What Is a Career Conversation and Why You Need to Have Them

Sam Cook


What Is a Career Conversation and Why You Need to Have Them

The saying “the grass is always greener on the other side” pretty much sums up what happened during The Great Resignation. Nearly 50.5 million people quit their jobs in the US alone, but there was a catch: 80% regretted their decision. The reality is that most people don’t want to quit; they feel forced to. Sometimes, the issue is low pay or a bad manager. But quite often, people leave because they don’t see a clear path forward in their career.

Holding career conversations with employees can be a great way to establish their development needs and discover exactly what they want to see from their careers. As they begin to develop their career path and advancement and growth plans, the company should look into how they can best support them.

Take it with you:

Download your FREE Career Mapping exercise to help guide your team members through career converastions

What Is a Career Conversation?

A career conversation is exactly what it sounds like: An honest and strategic conversation about what an employee might like to see from their career advancement. This is not just a case of assessing how the employee feels in the moment; effective career conversations also consider where the employee wants to go in the future.

Career conversations cover a variety of topics and important questions, including:

  • How do they feel about their current role?
  • Do they want to go into management or become a subject matter expert?
  • Are they looking for a career pivot into a different role or function?
  • Can they see themselves retraining and trying out a different industry completely?

Having this crucial conversation and supporting employees through career mapping and other tools is beneficial for both the employee and the company.

What Are the Objectives of a Career Conversation?

The objective of a career conversation is to find out what the employee wants their personal and professional development to look like. Even if two employees are hired to do the same job, they will inevitably want to take their careers in different directions.

Ideally, career conversations should meet 3 objectives:

  1. Alignment with overall organizational goals
  2. Professional growth and development
  3. Increased engagement

Each objective carries benefits for both the employee and the company. Aligning employees with company goals allows for more targeted career development. Workers can gain insight into how their career progression can benefit the company, while managers can truly understand their team members’ future aspirations.

Identifying professional growth and development opportunities helps a manager and employee to create actionable career steps and can feed into long-term plans to develop teams as a unit or identify high-potential employees.

Finally, increased engagement and motivation are just good all around. Happy employees lead to a good company culture and tasks being fulfilled efficiently. Employees feel valued and demonstrate high levels of job satisfaction, and managers can easily nurture relationships between team members.

When Should You Have Career Conversations?

An image of two employees engaging a career conversation on a couch in an office.

There is no right or wrong time to have career conversations with employees. You could sit down with someone during their onboarding period to talk about their plans for the future. If an employee has been at the company for a while but has yet to have a career conversation, schedule one during a quarterly or annual review. 

Regular career conversations can establish the direction an employee is headed in and what they hope to achieve in the future. If a manager is just discussing development activities with no context about how this might fit into an employee’s ideal career progression, valuable resources and time could end up being wasted.

How Do You Structure a Career Conversation?

Question: Let’s say you’re meeting with an employee who has been struggling with direction for the past year. You know that employee wants to stay, but it’s become evident they feel stuck in their career with your company. What do yo you?

There are two answers to this question:

  • Plan and hold a career conversation to help determine what this team member needs.
  • Match this employee with a career mentor who can meet with them regularly to help them build the skills, experiences, and insights they need to move in the career direction that suits their needs.

We’ll discuss the mentoring component further later. First, let’s examine how to create and structure those initial conversations on career direction.

Do the preparation!

Both the employee and the manager should prepare objectives for the conversation before it happens. Since both will have different points they wish to discuss, a little prep work can help them articulate their personal goals while also understanding the other’s viewpoint. It can also avoid wasting the valuable time of both parties. A Slack survey found that having more than 2 hours of meetings per day is about the extent most people can handle. Beyond that, workers begin feeling meetings cut into their productivity.

Employees should consider the goals they have achieved so far and the career opportunities they would like to see in the future. Managers should attempt to familiarize themselves with the employee’s current performance, role, and responsibilities to see how they align with company expectations. 


When holding career conversations, make sure that they always remain a dialogue. They should involve two or more people being prepared to offer honest and open opinions regardless of where the conversation might go. Even if you do not discuss what you initially prepped, an effective career conversation could still be achieved if new opportunities are identified and new tasks or goals are created.


