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Career Conversations


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AS DESCRIBED IN Chapter Three, all people have their own growth trajectories, and it’s a mistake to push everyone to be either a “superstar” or a “rock star.”

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.

They are your single biggest opportunity to move up on the “care personally” axis of the Radical Candor framework.

“You need a long-term vision and an eighteen-month plan,” she advised.

## Conversation One: Life Story

Look for motivators. Why did they make the decisions they did. "Please tell me more about that decision."

You are trying to get to know people and understand what they care about.

Is it a boundary violation? Don't push on issues people are uncomforable discussing.

When you understand what motivates someone, you understand their dreams.

The first conversation is designed to learn what motivates each person who reports directly to you. Russ suggested a simple opening to these conversations. “Starting with kindergarten, tell me about your life.” Then, he advised each manager to focus on changes that people had made and to understand why they’d made those choices. Values often get revealed in moments of change.

“You dropped out of graduate school after two years to work on Wall Street—please tell me more about that decision.” Answers like, “I couldn’t even afford orange juice on my grad school stipend, and I just wanted to make more money,” or “I was bored with all that theory and no practical, tangible application of the ideas I was working on,” enable you to begin to put together parts of the human puzzle. In the first case, you might write down “financial independence” as a key motivator; in the second, “see tangible results of work.”

## Conversation Two: Dreams

The second conversation moves from understanding what motivates people to understanding the person’s dreams—what they want to achieve at the apex of their career, how they imagine life at its best to feel.

This isn't about long-term goals or career aspirations or five-year plans.

We want to open this up to outcomes beyond the current job.

The goal is satisfying, meaningful work and productive relationships.

Possible questions:

“What do you want the pinnacle of your career to look like?” Because most people don’t really know what they want to do when they “grow up,” Russ suggests encouraging people to come up with three to five different dreams for the future.

Also as part of this conversation, make sure dreams are aligned with the values they expressed.

Homework from this conversation:

Ask each direct report to create a document with three to five columns; title each with the names of the dreams they described in the last conversation. Then, list the skills needed as rows. Show how important each skill is to each dream, and what their level of competency is in that skill. Generally, it will become very obvious what new skills the person needs to acquire. Now, your job as the boss is to help them think about how they can acquire those skills: what are the projects you can put them on, whom can you introduce them to, what are the options for education?

## Conversation Three: 18 Month Plan

Last, Russ taught managers to get people to begin asking themselves the following questions: “What do I need to learn in order to move in the direction of my dreams? How should I prioritize the things I need to learn? Whom can I learn from?”

it was much easier for managers to identify opportunities at work that would help them develop skills in the next six to eighteen months that would take them in the direction of at least one of their dreams.

Here’s what to do: make a list of how the person’s role can change to help them learn the skills needed to achieve each dream; whom they can learn from; and classes they could take or books they could read. Then, next to each item, note who does what by when—and make sure you have some action items.