Radical Candor by Kim Scott: Summary & Notes

Summary

A must-read for managers. This is one of those books so packed with information that you'll continue to revisit it like a textbook.

Not as relevant for me since I don't do much management (and am less interested in it), hence the 7, but a 10 for professional managers.

Notes

Introduction

• At the very heart of being a good boss is a good relationship.

Part I - A New Management Philosophy

1 - Build Radically Candid Relationships

• Bosses guide a team to achieve results.

Radical Candor

• The first dimension is about being more than "just professional." It’s about giving a damn, sharing more than just your work self, and encouraging everyone who reports to you to do the same.
• I call this dimension "Care Personally."
• The second dimension involves telling people when their work isn’t good enough—and when it is; when they are not going to get that new role they wanted, or when you’re going to hire a new boss over them; when the results don’t justify further investment in what they’re working on.
• This dimension I call "Challenge Directly."
• "Radical Candor" is what happens when you put "Care Personally" and "Challenge Directly” together.
• The most surprising thing about Radical Candor may be that its results are often the opposite of what you fear. You fear people will become angry or vindictive; instead they are usually grateful for the chance to talk it through.

Care Personally: The First Dimension of Radical Candor

• Fred Kofman, my coach at Google, had a mantra that contradicted the "just professional" approach so destructive to so many managers: "Bring your whole self to work."
• There are few things more damaging to human relationships than a sense of superiority.
• That’s why I detest the word “superior" as a synonym for “boss." I also avoid the word “employee."

Challenge Directly: The Second Dimension of Radical Candor

• Challenging others and encouraging them to challenge you helps build trusting relationships because it shows 1) you care enough to point out both the things that aren’t going well and those that are and that 2) you are willing to admit when you’re wrong and that you are committed to fixing mistakes that you or others have made. But because challenging often involves disagreeing or saying no, this approach embraces conflict rather than avoiding it.

What Radical Candor is Not

• A good rule of thumb for any relationship is to leave three unimportant things unsaid each day.

2 - Get, Give, and Encourage Guidance

“Operationalizing" Good Guidance

• There are two dimensions to good guidance: care personally and challenge directly.
• It’s also useful to be clear about what happens when you fail in one dimension (Ruinous Empathy), the other (Obnoxious Aggression), or both (Manipulative Insincerity).

Radical Candor

• In fact, a great way to get to know somebody and to build trust is to offer Radically Candid praise and criticism
• Radically Candid praise: "I admire that about you"
• Radically Candid criticism: To keep winning, criticize the wins

Obnoxious Aggression

• When you criticize someone without taking even two seconds to show you care, your guidance feels obnoxiously aggressive to the recipient. I regret to say that if you can’t be Radically Candid, being obnoxiously aggressive is the second best thing you can do. At least then people know what you think and where they stand, so your team can achieve results. This explains the advantage that assholes seem to have in the world.

Manipulative Insincerity

• Manipulatively insincere guidance happens when you don’t care enough about a person to challenge directly.
• People give praise and criticism that is manipulatively insincere when they are too focused on being liked or think they can gain some sort of political advantage by being fake—or when they are just too tired to care or argue any more.

Ruinous Empathy

• Ruinous Empathy is responsible for the vast majority of management mistakes I’ve seen in my career. Most people want to avoid creating tension or discomfort at work.
• Similarly, praise that’s ruinously empathetic is not effective because its primary goal is to make the person feel better rather than to point out really great work and push for more of it.
• Ruinously empathetic praise: "Just trying to say something nice"
• When giving praise, investigate until you really understand who did what and why it was so great. Be as specific and thorough with praise as with criticism. Go deep into the details.

Moving Toward Radical Candor

• "Is there anything I could do or stop doing that would make your lives better?"
• Balance praise and criticism: Worry more about praise, less about criticism—but above all be sincere.

3 - Understand What Motivates Each Person on Your Team

Rethinking Ambition

• A leader at Apple had a good way to think about different types of ambition that people on her team had so that she could be thoughtful about what roles to put people in. To keep a team cohesive, you need both rock stars and superstars, she explained. Rock stars are solid as a rock.
• The rock stars love their work. They have found their groove. They don’t want the next job if it will take them away from their craft.
• Superstars, on the other hand, need to be challenged and given new opportunities to grow constantly.

