Chapter 4. Encourage Learning Versus Knowing

As Satya Nadella accepted the role of CEO and embarked on changing the culture of Microsoft, one of the biggest challenges he encountered was getting back to the culture he had experienced more than 20 years earlier, when he had first joined the company.

In his book, Hit Refresh, Satya reflected on what the culture at Microsoft had become when he took the reins. “Our culture had been rigid,” he remembers. “Each employee had to prove to everyone that he or she knew it all and was the smartest person in the room. Accountability—delivering on time and hitting numbers—trumped everything.”1

My personal experience when I joined Microsoft a year before Satya took over as CEO was largely the same. I saw product teams jostle for position, trying to get their features shipped by being “airtight” and “bulletproof.” There wasn’t any time to talk with customers, because there were just too many specification sheets to write or meetings to discuss implementation details. Our time was consumed with trying to determine the right way to build something, never stopping to ask if it was the right thing to build in the first place. In the previous culture, the worst thing you could encounter was being proven wrong.

The individuals who succeeded in this culture were often seen as the know-it-alls. This wasn’t meant to be a disparaging term, because they did, in fact, know a lot about our products, businesses, and services. That’s incredibly valuable in a company with a diverse portfolio of products like Microsoft.

However, Satya was promoting a very different message. Although he valued the company’s deep technical knowledge and expertise, he also needed an organization that had the capacity to renew itself and learn new things. In short, the ability to learn was more valuable than the knowledge you had already acquired.

In numerous venues, I had heard Satya reference the work of Dr. Carol Dweck, one of the world’s leading researchers in the fields of personality, social psychology, and developmental psychology.

In her book Mindset: The New Psychology of Success, she summarizes 30 years of research that confronts the idea that our qualities are carved in stone (e.g., fixed mindset). Instead, she illustrates that adaptability, innovation, and creativity stem from a fundamental belief that our abilities are elastic; that they can be improved and built upon over time (e.g., growth mindset).

Through Satya’s insistence and sheer repetition, “growth mindset” became a term that shot its way through the hallways, team rooms, and board rooms.

In DevDiv, we saw this new desire to learn from customers become the “new currency” as product makers began adopting new skills and new methods to connect with customers. It became OK to admit that you didn’t know something, and time was spent on strategizing new ways to learn.

Coupled with the common language of learning discussed in Chapter 2, teams were formulating experiments and conducting customer interviews, demonstrating a growth mindset and a voracious appetite to learn. Put simply: it just wasn’t cool to be a know-it-all anymore. Now, it was cool to be a learn-it-all.

Our brains develop based on the output of millions of microexperiments. The learning that comes from these tiny experiments helps condition us to navigate an increasingly complex world.2 Effectively, our minds and bodies grow by learning; why should our organization’s growth be any different?

That’s why promoting learning is such an important culture hack. In this chapter, we explore how cultures thrive in environments that encourage learning and psychological safety. We discuss how to make change feel safe and how to encourage others to take a risk, learn new behaviors, and join you on your customer-driven journey.

Agents of Change: Margo

It was a typical evening when Margo clocked in for her shift in the oncology ward. She had just completed a three-month-long orientation as a new registered nurse, and although she felt supported by her team, she still felt overwhelmed with all that she still had to learn.

“I had great support from my peers,” she recalled, “but I was always asking questions. I was trying so hard to practice independently.”3

She stepped into a patient’s room, took his vitals, and reviewed his medication order. That’s when she noticed something odd. The medication order called for 44 units of Lantus for bedtime, but there was also an order for 44 units of regular insulin. She was under the impression the patient had already been given this dose of insulin, but she assumed that the process in place would’ve caught this order if it had already been administered.

She went to the Pyxis machine, an automated pharmacy distribution locker, placed her finger on the fingerprint scanner and collected the bags of IV medicine. “I totally relied on the computer and the system. I remember thinking, there is no way this can be in the computer and be wrong. The nurse practitioner wrote this order, a pharmacist reviewed it, and another nurse checked it…. Wouldn’t the computer catch it?”

