“What happens in your work life when you meet someone new and interesting? You connect with that person every once in a while, right? I’ll meet that person and reach out a few months later when I’m in town. And the pattern continues,” says Grant. “I always assumed that relationship building is something you can’t rush. But it’s the opposite. You want to spend a lot of hours in a row with people upfront. Does this sound like a nightmarish 14-hour first date, where there’s a big investment of time, high uncertainty and the risk you’ll run out of topics to discuss? Maybe. But if I want you to figure out whether I can trust you, the best thing I can do is look for consistency in your motivation and behavior, which is easier to see over a few long interactions instead of more short ones.”
Armed with this insight, Grant has tweaked the structure of his work life, including switching his undergrad class from twice a week for an hour and a half to once a week for three hours. So which seasoned CEO, thought leader or fellow professor did he pick this tip up from? Astronauts on the International Space Station. And that’s the premise of Grant’s new podcast, WorkLife, where he immerses himself in some of the world’s most unconventional workplaces, uncovering unexpected insights that can be applied broadly to the rest of us to make how we work better.
In this exclusive interview, the Originals and Option B author draws from his WorkLife podcast to spotlight lessons about four areas that are pivotal to any individual’s and organization’s success: creativity, criticism, trust and humility For each area, he also goes behind the scenes of the podcast, revealing his biggest personal takeaways, as well as valuable related advice that didn’t make it in the episode.
A BETTER WAY TO CULTIVATE CREATIVITY
Groups are often where creativity goes to die. Any startup that has scaled has probably witnessed how the faucet of ideas runs slower as the room gets more crowded. When looking to see how teams can continue to bring creative ideas to the table, Grant found a surprising source of inspiration: the writers’ room of “The Daily Show.” The well-oiled comedy-generating machine makes a show from scratch in less than a day. For Grant, that’s exactly where startups could learn about moving fast while stoking creativity.
According to Grant, companies can build their version of the writers’ room, by improving their brainstorming, encouraging burstiness, creating psychological safety and designing for diversity.
Swap brainstorming for brainwriting.
When we think about creativity, we often jump straight to brainstorming. It’s the default for most teams, but eventually brainstorming backfires. Grant cites evidence that groups generate fewer and worse ideas while brainstorming than when the very same people are working on their own.
Here are three specific problems with traditional brainstorming sessions:
Production blocks. “We can't all talk at once, so somebody’s ideas are not going to get heard,” Grant says. “And that's usually introverts or people who are members of non-dominant groups, so you miss out on ideas from a wide range of voices.”
Ego threat. “This is sometimes called evaluation apprehension,” says Grant. “Basically it’s the notion that you don’t want to look stupid, so you bite your tongue on some ideas, which are usually the most unconventional ones.”
Pull toward conformity. “We jump on the bandwagon of what's popular in the room, or what the boss seems to like,” says Grant. “We end up thinking convergently instead of divergently.”
So what’s the alternative? “There’s a way to get the best of both worlds: brainwriting. Here’s how it works: let people generate ideas individually, write them down, and submit them. If you know the group is nervous about ego issues or status hierarchies you should collect them anonymously,” says Grant. “Next, bring all the ideas together and let the group evaluate which ones have promise. It’s about leveraging the power of the group for idea selection, where people are actually better collectively, but letting individuals be creative first.”
Individuals are great at generating ideas. Groups excel at selecting ideas using the wisdom of the crowd.
When Grant walked into The Daily Show writers’ room, the first thing he noticed was that it was full of creative bursts. It sounds like a steady syncopation of voices in a room — and there’s a term for it in psychology: burstiness. On his podcast, Grant compares it to the best moments in improv jazz. “Someone plays a note. Someone else jumps in with a harmony. And pretty soon, you have a collective sound that no one had planned,” says Grant. “Most groups never get to that point, but you know burstiness when you see it. At the Daily Show, the room literally sounds like it’s exploding with ideas.”
A study from Carnegie Mellon associate professor Anita Williams Woolley found that the more innovative, productive software teams were burstier, which meant they were bandying about ideas more rapidly, as opposed to having longer lag times. “When you know someone is responding to you and about to engage with you, you bring more to the table,” Grant says. “But this isn’t to say we should all just go around interrupting each other more often in the name of creativity. While having people jump in and contribute boosts creativity, you have to manage those interruptions carefully so that they're an encouraging voice, not a silencing voice.”
