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What’s a career conversation anyway?

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People having a career conversation at a table

As managers we’re often told that we’re supposed to have meaningful career conversations with our team members. But what exactly is a career conversation?

One way to look at it is that career conversations support career development.

Supporting the career growth of every member of your team is the responsibility of any good manager and can really drive higher performance and job satisfaction.

Career conversations can come in many shapes and sizes and here are a few good ones to consider.

Conversations around the next promotion

This is probably the one that most people think of when they hear career conversation. These are definitely important but they’re the tip of the iceberg. A few examples:

  • How do promotions work?
  • Explaining your career paths/ladder.
  • Describe in detail what the next role looks like.
  • Letting them know where they stand in relation to the next role and what they need to do to get there.

Conversations about all the roles in your department

Discussing their next role is usually most pressing, but it’s also good to talk about other roles.

  • Pick a role that’s 2, 3, even 4 steps away. What is that role like? What skills/experiences are needed to perform at that role? Is that something that sounds appealing to them? If you have multiple paths (e.g. technical vs. management) make sure to do this with a role on each path.

What they love to do outside of work

These are good ones to have with brand new hires that are not showing any interest in discussing their career (yet). They also help build rapport.

  • What’s something you love to do outside of work that’s important to you?
  • What were you passionate about as a kid? What was special about that to you?
  • What do you dream of doing in the future?
  • If you didn’t have to work to earn money what would you be doing?

What they enjoy at work or would like to try

Looking for long term career goals is one approach, but another is to experiment and learn to find the best match quality between your strengths/interests and a role. These types of questions can provide good information.

  • What skill would you like to improve right now? Why?
  • What’s the project you’ve recently worked on that you felt most energized you (or produced the most flow)? Tell me more.
  • Describe the best day you’ve had at work recently. What did you do?
  • If you could work on any of our projects, which one would it be?

Conversations about their goals and career progress

A more classic approach is to try to figure out what their long term career goals are and work your way backward to find ways to make progress towards those goals now.

  • What work are you doing here that you feel is most in line with your long term goals?
  • What are your long term goals? Have you thought about them?
  • Could you see yourself making progress on more of your goals here? What would need to change?
  • Are you happy with your career progress so far? Why or why not?
  • Imagine that 10 years from now everything you could have hoped for professionally has happened, what does your job look like?
  • Who is someone that you admire and would like to model your career after?

Exploring their strengths and talents and what roles leverage them

You can approach this from your perspective or theirs. This is related to match quality which requires understanding what type of work brings out their best. For more on match quality and the benefits of getting varied experiences check out Range by David Epstein.

  • What strengths do they see in themselves? How do they use their strengths every day? What roles do they think fit their strengths best?
  • What was a time that they felt they were at their very best? What were they doing?
  • What strengths have you seen them use recently? What kind of roles leverage those well?
  • Extra ninja level bonus if you can help someone see strengths and potential they don’t think they have.

Conversations about career options outside of their department

Your first option will clearly be within the department but you shouldn’t be afraid to discuss other options. Letting your employees know that you support their career development even if it takes them away is a powerful message. I work with software engineers and here are some common options:

  • Product management
  • Project management
  • Sales/business development
  • Training
  • Consulting
  • Technical account management or technical sales
  • DevOps, data science, or some other technical role

Conversations about career options outside of the company

Yup, that’s right, I said it. But wait, aren’t we trying to retain our talent? Absolutely. Guess what, if they have their heart set elsewhere, they will leave. If they have a Taker reciprocity style they’ll probably take advantage of you but they were going to do that anyway. If they have a Matcher or Giver reciprocity style they should appreciate that you’re willing to support their career even if it takes them away. They’ll be inclined to reciprocate and reward you by staying longer and doing better work. They could also be great ambassadors for you when they leave.

For more on reciprocity styles check out Adam Grant’s Give and Take.

  • What skills/experiences are needed for that career change which you can develop here?
  • What changes to your current work would best allow you to pursue this goal?

These are some examples and there are plenty more! I got some of these questions from the Getlighthouse blog which is a great source for 1–1 questions and has some really good content on career development, and management in general.

It’s helpful to proactively plan career conversations but they can occur when you least expect them. Remember that the goal is career development. Look for any opportunity to pull information that helps you support it, and push information that helps them make decisions.

Do you have a favorite career conversation?

Originally published on on December 27, 2019.

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