Margo reentered the patient’s room and was still trying to justify why the medication order felt wrong, “I knew the order was wrong, but I was unable to say why. I told the patient, ‘I have your 44 units of Lantus and 44 units of regular insulin; is that what you do at home?’”

“The patient said yes, but who knows why—maybe he was poorly educated, maybe he didn’t feel empowered. I wasn’t skilled enough to ask open-ended questions, so I asked for confirmation.”

Margo administered the medication and went back to the floor to resume her duties.

About four hours later, she passed the patient’s room and noticed his call light was on. When she walked into the room, the patient had pulled out his IV and was lying in a contorted position. He was in a full seizure and was unresponsive. She called a code blue, and a flurry of nurses and physicians rushed into the room. Everyone was asking questions, trying to determine what could’ve caused the seizure.

In that moment, Margo knew that to save the man’s life, she’d have to own up to her mistake.

“His blood sugar is low, because I gave him too much insulin!” she finally admitted.

The staff used that information and was able to successfully resuscitate the patient. A tragedy had been narrowly averted.

The hospital administrators decided to use the situation as a learning moment for the entire hospital. They enlisted Margo to join the Root Cause Analysis (RCA) team to help unpack how the error occurred. The process required honesty and humility. She had to be willing to admit where she had made mistakes and examine why she was so reluctant to voice her concerns.

Not only did she keep her job at the hospital, she’s now a well-respected nurse leader. She uses the incident to help teach other nurses about the power of speaking up and asking questions, even if it means admitting that you don’t know something.

Essentially, Margo and many other nurse leaders like her are trying to chip away at the knowing culture within healthcare—the pressure to not make mistakes, to be perfect and accurate each time and in every circumstance. In Margo’s case, she was aware that something was off, but she didn’t have the curiosity to investigate or the courage to question the system. In social psychology, this is referred to as the bystander effect: when we are in the presence of others who are not addressing an urgent situation, we feel less inclined to intervene.

The reality is that mistakes happen all the time in healthcare. Many nurses are trained on how to avoid big mistakes, but not enough time is spent understanding how easy it is to fall into groupthink or operate on autopilot. Nursing requires a constant vigilance to question your assumptions and the willingness to speak up to ensure a patient’s safety.

“In nursing school, they treat error as something really rare,” Margo says. “[They show you] sensational cases, so you think that’s what med error is. We need to teach nurses you will make mistakes.”

What’s remarkable about Margo’s story is how the hospital dealt with the situation. Margo wasn’t reprimanded or fired. In fact, she was given counseling through the hospital’s Employee Assistance Network to ensure that she could process the situation in a healthy way. The organization helped her develop the courage to admit her mistake and help others learn the value of being curious and asking questions when you’re unsure.

Additionally the hospital realized that Margo was an incredible asset. She had unique, firsthand, experience of how the error occurred. It could not only use her experience to correct the system, but it could also have her coach others on how to avoid the mistake she had made.

That’s an exceptional example of encouraging learning over knowing.

The Importance of Acknowledging Mistakes

As part of her doctoral studies of organizational behavior at Harvard University, Amy Edmondson completed a study that followed the dynamics of teams and error reporting within two different hospitals. Her hypothesis was that teams who were more collaborative would produce fewer medical errors.

However, when she analyzed the data, she found that the opposite was true. She discovered that the teams who were more collaborative with their managers and colleagues actually produced more errors.4 She wondered how that could be. It didn’t make sense that teams with greater collaboration were prone to making more mistakes.

She went further into her research and uncovered the cause. It wasn’t that collaborative teams were producing more errors than their noncollaborative counterparts. It was that they were reporting more of them.

