3 Career Conversations With Employees Every Manager Must Have

This article is an excerpt from the Shortform book guide to "When They Win, You Win" by Russ Laraway. Shortform has the world's best summaries and analyses of books you should be reading.

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Do you know what your employees’ career goals are? Are you helping them reach those goals?

If you’re a manager, career development should be an ongoing process with each of your team members. Employee experience expert Russ Laraway recommends having three career conversations with employees, each conversation with a specific focus.

Continue reading to learn how to conduct these conversations and measure their effectiveness.

Career Conversations With Employees

One of Laraway’s focus areas for managers is career development: helping employees to plan and realize their long-term career goals, not just their current job goals. Notably, this focus area includes helping your workers advance their careers even if doing so means that they eventually leave your company.

We’ll examine Laraway’s suggestion of using three crucial career conversations with employees to build the foundation for their career development. Then, we’ll discuss how you can gauge your effectiveness in this area.

Conversation #1

In the first career conversation, ask your employee how they got to their current job role. Ask about their past—their education, their previous jobs, and why they applied for their current position. Knowing your employee’s history will give you a more thorough understanding of them as a person, including their interests, shortcomings, and job skills that may not come up in their current position. This understanding will make you better able to help them find and get their dream job.

(Shortform note: Discussing an employee’s history has benefits beyond just helping them with career development; it can also help you to forge a more personal connection with that employee, which also helps boost their engagement. In Trillion Dollar Coach, Bill Campbell describes the value of getting to know your staff as human beings—talking to them about their lives helps foster connections and reinforces job satisfaction.)

Conversation #2

In the first career conversation, ask about their goals and their aspirations. What do they hope to get from their current job? What do they hope to accomplish over the next year? Five years? What’s their ultimate career goal?

Conversation #3

In the first career conversation, work with the employee to create what Laraway calls a Career Action Plan (CAP). In short, this is a plan to get the employee from their current position to the dream position that they described in the second meeting. What skills will they need to develop? What work experience will they need? How can they accomplish this, and how can you help as their manager?

Tip: Set SMART Goals

Laraway suggests learning your employees’ goals, then helping them make career plans to reach those goals. However, he doesn’t offer a lot of concrete advice on how to do that. One useful strategy is to make a career plan using a series of what Charles Duhigg (Smarter, Better, Faster) calls SMART goals.

SMART goals are objectives that follow certain criteria. They must be:
Specific. Outline a targeted objective, not a vague aspiration.
Measurable. You must be able to measure the goal’s success—in other words, there has to be a way to know when you’ve reached it.
Achievable and Realistic. You must have the time, resources, and skills to complete this goal.
Timely. Have an expected timeline for accomplishing the goal.

Helping your employees set specific, feasible goals—and a timeline to go with them—will create a framework for their career development.

Measuring Your Effectiveness

To find out how effectively you’re helping your workers with their career development, Laraway suggests asking employees to rate you in the following two categories.

1) Constructiveness. Ask: How well does your manager support your career development? How helpful is your manager’s advice about your career? How frequently does your manager encourage you to take on new challenges or learn new skills that may help you in the future?

(Shortform note: One thing Laraway doesn’t discuss in this section is the importance of helping your employees play to their strengths. Ideally, someone’s dream job will be something they have a natural aptitude for, but that’s not always the case—and sometimes they don’t even realize what they’re good at. An attentive manager can help by recognizing and highlighting what the employee does well and what they seem to enjoy. Then, as you continue working with that employee, you might find opportunities to tweak the career plan you’ve created to better suit their talents and interests.)

2) Care. How strongly do you agree with the statement, “My manager cares about me as a human being, not just as an employee?”

(Shortform note: In Radical Candor, Kim Scott writes that in order to truly care about your employees, you have to practice self-care first. Her reasoning is that it’s hard, if not impossible, to truly care about other people when your own needs aren’t being met or you’re distracted by your own problems. She adds that self-care looks different for each person: Some people need to meditate quietly in the morning to prepare for the day, while others need to go to the bar with friends after work. In short, doing whatever keeps you happy, healthy, and focused will be good for you and for your team.)

3 Career Conversations With Employees Every Manager Must Have

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Elizabeth Whitworth

Elizabeth has a lifelong love of books. She devours nonfiction, especially in the areas of history, theology, and philosophy. A switch to audiobooks has kindled her enjoyment of well-narrated fiction, particularly Victorian and early 20th-century works. She appreciates idea-driven books—and a classic murder mystery now and then. Elizabeth has a blog and is writing a book about the beginning and the end of suffering.

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