Effective Career Planning Conversations with Your Boss


To invite managerial direction, perspective, and support for your organization-specific career thinking (i.e., you are there to talk about career plans that fit with THAT company’s needs/direction).

The conversation is wildly successful when:

  • Your manager has heard and responded to your ideas about where you’d like your career to go next and why.
  • There is a substantive ‘give and take’ about how your individual career goals mesh with the organization’s needs and direction.
  • You get confirmation or new information about any skill, experience, relational GAPS between where you are now and where you’d be IF organization saw you as ‘top talent’ for that role or direction.
  • You understand the next career-related steps your manager is recommending for you in terms of development planning, skill demonstration, or sponsorship support.
  • You and your manager are clear on immediate next steps for communication or action based on this conversation.

A career discussion is different than a job interview or performance review in that:

  • The amount of information exchanged has mostly to do with what you share and what you ask
  • You want to present as complete a picture as possible of your thoughts WHILE conveying humility, willingness to learn and acknowledge the potential downsides, competing interests, and alternative views of your self-assessment and career path ideas

Although the set up and flow of the discussion will have mostly to do with the specific people and content involved, here are some concrete suggestions that might be helpful.

Step 1: Preparation

  • Confirm that your manager is available for a separate discussion about your career planning and goal setting
  • Schedule a time and place with some privacy and limited distraction
  • If requested, prepare and share an agenda in advance
  • Summarize your thoughts related to the agenda topics
  • Think through how best to connect your desires/objectives to real organizational needs

Step 2: Conduct the Discussion

  • Set the stage. Start slow to go fast. Rather than dive into the specific content, be open to some small talk initially.
  • Clarify the purpose and objectives for the discussion, ie to get your manager’s perspective on:

Where you’d like your career and contribution to advance in the organization (what specific ‘next steps or moves’ for you are most interesting and why)

How your desires/objectives support organizational goals

The gaps in your experience or skill set that need to be filled out (we ALL have gaps between where we are now and BEING GREAT at where we want to be next)

What relational/organizational support you think you need to proceed

  • Support your ideas with data where possible
  • Invite a candid response. What do you like? What questions do you have? What might be missing? What concerns might you have?
  • Listen and acknowledge what you learn. Stay open minded. Listen for understanding not to respond. Ask questions for clarification. Do not get defensive.
  • For sensitive or complicated matters, share that you will give the content some thought and set up a future discussion on that matter
  • Suggested Topics:

Your favorite achievements or experiences from the past year or two

‘New’ or ‘re-confirmed’ insights into what matters most to you in terms of go-forward career success and growth

Possible new/revised career goals and their link to a career plan

High level timeframe or circumstantial factors to integrate

Ways to enrich current position related to goals

Facts supporting realism and relevance of goals

Assets supporting goal achievement

Areas needing development to achieve goals

Areas needing manager support to achieve goals

Patterns or conclusions that your manager might see differently

Possible next step

Step 2: Close the Discussion

    • Summarize what you learned
    • Define next steps and responsibilities starting with yourself
    • Agree to timing for follow-up
    • Ask if the manager wants a write-up of any kind
    • Express appreciation and support


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