How to have career conversations with your employees

The what, why, and how of career conversations for managers.

A couple of years ago, I stumbled upon a concept that changed my entire perspective on leadership. That concept was Servant Leadership.

In 1904, a man called Robert Greenleaf challenged the most common leadership models by stating that great leaders focus on the growth and development of their teammates.

This, to me, was a big eye-opener.

While the majority of leadership styles I had seen and heard about before portrayed the leader at the top of a pyramid, this model put the leader at the bottom — serving the needs of the employees.

It’s been over 100 years since Greenleaf first wrote about this concept, but Servant Leadership is extremely relevant in today’s fast-paced world.

In fact, Russ Laraway, co-founder of Candor, Inc. and former military leader, mentioned it during his talk at the First Round CEO Summit two years ago:

“One way to know if you’re exhibiting service leadership is if the people under you are growing and developing,” said Laraway.

Sounds great. But how can you, as a manager, make sure that your direct-reports are developing personally and professionally? How can you become a servant leader, in practice?

Great leaders like Kim Scott, Russ Laraway, and Sheryl Sandberg argue that having career conversations is one of the best ways to serve your direct-reports and help them grow.

In a recent survey conducted by Right Management, 82 per cent of respondents said they would be more engaged in their work if their managers would have regular career conversations with them. And 75 per cent said they would be more likely to stay at their current company.

In spite of what these results show, many organizations and teams have stopped giving career conversations the importance they deserve. In fact, only 16 per cent of employees say they have ongoing conversations with their managers about their career, according to the same survey.

Most of the time, this happens because managers don’t know how and why to talk about career progression with their employees.

And this is where the Fellow.app team steps in 👋 — We want to help you be a great manager and make work better for everyone on your team. For this reason, we gathered some great advice from industry leaders on their career conversations with employees. Excited? You should be. After reading this post, you’ll become a servant leader!

What are career conversations?

Career conversations are ongoing discussions that help you identify your direct report’s professional goals and the steps needed to reach them. Kim Scott, the author of Radical Candor, argues that you should have these conversations with each person who reports directly to you.

“To understand a person’s growth trajectory, it’s important to have career conversations in which you get to know each of your direct reports better, learn what their aspirations are, and plan how to help them achieve those dreams,” says Scott.

Kevin Sheridan, a New York Times best-selling author and employee engagement expert, says that one of the biggest (and most common) mistakes that managers make is not meeting with their direct reports to discuss career development, learning, and promotion opportunities:

“People want to advance in their career, rather than feeling stagnant. Whether it’s learning a new skill set, exploring new responsibilities, or getting a title change, all employees have goals. Managers need to be keyed in on those goals,” says Sheridan.

Why are career conversations important?

1) Career conversations boost employee engagement and retention

In a study conducted by Right Management, 82 percent of respondents said they would be more engaged at work if their manager showed more interest in their career progression.

“Regular career conversations would make them more likely to engage with their work, share ideas, and look for career growth and longevity in their current organization,” says the study.

The connection between career conversations and employee engagement is clear: employees are more likely to enjoy their work when their daily tasks and responsibilities align with their long-term career goals.

“If you know what motivates people because you’ve taken the time to ask about their life, and if you know what people’s dreams are, then you’re going to do a better job giving the right work to the right people,” says Kim Scott.

There’s a similar connection between career conversations and employee retention. For instance, a study conducted by LinkedIn shows that the top reason why people leave their companies is that they didn’t see opportunities for career advancement.

One of your responsibilities as a manager is to hire and retain top talent. In order to do this, you need to show your direct reports that you care about their development, and provide resources and opportunities that contribute to their growth.

2) Career conversations foster self-awareness in the workplace

Believe it or not, most people don’t spend too much time thinking about their personal values and desired career path.

“We plan a lot of things. We plan our families, plan our weekends, plan our vacations and plan our meals. It’s a little crazy to me that we don’t often put a lot of energy, intentionality, or conscientiousness toward our careers,” says Russ Laraway.

That’s why career conversations are such an important part of servant leadership.

Scheduling specific times to talk about career goals and aspirations will help your direct reports reflect on what’s important for them and what they want to accomplish in their career.

What activities and projects do they enjoy most? What kind of work environments do they prefer? What new skills would they like to learn? Where do they see themselves in ten years? How do their personal values relate to their job?

These are all questions that will help your employees become more self-aware.

3) Career conversations help you develop positive relationships with your team

Asking your direct reports about their aspirations is a great way to get to know them and show that you care personally about them.

