Pyn • Career Journey

How to have a career development conversation with your employee

Your report has been on your team for 10 months. Time to create a career development plan! Here’s what to do over the next 2 weeks. 

Before the career development conversation: Know your role and goal

Your role: align and listen

Research shows that managers who give their team members responsibilities and tasks that align with their goals for the future are much more successful in building engaged teams. This career conversation is designed for you and your report to decide on those tasks that do just that!

It's about helping them find the right fit, not just the next step on the career ladder.

During a career conversation, you’ll do more listening and asking questions than you might be used to.  According to research by manager training provider LifeLabs, top motivators ask about 10 questions every 15 minutes! And this conversation is definitely a time to be curious, listen more, and talk less.

Note for remote managers

We know your memory is top-notch, but you'll still want to take notes in these conversations. To avoid giving the appearance of being disengaged and looking away from the camera as you write things down, just let your direct report know what you're doing and why. "I'm going to take notes during our conversation - so if I'm not making eye contact, that's why. You have my full attention".

The goal: create short- and long-term action plans

Your goal is to work with your direct report to create short-term (3 months) and longer-term (18 months) action plans. 

Before the career development conversation, have the “life story” chat. 

This an opportunity to look backward and discover the story of how your employee got to where they are today. Through it, you’ll both discover some clues to help paint a picture of their future. 

  • Schedule two meetings for about one hour each (i.e., one for the life story chat and one for the career development conversation).
  • Explain in your meeting invites what you’ll discuss. “You’ve been on the team for a while and I’d love to schedule a career development conversation in a couple of weeks. But before we do that - it’d be good for me to truly understand your journey so far. We’ve never had the time to properly do that!”     
  • Start the life story chat simply by asking: “Starting at High School, tell me about your life.”
  • Ask a lot of probing questions, especially to understand pivots or transitions.  
  • Be curious. Listen! 
  • Resist the urge to talk about your own experience unless they ask. Remember, this isn’t about you. 

Pay close attention to their major pivots and transitions. Why did they make them? What did those transitions teach them about what they love and loathe about their work? This is data you can both use and reference in the career development conversation. 

During the career development meeting: use the GROW Model to identify career goals 

Great, you have a general sense of their life journey. Now it’s time for the actual career development conversation. Use the GROW model - a technique to structure a conversation to generate new thinking and action. 

GROW stands for Goal, Reality, Options, and Way Forward. 

  • G: goals and aspirations
  • R: current situation, internal and external obstacles
  • O: possibilities, strengths, and resources
  • W: actions and accountability   

Instead of skipping straight to action, coaching someone through this model helps them clarify what’s important and uncover what might get in the way of achieving their goals.

You don't need to ask each question but make sure you follow the model in order starting with Goal.

Goal: What’s their dream job?

Together, identify what your team member wants to grow into. Even though this sounds easy, it may be the hardest part of a career conversation. 

Ask questions such as  

  • “If money or your current skills weren’t an issue, what would be your dream role?”
  • “What are your interests?”
  • “What parts of your past work did you enjoy most?” 
  • “What size company do you imagine working for?”
  • “Do you imagine a very senior individual contributor type role or a very senior manager type role?”

Reality: Discuss the current reality

Now that you have a sense of what this person’s goal is, identify their current reality. Ask questions like:

  • “Do you feel challenged or stretched in your current role? What would make it more challenging? What isn’t challenging for you?"
  • “What do you think your teammates and other stakeholders feel you are best known for?”
  • “What feedback have you received from other people on your strengths and development areas?”

Options: Discuss their options

Generate multiple options for closing the gap between goal and reality (where they want to go and where they are today).

Collaborate on a list of education, experiences, and exposure that will get them closer to their dream job. 

  • “What can you do right now to further develop skills that would be useful in reaching that goal we talked about earlier?”
  • “What stretch assignments, big projects, or experiences could you pursue?”
  • “What networking or mentorship options are there?”
  • “What books or other learning do you know that could help you explore?”

Write down the Way Forward: create a short- and long-term plan

Way Forward: What will you do? Identify achievable steps to move from reality to goal. 

👉 Download this career action plan to jointly commit to your employee’s development. 

Create a shared document with your direct report, so you can both collaborate on it during your conversation. Agree on about three action items under the short-term “Develop Role” category and about three action items under each of the longer-term “Develop Skills & Network” and “Develop into Different Role” categories. When writing down action items, clearly indicate who will do what by when.

Develop current role: short-term (3 months)

What adjustments can they make in their current role that will help them move toward their ultimate career goal? For example, mentoring junior team members through weekly 1-1s is a great step towards becoming a people manager. 

Develop skills and network: longer-term (18 months)

What skills do they need to acquire? Maybe there are relevant training courses to complete or books to read. For example, a recruiter wanting to move to HR operations could do some employment law course work.  They could also connect to people in your combined networks who could help them uncover opportunities.   

Develop into different role: longer-term (18 months) 

Is there a different role they can do over the next 18 months that will help them get closer to the career of their dreams? Work together on a plan to bridge that gap either through stretch assignments, mentorship, training, or experience.

Send this message automatically using Pyn

Back to key moment
Next Career Journey Pyn
Your report hit their 3 months mark. Time for a lightweight career conversation.
View next pyn