In his book The Best Place to Work, Dr. Ron Friedman examines Edmondson’s study and arrives at a simple conclusion. “When consequences of reporting failure are too severe,” he writes, “employees avoid acknowledging mistakes altogether. But when a work environment feels psychologically safe and mistakes are viewed as a natural part of the learning process, employees are less prone to covering them up.”5

In collaborative environments, employees feel safe to recognize and discuss their mistakes. This leads to more error reporting. Therefore, we can’t assume that when we don’t see mistakes, this means they’re not happening. Creating a culture that expects perfection is going to diminish employees’ desire to share expertise and learning.

Edmondson says, “We need to hear from people; and yet the research, the data, are overwhelming that many people feel that they can’t speak up at work.”6

Know-it-all cultures spring from the desire to prove that you’re always right or to defend a position to save face. Learning cultures require humility and the admission that you don’t have all the answers.

As Edmonson uncovered, in knowledge economies and especially in product development, the landscape is constantly changing. It’s virtually impossible for one person to be involved with all aspects of a product’s life cycle. Therefore, you need to build teams that hold a learning-first mindset so that you ensure you’re getting the most up-to-date thinking.

In this chapter, we discuss ways that you can hack your organization to a culture that values and encourages learning over knowing.

Celebrate Learning, Not Failure

When talking about building a culture that values learning, some people believe we’re asking them to accept failure. They’ll say, “I don’t want a culture where everyone feels that failure is acceptable!”

Although failure is a pathway to learning, it can also be a signal that someone is underperforming or needs more support for the task you’ve assigned them. The key is determining which is which. We must decide whether what we’re seeing is learning or failure. Let’s explore this idea by using an imaginary scenario.

Example Scenario: Learning versus Failure

Let’s imagine a services firm finds out that a massive potential client is considering the firm for a big project. This is an incredible opportunity for the firm, so it builds a small team to develop a compelling presentation and secure a deal with the client.

Now, let’s assume that we have two teams: Team 1 and 2. Each of them is assigned this opportunity, but each team sees the opportunity differently.

Team 1: An opportunity to demonstrate an efficient and exacting vision

Team 1 spends the first week sorting out who is going to present to the client and in what order, saving itself valuable time to bring creative assets together. To keep decision making at a minimum, the team keeps the presentation materials locked down from the rest of the firm. It’s too easy for a project like this to turn into a “design-by-committee” workshop. Keeping the working group small will streamline the decision process.

Team 1 brainstorms some ideas and is confident it has come up with a vision that will inspire not only the client, but the entire firm. After it has a rough idea in place, Team 1 consults with an outside agency to help with the creative work. The team admits that it’s a bold direction, but aren’t the partners always asking for more innovative ideas?

The afternoon before the client and his team arrives, Team 1 finally presents its work. In a closed-door meeting with the partners of the firm, it unveils its new media strategy as well as its presentation for the client proposal. Team 1 presents its bold strategy for the new client proposal: on the day of the client arriving, the firm will announce a pricing restructure and bundled services offering. This is something the firm’s existing clients have been asking for, and announcing it the day the client arrives for the proposal will generate a lot of excitement.

The head of sales tells Team 1 that her team had already tested a similar pricing structure with some existing clients, and it received a negative reaction. She’s concerned that Team 1 might have over-indexed on the value of the new bundling options in its presentation.

The head of the account management team asks whether Team 1 had a chance to connect with the client’s account manager. Team 1 shuffles its response, but it’s clear it hadn’t. He tells the room that, from what he’s heard, the client is a “numbers guy” and might have some deep questions about pricing. He suggests that the team should “stick with the pricing structure that we already know, rather than try to introduce a new model in front of an important potential client.”

The pricing idea Team 1 proposes is interesting, but the firm will need more time to figure it out. Team 1 is instructed keep the new media campaign, but to stick with the current pricing structure.

Team 1 works overtime to reorganize the presentation. It removes any mentions about the new pricing ideas. To save time, the team goes with the slides that the head of sales already had. Although the story has gaps, Team 1 is resourceful, getting the last-minute information they need to propose the current pricing structure. Tensions with the other group is high, but that can always be sorted out later. After all, big proposals like this are bound to generate a bit of “politics.”

