Leading with Vulnerability: Ryan Holiday’s Masterclass Through a CS Lens

By Kristen Hayer

One of my goals for 2025 is to spend more time on personal development. For me, this includes yoga, watercolor painting and taking classes on the Masterclass app. The class I started with explores how ancient philosophies – stoicism, epicureanism, cynicism, and Socratic wisdom – can help you solve modern problems. Ryan Holiday, who is the host of The Daily Stoic, leads the program. I kicked things off with the class on Communication.

I was hoping to find some ideas or stories to share for our classes that cover communication skills and Masterclass didn’t disappoint. I’d highly recommend this particular Masterclass, which also covers Relationships, Resilience, and Growth. But I wanted to share something important I took away that I think applies to communication between leaders and team members.

In our CS Manager course, we talk a lot about the importance of one-on-one meetings with each of your direct reports. A part of that meeting should be a space where the manager can offer feedback to their direct report. Of course, feedback can happen anytime, but we feel it is useful to carve out specific time for it as well.

In the Masterclass they talked about Socrates’ advice for giving feedback to someone. He said that it needed to pass the test of being 1. True, 2. Good, and 3. Useful. If the advice you’re offering doesn’t meet those criteria, Socrates would have argued that you shouldn’t give it.

Ryan and the other experts that are a part of this class extended this philosophy to a practical approach for offering feedback or advice. They had 3 ideas that I think are useful, especially if you’re not super comfortable offering feedback.

Create a Platform of Emotional Safety – One of the best ways to do this as a leader is to have weekly one-on-ones with your direct reports. While driving performance is the overall objective of those meetings, building a solid relationship is a big piece of that. Having a trusting relationship with your direct reports creates that platform of safely that allows you to offer advice that will be taken in the way it was intended.

Lead with Vulnerability – Being willing to share your own stories about how you messed up, or things that you did wrong helps your team members understand that you’re offering advice from a place of humility and understanding, not a place of perfection. This approach further opens the channel of communication and positions the other person to learn from your mistakes.

Break Up the Feedback – While you might have a long list of things your team member could have done differently, don’t bombard them with that all at once. Pick one or two things to focus on at a time, and if other items surface again later, tackle them then. My personal advice along these lines would be to ask the team member what they would have done differently. If their internal criticism echoes some of the items on your list, those are ones you don’t need to cover.

I found this ancient advice so timely and powerful that I wanted to share what I learned with all of you. I’d love your thoughts. Does this resonate? How do you provide feedback to your teams? Engage with me on LinkedIn to add your perspective!

Are you a first-time or newly promoted front-line leader? Our Leading as a Manager course is designed for you! Classes focus on practical leadership training, woven in with context specific to the Customer Success field. Visit TheSuccessLeague.io to learn more about this and our other offerings.

Kristen Hayer - Kristen founded The Success League in 2015 and currently serves as the company's CEO. Over the past 25 years Kristen has been a success, sales, and marketing executive, primarily working with scaling tech companies, and leading several award-winning customer success teams. She has written over 100 articles on customer success, and is the host of 3 podcasts about the field. Kristen has served as a judge for the Customer Success Excellence awards, and is on the board of several early-stage tech companies. She received her MBA from the University of Washington in Seattle, and now lives in San Francisco.