If you’re leading a meeting or an offsite session, remember that people may engage differently around gender, style and personality. “For example, Anita’s study identified some differences between men and women. Interruptions were associated with more burstiness and better performance for mostly male teams, and they were associated with less burstiness and lower performance from mostly female teams,” says Grant. “From the initial data, it seems that men are more likely to view interruptions as a sign of engagement, while women are more likely to see them as a signal that the people don’t value their ideas. So take note, group leads: assert — and insert — yourselves in group discussions to ensure burstiness doesn’t stifle some participants’ ideas. It doesn’t have to be awkward. My favorite way to do this is to go around the room and have everyone share an idea before anyone else jumps in. Or if you collect a bunch of ideas in writing, hand them out randomly so that people are pitching each other’s ideas.”
Charge your ‘credit’ card, leaders.
While brainwriting and burstiness fuel the creativity of Daily Show writers, Grant also observed an important contribution from the show’s host Trevor Noah. He had clearly created a safe environment, where no one was afraid to toss out a joke that might tank. Many refer to this as psychological safety. It can take time to build — time that startups don’t frequently have.
“Leaders build psychological safety through moments of vulnerability, often by sharing their shortcomings or failures to signal to others that they, too, can admit mistakes and take risks without bad things happening,” Grant says. “That does work. But Trevor also did something more incremental and subtle: quick interjections to give credit where it was due. When you’re in a creative group, it’s easy to lose track of who said what. In the case of Daily Show — and fast-moving startups — it’s an environment where all the praise and blame goes to the leader. Pass down the credit through quick, verbal kudos.”
Looking beyond the Daily Show, Grant has a few more recommendations for encouraging people to share new ideas. “When you’re solving a creative problem, think about accountability more systematically,” says Grant. “First is outcome: did you succeed or fail? And the second is the thoroughness of the process: was it a good decision process, a creative process or a bad one?”
Grant likes to think about accountability as a 2x2 chart plotting out the various combinations of answers to these questions. Organized in this fashion, it’s easier to see how one might undermine creativity.
“One way to undermine creativity is to reward lucky successes. This is when you’ve had a bad process, but a good outcome — but you still celebrate it. Instead, be honest about that lucky break, because your team will sense it came from good fortune,” says Grant. “The second is way to squash the flow of ideas is to punish failed outcomes that had a good process. This should be flipped. We should be looking for examples of creative ideas that either failed, but were tested in a smart way, or risky experiments that were worth trying to see their results. You need to make it safe for people to keep running those kinds of experiments.”
Finally, Grant has a bone to pick with tech culture. “Leaders talk a big game about taking risks or failing fast, but they’re missing the mark. Conversations about celebrating failure in Silicon Valley crack me up,” Grant says. “Who thinks that’s a moment of joy? You don't want to celebrate failure, you want to normalize it. Make it a common, expected and accepted part of creativity and innovation. Take an approach like that of Etsy, where there’s a practice of sending company-wide emails normalizing errors. If you do something like that, you're in a much better position to get people to take risks, which is what creativity requires.”
Review applications blind with diverse interview panels.
Whether it’s comedy or business, creativity requires getting the right mix of people in the room. “Like orchestras that hired more women after they had musicians audition from behind a curtain, the Daily Show uses a blind review of application packets when hiring writers, so they’re not biased toward or against any particular demographic groups. Other late night shows tried it too,” says Grant. “But the other late night shows still hired a bunch of white men. Why? They had a bunch of white men evaluating the applications. Evaluators gravitate towards comedy that came from people like them. Since The Daily Show had a more diverse group of leaders reading packets, they were more likely to recognize the potential in a diverse range of candidates.”
It’s not enough to just disguise the candidate’s identity — you also have to have a diverse pool of evaluators.