No matter what is discussed, make sure there is some degree of follow-up. Depending on the nature of the discussions, this could take a few forms. It could be as simple as a round-up email discussing what the manager and employee talked about with the next steps for both to take. It could also be a little more in-depth, with the promise of an introduction between the employee and another team member that could blossom into a mentoring relationship.

The next session should also be set up in the follow-up. Ongoing career conversations require semi-regular input if they are going to prove useful to employees. At a minimum, they should form part of an annual performance review, but many find that they have more of a clear understanding of the paths open to them if they discuss it on a quarterly or even more regular basis.

How Do You Discuss Career Aspirations?

It can be daunting for an employee to sit there and discuss potential career paths with a manager or supervisor as it is. However, when the employee has no intention of staying in a role for more than a few years, they can feel nervous about bringing up future plans to a manager. After all, that future plan involves them leaving a company that might have so far offered them a lot of career support. 

Discussing career aspirations shouldn’t be so daunting. Neutral questions can help a manager understand what the professional development of an employee might look like without having to discuss any sort of longevity.

These questions could include:

  • What would you describe as your biggest passion?
  • What are your strengths?
  • Where do you wish to improve and why?
  • Which new skills do you wish to learn and why?
  • Which of your recent assignments have been satisfying or interesting? Which haven’t?
  • What support would you like from management to reach your goals?

Most employers now recognize that average employee tenure has been getting shorter. LendingTree found that since 2019, tenure for all workers has dropped about 11%.

Few employees retire at the company where they started. As a consequence, HR and talent development leaders need to pivot their focus on keeping people as long as possible without worrying about them quitting.

Which is to say: Yes, people are going to quit eventually. But if you're strategic about helping them navigate their career within your company by having meaningful conversations that include effective follow-through, you can keep them for longer.

That means investing time, energy, and resources into retention strategies that impact employees from the moment they're hired.

How Do You Set Goals During a Career Conversation?

Setting career goals is a vital part of these important conversations. In doing so, you will have metrics that can be discussed during check-ins, and will also give employees something tangible to work towards.

Focus on what the employees actually want to do

Each individual employee is going to have a different idea of what their career path should look like. Therefore, they should be the ones to guide their development plans. Though a manager might want to guide their direction and potentially offer connections they might not have on their own, the initial idea should come from the employee. It is their future after all!

Keep it REAL!

Any goal should be a REAL one! This means that it is:

  • Relevant
  • Experimental
  • Aspirational
  • Learning-based

You might have heard of SMART goals before. We love to use the SMART goals for measuring performance, but that does not always make them the best option for setting developmental objectives. The REAL goals are a bit better at finding the subject and need at the heart of someone's goal and can help them achieve these more easily than other structures.

Check out our blog about REAL goals in action to find out more about how they can help your goal-setting!

Have short, medium, and long-term goals

Even when using the REAL goals template, it can be difficult to pick a really good timeframe for you to achieve your goals. This is why it is often a good idea to break them down even further into short-, medium-, and long-term goals.

Short-term goals should be achievable within the next 6 months. Medium-term goals are to work on over the next year, hopefully in time for your next annual appraisal. Finally, have long-term career goals that could take 18 months or even longer to complete.

Follow Up Career Conversations with Mentoring

Two employees continuing a career conversation on a couch in an office setting.

Career conversations are only the first step in helping employees navigate their roles within your company. And that's because these conversations are more about understanding. A career conversation can help your team members understand:

  • More about their current role
  • What the future career path for their role looks like within your company (and even after)
  • How they can continue to progress toward internal mobility, such as future promotions or career pivots

These conversations cover a very important "what." A career mentor can help them understand the "how."

That's where structured, formal mentoring and mentoring software come in.

MentorcliQ can help you provide career mentoring to every employee in your organization without having to requiring you to hire an arm of HR specialists and program admins. The software is designed to automate enrollment and matching, saving you countless hours and potentially millions of dollars in program management alone.

What's more, companies that use MentorcliQ see a 32% reduction in turnover (and an average 62% when employees are engaged in both ERGs and mentoring).

Career mentoring leverages your existing employee population to get the most out of the internal knowledge that exists within your organization. It also takes advantage of the excellent culture you've created already, or helps you build the culture of retention and development that you want.

Need to know more: Here are two things you can do today to get started:

🧐 Explore our blog post on Career Mentoring: Critical Elements for Success.

👉 Book a Demo to see how easy it is to give everyone in your company a career mentor.

Sam Cook

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