How to Practice Radical Candor With Your Boss 3 | 9
On this episode of the Radical Candor podcast Kim, Jason and Amy discuss clearing the cruft and the art of upward feedback. It's true that it can be...
4 min read
Brandi Neal Mar 22, 2023 12:01:15 AM
Table of Contents
On this episode of the Radical Candor podcast, Kim, Jason and Amy dig into the digital advice mailbag and answer questions from Radical Candor listeners and readers. What happens when people think you're too young to lead? How can you stop paying the a**hole tax? How can you be more present at work when everything is stressful all of the time? Listen to find out!
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Folks regularly write into our advice email with questions about how to practice Radical Candor. So, on this episode, we’re going to reach into the Radical Candor advice mailbag and answer some of your questions.

Hello! I discovered y’all when my partner, who works at an apartment complex, found your book in an abandoned apartment. She brought it home and it just seemed so fitting given my current situation. Funny how things work! All that to be said…
I’m currently 28 years old and am the manager of a small(ish) company in [the South]. We have 10 employees currently but do some fairly large business, about $1.7M per year.
I am currently in year three of a four-year transition to become the owner of the company and will be 30 at that time. While I feel incredibly blessed to be in this position, and 95% of it is great, I really struggle with garnering respect from potential hires.
I have had on multiple occasions people say they “didn’t want to work for a kid” to my face. And I suppose I get that. But it weighs on me heavily at the same time. Are there steps I can take to set an example of maturity and leadership?
For the more tenured employees that work for me, they all say I do a good job and it’s just a matter of growing gray hair. Perhaps it is. I figured if anyone has some solid advice, it would be the wonderful folks at Radical Candor.
I have an insurmountable problem, it won't matter how much I apply Radical Candor when my CEO undoes everything I do.
I'm now leaving my fourth job working for someone who has never read any management books and is making very basic mistakes, like publicly humiliating people, thinking that job satisfaction is irrelevant because they are paying and that's all that matters, refusing to buy the tools people need to work, randomly breaking processes without warning, explanation or apology, demanding employee install spyware on their computers and refuse to pay for the time they went to the toilet.
I keep reading books like Radical Candor but I feel it's useless. What's the point of learning to have better one-on-ones when my boss tells me "They are just contractors, they do as they are told, stop having 1:1s with them" (I still have them, just in secret). This has been my life for the past seven years.
Do you have a solution?
Here I'm thinking that maybe there's a job board or networking group where you only get access if you buy into the ideas of Radical Candor, where a CTO like me can find a CEO that's not destructive.

First of all: your work made me a better person and my 40-person startup company a better company.
Second: I feel like I am shit at communication. People give me feedback about feeling stressed and pushed when meeting with me about work. They also feel I am rushed and unavailable. (Obviously, this is the gist of their stories between the flowers and the sandwich spread).
Generally, I feel my leadership communication is quite shit, lol! Do you have tips on resources or practices I can perform to become a better communicator as a leader?
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Episodes are written and produced by Brandi Neal with script editing by Amy Sandler. The show features Radical Candor co-founders Kim Scott and Jason Rosoff and is hosted by Amy Sandler.
The Radical Candor Podcast theme music was composed by Cliff Goldmacher. Order his book: The Reason For The Rhymes: Mastering the Seven Essential Skills of Innovation by Learning to Write Songs.
Sound editing by PodcastBuffs.
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When you get feedback like "I don't want to work for a kid," get curious rather than defensive. Ask directly: what specifically worries them about working for a younger manager? Pressing for specifics can surface genuinely useful advice about how you can lead more effectively. Your tenured employees already say you do a good job — that's real evidence. Confidence built on results, combined with genuine curiosity about others' concerns, tends to matter more than gray hair over time.
Before accepting any job, trust your gut about the person who will be your boss — if you're not genuinely excited to work for them, try not to take the role. Before signing, find someone who has worked for that person and ask candidly what it was like. You can even try getting into a disagreement with them during the interview process to see how they handle pushback. No amount of Radical Candor on your part can fully compensate for a destructive boss above you.
The "a**hole tax" refers to the very real personal and professional cost you pay when you work for a bad boss — lost time, energy, morale, and career momentum. The best way to stop paying it is to be more deliberate before accepting a new role. Research your prospective boss, talk to people who've reported to them, and if possible, manufacture a moment of disagreement during the interview to see how they react under pressure.
If your team is giving you feedback that you seem stressed, rushed, or unavailable, a few practical habits can help. Block dedicated "think time" on your calendar so you can clear your head before engaging with others. Schedule "wander time" — a short walk around the office or building — so you can connect with people in a more relaxed, spontaneous way. You can also set up virtual office hours once a month to give people a predictable, low-pressure window to reach you.
It can feel pointless to practice good management when your own boss actively undermines it — publicly humiliating people, blocking tools, or forbidding one-on-ones. The honest answer is that Radical Candor has real limits when leadership above you is destructive. The most durable solution is choosing your next employer more carefully: vet the culture, talk to former employees, and evaluate the boss before you accept an offer. Good management skills still matter — you just need an environment where they're allowed to work.
Three ways to put this into practice.
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