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.