Career conversations are a critical ingredient of high-performing teams. Your employees are going to grow with or without you. You can either be a part of that growth or wave goodbye when employees leave for better opportunities. It’s a hard lesson I’ve learned from managing teams myself, and the reason I founded Groove—to help managers and employees create a sounding board to find their career true-North.

When career conversations are forgotten or done poorly they impact your team and business more than you may realize. Lack of career development is the #1 reason employees leave companies. Psychological safety (or the belief that you won’t be punished when you make a mistake), grows with open conversations about career.

This conversation is a keystone in building trust between managers and employees. Doing it well shows an employee that a manager cares and is willing to invest time and energy into them.

Here are four unconventional ways to make this conversation great. 

1. Remember a career conversation is not a performance conversation 

Performance and career are fundamentally different. A performance conversation is about looking backward. A career conversation is about looking forward. Performance is about how an employee is helping the company. Career is about the employee’s desires, plans, and skills. 

No one (neither manager nor employee) looks forward to a performance conversation. It’s tempting to combine the conversations to save time. But there’s a distinct difference when you show an employee you care about them as a person, not only the work they do. It’s sadly rare for most managers to genuinely say “I’d like to spend time listening while you tell me more about you.” 

My recommendation is to set aside at least 45 minutes to focus on a conversation about someone’s career. This should happen at least every six months, though quarterly is ideal.

2. Skip the typical first question

Don’t start the conversation with the tired and daunting question “Where do you see yourself in five years?” Most people answer this question with a role. Usually, it’s a little “higher” than where they are right now. But in our fast-changing world roles are less relevant than they’ve ever been.

Future ideas of what you want flow with more clarity when you first talk about what matters most to you.

A better way to start this conversation is to ask “what matters most in your career?”

3. Talk about more than compensation

Many people today have a tough time articulating their values in terms other than economics.

We often think about salary and benefits when getting a new job. But other factors such as culture, flexibility, or autonomy end up being the things that can make work great or cause serious stress.

Spending time talking about what values are most motivating to someone can help put desires, requests, and plans into context. 

Compensation matters at work. But it provides limited motivation. Studies show the diminishing return of increased compensation on your happiness.

While your specific plan may change over time, your values shift less often. Understanding what you actually want makes it more likely you’ll achieve it even when circumstances shift.

4. Don’t make a set plan—instead focus on career experiments

Today’s work environment changes faster than ever before. What a freshman in college learns in class is less likely to be relevant when they graduate than in years past. So how can you make a plan when things will change?

Take a leaf from how tech companies build products. You create a flexible roadmap. Create a 1-page document that lists out your career “why”, what success looks like, and how you’re going to get there.

Writing down a linear plan of “how” is destined to fail. Instead, start by identifying and committing to small career experiments

How this can benefit you and your employees

Done well this conversation leads to positive outcomes for everyone. You create more psychological safety on your team by showing your employees you want to hear about their background and needs. You understand your employees in a way that can increase the productivity of your team. And by giving your employees more sense of progress, they are more likely to want to stay with your team and company.

One of my best career conversation experiences was when I managed a call center with around 80 employees. I made sure to have open conversations with employees where I asked about their motivations at work and future aspirations.

One of my call managers brought up things he liked about his current role, but also shared that he wanted to go more into org design and development. 

When I learned about this aspiration, I wrote it down so that I’d remember. Over time I found small ways to give him chances to help us with org development work for our 80-person team. He ended up coming up with great solutions for current challenges and he got a chance to practice new skills he was passionate about. It was a win for everyone. 

Having the conversation and framing it as outlined above is a good start. It shows employees that their aspirations are understood and even appreciated. When managers have those conversations regularly, businesses can retain their best talent, even as those employees develop beyond the roles they were hired for. 

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