Growth Management

• The most important thing you can do for your team collectively is to understand what growth trajectory each person wants to be on at a given time and whether that matches the needs and opportunities of the team.

Understanding What Matters and Why

• "Steep growth" is generally characterized by rapid change—learning new skills or deepening existing ones quickly. It’s not about becoming a manager—plenty of individual contributors remain on a steep growth trajectory their entire careers, and plenty of managers are on a gradual growth trajectory. Nor should steep growth be thought of as narrowly as “promotion." It’s about having an increased impact over time.
• Gradual growth is characterized by stability. People on a gradual growth trajectory, who perform well, have generally mastered their work and are making incremental rather than sudden, dramatic improvements. Some roles may be better suited to a rock star because they require steadiness, accumulated knowledge, and an attention to detail that someone in a superstar phase might not have the focus or patience for.
• Most people shift between a steep growth trajectory and a gradual growth trajectory in different phases of their lives and careers, so it’s important not to put a permanent label on people.

The Problem With “Passion"

• It’s a basic axiom that people do better work when they find that work meaningful. I don’t disagree with this basic premise. However, bosses who take this to mean that it is their job to provide purpose tend to overstep. Insisting that people have passion for their job can place unnecessary pressure on both boss and employee.
• A wise man once told me, "Only about five percent of people have a real vocation in life, and they confuse the hell out of the rest of us."

4 - Drive Results Collaboratively

• First, you have to listen to the ideas that people on your team have and create a culture in which they listen to each other. Next, you have create space in which ideas can be sharpened and clarified, to make sure these ideas don’t get crushed before everyone fully understands their potential usefulness. But just because an idea is easy to understand doesn’t mean it’s a good one. Next, you have to debate ideas and test them more rigorously. Then you need to decide—quickly, but not too quickly. Since not everyone will have been involved in the listen-clarify-debate-decide part of the cycle for every idea, the next step is to bring the broader team along. You have to persuade those who weren’t involved in a decision that it was a good one, so that everyone can execute it effectively. Then, having executed, you have to learn from the results, whether or not you did the right thing, and start the whole process over again.

LISTEN

• "Give the quiet ones a voice."—JONY IVE
• Google CEO Eric Schmidt took the opposite approach, urging people to "Be loud!" I love this, too.
• I’ve always found that saying what I think really clearly and then going to great lengths to encourage disagreement is a good way to listen. I tend to state my positions strongly, so I have had to learn to follow up with, "Please poke holes in this idea—I know it may be terrible. So tell me all the reasons we should not do that."

Create a culture of listening

• It’s hard enough to get yourself to listen to your team members and let them know you are listening; getting them to listen to one another is even harder. The keys are 1) have a simple system for employees to use to generate ideas and voice complaints, 2) make sure that at least some of the issues raised are quickly addressed, and 3) regularly offer explanations as to why the other issues aren’t being addressed.

DEBATE

Create an obligation to dissent

• I once interned at McKinsey for a summer, and what impressed me most about the company was its ability to spur productive debate. How’d they do it? McKinsey had very consciously created an obligation to dissent. If everyone around the table agreed, that was a red flag. Somebody had to take up the dissenting voice.

DECIDE

PERSUADE

EXECUTE

• Here are the three things I’ve learned about getting this balance right: Don’t waste your team’s time; Keep the dirt under your fingernails; and Block time to execute.

Don’t waste your team’s time

Keep the "dirt under your fingernails"

• You need to learn to toggle between leading and executing personally. Don’t abandon the first for the second; integrate the two. If you get too far away from the work your team is doing, you won’t understand their ideas well enough to help them clarify, to participate in debates, to know which decisions to push them to make, to teach them to be more persuasive.

Block time to execute

• Often, execution is a solitary task. We use calendars mostly for collaborative tasks—to schedule meetings, etc. One of your jobs as a manager is to make sure that collaborative tasks don’t consume so much of your time or your team’s time that there’s no time to execute whatever plan has been decided on and accepted.