The client and his team arrive. Almost immediately, the presentation is full of false starts. Just as the head of the account management team predicted, the client seems intent to ask questions around the pricing structure. Team 1 struggles to answer complex questions around pricing and services. The head of the sales team jumps in to smooth out the rough spots and they’re able to continue.

With very little time remaining, Team 1 unveils the new media campaign. Rather than inspiring the client, the media appears to be boring them. One member from the client’s team pulls out his phone to check his email.

When the presentation ends, the client asks for an example that demonstrates the firm’s commitment to its customers. Team 1 stumbles over the answer, but the account manager was able to tell a great story that has the client smiling. The client begins to relax and engage, but time runs out. The client thanks the firm for its proposal and leaves.

There are a few follow-up attempts, but the client is never heard from again.

Team 2: An opportunity to demonstrate a learning and collaborative vision

Now, let’s go through the same example scenario with Team 2.

This team starts the project by looking over the presentations the firm has given over the previous three years. One member of the team has a knack for identifying patterns in analysis. The team decides to take advantage of her strength and puts her in charge of determining whether there are any patterns that can be found in successful pitches from the past.

Through her analysis, the team discovers an interesting finding. It appears that when a sales pitch incorporates testimonials from current clients, it is accepted 78% of the time. The team is excited by this insight, but it wants to check its assumption that customer testimonials have a positive effect on the outcome of sales pitches. The team decides to share the new insight with the head of the sales team. The team lead supports the finding and suggests that she sees customers always light up when they talk about success stories from other customers.

However, she’s concerned that the team’s presentation is light on specifics around pricing. She’s heard stories about this client. “He’s a numbers guy,” she says. “He’s going to want to see what this all costs. It’s nice to have a glitzy presentation, but make sure your numbers are rock solid.” With her help, Team 2 reworks its presentation to touch on key points regarding the firm’s pricing structure.

Working with the account management team, Team 2 creates a handful of customer stories that speak to the relationship the firm builds with its customers. The media is fun, authentic, and speaks to the values of the firm. When some of the sample design work is floated around the offices, people are excited and express how much they like the new messages.

The team works with marketing and design to craft a compelling theme for its presentation, calling it “The Power of Together.” The presentation highlights how the firm partners with its clients to improve their businesses.

The afternoon before the presentation, the team sends out the latest version of the presentation. There’s no need to meet, because many of them have been involved in helping put the presentation together. Team 2 encouraged co-discovery with their colleagues, and all that’s left is to wish one another good luck.

At the beginning of the presentation, the client states that before they get to anything, he wants to discuss pricing structures. Thanks to the suggestions from the head of the sales team earlier, Team 2 was prepared and is able to confidently address the client’s pricing questions and keep the presentation on track. After a series of back-and-forth questions, the client seems satisfied and begins to relax.

Seeing that he’s ready to move on, Team 2 unveils its “The Power of Together” message. As part of the presentation, the team plays a video in which some of its premiere clients talk about their experiences with the firm. It’s a touching video, and the partners beam as it’s being played. The client smiles and nods to his team during the video. It appears to be a hit.

When the video finishes, the client says, “Wow. It’s great to see what your customers think of you and see examples of what we could do together.”

The client’s team generally agrees, but unfortunately one member is still uneasy. He mentions that the firm has never worked with a client in the same industry as the project they’re considering.

Although he was inspired by “The Power of Together” message, he wasn’t sure the firm could manage this project’s unique business model. The client eventually agrees that the firm might not be right for this project, but as he’s leaving, he mentions to the account manager that he has another project that he believes the firm would be better suited to help with.

So in this scenario, both Team 1 and Team 2 failed to deliver the desired outcome. The client didn’t choose either team’s proposal for his project.

