By Cheryl Schenk, Director of Enrollment Management

As a leader, I’ve found a transformative framework for building trust and genuine collaboration is Kim Scott’s Radical Candor¹. At its core, Radical Candor is about balancing two essential leadership behaviors: “Care Personally” and “Challenge Directly.” These principles have become the foundation of how I engage with our Enrollment Management team at Eastside Prep, as well as the wider community. As we embark on this year’s theme, Act Responsibly – Care Through Clarity, the succinct conceptual framework Kim Scott outlines in Radical Candor is a helpful starting place.

WHAT MAKES CANDOR, WELL, RADICAL?

If you’re familiar with the Radical Candor framework, you know that Scott maps out a graph with quadrants of communication, in which “Care Personally, Challenge Directly” is the top right quadrant, the goal. The other quadrants, therefore, represent when we only do one of these things, or neither of them. Caring personally without challenging directly is what Scott calls “Ruinous Empathy,” and it’s a cultural liability when we are emotionally invested in those around us, yet we don’t have the skills, encouragement, or mutually agreed upon framework with which to share direct feedback.

Growing up in suburban New Jersey, I experienced cultural norms of conversing with both strangers and acquaintances very directly, yet interactions felt different for me when I arrived in the Pacific Northwest and strangers didn’t interact that much on the streets of Seattle. Geographies, institutions like companies and schools, and groups of people each have their own cultures, and communication needs to be understood through those cultural lenses. In her practice of implementing Radical Candor in different settings, Scott has adapted the framework language to mirror diverse cultural norms. For example, when consulting with a Google team in Tokyo, they were reluctant to point out problems to a product team because it felt disrespectful to do so, as this entailed contradicting others in a group setting². Scott encouraged the team to be “politely persistent” as politeness was the cultural currency of Caring Personally for that team, and being persistent offered a way of challenging the product team while saving face.

Even if a group is ready to implement a framework like Radical Candor, it can still feel countercultural, or personally difficult. A direct statement of feedback without a safety net of care can feel harsh—or as Scott puts it, “Obnoxious Aggression.” I’ll provide some examples through which Radical Candor forms the foundation of how our Enrollment team engages. Through intentional practices like Career Conversations, 1:1 Meetings, and generally fostering a team-wide culture of candor, I’ve seen firsthand how this model cultivates stronger relationships, clearer communication, and reduces stress.

CAREER CONVERSATIONS: CARING PERSONALLY THROUGH LONG-TERM INVESTMENT

One of the most powerful ways I demonstrate that I care personally about our team is by investing in their long-term growth through structured Career Conversations. These are not performance reviews—they are dedicated spaces to explore each team member’s aspirations, motivations, and evolving goals. This conversation kicks off during a new team member’s onboarding as an extension of their hiring process.

Understanding the Whole Person: In these conversations, I start by asking about the story of their work life leading up to joining our team. I want to understand what experiences shaped them, what they value, and what drives them. This helps me see them as whole people, not just as a person fulfilling job functions for the organization. It also helps to build the trust necessary for honest dialogue.

A Strengths-Based Model: We discuss how to bridge the gap between where they are now and where they want to go, through their role at EPS, and beyond. Each new EPS employee identifies their top five strengths through the CliftonStrengths³ assessment tool. These strengths provide key indicators for what motivates an individual internally, how they prefer to contribute, and which domains shape how they interact with the world. For example, our team has the largest number of strengths in the “Relationship Building” domain—no surprise given the people-centered nature of admissions and enrollment. Yet within that domain, an individual with the “Relator” strength will bring different skills than one with the “Empathy” strength. Strengths provide a language through which we can discuss how they see themselves and want to grow. By aligning their growth with the organization’s needs, I show that I care about their future while also challenging them to take ownership of it.

1:1 Meetings: A Weekly Practice of Candor and Connection: Radical Candor comes to life in real time through 1:1 meetings—where both support and challenge happen through an open conversation. Some team members schedule these weekly and others opt to schedule in an alternate cadence based on their needs.

Holding Space: Every 1:1 kicks off with a general prompt from me: “What do you want to talk about today?” The conversation will typically flow from whatever needs they’ve already identified in our shared OneNote. Listening actively, asking follow-up questions, and holding space for whatever they need to share. This emotional safety is what makes it possible to have the harder conversations when needed.

Giving and Receiving Feedback: I use 1:1s to give feedback that is both kind and clear. For example, if someone missed a deadline, I might say, “I know you’ve had a lot on your plate, and I appreciate your effort. That said, the delay impacted the team’s timeline. How can we prevent this next time?” This approach demonstrates my empathy for deadline pressures, while also holding them accountable. I also invite feedback on my own leadership. I ask, “What’s one thing I could do better to support you?” This models vulnerability and reinforces that candor is a two-way street.

Coaching in the Moment: Sometimes, 1:1s are where I challenge directly by coaching someone through a tough situation. Whether it’s navigating a conflict, preparing for a presentation, or making a difficult decision, I use these meetings to help them think critically and grow. I try to paint pictures of multiple actions to take, while asking questions that help them find their own. Again, communication is rooted in culture and that’s unique to each of us on a team with diverse backgrounds, so each member needs to find what works for them.

SETTING A TONE OF CANDOR AS A TEAM

While individual conversations are essential, Radical Candor must also be a team norm. I work intentionally to create a culture where candor is expected, respected, and practiced by everyone—not just between me and my colleagues.

Modeling Candor Publicly: I make a point to model candor in team meetings. If I make a mistake, I own it. If I disagree with an idea, I say so respectfully. I also praise publicly and criticize privately, reinforcing that feedback is about growth, not shame.

Encouraging Peer Feedback:
We share a practice, particularly after events, where team members give each other warm and cool feedback after major projects—what went well and what could be improved. This normalizes feedback as a gift, not a threat. When necessary, I can provide direction to the team on delivering feedback with care and receiving it with openness. Having protocols helps with this, for example, “first we’ll each share out our individual highlight from the event, and next, we’ll each share something that felt like a missed opportunity.” On larger teams, pair-and-share activities can help encourage all voices to join the conversation before a large group share-out occurs.

Building Team Safety:
To support this culture, I regularly check in on team dynamics. I ask questions like, “Is there anything we’re not talking about that we should be?” These questions surface unspoken tensions and help us address them before they fester. We also take time in the majority of our weekly team meetings to go “around the room” and hear from individuals about what they are seeing from their perspectives, as well as the texture of the individual work they are tackling.

CONCLUSION: LEADING WITH HEART AND BACKBONE

Radical Candor is not a one-time tactic—it’s a daily discipline. It requires emotional intelligence, courage, and consistency. By caring personally and challenging directly through Career Conversations, 1:1 Meetings, and team-wide candor practices, I’ve built a team that trusts each other, grows together, and helps build the reputation of EPS as a place of learning and caring. It’s not always easy. Sometimes candor feels uncomfortable. It can feel counter to a culture in which saving face is most highly valued. But I’ve learned that discomfort is often the price of clarity—and clarity is a gift. When people know where they stand, what’s expected, and that they are genuinely cared for, they thrive. And when they thrive, so does the team.

References:

1. Scott, Kim. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity. New York: St. Martin’s Press, 2017.

2. Davies, Nahla. “Feedback on Diverse Teams.” Radical Candor, www.radicalcandor.com/blog/feedback-on-diverse-teams

3. CliftonStrengths, www.gallup.com/cliftonstrengths