LEARN

• "Consistency is the hobgoblin of little minds."—Ralph Waldo Emerson, Self-Reliance
• When managing a large team, I found there were two enormous pressures that tempted me to quit learning.

Pressure to be consistent

• We are often told that changing our position makes us a "flip-flopper" or "erratic" or "lacking principles." I prefer John Maynard Keynes’s idea that "When the facts change, I change my mind."
• The key, of course, is communication. Someone might reasonably complain, "Just two months ago you convinced me of X and now you’re telling me maybe not-X after all?" You obviously can’t change course like this lightly, and if you do, you need to be able to explain clearly and convincingly why things have changed.

Burnout

• Sometimes we’re overwhelmed by our work and personal lives, and these are the moments when it is hardest to learn from our results and to start the whole cycle over again. That’s why you are at the very center of the wheel that moves you forward as a manager. You’ve got to take care of yourself, first and foremost. That’s easier said than done, of course.

Part II: Tools & Techniques

5 - Relationships

Work-life integration

• Be relentlessly insistent on bringing your fullest and best self to work—and taking it back home again.
• Don’t think of it as work-life balance, some kind of zero-sum game where anything you put into your work robs your life and anything you put into your life robs your work. Instead, think of it as work-life integration.

Figure out your "recipe" to stay centered and stick to it.

• The world is full of advice here, and what is enormously meaningful for one person is pure crap for another.
• Do whatever works for you. The key, I’ve found, is to prioritize doing it (but not overdoing it) when times get tough.
• Here’s what I need to do to stay centered: sleep eight hours, exercise for forty-five minutes, and have both breakfast and dinner with my family. If I skip one or two of those things for a day or two, it’s OK. But that’s the routine. Also, every so often I need to read a novel (ideally one a week), go away for a romantic weekend with my husband (ideally four times a year), and take a two-week vacation with siblings and parents (once a year).

Calendar

• Put the things you need to do for yourself on your calendar, just as you would an important meeting.

Building trust

• Probably the most important thing you can do to build trust is to spend a little time alone with each of your direct reports on a regular basis.

Recognizing your own emotions

• What did I need to do to make sure that my whole team didn’t have a worse day just because I was having a bad one?
• The best you can do is to own up to how you feel and what’s going on in the rest of your life, so others don’t feel your mood is their fault.
• I learned simply to say something along the lines of, "Hey, I’m having a shitty day. I’m trying hard not to be grouchy, but if it seems like I have a short fuse today, I do. It’s not because of you or your work, though. It’s because I had a big argument with a friend [or whatever]."
• If you have a truly terrible emotional upset in your life, stay home for a day.

Master your reactions to others’ emotions

• To build Radically Candid relationships, do not try to prevent, control, or manage other people’s emotions. Do acknowledge them and react compassionately when emotions run high. And do try to master your reactions to other people’s emotions.

6 - Guidance

• In order to build a culture of Radically Candid guidance you need to get, give, and encourage both praise and criticism.

Here are some tips/techniques I've seen work to get the conversation flowing:

• You are the exception to the "criticize in private" rule of thumb. Michelle Peluso, CEO of Gilt Groupe, explained the benefits of criticizing herself publicly. In an interview with The New York Times she said, I’ve always taken a slightly different approach with 360 reviews. We’ll share them with each other on the executive team, and I’ll start with mine—‘Here is where I’m good, and here is where I’m not doing so well.’ I’ll even tell the whole company and say, ‘Here is where I want your help.’ That makes it a bit safer for other people to do the same, and you can build trust."

Be humble

• I start with being humble because it’s absolutely essential when delivering both praise and criticism.
• Furthermore, a common concern that people raise about giving feedback is "What if I’m wrong?" My answer is that you may very well be wrong. And telling somebody what you think gives them the opportunity to tell you if you are. A huge part of what makes giving guidance so valuable is that misperceptions on both sides of the equation get corrected.

Here are some techniques I've found helpful to make sure I'm being humble when giving praise and criticism:

• Situation, behavior, impact. This simple technique reminds you to describe three things when giving feedback: 1) the situation you saw, 2) the behavior (i.e., what the person did, either good or bad), and 3) the impact you observed
• Situation, behavior, and impact applies to praise as well as to criticism.

