How to be a Better Leader by Developing “Radical Candor”

The best boss Cares Personally and Challenges Directly

Jordan Rothstein
The Startup
6 min readFeb 14, 2019

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My goal as a manager is to create a bullshit-free environment where people love what they do and who they do it with. Easier said than done. As an outsider, I think Google does a great job creating a culture where conflict is encouraged and pulling back punches is frowned upon.

Radical Candor is the secret to being a good boss.

I recently finished Kim Scott’s New York Times Bestseller Radical Candor: Be a Kickass Boss Without Losing Your Humanity. The book, which I thoroughly enjoyed, takes you along a journey sharing amazing stories from tech giant executives (Apple, Google, Twitter, and so on) and sheds light on best management practices as they relate to Kim’s “radical candor” philosophy.

Think of this article as a book review, or Radical Candor for Dummies, if you will. I highly recommend the book for those in management positions.

Since reading this book, every conversation I’ve had with my team of 16 has shifted. I keep this philosophy in the back of my mind and always try to be radically candid with everyone I directly manage. Kim does a great job explaining in her final chapter how you can use the tools you’ve learned to introduce this management strategy to your team.

A Brief Introduction— Who Is Kim Scott?

  • New York Times and Wall Street Journal Bestselling Author
  • Led AdSense, YouTube, and Doubleclick Online Sales and Operations at Google
  • Developed and taught a leadership seminar at Apple
  • CEO coach at Dropbox, Qualtrics, Twitter, and several other tech companies.

What is Radical Candor?

Kim explains that good management can be broken down on a two-by-two chart with the axis Challenge Directly and Care Personally. By doing both of these at the same time, you will get the best work from your team while building the best relationships of your career. Simply put, Radical Candor means saying what you really think while also giving a damn about the person you’re saying it to. So how do we build a radically candid relationship?

1. Care Personally

Aka, give a damn. The key to building a good relationship with your direct reports is to genuinely care about them. Get to know them on a personal level. Are they married with kids? Single mom? What are their hobbies? Do they have a long commute? These details are great conversation starters to show you care. Most bosses do actually care about their team members, but they fail to demonstrate it. Take the time out of your week to do quick check-ins with your team one-on-one and ask how they’re doing. E.g. How was the commute today? Did you watch that tennis match last night? Are you taking your son to see the new Spiderman movie?! 🕷

Don’t be afraid to get a little personal, but be careful not to cross any lines. Politics, religion, sex, race, ethnicity, and health are all topics you should probably avoid. Caring personally about your peers makes it easier to challenge them directly, and your feedback is much better received.

2. Challenge Directly

Caring personally can be detrimental to a working relationship unless you fulfill the Challenge Directly quadrant. This means offering direct feedback if you don’t feel a person is fulfilling their duties to the exceptional level you desire. Believe it or not, people actually enjoy receiving feedback as long as it’s presented in the right way. Don’t hold back your punches, but make sure you show them you care before dishing out a direct criticism.

The best way to challenge directly is to start by offering some positive feedback. What is going well in their role? When critiquing a design, which I often do, start by saying what you like about it. Is there any standout thing they do that you really enjoy? Let them know! Then, ease into the critique.

The Bullshit Sandwich:

Be careful of the bullshit sandwich, when you give praise, followed by feedback, and ending with praise again.

If you don’t Care Personally and Challenge Directly, you may end up losing an employee with an exit interview that looks something like this:

Michael Scott Interviews Toby on The Office

What happens when you fail to Care Personally and Challenge Directly?

The common mistakes of failing to provide Radical Candor are explained by Kim Scott below.

  1. Obnoxious Aggression™ is what happens when you challenge but don’t care. It’s praise that doesn’t feel sincere or criticism that isn’t delivered kindly. This is when you behave like a jerk, which if you’re like me, happens when I’m short on patience.
  2. Ruinous Empathy™ is what happens when you care but don’t challenge. It’s praise that isn’t specific enough to help the person understand what was good or criticism that is sugarcoated and unclear. This happens when you don’t want to hurt their feelings and you’re too nice.
  3. Manipulative Insincerity™ is what happens when you neither care nor challenge. It’s praise that is non-specific and insincere or criticism that is neither clear nor kind. The result of manipulative insincerity is passive aggressiveness, backstabbing, and usually results in an unhealthy work environment.
Jack Sharp @ Unsplash

Rock Stars v. Superstars

Understanding the differences between rock stars and superstars really helped me put people in the right place. I always understood the different personalities at my company, but this concept gave it a label that I can understand and communicate with my team. Rock stars and superstars are equally valuable but have much different growth trajectories that you need to care for.

Who are the rock stars?

The rock stars are the people that are happy in the position they’re in, don’t need to move into management roles, and don’t have the goal of running a department or the company. They come in, get the job done, and perform exceptionally well. Rock stars should grow internally by constantly improving their craft, teaching their coworkers through experience, and staying on top of trends. Eventually, they will get to pick and chose the projects they want to work on as they start to mentor their peers.

Who are the superstars?

The superstars are the individuals that want to move upwards in an organization, taking on new responsibilities and challenges as they grow. They are usually eager to lead teams, and eventually, they will want to run a department or join the executive team. Not everyone has the same goals, and it’s important to pull this information out of them during interviews and check-ins. Make sure you’re aligning their responsibilities with their long-term goals and you will get the best work out of them.

Kicking Down and Kissing Up

The last concept I wanted to share from the book is “Kicking Down and Kissing Up”. It’s an expression to describe the situation where middle-level employees in an organization are polite and flattering to superiors but abusive to subordinates. I would add that this applies to small business in the case where people are nice to clients, but when clients get angry, they pass this anger along to their employees. I’ve seen this so much in my career and it drives me crazy.

If you choose not to read Radical Candor, I hope the lessons encourage conscious change in how you interact with your team. Let’s strive to build companies that promote conflict, support meaningful relationship, and encourage growth. XO

Kim Scott explaining it first hand.

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Jordan Rothstein
The Startup

Stream of consciousness from a passionate entrepreneur. CEO @ King Tide. A Digital Product Studio. Rise Together.