The idea of “care personally and challenge directly” was popularized recently by Kim Scott’s book, Radical Candor.  Kim worked with Google, Apple, and with Cheryl Sandberg directly.  In her book, she shares how to be a “kick-ass” boss without losing your humanity.  More importantly, she unpacks how to create relationships that will last a lifetime.  She shares about an experience receiving feedback from her boss Cheryl Sandberg where she felt she did well, but her boss felt there was room to improve. While these are great examples from high level leaders, how do we apply it to smaller teams?  By implementing the same principles.

two people sitting in cafe with laptops having a conversation to illustrate care personally




The key idea is that you need to be able to care personally about people as well as challenge them directly.  Psychologically, people need to know you care about them before you challenge them.  Even Theodore Roosevelt knew that “People need to know how much you care, before they care how much you know.”


Think about coaches and their teams.  During games, especially bad ones, you’ll see a football coach losing his mind.  They often yell at their players, and sometimes they even yell at the referees.  But why do the players put up with that kind of verbal abuse?  Because of what we don’t see.  


Between the games, that coach is investing time, energy, and heart into each of the players.  They know that their coach cares about them because of all that time building relationships and working through training.  This means that, if the coach gets emotional and tough during a game, they trust the motivation behind it.  The players can receive even difficult feedback because of their relationship with the coach.


Many entrepreneurs and owners are extremely focused on goals.  Especially if you’ve built your business by bootstrapping and shouldering a large workload, building relationships may not be a high priority.  However, it is important that your team knows you care about them!  They will communicate better, commit to the team’s goals, and enjoy working with you when you’ve developed a relationship. 


So how do you genuinely develop relationships within your team?  Consider getting to know important details about their lives.  Make time to receive feedback from them during the work day.  Take time to learn how you can help them in their careers.  Encourage cooperation instead of competition.  Avoid micromanaging your team during task work.  And, sometimes most importantly, show the same level of respect to every person on your team.  Then, when it’s time, you will be able to provide candid feedback directly.



multiple people sitting at a desk with computers having a conversation illustrating challenge directly




Being direct allows you to provide much-needed feedback.  It also enables you to hold your team accountable and continue to develop their skills.  Another way to describe this is a culture of accountability.


How do you create a culture of accountability? There are a few ways to do this.  They include owning mistakes at a leadership level to set an example, clearly communicating expectations, actively seeking commitment from your team, and being open to feedback.


The good news is that, when you’ve developed relationships with your team, there will be many touch points for feedback.  For example, if you’re working on a project with clear expectations, it is easy to check in and see if the trajectory and completed tasks align with those expectations.  If you’ve blocked time to receive feedback one on one with your team members, you can also provide feedback to them.  If the team overall has an issue, address it with the team.  This keeps communication lines open and clear.


The bottom line is this: You can coach ‘em as hard as you love ‘em. Your team becomes like your family. Sometimes you’re gonna fight like your family, but they have to know you care about them.  When you take time to develop relationships and consistently provide feedback, your team will be strong and effective.


five people sitting at a table with laptops open




radical candor graph showing care personally and challenge directly

Four quadrant graph from Kim Scott’s “Radical Candor.”

Leaders will often fall too deeply into the caring or the challenging.  While this is natural, it’s important to be aware of the consequences.  Kim calls the sweet spot between this two “radical candor.”  On the other side of the spectrum, you’ll find “manipulative insincerity.” Kim explains that this is praise that is non-specific and insincere, or criticism that is neither clear nor kind.  So what happens if you err too far on the side of caring personally?  It becomes “ruinous empathy.”  This is what happens when you care about someone personally, but you fail to challenge them directly.  


You may also err on the side of challenging too often, aka “obnoxious aggression.”  This is also called “brutal honesty” or “front stabbing.”  Unfortunately, some confuse Radical Candor with Obnoxious Aggression.  “It’s not Radical Candor just because you begin with the words, ‘Let me be radically candid with you.’ If you follow that phrase with words like, ‘You are a liar and I don’t trust you,’ you’ve just acted like a garden-variety jerk. It’s not Radical Candor if you don’t show that you Care Personally.” — Kim Scott




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