Be helpful

• Stating your intention to be helpful can lower defenses. When you tell somebody that you aren’t trying to bust their chops—that you really want to help—it can go a long way toward making them receptive to what you’re saying.
• For example, in your own words, say something like, I’m going to describe a problem I see; I may be wrong, and if I am I hope you’ll tell me; if I’m not I hope my bringing it up will help you fix it.
• Show, don’t tell. It’s the best advice I’ve ever gotten for story-telling, but it also applies to guidance. The more clearly you show exactly what is good or bad, the more helpful your guidance will be**.**
• Finding help is better than offering it yourself. When Sheryl Sandberg offered to get me a speaking coach, she did have to budget for it, but she didn’t have to sit there watching me practice presentations for hours. It took some of her time but not too much.
• Guidance is a gift, not a whip or a carrot. It took me a long time to learn that sometimes the only help I had to offer was the conversation itself.

Give feedback immediately

• Giving guidance as quickly and as informally as possible is an essential part of Radical Candor, but it takes discipline—both because of our natural inclination to delay/avoid confrontation and because our days are busy enough as it is.
• Say it in 2–3 minutes between meetings. Just saying it right away in a minute or two, three at most, will take less time than scheduling a meeting for later, let alone having it—and it won’t stick around in your mind, worrying you at odd moments.
• Keep slack time in your calendar, or be willing to be late. Prioritizing something generally means making time in your calendar for it. But how do you make time in your calendar for something that is "impromptu"? You can’t. Better to talk to the person right away. But in order for that to happen, you must do one of two things. One, keep slack time in your calendar, either by not scheduling back-to-back meetings or by having twenty-five- and fifty-minute meetings with hard stops, not thirty- and sixty-minute meetings. Or, simply be willing to be late to your next meeting.
• Don’t "save up" guidance for a 1:1 or a performance review. One of the funniest things about becoming a boss is that it causes an awful lot of people to forget everything they know about how to relate to other people.
• Guidance has a short half-life. If you wait to tell somebody for a week or a quarter, the incident is so far in the past that they can’t fix the problem or build on the success.
• Unspoken criticism explodes like a dirty bomb. Just as in your personal life, remaining silent at work for too long about something that angers or frustrates you makes it more likely that you will eventually blow up in a way that makes you look irrational, harms your relationship, or both.
• Avoid black holes. Be sure to let people know immediately how their work is being received. If you ask somebody to do work to help you prepare for a meeting or a presentation where that person won’t be present, be sure to let them know the reaction to their work.

In person (if possible)

• Remember, the clarity of your guidance gets measured at the other person’s ear, not at your mouth. That’s why it’s best to deliver guidance in person.
• Unfortunately, giving guidance in person is not always possible. When that is the case, here are some things to keep in mind:
• Immediate vs. in person. If the person is in another city and giving guidance in person means waiting more than a few days, then optimize for immediacy unless what you’re talking about is a big deal.
• Hierarchy of modes. A video call, if you have high-speed internet access, is second best. If the connection is spotty, use phone for voice and video as a bonus, muting your computer. Phone is third best. Email and text should be avoided if at all possible.
• Multiple modes. I found that praising people at a public all-hands meeting was a great way to share significant accomplishments. However, I often found that following up in person at a 1:1 carried more emotional weight, and following up with an email to the whole team carried more lasting weight.
• Reply All do’s and don’ts. If you must criticize or correct somebody over email, do not Reply All. Never. Even if there’s a small factual error that went out to a lot of people, reply just to the person who made the factual error and ask that person to Reply All. For praise on small things, I found that a quick Reply All email worked pretty well.
• Being in a remote office is hard. If you are in a remote office, or if you are managing people in remote offices, it’s really important to have quick, frequent interactions. This will allow you to pick up on people’s most subtle emotional cues.

