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What Level Career Conversationalist Are You?

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Levels of career conversations
Photo by Jordan Opel on Unsplash

That’s likely a question that you’ve never asked yourself, but as a manager, it’s an important one. Career conversations are an important part of career development. We’re going to define 5 levels that will make it easier for you to have a better career conversation. Through self-reflection or 360 feedback, it should be relatively easy to know where you stand. You can then set the next highest level as a tangible goal to improve.

Each level builds on top of the previous one. Let’s dive in.

Level 0


  • Manager never initiates any conversations with employees about their careers or development.
  • If the employee brings up a career conversation the manager is not helpful. They’re either dismissive, unsupportive, ignorant, or don’t offer any insights. 

Grade: F

You don’t want to be this manager! The good news is that it’s hard to be at this level. The most likely explanation is that you don’t believe in supporting your employees’ careers and development. You may believe that it’s not your job or that it’s not in the best interest of the organization. If so, I think you’re mistaken, though I would be curious to understand that point of view better. Here are some of the potential risks of not supporting them:

  • Decreased engagement
  • Decreased motivation
  • Decreased innovation and creativity
  • Lack of trust and goodwill

Tips for improvement:

  • Be prepared to answer the following questions from your employees:
    • How do promotions work?
    • What are the different career paths?
    • What is my next role, and what does it take to get there?
    • What should I be working on to progress in my career?
  • Discuss this with your manager, HR, and peers. You want your answers to be accurate and consistent with the rest of the department.

Level 1


  • Manager doesn’t initiate conversations about careers and development.
  • Manager is helpful when the employee initiates a career conversation. 

Grade: C

This is better than nothing. At Level 1 you may think that you don’t have time to support their careers and that it’s their responsibility. You’re at least providing value to them. If you’re good at responding when they initiate a career conversation, you may even add a lot of value. You can do much better though. Here are some of the downsides of this level:

  • It’s not equitable. The people that are comfortable and skilled at initiating career conversations will benefit more than those who aren’t.
  • It’s hard to know what you don’t know. The employee can only bring up career topics and options that they’re familiar with. This could leave some valuable conversations out.
  • The employee is making all the effort which is not as good at building trust and goodwill. If there’s little trust the employee is less likely to share their career goals.

Tips for improvement:

  • Schedule multiple times throughout the year to have career conversations.
  • Prepare for each conversation. Make sure you understand career progressions in your department well. Anticipate common questions.

Level 2


  • Manager initiates some career conversations, usually at review time. 
  • Manager discusses the employee’s career options in the department (e.g. career ladder and/or different tracks).
  • Manager discusses the employee’s next role, where they stand, and how to get there. 

Grade: B

This is pretty good. You could consider this your target level or your minimum requirement. At Level 2 you’re taking an active role in the career conversations. Your focus is helping employees progress their careers at your company. This is reasonable and will provide solid value to the employee. You can still do better! Here are some of the downsides of this level:

  • The default progressions in your department may be limiting to some employees.
  • Focusing on the next role may feel transactional and less inspiring.
  • The focus is on the benefit to the company which is sub-optimal for building trust and goodwill.

Tips for improvement:

  • Expand the scope of your career conversations. Get curious about them as individuals and about their career goals:
    • What are their personal goals?
    • How much is career growth important to them?
    • What kind of growth are they looking for right now?
    • What are they passionate about?
    • What do they want to learn?
  • Expand the career options that you’re comfortable discussing beyond the next role in your department.
  • Talk about career and growth frequently in your 1-1s.
  • Experiment with a variety of different conversations and questions.

Level 3


  • Manager discusses the employee’s Career with a capital C. 
  • Manager takes a more holistic view of their career unconstrained by the roles available in the department, or even the company.
  • Career conversations explore short-term and long-term goals. 
  • Conversations occur more frequently throughout the year. 
  • Employees trust the manager enough to shares their true career goals. 

Grade: A-

This is a great target level for all managers. The big difference at this level is that for the first time we’re putting the goals of the individual on par with the goals of the company. We’ve made the transition to servant leadership in the belief that the best way to serve the company is to serve the company and the individual. We’re proactively supporting the individual. This not only builds trust and goodwill; it also adds a lot more value to them! If they trust you, they are more likely to tell you what they really want. This gives you a much better chance to find them work they love. It’s not crazy to say that if you do this well you could have a profound effect on someone’s career, maybe even their life.

Tips for improvement:

At this level improvement becomes harder. Progressing through the earlier levels is mostly a question of taking the time to perform various actions. To progress beyond Level 3 you have to view career conversations as a skill and get serious about working on it.

Level 4


  • Manager inspires the employee. 
  • Manager motivates the employee.
  • Manager expands the employee’s realm of career possibilities.
  • Manager sees potential that the employee doesn’t see in themselves.

Grade: A+

The Picasso of career conversations! This is Level 3 executed at an expert level. The other levels are attainable through effort and knowledge. This one is not. This level requires superb emotional intelligence, listening, and job crafting skills. You need to have a great feel for asking insightful questions. You have to know when and how to push people out of their comfort zones and when to reassure and build up their confidence. You have the humility to coach people to find their own path instead of imposing your vision.

This level requires the skills and the dedication to apply them, one good career conversation at a time. This is really hard to do consistently. Which is exactly what you want for an expert level!

Final thoughts

These levels are not perfect. They’re not going to be neat and precise, and they don’t capture all the subtleties of career conversations. You may find that you don’t fit nicely in any of them. You may reach a higher level with one employee versus another. As imperfect as they are, they can be helpful. The benefit of these levels is using them for a quick self-assessment:

  • What level are you at with each of your team members?
  • What would you have to change to move up one level?

If you realize that you’re not at the level you want to be, don’t be too hard on yourself. You have a lot on your plate and chances are you’ve had little to no training on career conversations.

Being a better career conversationalist is a great way to add value to each of your team members. Each career conversation is an opportunity to build trust, increase engagement, and job satisfaction. If you can have them often and skillfully your team will be more likely to stay, perform at a high level, and be happy. Challenge yourself to get to the next level!

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