Google and Apple alum shares the surprising secret to being a good boss
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Kim Scott (@kimballscott) has built her career around a simple goal: Creating bullshit-free zones where people love their work and working together.
She first tried it at her own software startup. Then, as a long-time director at Google, she studied how the company's leaders created an environment where the joy that people took in their work felt almost tangible. As a faculty member at Apple University, Scott learned how Apple takes a different path but is equally committed to creating the conditions where people can do the best work of their careers and love doing it.
Along the way, she managed a lot of teams in various states of euphoria and panic. And while she did a lot right, she'd be the first to admit everything she did wrong.
The good news is that Scott, now an acclaimed coach for companies like Twitter, Shyp, Rolltape, and Qualtrics, has spent years distilling her experiences into some simple ideas you can use to help the people who work for you love their jobs and do great work.
"At Google, I was really curious — did creating such a great work environment require having the world's greatest business model? The answer is no. Luckily, there are some things that any of us can do, even before the profits start rolling in."
The single most important thing a boss can do, Scott has learned, is focus on guidance: giving it, receiving it, and encouraging it. Guidance, which is fundamentally just praise and criticism, is usually called "feedback," but feedback is screechy and makes us want to put our hands over our ears. Guidance is something most of us long for.
At First Round's recent CEO Summit, Scott shared a simple tool for ensuring that your team gets the right kind of guidance — a tool she calls "radical candor."
What Is Radical Candor?
To illustrate radical candor in action, Scott shared a story about a time her boss criticized her. "I had just joined Google and gave a presentation to the founders and the CEO about how the AdSense business was doing. I walked in feeling a little nervous, but happily the business was on fire. When we told Larry, Sergey and Eric how many publishers we had added over the previous months, Eric almost fell off his chair and asked what resources they could give us to help continue this amazing success. So... I sort of felt like the meeting went okay."
But after the meeting, Scott's boss, Sheryl Sandberg, suggested they take a walk together. She talked about the things she'd liked about the presentation and how impressed she was with the success the team was having — yet Scott could feel a "but" coming. "Finally she said, 'But you said um a lot.' And I thought, 'Oh, no big deal. I know, I do that. But who cared if I said um when I had the tiger by the tail?'"
Sandberg pushed forward, asking whether Scott's ums were the result of nervousness. She even suggested that Google could hire a speaking coach to help. Still, Scott brushed off the concern; it didn't seem like an important issue.
"Finally, Sheryl said, 'You know, Kim, I can tell I'm not really getting through to you. I'm going to have to be clearer here. When you say um every third word, it makes you sound stupid.'"
"Now, that got my attention!" Scott says.
For all of us raised in a culture that preaches, "If you can't say something nice…", that criticism might not sound so nice. But Scott knows now that it was the kindest thing Sandberg could have done for her. "If she hadn't said it just that way, I would've kept blowing her off. I wouldn't have addressed the problem. And what a silly thing to let trip you up." (Incidentally, she did work with that speaking coach, and kicked her umhabit handily.)
It sounds so simple to say that bosses need to tell employees when they're screwing up. But it very rarely happens.
In the years since, Scott has worked to operationalize what it was that made Sandberg such a great boss.
To help teach radical candor — this all-important but often neglected skill — to her own teams, Scott boiled it down to a simple framework: Picture a basic graph divided into four quadrants. If the vertical axis is caring personally and the horizontal axis is challenging directly, you want your feedback to fall in the upper right-hand quadrant.
That’s where radical candor lies.
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"The vertical axis is what I call the 'give a damn' axis," Scott says. "Part of the reason Sheryl was able to say to me so bluntly, 'You sounded stupid,' was that I knew that she cared personally about me. She had done a thousand things that showed me that."
From inviting recent New York transplant Scott to join her book group, to encouraging her to take time off to care for a sick relative, Sandberg didn't just invest in her professionally, but showed she truly cared about her. And she did that for everyone on her team. "Caring personally makes it much easier to do the next thing you have to do as a good boss, which is being willing to piss people off."
That's right, the horizontal axis is what Scott calls the "willing to piss people off" axis. Challenging others is difficult for many people; saying anything short of positive feels impolite. But once you become a boss, it's your job to do be equally clear about what's going wrong, and what's going right.