Praise in public, criticize in private

• A good rule of thumb for guidance is praise in public, criticize in private. Public criticism tends to trigger a defensive reaction and make it much harder for a person to accept they’ve made a mistake and to learn from it.
• Corrections, factual observations, disagreements, and debates are different from criticism. It’s vital to be able to correct somebody’s work, to make a factual observation, or to have a debate in public.
• But criticizing a person should be done in private—"There’s a typo on slide six," or "There are a lot of typos in this presentation, and given the nature of our work we need to be 100 percent accurate," or "There are a bunch of typos here but they don’t matter too much at this stage," or "You missed your number by 5 percent," or "I disagree with what you just said." Those kinds of corrections could go out over email or be said in a public meeting. Here is an example of criticizing the person: "When you give several important presentations that are all riddled with typos that a simple spell-checker would catch, I start to wonder what’s going on. Can you explain?" That sort of thing needs to be a private conversation.
• Adapt to an individual’s preferences. While the majority of people do like to be praised in public, for some any kind of public mention is cruel and unusual punishment
• Group learning. I’ve rarely encountered anyone who will admit that they like to be praised publicly. So whenever I praised in public I would explain that I wasn’t doing so because the person wanted public praise, but so that everybody could learn from what had happened

Don’t personalize

• The "fundamental attribution error" will harm the effectiveness of your guidance. This phrase was coined by Lee Ross, a social psychologist from Stanford. We’ve touched on this already, but it’s useful to repeat because it is so central to healthy human relationships, whether with spouses, children, friends, or the people who report to you. Making a fundamental attribution error is using perceived personality attributes—"You’re stupid, lazy, greedy, hypocritical, an asshole, etc."—to explain someone else’s behavior rather than considering one’s own behavior and/or the situational factors that were probably the real cause of the other person’s behavior. It’s a problem because 1) it’s generally inaccurate and 2) it renders an otherwise solvable problem really hard to fix since changing core personality attributes is so very difficult and time-consuming.
• Say "that’s wrong" not "you’re wrong." He stopped saying, "You’re wrong," and instead learned to say, "I think that’s wrong." "I think" was humbler, and saying "that" instead of "you" didn’t personalize. People started to be more receptive to his criticism.
• The phrase "don’t take it personally" is worse than useless.
• How not to personalize even when it really is personal. It’s easier to understand how to avoid personalizing guidance when you’re talking about a person’s work. But when you’re talking about something that is more personal, it’s even harder. One woman I worked with had body odor to the point that it undermined her effectiveness. But how to raise the issue? I tried hard to make the conversation about her colleagues’ noses, not her armpits. She wasn’t American, but we were working in the U.S., so I laughed a little bit about American culture. I tried not to be prescriptive about the solution—maybe she had an allergic reaction to deodorant, or a health concern—but I did make clear that the status quo was undermining her otherwise strong performance.

7 - Team

CAREER CONVERSATIONS

• He taught every manager on his team to have a succession of three forty-five-minute conversations with each direct report over the course of three to six weeks.

Conversation one: life story

• The first conversation is designed to learn what motivates each person who reports directly to you. Russ suggested a simple opening to these conversations. "Starting with kindergarten, tell me about your life."
• Then, he advised each manager to focus on changes that people had made and to understand why they’d made those choices. Values often get revealed in moments of change.
• Remember, you’re not looking for definitive answers; you’re just trying to get to know people a little better and understand what they care about.

The second conversation: dreams

• The second conversation moves from understanding what motivates people to understanding the person’s dreams—what they want to achieve at the apex of their career, how they imagine life at its best to feel.
• Russ recommends that you begin these conversations with, "What do you want the pinnacle of your career to look like?" Because most people don’t really know what they want to do when they "grow up," Russ suggests encouraging people to come up with three to five different dreams for the future. This allows employees to include the dream they think you want to hear as well as those that are far closer to their hearts.
• Ask each direct report to create a document with three to five columns; title each with the names of the dreams they described in the last conversation. Then, list the skills needed as rows. Show how important each skill is to each dream, and what their level of competency is in that skill.
• Generally, it will become very obvious what new skills the person needs to acquire. Now, your job as the boss is to help them think about how they can acquire those skills: what are the projects you can put them on, whom can you introduce them to, what are the options for education?
• The final part of Russ’s second conversation involves making sure that the person’s dreams are aligned with the values they have expressed. For example, "If ‘hard work’ is a core value, why is one of your dreams to retire early?" Inquiring about the dreams people describe is an important way to push for candid, meaningful conversations.