When it comes to assessing talent, you need to have people who have different tastes, backgrounds and criteria doing evaluations. Otherwise the applicants you need may never have a real shot. “Leaders have as much responsibility for the diversity of the hiring managers or evaluators as they do for the diversity of the applicant pool. Otherwise, you can’t make sure that you're not systematically biased against the very backgrounds that will bring new, creative ideas and insight,” says Grant.
CREATING A CULTURE OF CRITICISM
Those of us who hesitate to float those crazy, wild ideas often pause for fear of what others might say. In “How to love criticism,” Grant explores the merits of how to create a workplace where people constantly criticize each other — and enjoy it. If Grant could send startups to one company to learn about criticism, it’d be Bridgewater. Here’s what the global investment firm that manages $150 billion has to teach startups.
Play the tape to reduce the need to impress.
Bridgewater has become well known for taking criticism to new heights with its honest and transparent culture. In fact, the hedge fund is so obsessed with the notion of radical transparency that they record video or audio of almost every meeting.
At first blush, this idea seems a little out there. Wouldn’t it be very stressful to work in an environment where your conversations were taped? “It was way less creepy than I had initially anticipated,” says Grant. “People adjust really quickly. The founder, Ray Dalio, told me it’s similar to a reality show. You know when you're watching the second hour of Survivor or The Bachelor, and you're just sitting there wondering to yourself, ‘How in the world are these people acting this way when they’re on national television?’ It’s because they only pay attention to the camera for so long."
Instead of seeing Orwellian overtones, employees get to keep an eye on the boss—it’s not uncommon for them to criticize Dalio himself. They view the tapes as a tool for learning, whether it’s spotting behavior patterns or getting a new perspective from colleagues who interpreted a decision differently. “It’s an opportunity to review the ‘game tape.’ But, aside from forgetting about the camera, how do people get over that initial hump of fear from being recorded? People start to realize that if their goal is to be valued or respected, then the best thing they can do is focus less on proving themselves and more on improving themselves,” says Grant. “Often, a good impression is a byproduct of deep engagement in a conversation, a desire to learn, or thoughtful work, as opposed to something you aim at directly.”
“Ironically, if you want to make a good impression, focus less on impressing people.”
For Grant, this lesson from Bridgewater influenced him on a very personal level. “Early on in my career, I wanted my students and colleagues to like me,” he says. “Now I’m more interested in whether people respect my viewpoint. I'm actually thrilled if somebody says, ‘I disagree with your thesis, but it really got me thinking.’ That’s what makes Bridgewater stand out. People are invested in putting the process of thoughtful disagreement on the table. This is something all companies — especially startups — could seek out. Admit you may be wrong but offer to put an argument or counterpoint on the table. That’s what they do at Bridgewater. It gets people curious, not combative.”
Assemble a challenge network.
If your startup’s not ready to create a carefully designed culture of criticism with methods like audio or video recording, that’s okay. You can recreate this effect with a group called a challenge network. “You know the value of a support network, but you also need a challenge network. For the past few years I've had a core group of people, who all have one thing in common: they believe in the potential of my work, but they're the first ones to call BS when it falls short of that potential. They’re my challenge network. So when I finish a draft of an article, I’ll send it to them. They’ll call out if I haven't made a convincing point or substantiated my argument well,” says Grant. “They're really good at calling that out and I value it tremendously, but I had never thought to tell them they were my challenge network.”
Inspired by Bridgewater, Grant has formalized his challenge network. “Now, whenever I get an email from someone in this group, I’ll write back and say, ‘Hey, I probably should've told you this sooner, but you're actually a founding member of my challenge network. Here's what I've valued so much about the constructive criticism that you've given me, and please keep letting it fly.’ And they have — the gloves really came off,” says Grant. “As entrepreneurs and leaders grow more influential or senior, people become more hesitant to tell them the truth. You can counter this by inviting people into your challenge network and letting them know how much you rely on them. It’ll open the door for more unvarnished, constructive criticism.”
Move from proving to improving mode.
Whether you leverage a challenge network or have a culture like Bridgewater that has formalized a culture of transparency, shifting your mindset around constructive feedback is key. “When we’re faced with criticism, our egos kick in, putting up barriers as self-defense. This is proving mode, the primal, emotional reaction from the lower-level of your brain,” says Grant. “But thankfully there’s a higher setting to unlock: improving mode. That’s the side of you that wants to get better, recognizing that you’re always a work in progress.”