I would argue that criticizing your employees when they screw up is not just your job, it's actually your moral obligation.
"John Stuart Mill explains it very well. He said, 'The source of everything respectable in man, either as an intellectual or as a moral being, is that his errors are corrigible.' The whole strength and value of human judgment depends on the one property that it can be set right when it is wrong.' You have to tell people when you think they're wrong or their work isn't good enough," Scott says.
Radical candor, then, results from a combination of caring personally and challenging directly. But what does it look like in practice?
Scott has created an acronym to help people remember: HHIPP. "Radical candor is humble, it's helpful, it's immediate, it's in person — in private if it's criticism and in public if it's praise — and it doesn't personalize." That last P makes a key distinction: "My boss didn't say, 'You're stupid.' She said, 'You sounded stupid when you said um.' There's a big difference between the two."
Consider Your Alternatives to Make the Best Choice
If you think this all sounds like a lot of work, you're right. Radical candor requires you to undo the "if you don't have anything nice to say don't say it at all" training that's been beaten into your head since you learned how to talk. This is hard.
But if you're wondering whether it's worth it, you need only consider the alternatives — the other three quadrants of that graph.
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"Now, let me be totally clear. I hate working with jerks. You're not shooting for second best," Scott says. But when you challenge directly without caring personally, you fall into the quadrant that Scott calls obnoxious aggression. Which is bad, but better than not challenging directly.
If you can't offer radical candor, the second best thing you can do is be an a--hole.
She vividly remembers her own career's most memorable workplace jerk. He started out as obnoxiously aggressive — then things went from bad to worse.
"He had an advisor who was trying to help him brush up his reputation. Unfortunately, this advisor didn't teach him to care personally and just advocated that he quit challenging people so directly." As a result, this jerk rolled over into the worst possible quadrant on the graph: manipulative insincerity.
"Rather than starting to care personally when he challenged us, he just quit challenging us. This was much worse. Rather than asking people what they thought about things and then yelling at them harshly when he disagreed, he started doing sneaky things," she says. "For example, he walked into a friend's office, hit the speaker phone button, and ordered him to call another colleague and ask her what she thought of him. 'But don't tell her I'm in the room,' he ordered." Scott couldn't believe it.
"Most of us left that kind of behavior behind in middle school. It's actually pretty rare. The vast majority of management mistakes happen in the quadrant that I call ruinous empathy," she says.
It's a quadrant she's spent some time in herself, leading to what she describes as the worst moment of her career.
"There was this guy who was working for me. We'll call him Bob. I really liked Bob. The problem was that Bob was absolutely terrible at his job," she says.
Whenever Bob would express worries about his performance, Scott would try to reassure him. But after nearly a year, she realized that Bob's weak performance was impacting her whole team — and she was in danger of losing several top performers as a result. Trying to be "nice" to Bob, she'd been unfair to the people who were doing great work. And things didn't work out so well for Bob, either.
"Having never criticized Bob for 10 months because I was trying to spare his feelings, I was now sitting in front of Bob firing him. Not so nice after all," says Scott. "When I told him, Bob pushed his chair back, looked at me, and said, 'Why didn't you tell me? Why didn't anyone tell me?'"
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Encourage Your Whole Team to be Radically Candid
Scott realized that she'd failed Bob and encouraged the rest of her team to fail him, too. "The kind of praise that I gave him was a fake-out, a bunch of false reassurances. I never asked Bob what he thought, because I had written him off, frankly. Worst of all, I had failed to create the kind of culture in which everyone in the company would tell Bob when he was going off the rails," she says. "Not to be mean, but to help him."
It was one of the biggest mistakes Scott made as a boss, and she quickly learned from it — for her own good, and to help spare future employees from the same painful situation.
In the years since, she's mined her vast management experience for other valuable takeaways, and arrived at the four key things that any manager can do to create an environment of meaningful guidance:
1. Find opportunities for impromptu feedback.
Again, the goal with day-to-day guidance is to to push toward radical candor. Scott urges managers to go so far as to print out the quadrant system, post it near their desks, and explain what it means to their teams.
