Podcast

How to Choose a Radically Candid Boss 3 | 12

Name: How to Choose a Radically Candid Boss 3 | 12
Uploaded: 2021-12-14T07:59:25Z
Description: How to Choose a Radically Candid Boss 3 | 12

Brandi Neal · Dec 13, 2021

If you're in the market for a new job and you are lucky enough to have multiple offers, or you’re in a position where you can afford to wait for the right opportunity, you don’t have to pay the asshole tax. On this episode of the Radical Candor podcast, Kim, Jason and Amy talk about how to suss out whether your potential new boss is going to help you move toward the direction of your dreams or get in your way. Listen now to the last episode of 2021 to learn how to find a Radically Candid boss.

Listen to the episode:

How to Choose a Radically Candid Boss: Episode at a Glance

Kim’s been getting a lot of questions from people about how to choose a new job and noted that one of the most important things you can do is to choose your boss wisely.

One of the first steps to avoiding a bad boss is knowing what you’re looking for in a boss.

Think about things like, how much autonomy you want in the job? Do you want a boss who’s going to be a mentor? Is this someone you could imagine going to with problems?

"First of all, trust your gut. That’s far more important than any list of criteria from me or anyone else. If you are not dying to work for this person, don’t take the job," Kim advises. "If you’re not sure what you think of them, start by making a list of pros and cons. Keep wrestling with it until you get to what is for you the determinative factor. For me, it’s can this person help me take a step in the direction of my dreams, or will they trip me up?"

Radical Candor podcast

Can this person help me take a step in the direction of my dreams, or will they trip me up?" — Kim Scott

You want a boss who is respectful of the people who work for them, not a boss who tries to lord power over their employees or who thinks the job is a value judgment rather than a responsibility they’ll be held accountable for. Ask your potential new boss:

What is your management philosophy?
- A lot of bosses won’t be able to articulate exactly what a boss does. "It took me a long time to do it when I was writing Radical Candor — bosses get feedback from and give feedback to teams to achieve results," Kim says. "But you want them to have some idea of what their responsibilities as a boss are."
- Dig into the details here. If someone says something that sounds buzzwordy or that you’re not sure what it means, ask them for a specific example of what they mean.
- Beware of absentee and micromanaging philosophies.
You want a boss who solicits feedback and then responds well to it — who has a growth mindset.
- Ask your prospective boss about a failure. Who told them they were failing, and what did they learn from the experience? If they tell you about a time when one of their employees told them they were screwing up and they responded well, that’s a really good sign
- Ask your prospective boss how they like to receive feedback. (Your real question is, will you take feedback if I give it to you)
- Try giving your prospective boss feedback about something you observed during the interview process, and notice how they respond.

Radical Candor Podcast

If you are worried about the broader culture, make sure you're working for a shit umbrella, not a shit funnel." — Kim Scott

Once you have an offer and know who your boss is going to be, talk to other people who have worked for them. You better believe that your new employer is doing backdoor reference checks on you. Do some backdoor reference checks on your boss. If people were miserable working for that person, don't take the job. You'll soon be miserable too.

"It's true that your boss's boss can have a huge impact on how your boss behaves. But I've worked for some people who are incredible shit umbrellas — who shielded me from toxicity they were experiencing," Kim says. "Others, however, are like shit funnels... If you are worried about the broader culture, make sure you're working for a shit umbrella and not a shit funnel."

Radical Candor Podcast Checklist

Think about what matters to you in a boss. Pay attention to how the manager treats you throughout the interview process. Trust your gut.
Ask the manager specific questions about how they intend to manage you.
Research the manager online, and if possible find former employees and ask for their honest perspective about working for the manager.

Radical Candor Podcast Resources

The Radical Can dor 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.

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FAQs

How do I know if a potential boss practices Radical Candor before accepting a job offer?

Pay close attention throughout the interview process itself — the way a manager treats you during interviews is a preview of how they'll manage you. Ask them about a past failure and who told them they were failing; a boss who received critical feedback from an employee and responded well is a strong sign. You can also try offering a small piece of feedback about something you observed during the process and watch how they react. Finally, do backdoor reference checks with former employees to hear honest perspectives.

What questions should I ask a prospective boss during an interview?

The Radical Candor podcast recommends asking:

What is your management philosophy? — A good boss should be able to articulate their responsibilities, even if imperfectly. Push for specific examples if their answer sounds buzzwordy.
Tell me about a failure — How did they learn, and who told them they were failing?
How do you like to receive feedback? — This reveals whether they're open to hearing hard truths from their team.

Dig into vague answers and trust your gut about whether their responses feel genuine.

What is the 'asshole tax' in the context of choosing a boss?

The 'asshole tax' refers to the hidden cost you pay — in stress, lost growth, and diminished wellbeing — when you work for a bad boss. Kim Scott's point is that if you have multiple job offers or can afford to wait, you don't have to accept a role under a toxic or ineffective manager just for the paycheck or title. Choosing wisely upfront saves you from paying that steep personal and professional price down the road.

What is a 'shit umbrella' vs. a 'shit funnel' and why does it matter when job hunting?

A 'shit umbrella' is a boss who shields their team from toxicity coming from upper management or a dysfunctional broader culture. A 'shit funnel,' by contrast, passes all that dysfunction straight down to their reports — or even amplifies it. Kim Scott emphasizes that even if you're worried about the broader company culture, having a boss who acts as a shit umbrella can make the job workable. When researching a prospective boss, try to determine which type they are.

Why does Kim Scott say trusting your gut is the most important factor when choosing a boss?

Kim advises that no checklist of criteria outweighs your instinctive read of a person. If you're not genuinely excited to work for someone, that hesitation is meaningful data. She suggests making a pros-and-cons list and wrestling with it until you identify your 'determinative factor' — for her, it's whether this boss can help move her toward her dreams or will get in the way. Analytical frameworks are useful, but gut feeling often surfaces what logic misses.

What are the warning signs of an absentee or micromanaging boss?

During the interview, listen for management philosophies that signal either extreme: a boss who gives employees zero guidance or one who wants to control every detail. Ask how much autonomy you'll have in the role and whether they see themselves as a mentor. Vague or evasive answers about their management style, an inability to describe their responsibilities as a boss, or an unwillingness to share a genuine failure story are all red flags worth taking seriously before you accept an offer.

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