrases when used by managers, tend to elicit only a professional response or something which manager wants to hear, and not an entirely human one which the employee actually wants to achieve. The book Radical Condor recommends asking — “what do you want the pinnacle of your career to look like?”. Ask “why” questions and check if the person’s dreams are aligned with the values they had expressed.
  3. The ask: At the end of the meeting, you should ask your direct report to come up with a list of the skills they would need to achieve their dream in the next meeting.

Meeting 2: Add wheels to the dream

The 2nd meeting should focus on adding wheels to the dream and career development journey:

  1. Prioritize the skills: Review the skill list that the employee would have come up with. Ask them why they think these skills are needed. Discuss and distill it down to include only the most important ones. Ask them to assess themselves on those skills. Ask which ones they would like to work on first.
  2. Align dreams with current work: Identify opportunities at work that would allow your direct reports to develop and hone those skills over the next six to eighteen months. This would require thinking about aspects like — how the person’s role can change to help them learn those skills, whom they can learn from, the classes they could take, and books they could read. If you don’t have all the answers and come back with it in the next meeting. This translation and alignment of future dreams with current work is inspiring for people and also makes the team stronger.

Keep the engine running

Career conversations have to be an ongoing agenda between managers and employees. Schedule regular 1:1s, and discuss progress on developmental goals, give specific feedback, share your own experience of growing as a professional, connect them to the right people, and introduce them to theories, books, and frameworks that may help them. There would be moments when they would want to give up on a few skill goals, particularly if they face setbacks. In those moments, you need to inculcate a growth mindset and motivate them to keep going.



Mayank Prabhakar

Product Manager in HR/People Tech domain. I explore and write about emerging research to solve people and org problems through tech.