"Get a couple of stickers, one color for praise and one color for criticism, and ask people to put stickers where they think your last interaction was on the graph," she says. "You'll be surprised how clear people will be with you about their reactions to the kind of guidance you're giving them."
2. Make backstabbing impossible.
"This is one of the most important things you can do to foster a culture of guidance between the people who work for you," says Scott. But that means more than squelching obviously political or passive aggressive behavior; bosses also need to avoid acting as well-meaning but ultimately harmful go-betweens. Scott learned this one the hard way, too, trying to act as diplomat for two reports who couldn't get along.
By trying to play shuttle diplomacy, I created exactly the kind of toxic political environment that I was trying to avoid.
If she had it to do over, she would have insisted that these colleagues speak with each other directly about their conflict first — before involving her. Only if that route were exhausted would she have become involved, and then only with both parties present.
"I read about a leader who said he would always try to come up with the worst possible solution for both people when they came to him unable to resolve a disagreement. Because he didn't want to hear about it," Scott says.
She encourages the opposite approach, though. "The problem is that if you don't genuinely try to come up with something that works for both people, then conflicts become too difficult to resolve in your organization, and people will avoid them. They won't challenge each other directly. Instead, you'll get a passive aggressive culture. So try to make a good faith effort to help people find a solution, and find it quickly."
3. Make it easier to speak truth to power.
"If you're a manager of managers, you need to make sure that everyone on your team feels they can criticize their boss," Scott says. But she's quick to note that this does not mean encouraging your team to be boss killers. Instead, she recommends putting this advice into practice with a simple meeting — commonly called a "skip-level meeting," though that sounds hierarchical, so she prefers to call them "manager guidance sessions."
The process is straightforward: First, let your managers know that you'll be scheduling a meeting with their direct reports. Get them comfortable with the idea, and make it clear that this meeting is intended to be helpful to them. Then explain the process to the reports, again making it clear that the goal of the meeting is to help their boss be a better manager — and that the meeting is not for attribution.
"In other words, I would tell the manager what everybody said but not who said it. Not because I wanted to foster secrecy, but because I wanted to help get the information out there," says Scott. "If there were too many things the team didn't feel comfortable saying directly to their boss, and if it wasn't getting better over time, that became the top thing I worked with the manager to change."
When it comes to the nuts and bolts of the meeting, Scott has two key recommendations: Take the notes yourself — don't farm that task out — and send them to the manager in question as soon as the meeting is over. "Taking notes yourself is a very important way to show people that you're listening, and to get corrections. And I would tell people that at the end of this meeting, I was going to share the document. We're not going to have time to go back and edit, because we're all too busy. That had a way of focusing the conversation."
To prevent the meeting from devolving into a gripe session, force the team to prioritize issues. "I would say, 'Changing behavior is hard; you can't ask your boss to get a personality transplant as a result of one 45-minute meeting. What are the one or two things you want your boss to do differently?'" says Scott.
Then, armed with that short wish list, talk with the manager in question. Now it's the boss's turn to be specific about concrete ways that they can address the team's concerns. Make sure the boss doesn't just communicate the action plan to the team, but over-communicates it. Then, follow up to make sure the boss actually does what he or she promised to do.
"These meetings are a way of avoiding the situation where stuff is happening down in your organization that makes your skin crawl when it comes to light," Scott says. "You wonder, 'How could this have happened? Why didn't I know about it?' You want to learn about those things in a way that supports both the managers who are working for you and the people who are working for them."
4. Put your own oxygen mask on first.
There's a reason you hear this every time you board a plane — it's good advice. "You can't possibly give a damn about other people if you don't give a damn about yourself. At one point, when I was having a very stressful period in my career, I realized that the most important thing I could do for my team was not hire great people. It was not to raise a lot of money. It was actually to take a run every morning," Scott says.
She got pretty religious about it, running around the reservoir near her New York apartment every morning. Then one day, during a particularly difficult time at work, there was a big storm, lightning, hail and all. She thought about bailing, but quickly reconsidered and laced up her shoes. Scott had learned to take her commitments to herself as seriously as any other professional responsibility.
"There were usually hundreds of people running around the reservoir, but there was just one other nut out there that morning. As I got closer to him, I realized it was my cofounder," she says. "A lot of things were going wrong, but we were doing something right."
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