As Julie Zhuo, Facebook’s VP of Product Design argues in the book The Making of a Manager , your job as a leader is to understand your fellow teammates’ goals, the projects that are suited to their strengths and interests, and the tasks they need support with.

Learning about these things will help you develop closer relationships with them, as they’ll see you as a coach and mentor — and not only as their boss.

“Think of yourself as a coach who is there to support and help your people reach their goals,” says Zhuo.

When should you schedule career conversations with your direct reports?

If you’ve never had career conversations with your teammates, this might seem like a lot of extra work. However, most managers have these talks during their usual one-on-one slots — which as we have discussed in previous posts, should be scheduled weekly or bi-weekly, depending on the task-relevant maturity of each direct-report.

We’re not saying that every one-on-one meeting should address professional development; we know that wouldn’t be realistic. There are other things to talk about, such as weekly challenges, team dynamics, and strategies to help your direct-report on their day-to-day work.

However, leaders like Sourov De, co-founder and president of Stryve argue that you should have these conversations twice a year:

“It works pretty well. We haven’t had a full-time employee leave in the 9 years we’ve been in business. That’s a 100% retention rate for our full-time employees. It’s something we’re really proud of,” he says.

How can you structure your career conversations?

Russ Laraway is a career conversation expert. The approach he developed during his time at Google was so successful that it led to a 10-point bump on engagement scores across the organization.

Would you like to empower your employees, and become a servant leader — just like Laraway did? Start by choosing three consecutive one-on-one slots in your calendar. This means that your career conversation should be scheduled over the course of three to six weeks.

The next step in Laraway’s approach is to address the following three topics; one in each of those meetings:

One-on-one meeting #1: Life story

According to Laraway, managers must understand the past and the future in order to help their direct-reports grow. This is why he suggests that you start your first professional development conversation with this simple opening question:

“Starting with kindergarten, tell me about your life.”

This will help you understand the life events and stories that have shaped your direct reports’ dreams and aspirations.

“It’s amazing what you can learn from a person’s life story if you pay close attention to and ask about their major pivots and transitions. Why did they make them? What did those transitions teach them about what they love and hate about their work?” says Laraway.

For instance, learning that your direct-report has always enjoyed competitive sports will be helpful to understand what type of environments motivate them. Since they are highly competitive, you could come up with targets and ideas to make their work more exciting and competitive. On the other hand, if they say they have always enjoyed group activities or collective arts, you can determine that being part of a team is a big motivator for them.

One-on-one meeting #2: Dreams

Your second career conversation will focus on dreams and aspirations. Laraway recommends that you start this conversation with one question:

“What do you want the pinnacle of your career to look like?”

This is a hard question for many of us. This is why he suggests that you encourage your direct-reports to come up with three to five different ideas.

In order to make your one-on-one more productive, you can use Fellow.app to plan a meeting agenda ahead of time. This will allow your direct-reports to come up with a list of ideas prior to the meeting👌

After going over that list of “dream jobs,” you can collaborate on a list of skills they can start developing to achieve those roles.

The second part of this meeting is figuring out how you, as their manager, can help them develop those skills. As mentioned in Hannah’s example, you can find mentorship opportunities, workshops, projects and responsibilities that best meet the needs of your employees.

Be the coach they remember for helping them reach their end-goal.

One-on-one meeting #3: The 18-month career action plan

In the book Lean In, Sheryl Sandberg, Facebook’s COO, argues that in order to work towards a long-term vision, you need to create an 18-month plan. This is something you can help your direct-report create during your one-on-one:

“I try to set more personal goals for learning new skills in the next eighteen months. It’s often painful, but I ask myself “How can I improve?” If I am afraid to do something, it’s usually because I’m not good at it or perhaps I’m too scared to even try,” says Sandberg.

Speaking out loud about our dreams (especially when our boss is in the room) is not the easiest thing to do. However, Laraway’s three-step framework will empower your fellow teammates to track professional development and see a clear purpose in everything they do at work.

It will also help you find the projects and responsibilities that best align with their dream job. As Marcus Buckingham argues in the book First, break all the rules:

“When developing someone, help them find the right fit… not simply the next rung on the ladder.”

Now that you know about the importance of having career conversations with your direct reports, it’s your turn to be a servant leader and help them grow — because as Sheryl Sandberg argues:

“Leadership is about making others better as a result of your presence and making sure that impact lasts in your absence.”

If you enjoyed reading this article, we think you’d enjoy using the app we built for managers like you.

Fellow is the smart app that makes it easy for managers and their teams to have effective one-on-ones and team meetings, exchange feedback, and track goals — all in one place!