Yet, it’s difficult to suggest that Team 2 failed. Even though it was unable to secure the new client, it was able to move the firm forward with valuable new knowledge. Team 2 recognized the individual talents and passions of one team member. Through her analysis, the team identified an important insight into the power of customer testimonials on sales presentations. This could be an important differentiator in how the team pitches new clients going forward.

Team 1 was not only unable to secure the client, but it left the firm in a worse position at the end of the project. The upcoming months will be consumed with infighting about changes to the pricing proposal.

With Team 1, the outcome is a lost client and a wealth of new problems. With Team 2, the outcome is a lost client, but an exciting opportunity to improve going forward. The team demonstrated a positive way of working, utilizing one another’s strengths, and created a model of how they should engage future projects going forward.

The partners of the firm should celebrate Team 2’s efforts. They should point out the innovative way in which it employed past sales presentations to gain useful insights. Congratulating Team 2 on its efforts presents an opportunity for the partners to show the rest of the firm that these sorts of calculated risks will be rewarded, even when they don’t deliver the desired result. By celebrating Team 2, the partners are building the psychological safety for everyone to try new things, even in high-risk situations like pitching a big client. In this case, they can celebrate the learning, not the outcome. They can use this opportunity to encourage a learning mindset over a knowing one.

When successful outcomes are the only things that are recognized, employees will be more inclined to trust conservative approaches on new projects. If you want to promote innovative thinking, you must be willing to reward someone who’s showing a learning mindset. Seeing examples of their peers being rewarded not only for positive outcomes but also for developing new learning for the firm, will encourage them to engage in similar risk-taking and learning-first behaviors.7

Lead with Questions, Not Answers

In his book The Practice of Management, famed management consultant Peter Drucker wrote, “The important and difficult job is never to find the right answer, it is to find the right question.”8

To build a culture that is rooted in learning, you must be comfortable asking questions. As a leader, you might find it difficult to ask questions because you feel intense pressure to have all the answers. Many leaders believe it’s their job to make the final decision and pride themselves on having enough knowledge in their given area that they are prepared to answer any question that comes their way. After all, wasn’t that why they were given the leadership position in the first place?

However, the best leaders know the correct questions to ask. They not only ask questions to enrich their own understanding, but to help others learn as well. They use questions to advance debate, not to score points or make passive-aggressive arguments. For these leaders, questions are a powerful instrument that help bring clarity in complex conditions.

John Montgomery, corporate vice president, is responsible for leading all of program management, UX research, and design within the Developer Products Division at Microsoft. He believes asking questions is a powerful way to reinforce a learning mindset within his teams. John has a unique background compared to other leaders you might meet at Microsoft. He studied Russian language and literature at Harvard and even wrote articles in a variety of technology magazines for Ziff-Davis Publishing.

“My background is very different from most of the people that work at Microsoft,” he says. “I don’t have a computer science degree. I was never a professional software developer and so, in a lot of cases, I find myself genuinely not knowing answers to questions. My background was as a journalist, and as a journalist, a lot of your job is to ask people questions to uncover what they know and to get them to tell stories.”9 Montgomery continues:

[The process of asking questions] very often helps [teams] see things through different perspectives and different lenses. It can move them in different directions, because they hadn’t considered something. I would say [as a pattern of leadership] that question and curiosity is something I try to bring, and I try to encourage it in others.

As a leader, John models that he’s comfortable admitting what he doesn’t know. He projects a curiosity and a desire to learn and he gives his reports the space to do the same.

“A completely fair answer to every question is, ‘I don’t know, but I can go find out,’” he admits, “and in terms of growing that, I think there is a core requirement of all program managers to approach things from that lens of asking questions.”

If your organization has a strong knowing culture, it can be difficult to admit when you don’t know the answer to something. In a knowing culture, people sit quietly in meetings listening to the presenter even though they have no idea what that person is talking about. Yet, when the presenter asks, “Does that make sense?” everyone nods to one another in unison.

Later, you ask a colleague, “Hey, I didn’t understand the part about our new global sales quotas. Do you get that?”