The constant feedback loop at a place like Bridgewater is designed to help you uncover that improving voice. Here are two strategies for startups looking to do the same:
Go public. “One of the best ways to get into improving mode is to ask people to criticize you in public or to criticize yourself in public. It can push you to stop being defensive. Because if you're not showing a genuine interest in developing yourself, everyone in that room is going to know it,” says Grant. “I know one leader whose company grew to around 100 employees, and he felt people were just managing up and not telling the truth. So he called an All Hands and said, ‘I want you all to tell me everything I'm doing wrong and we're going to stay here until we've got it all on the table.’ And he started off by criticizing himself, which made others more comfortable.”
Get meta on feedback. As a professor who gets feedback from students, Grant knows a thing or two about responding to it. “Mid-course, I ask for feedback and I take the comments and send them out to all the students, typed up verbatim. But I like to take it a step further. In the next class, I stand up and analyze the comments, identifying themes and outlining changes I’ll make in response,” says Grant. “Then I ask for their feedback on my response to their feedback. ‘Give me some meta feedback.’ What’s interesting is that they’ve already made their judgement about the class. But when I go up there and give my reaction, well then I’m being evaluated on how well I’m taking it. And at that point the only thing that you have to prove, is that you are willing to improve.”
BUILD TRUST BY GOING DEEPER
A culture of criticism is predicated on a trust that your team has your back — that they have a legitimate interest in helping you get better. But that trust isn’t always easy to develop quickly. Grant found some powerful insights from talking to the astronauts on the International Space Station. “Astronauts do things a little differently to build trust. Multinational teams are put together to do complex work in a dangerous setting, so they need to build trust, fast,” says Grant. “To replicate that environment, they do intense training in the wilderness, where astronauts spend a lot of hours in a row with someone. The idea is to create a big investment of time with high uncertainty.”
It got Grant thinking differently about building trust. Here’s why:
Surface-level small talk disintegrates. “When you have a long interaction with somebody, you move past the pleasantries, and you have no choice but to just start going deeper,” he says. “That’s the only stuff left to talk about.”
The masks come off. “It’s really hard to maintain a front when you’re in your eighth hour together. The real you comes out,” Grant says. “You stop managing impressions. You stop trying to create the perfect interaction. It turns into something more like what you have with family, friends or colleagues you've known for a long time.”
Working forges bonds. “I thought you were supposed to build trust through conversation,” says Grant. “But astronauts taught me that the trust is often built through working and solving problems together.”
Based on these insights, here are two ways you can go deeper in your relationships earlier on:
Front load the ‘blitzing’ in a collaboration. “I collaborate in ‘blitzes,’ where we block out a day from 8 AM until we run out of energy, just sitting and working together,” Grant says. “But I always saw that as for implementing ideas, not as a technique for building a relationship from the start. Shift to to do more of that upfront, scheduling multi-hour blocks early in a working relationship.”
Extend it further to your hiring practices. It’s important to get a taste of what it's like to actually work together. “Before you hire someone, you want to spend time working with them in a long stretch,” Grant advises. “Once they’ve passed the regular hurdles, hire them on a temporary contract, if they're open to it.”
Our thinking around trust tends to be skew narrow and unbalanced.
Grant expected that people would form trust in similar ways. Social scientists define trust as being based on three judgements — the first having to do with capability and the second two dealing with character:
Competence. Do you have the appetite, aptitude and skills to get the job done?
Benevolence. Do you have good intentions toward me?
Integrity. Do I think you have sound principles and that you'll act on them? Do I see consistency between your words and your deeds?
But in practice, Grant found that people differ in how much weight they place on competence versus character. “When it comes to forming trust, some might focus only on capabilities or technical skills. That's a dangerous way of looking at trust, because it's when toxic superstars get elevated. You end up polluting your culture because you overlook those other dimensions of trustworthiness,” says Grant. “And on the flipside, there are plenty of people who said, ‘Look, if you demonstrate that you care and that you have integrity, that's enough for me.’ That might be okay if this is a cousin that you want to trust with a secret, but if you're going to work with this person, you want to know that they have relevant knowledge and skills.”
