skip to Main Content

How To Have Radically Candid Career Conversations Like a Boss

In order to build a successful team, you need to truly understand each person’s long-term ambitions and how their current circumstances fit into their life and career goals. You can only achieve this is by getting to know each member of your immediate team personally. Helping each person on your team grow in the direction of their dreams is part of being a kick-ass boss, and it’s the key to successful growth management. This is why you can’t skip having career conversations.

The Quick & Dirty On Career Conversations

Each individual person is on their own growth trajectory, and, as a boss, it’s a mistake to push everyone to be either a “superstar” or a “rock star.” To be successful, you need to balance growth and stability.

Career conversations will guide you through career planning with your direct reports so you can learn what is important to them, understand where they want to go and work collaboratively with them to build the best possible plan of action to benefit each individual person as well as the team as a whole.

Only when you get to know your direct reports well enough to know why they care about their work, what they hope to get out of their careers and where they are in the present moment in time, can you put the right people in the right roles and assign the right projects to the right people.

The bottom line is that having career conversations with each person who reports directly to you is the only way to understand their growth trajectory. Not only are these conversations crucially important to understanding how to help your people grow, they’re vital to understanding how you can help them grow relevantly.

To ensure the career conversations you have are both rewarding and effective, Radical Candor recommends a structure for a series of conversations between managers and direct reports created by Russ Laraway, VP of people operations at Qualtrics, who developed a particularly effective approach for having career conversations during a difficult period at Google. We recommend you begin having these conversations with people you’ve been working with the longest.

Start with the Past – Life Story

The first step is understanding people’s motivations and values, the things that drive them. 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 those choices? What did those transitions teach them about what they love and hate about their work?

Talk about the Future – Dreams

Step two is understanding where people want to be at the pinnacle of their careers. While some bosses are skeptical that younger workers know what they want to be when they grow up, everyone has dreams, and you just have to help people make them a little more tangible. Other managers worry about asking their reports to hone in on a single vision too early in their careers.

Don’t use these concerns as excuses to avoid having career conversations. People change, and their dreams can change. This is why it’s important to have regular career conversations. Just like soliciting criticism from your team, it’s not a one-and-done practice.

Plan for the Present – Career Action Plan

With an understanding of the past and the future, you can now create a relevant and thoughtful action plan with clear owners and clear timelines. (Listen to Career Conversations on the Radical Candor podcast.)

Once you’ve gotten the hang of these conversations, you’ll look forward to them. They are your single biggest opportunity to move up on the “Care Personally” axis of the Radical Candor framework. In fact, these conversations are the very first thing we recommend you do when rolling out Radical Candor with your team.

Yes, career conversations do take time, but they can occur in your usual 1:1 slots. And they will generate some of the most enjoyable and productive conversations you have as a boss.

There are few pleacareer conversationssures greater than being part of a team where everyone loves their job and loves working together, and it’s absolutely within your power to build a team that looks forward to coming to work every day.

Read our Career Conversations post by Russ Laraway to learn more about how to have effective conversations with your team.