Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

Emily Azevedo By: Emily Azevedo

Mainsail Partners recently hosted our annual CEO Summit in Napa Valley, CA, where 25 of our portfolio CEOs and board members gathered for two days of networking and knowledge sharing. We find that these events have proven to be productive and impactful and provide portfolio executives with the opportunity to swap ideas, test new concepts in small group settings, learn from industry trailblazers and, of course, enjoy beautiful Napa Valley.

This year’s speaker line-up was stacked with talent that covered a wide range of topics including leadership, M&A strategies and a feedback philosophy known as “Radical Candor.” You might be familiar with “RadCan” from Season 5 of “Silicon Valley” when characters professed to be practicing Radical Candor, but really provided some hilarious examples of Obnoxious Aggression; in other words, acting like a jerk.

The show is satirical, but the episode strikes a nerve: we could all work on our feedback. It also shows how easily the philosophy can be misused if people don’t include caring with their challenge.

At the heart of this movement is Kim Scott, author of  Radical Candor: Be a Kickass Boss without Losing your Humanity and co-founder of Radical Candor, LLC, the executive education company based on the book. Since hitting shelves in March 2017, the Radical Candor philosophy has spread like wildfire and is increasingly prevalent among management teams. These days, Kim is hard at work on her next book and accepts very few speaking engagements, so we were particularly excited to welcome her as one of our 2019 CEO Summit speakers.

Prior to publishing “Radical Candor,” Kim worked at Google where she led AdSense, YouTube and Doubleclick Online Sales, reporting directly to Sheryl Sandberg. She unofficially became known as the “High Priestess of the Long Tail,” because she placed ads on pages that normally didn’t have them, mostly for small publishers. Kim has also been a member of the faculty at Apple University and an advisor at Dropbox, Qualtrics, Twitter and several other Silicon Valley companies.

Kim’s talk was the topic of much discussion at our CEO Summit and we’re excited to share our recap with the greater Mainsail community.

Care Personally and Challenge Directly

Kim begins by breaking down variations of feedback into a 2×2 matrix with two axes: Care Personally and Challenge Directly.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

The vertical Care Personally Axis, also known as the “give a damn” axis, ranges from rage at the bottom to love at the top. As you move up this axis, you care increasingly for the person to whom you’re providing feedback.

The horizontal Challenge Directly Axis, or the “willingness to piss people off” axis, spans from “silence” on the left to “challenge directly” to the right. Challenging people is often the best way to show you care. It does not mean that whatever you think is the truth; it means you share your (humble) opinions directly.

Ruinous Empathy

In this quadrant, we care deeply, but we’re reluctant to challenge because we’re afraid of hurting someone’s feelings. A perfect example is if someone on your team frequently interrupts in meetings, but you don’t correct them for fear of hurting their feelings. Your intentions are kind, and it’s not as though you don’t care, but the results are ineffective because you are not being direct. Kim gave a great example of an executive that she fired who was completely blindsided. The reaction was “I had no idea this was coming; I thought you cared about me? Why didn’t you tell me I was doing X ineffectively?”

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

Manipulative Insincerity

Here, we are both unwilling to challenge and unable to care. For example, you’re in a debate with someone and just give in because you decide you don’t care enough. It can sound like this: “OK, you’re right, I’m wrong.” Even though you don’t really mean it. Manipulative Insecurity looks a lot like passive aggression and makes for a toxic workplace environment.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

Obnoxious Aggression

This is one of the more damaging quadrants, in which we are perfectly willing to challenge, but don’t show that we care—otherwise known as being a bully. It can happen, for example, when a boss belittles an employee, embarrasses them publicly or throws them under the bus. Though Obnoxious Aggressors might experience quick wins, very rarely do they succeed or find long-term satisfaction.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

Radical Candor

As Scott puts it, “Radical Candor happens when you say what you really think and allow yourself to challenge others and be challenged in return.”  Unlike Obnoxious Aggression, radically candid feedback comes from a place of concern; it’s kind and clear, specific and sincere.  And unlike Ruinous Empathy, Radical Candor addresses problems directly, instead of letting them fester.

Practicing Radical Candor happens in three minutes or less. It’s in-person, succinct and impromptu. It comes from a place of deep caring and it’s presented in a straightforward, clear way.

In the case of the interrupter, the Radical Candor approach could involve pulling them aside to address it immediately after it happens in a meeting, suggesting that the habit might prevent them from advancing in their career.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

3 Rules for Radical Candor

Whether you’re giving, receiving or encouraging feedback (be it praise or criticism), Scott provides a few ground rules:

1.) Get it

  • Make it routine. Build receiving feedback into all of your 1:1s.
  • Ask a go-to question: “What can I do that will make it easier to work with me?”
  • Count to six. Embrace the discomfort. Let them talk.
  • Listen with the intent to understand, not to respond.
  • Reward the candor.

2.) Give it

  • Keep it succinct: 1 to 3-minutes.
  • Be humble. Work toward a shared truth.
  • Be helpful. Provide specific guidance.
  • Do it immediately and in person.
  • Praise in public; criticize in private.
  • Keep it objective. Don’t address personality traits.

3.) Encourage It

  • Share your Radical Candor stories—good, bad and ugly.
  • Eliminate the phrase “Don’t take it personally.” This is a quick way to minimize the other person’s emotions and destroy trust.
  • Don’t be a go-between. Encourage people to resolve issues themselves.
  • Don’t back off. Watch out for Ruinous Empathy!

It’s Time to Get Radical

From the time we’re toddlers we’re told, “If you don’t have something nice to say, don’t say anything at all.” Radical Candor is here to help you break that rule.

Whether in your personal or professional life, feedback is unavoidable and essential to success. Radical Candor provides a framework to provide, accept and encourage feedback in a productive, constructive manner.

Thanks to Kim Scott for presenting at this year’s Summit. You can learn more about Kim Scott at radicalcandor.com.


Emily Azevedo
Emily is Vice President of Talent at Mainsail Partners and works with the firm’s portfolio companies on their talent needs, including executive leadership, recruiting, compensation and onboarding.
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