People’s narrow thinking around how they would decide to trust someone wasn’t the only surprise to Grant. “I don't think it fully crystallized for me until after we did the episode on trust, but I came away convinced of something that psychologists first demonstrated a few decades ago: to judge character, we rely mostly on negative examples,” says Grant. “So, if you want to know if someone's a good person, bad is stronger than good. Finding out that they lied, cheated, stole, or took advantage of someone will carry much more weight than finding out that they cared, they were honest, they were helpful, or they were just. All it takes is one violation for that to come crashing down.”
But when it comes to competence it’s the opposite. “We actually judge ability by positive examples, not negatives. You don't judge whether Serena Williams is a good player by how many shots she misses,” says Grant. “You judge her by her peak performance. When she hits a winner, it’s a signal to you that she has a rare set of capabilities — even if she doesn't display them perfectly in every moment.”
The takeaway is to be more systematic in how you evaluate capability and character. “When you evaluate people, recognize that these different domains are weighed in opposite ways. When you judge competence, pay less attention to a small error that somebody makes here and there and look more at their maximum performance. How good are they on their best day—and how often do they show up at their best? Now, of course an error could be a sign of low attention in detail, but that's no longer a question of competence, it’s a question of motivation,” says Grant. “And when we’re trying to judge people's character, rely less on the positive examples. Just because somebody has spent some time being helpful doesn't mean that they're not a taker. Just because somebody had shown unusual honesty in one situation doesn't mean that they have integrity.”
TAKING A HEALTHY DOSE OF HUMILITY
“Many companies are adamant about only hiring ‘rockstars,’ ‘ninjas’ or the latest buzzword du jour,” says Grant. “Yet from Wall Street to World Cup soccer, there’s evidence that having too many top players can actually be a problem.”
If one more executive says to me, ‘I only hire A players,’ I'm probably going to vomit.
Grant believes startups should learn from a philosophy that Celtics coach Brad Stevens crystallized in Butler’s basketball program. Humility is at the heart of Butler’s value system, and this small school has beaten the odds multiple times to upset the #1 team in the country and make NCAA championship games. Here are more insights into why humility matters, how to build it into your culture, and how to hire for it.
Don’t mistake humility for weakness.
There’s a clear difference between weakness and humility, but it’s often conflated or confused. “When I first started talking about humility, people would always say, ‘You can't be humble and wildly successful,’’’ Grant observes. “But I can make a list of people who are, and there’s fascinating research by Brad Owens showing that humble leaders have more productive employees and more innovative teams—and the team humility is associated with better team performance.”
Grant has long wrestled with this contradiction. “Eventually what I realized was that the idea people have in their head about humility is wrong,” he says. “A lot of people think humility means having a low opinion of yourself. When you hear people say things like, ‘I'm so humbled by this award,’ that’s not correct. That literally means ‘I am lowered in dignity or importance.’ Being humbled is actually about getting crushed, not about being recognized or successful. What you mean to say in that context is ‘I'm honored.’”
Instead we need to think of it more as being grounded. Which can go hand in hand with confidence. “Humble confidence is saying, ‘I believe I can excel here, but I also know I'm human,” says Grant. “I'm flawed. I'm not going to be perfect. I always have something to learn.”
Humility points you to the horizon.
For startups especially, humility is a way to go after the long game. “Humility is critical to sustaining success, because otherwise teams rest on their laurels and get complacent,” Grant says. It’s hard to stay great when you let success go to your head and you stop focusing on learning. And when companies get too comfortable, that’s when they get disrupted, or when founders overlook major problems.”
Teach individuals and teams to recognize that once they’ve ‘made it,’ their work is far from done. When Grant talks to people who have sustained success, one thing they have in common is a mentality of focusing on what they can do better. “That may seem like insecurity. But Grant disagrees. “It’s just recognizing that if you step on the brakes or take your foot off the gas, there will always be other people who won't. Or there will be products that you'll end up responsible for that don't live up to your standards.”
