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Retain Your Team During the Great Resignation 3 | 11

Retain Your Team During the Great Resignation 3 | 11

Table of Contents

You’ve likely heard about the Great Resignation — perhaps you’re even one of the millions of people who’ve bid their jobs farewell over the past few months. On this episode of the Radical Candor podcast, Kim, Jason and Amy talk about how bad bosses, lack of transparency and poor communication are leading to a mass exodus of mid-level workers. How can you retain your team? Listen to find out how a series of small adjustments can help!

Listen to the episode:

The Great Resignation: Episode at a Glance

Gallup CEO Jim Clifton said in the Gallup State of the American Workplace study, “The single biggest decision you make in your job — bigger than all the rest — is who you name manager. When you name the wrong person manager, nothing fixes that bad decision. Not compensation, not benefits — nothing.”

As a boss, job one is you’ve got to treat everyone who works for you as a human being. This means actually talking to them about everything from their career goals to how they like to work — what works best for them versus what works best for you. Focus on being a partner, not an absentee manager or a micromanager.

This is always important, but it’s even more important to remember when your whole team is remote. Remember that everyone is different, which is why you need to ask each member of your team what works for them. While some people may want to hop on the phone several times a day to talk, others might find this disruptive and stressful. Don’t assume that what works for one person will work for every person.

If you have a manager who doesn’t communicate with you, you’re more likely to become part of the Great Resignation because humans do not handle uncertainty well. As Brené Brown says, "Clear is kind, unclear is unkind."

In order to retain your team, Gallup suggests having "stay conversations" with your direct reports. "Stay conversations are one-on-one conversations designed to learn more about the employee, including their passions and career goals, what they value in life, and what they need to be more successful in their role." 

At Radical Candor, we call these Career Conversations. 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.

Career Conversations are something created by Kim's former Google colleague and Candor, Inc. co-founder Russ Laraway. (Get Russ's book: When They Win, You Win: Being a Great Manager Is Simpler Than You Think.)

radical candor podcast Russ Laraway & Kim Scott

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, but they’re also vital to understanding how you can help them grow relevantly. Russ has created a Career Conversations tool you can use with your team!

Radical Candor Podcast Checklist

Tip 1
Get to know each member of your team as a human being. Don’t assume that what works for one person will work for every person.

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 — are they in rockstar mode or superstar mode, can you put the right people in the right roles and assign the right projects to the right people.

Tip 2
Have regular two-minute impromptu conversations with your team members. If you work remotely, text them or ping them and ask if they have two minutes to chat.

The atomic building block of Radical Candor is the two-minute impromptu development conversation. You don’t want to try to operationalize impromptu chats. The motivations of both the feedback giver and the feedback receiver need to be intrinsic.

The motivation to solicit guidance and to act on it is the desire to improve, to grow, to do good work and then make it better, to build strong relationships and then make them stronger.

“I’m listening to you because I want to develop the skills and the team I’ll need to succeed.”

The motivation to give guidance is mostly altruistic—to help another person and the team as a collective flourish.

“I’m telling you this because I want to help you develop the skills you need to succeed and because it’s not fair to your peers if I don’t tell you.”

If you tie each two-minute conversation too explicitly to extrinsic motivators like bonuses, promotions or termination, you can ruin the motivation for them. If an employee thinks each two-minute impromptu conversation is going to impact their compensation or future career prospects, they will be less open to hearing what was said and more prone to fight it.

Tip 3
Have Career Conversations with each member of your team and revisit them often so you understand who is in rockstar mode and who is in superstar mode and how that aligns with the goals of the overall team.

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.

Talk about the Future – Dreams: Step two is understanding where people want to be at the pinnacle of their careers.

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

But remember, 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.

Don’t put people in boxes and leave them there.

Radical Candor Podcast Resources

 

The Radical Candor Podcast theme music was composed by Cliff Goldmacher. Order his book: The Reason For The Rhymes: Mastering the Seven Essential Skills of Innovation by Learning to Write Songs.

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Key Questions Covered

What is causing the Great Resignation, according to Radical Candor?

According to Kim Scott, Jason, and Amy on the Radical Candor podcast, the Great Resignation is largely driven by bad bosses, lack of transparency, and poor communication. When managers fail to treat employees as human beings, avoid regular check-ins, or leave people in uncertainty about their roles and futures, workers leave. Gallup CEO Jim Clifton reinforces this, noting that naming the wrong person manager is the single biggest workplace mistake — and nothing, not compensation or benefits, fixes it.

What are Career Conversations and how do they help with employee retention?

Career Conversations are structured one-on-one discussions — developed by Russ Laraway, Kim Scott's former Google colleague — that help managers understand each direct report's motivations, values, and long-term goals. They unfold in three steps: (1) explore the employee's past life story to understand what drives them, (2) discuss their future dreams and career pinnacle, and (3) build a present-day action plan with clear owners and timelines. By understanding where people want to go, managers can assign the right roles and projects, significantly improving retention.

What are 'stay conversations' and how are they different from exit interviews?

Stay conversations are proactive one-on-ones designed to learn what employees value, what their career goals are, and what they need to succeed — before they decide to leave. Unlike exit interviews, which happen too late, stay conversations help managers address concerns and align opportunities while the employee is still engaged. At Radical Candor, these are called Career Conversations, and they serve the same purpose: keeping your best people by showing genuine interest in their growth and well-being.

How do two-minute impromptu conversations help retain employees?

The two-minute impromptu conversation is described as the atomic building block of Radical Candor. These brief, informal chats — even a quick text or ping on a remote team — keep the lines of communication open and signal to employees that their manager is present and invested. The key is keeping them intrinsically motivated: they should feel like genuine moments of connection and development, not performance evaluations tied to bonuses or promotions. Tying them to extrinsic rewards makes employees defensive rather than open.

How should managers handle the fact that every team member is different?

The Radical Candor framework emphasizes that you cannot assume what works for one person works for everyone — especially on remote teams. Some employees thrive with frequent phone check-ins; others find that disruptive. The solution is simply to ask each person what communication style and working arrangement works best for them. Getting to know each team member as an individual human being — their goals, preferences, and current mode (rockstar vs. superstar) — is the foundation of good management and effective retention.

What is the difference between rockstar mode and superstar mode?

In the Radical Candor framework, 'rockstar mode' describes employees who are excelling in their current role and prefer stability and mastery over rapid advancement — they are the backbone of a high-performing team. 'Superstar mode' describes employees who are eager to grow quickly, take on new challenges, and move up. Understanding which mode each team member is in helps managers assign the right projects, set appropriate expectations, and support each person's growth in a way that feels relevant and motivating to them personally.

Keep going.

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