Conversation three: eighteen-month plan

• Last, Russ taught managers to get people to begin asking themselves the following questions: What do I need to learn in order to move in the direction of my dreams? How should I prioritize the things I need to learn? Whom can I learn from? How can I change my role to learn it? Once people were clear on what they wanted to learn next, it was much easier for managers to identify opportunities at work that would help them develop skills in the next six to eighteen months that would take them in the direction of at least one of their dreams.
• Here’s what to do: make a list of how the person’s role can change to help them learn the skills needed to achieve each dream; whom they can learn from; and classes they could take or books they could read. Then, next to each item, note who does what by when—and make sure you have some action items.
• Helping people clarify values and dreams and then aligning them as closely as possible with their current work will invariably make your team stronger. Each individual will be more successful and happier, and together you’ll achieve results "unexpected in common hours."

HIRING: YOUR MENTALITY AND YOUR PROCESS

Here are some simple things you can do to make sure you’re hiring the right people:

• Job description: define team fit as rigorously as you define skills to minimize bias. The hiring person—not a recruiter!—should write the job description, basing it on the role, the skills required for the role, and the team fit criteria. Defining team fit can be hard, which makes it tempting to leave out. Try to describe your culture in three to four words. It could be detail-oriented, quirky, and blunt. Or maybe it’s big picture, straightlaced, and polite. Whatever you choose, be disciplined about interviewing for those things.
• Blind skills assessments can also minimize bias. Interviewing takes time, filling out interview feedback reports takes time, and so it’s important to be very selective about who gets invited to interview.
• An example of a good prescreen is a skills assessment: ask potential candidates to do a project or solve a problem related to the job they’re applying for.
• Use the same interview committee for multiple candidates, to allow for meaningful comparisons. If you can avoid it, don’t make unilateral hiring decisions. Because interviewing is so subjective and prone to bias, you’ll improve your odds of making good decisions by getting multiple perspectives.
• Four people is about the right size for an interview committee.
• It’s also helpful if at least one of the interviewers is on another team.
• Casual interviews reveal more about team fit than formal ones. I am sure that there is good interview training out there somewhere, but I’ve never encountered it. My experience is that interviewing is a learning-by-doing skill. Let people develop their own style. I love stories, so my whole interview technique is just to ask people to give me the oral version of your résumé.
• Another good practice is to have people intentionally create more casual moments—take candidates to lunch, walk them to the car.
• An important part of my team’s culture was Bob Sutton’s "No Assholes" rule. One candidate I was about to hire was so rude to the scheduler that she cried.
• Make interviews productive by jotting down your thoughts right away. Write down your interview feedback; doing that is as clarifying for you as it is for the rest of the committee, and it will result in better hiring decisions. Write down your thoughts on each of the skills, if you’re interviewing for skills, as well as for each of the team fit criteria identified.
• I know, you’re busy and you don’t have time to write everything down. Here’s a tip: schedule an hour, interview for forty-five minutes, and write for fifteen. This arrangement will force you to have a more focused interview and to make a better recommendation about whom to hire.
• In-person debrief/decision: if you’re not dying to hire the person, don’t make an offer. The best advice I ever got for hiring somebody is this: if you’re not dying to hire somebody, don’t make an offer. And, even if you are dying to hire somebody, allow yourself to be overruled by the other interviewers who feel strongly the person should not be hired. In general, a bias toward no is useful when hiring.