Here are a couple of techniques to foster humility in yourself and your teams:
Do the grunt work — it’s contagious. A tactic that comes to mind for Grant is from JetBlue, where everyone cleans the plane after it lands, including the pilots. “Think about the humility it requires to say, ‘You know what, it doesn’t matter that I've got these stripes on my shirt and I'm the person in charge around here. I will still stay around and clean up garbage,’” says Grant.
“One of the people whose humility I admire the most is Sarah Robb O'Hagan, the CEO of Flywheel. She previously ran Equinox and was the president of Gatorade, yet remains very humble. When she joins a new team, she's often the first person to volunteer to do the grunt work,” says Grant. “It's like the professional equivalent of signing up to run a Tough Mudder. It’s telling, but it's also inspiring and contagious. People say, "Wow, our boss doesn't see anything as beneath her. She's willing to do everything in her power to support us and make this company successful."
In your own organization, go out of your way to sign up for grunt work that might technically be beneath your pay grade. It signals not only that you don’t think you’re better than anyone, but also that you’re really committed to the success of the team. In order to extend that attitude throughout your culture, lead by doing and refusing to maintain a power distance.
The key to showing humility and making it contagious is leveling the playing field.
Spend time doing the work of your team. One of Grant’s colleagues at Wharton, Sigal Barsade, recommends that leaders spend 10% of their time doing the actual work of their employees. Not only does it give you the benefit of perspective, but it can also create what’s called moral elevation, that warm and fuzzy feeling you get when you see someone else doing good works.
Interview for humility. For Butler’s basketball program, it all starts with recruiting. It’s about keeping big egos off the team and not sacrificing culture for talent. Grant unearthed a great recruiting question their scouts use to surface true humility: Would you rather your team win but you only score 5 points, or score 20 points but your team loses?
"Who do you owe your success to?" When listening, see if the candidate uses words such as “I” or “me” a lot, instead of giving credit to others. Also watch out out for phony humility from people looking to game the system or name drop. “What differentiates a faker from a truly humble person is often that the fakers are really focused on impressing you and managing up and kissing up. So they will name people above them in the hierarchy,” says Grant.
"Who have you learned the most from in your career?” A mark of humility is a willingness to learn from someone who might not be in a position to teach you anything. “Humble people recognize you can learn from anyone and everyone,” says Grant. “Take the student who was admitted to Yale and who asked his school’s janitor to write his recommendation letter. The appreciation and curiosity that the student showed towards somebody who's literally at the bottom of the totem pole in that high school. That's humility.”
Ultimately, Grant’s mission with his WorkLIfe podcast is to help teams and individuals learn from organizations that are getting it right, even if their workplaces are unconventional. Here are a few takeaways to stoke creativity, embrace criticism, garner trust and reward humility.
Swap brainstorming for brainwriting. Let individuals generate ideas solo. Convene groups to select ideas.
Encourage bursts of interruptions. Creativity will compound, but moderate the conversation to ensure burstiness doesn’t hinder specific members of your team.
In creative, bursty environments, issue credit immediately and frequently. It’s easy to lose track of people’s contributions.
Review applications blind with diverse interview panels. It’s not enough to just hide the candidate’s identity — you also have to have a diverse pool of evaluators.
After getting consent, consider recording meetings from time to time so people can review their own behavior. Employees can use recordings as a tool for learning, whether it’s spotting behavior patterns or getting a new perspective from colleagues who interpreted a decision differently.
Assemble a challenge network. Find and foster a panel of people who believe in the potential of your work, but are the first ones to call BS.
Move from proving to improving mode. Do this by publicly sharing feedback on your performance and get feedback on how you handled criticism.
Front-load and extend the amount of time with others to build trust. The best way to build trust is to show consistency in motivation and behavior, which is easier to demonstrate over long interactions early on.
Assess trust through a balance of capability (competence) and character (benevolence and integrity), not just one of those factors. Don’t judge capability only by one’s high points. Avoid assessing character only through negative examples.
Don’t mistake humility for weakness. Instead look for humble confidence: a belief one can excel but is also human.
Spend 10% of your time doing the work your team does. Do the grunt work. It’s contagious.
Interview for humility. Ask: “Who do you owe your success to? Who have you learned most from over your career?”