8 - Results

• Your role will to be to encourage that process of listening, clarifying, debating, deciding, persuading, and executing to the point that it’s almost as if your team shares one mind when it comes to completing projects, and then learning from their results
• One of your most important responsibilities to keep everything moving smoothly is to decide who needs to communicate with whom and how frequently. This means meetings. Obviously, every meeting comes with a significant cost—time—so it is important to minimize the duration, frequency and number of people required to attend. The most important of these meetings is the 1:1 with each of your direct reports.
• 1:1 Conversations
• Staff Meetings
• Think Time
• "Big Debate" Meetings
• "Big Decision" Meetings
• All-Hands Meetings
• Meeting-Free Zones
• Kanban Boards
• Walk Around
• Be Conscious of Culture

1:1 CONVERSATIONS

• Employees set the agenda, you listen and help them clarify
• 1:1s are your must-do meetings, your single best opportunity to listen, really listen, to the people on your team to make sure you understand their perspective on what’s working and what’s not working.
• Here are a few things you can do to make sure you and each of your reports are getting the most out of these 1:1 meetings:

Mind-set

• Your mind-set will go a long way in determining how well the 1:1s go. I found that when I quit thinking of them as meetings and began treating them as if I were having lunch or coffee with somebody I was eager to get to know better, they ended up yielding much better conversations.

Frequency

• Time doesn’t scale, but it’s also vital to relationships. 1:1s should be a natural bottleneck that determines how many direct reports a boss can have. I like to meet with each person who works directly for me for fifty minutes a week. But I can’t bear more than about five hours of 1:1 time in my calendar.

Some good follow-up questions

• Here are some follow-up questions you can ask to show not only that you are listening but that you care and want to help, and to identify the gaps between what people are doing, what they think they ought to be doing, and what they want to be doing:
• "Why?"
• "How can I help?"
• "What can I do or stop doing that would make this easier?"
• "What wakes you up at night?"
• "What are you working on that you don’t want to work on?"
• "Do you not want to work on it because you aren’t interested or because you think it’s not important?"
• "What can you do to stop working on it?"
• "What are you not working on that you do want to work on?"
• "Why are you not working on it?"
• "What can you do to start working on it?"
• "How do you feel about the priorities of the teams you’re dependent on?"
• "What are they working on that seems unimportant or even counterproductive?"
• "What are they not doing that you wish they would do?"
• "Have you talked to these other teams directly about your concerns? If not, why not?"

Encourage new ideas in the 1:1.

• It’s worth keeping Jony Ive’s quote, "new ideas are fragile," top of mind before a 1:1. This meeting should be a safe place for people to nurture new ideas before they are submitted to the rough-and-tumble of debate.

Here are some questions that you can use to nurture new ideas by pushing people to be clearer:

• "What do you need to develop that idea further so that it’s ready to discuss with the broader team? How can I help?"
• "I think you’re on to something, but it’s still not clear to me. Can you try explaining it again?"
• "Let’s wrestle some more with it, OK?"
• "I understand what you mean, but I don’t think others will. How can you explain it so it will be easier for them to understand?"
• "I don’t think ‘so-and-so’ will understand this. Can you explain it again to make it clearer specifically for them?"
• "Is the problem really that they are too stupid to understand, or is it that you are not explaining it clearly enough?"

Signs you’ll get from 1:1s that you’re failing as a boss

• Cancellations. If people who report to you cancel 1:1s too often, it’s a sign your partnership is not fruitful for them, or that you’re using it inappropriately to dispose of criticism you’ve been stockpiling.
• Updates. If people just give you updates that could simply be emailed to you, encourage them to use the time more constructively.
• Good news only. If you hear only good news, it’s a sign people don’t feel comfortable coming to you with their problems, or they think you won’t or can’t help. In these cases, you need to ask explicitly for the bad news. Don’t let the issue drop till you hear some.
• No criticism. If they never criticize you, you’re not good enough at getting guidance from your team. Remember that phrase: What could I do or stop doing that would make it easier to work with me?
• No agenda. If they consistently come with no topics to discuss, it might mean that they are overwhelmed, that they don’t understand the purpose of the meeting, or that they don’t consider it useful. Be direct but polite: "This is your time, but you don’t seem to come with much to talk about. Can you tell me why?"

EXECUTION TIME

• At Google, different teams tried declaring "No-Meeting Wednesday" or "No-Meeting Thursday." None was ever able to stick to it. Greg Badros, an engineering leader at Google and Facebook, set a goal of ending 25 percent of his meetings early. I loved that, but I don’t think he ever hit the goal.
• I have found that the most effective solution is simply to fight fire with fire. For the same reason, I blocked off think-time in calendar; I also found it necessary to block off time in my calendar to be alone and execute.