Your colleague looks at you and shrugs, “Yeah, I didn’t understand that, either.”

You’re left asking yourself, “Then why did we all agree that we understood?!” Better yet, “Why did I say I understood?!”

It’s more than just admitting you’re confused or that you need help understanding; some people feel uncomfortable asking questions because they don’t want to be perceived as being difficult or wasting everyone’s time. There’s a fear that you might ask a question that everyone knows the answer to, leaving the group to look at you and say, “Really?! You didn’t know the answer to that?!

Yet, asking questions should be viewed as the ultimate sign of respect. When someone asks you a question, they’re saying, “What you’re saying matters to me. I want to make sure I understand you.”

That’s why John and other leaders who are naturally inquisitive end up creating large networks that span cross-organizational boundaries. They want the bigger picture, and they’ll keep asking questions until they get it. They are shining examples of a learning culture because their pursuit of knowledge outweighs their need to create an illusion of knowledge.

In the book The Innovator’s Method, the authors refer to these types of leaders as chief experimenters. These leaders rapidly test their assumptions and will often experiment by asking questions directly of the customer.

Be a Multiplier

At the start of this book, I referenced Liz Wiseman’s work of identifying and unlocking the power of multipliers. These are people who make everyone around them smarter by helping them reveal their own ideas and discover their own potential.

Conversely, she says that diminishers are those who detract from others’ ability to learn and grow. These individuals care more about showcasing their own knowledge and operate with an assumption that others need their expertise to solve problems. It’s a vicious cycle in which they jump in on every project, offering a rapid-fire succession of opinions. Meanwhile, they lament that they’re the only ones who are engaged and willing to offer ideas.

The truth is that we all are capable of being a multiplier and a diminisher. For example, on low-priority projects, we might be willing to allow others to step in and experiment with new ways of working, but on critical projects, we assume the role of dictator, carefully controlling the outcome. It can be challenging to maintain a growth mindset and encourage learning when projects have more importance and visibility, but it’s in those moments that it’s most essential to do so.

Wiseman refers to people who end up in this situation as acting like an “Accidental Diminisher.” These are situations when our intention is to support others, but our actions stifle their autonomy and creativity.

It’s true. When I’m excited about an idea, I leap first and stitch the parachute on the way down. I fully admit that it can be an exhausting personality trait to be around. In many ways, this behavior can have diminishing effects. If you’re an idea-generating machine like me, be aware that you might be exhausting your colleagues. If you’re in meetings and you’re the only one proposing ideas, perhaps you’re diminishing others’ ability to process the conversation and jump into the discussion. Try taking breaks or asking others about their ideas.

One experiment that Wiseman suggests is to “play fewer chips.” Essentially, if you know you’re going to go into a meeting that will require a lot of ideation, try giving yourself a mental count of how many chips you’re willing to use. Each chip represents a comment, suggestion, or idea. If you go into a meeting with a plan to spend only five chips, you might find that you are far more judicious with your feedback.

What I’ve come to realize is that the energy I have around ideation is infinitely more valuable and rewarding when I use it to help others generate their own ideas. Multipliers build on the superpower of those around them. They improve collaboration and overall performance of the team by doing the following:

  • Asking questions to encourage learning, not to encourage skepticism

  • Operating with an assumption of positive intent and a belief that ideas are better when influenced by multiple perspectives

  • Championing the work of others as they build on top of their efforts

  • Resisting the urge to discount the ideas of others because they value multiple points of view

According to Wiseman’s research of more than 150 executives across the Americas, Europe, Asia, and Africa, the “Multiplier Effect” had the power to double, and in some cases nearly triple, the productivity and output of teams.

Employees of multipliers were more engaged, more innovative, took more risks, and were more satisfied with the work they were doing. The research confirmed that multipliers not only access people’s current capability, they stretch it. They get more from people than they knew they had to give. Employees reported actually getting smarter around multipliers.10

Consider situations in which you can encourage others by being a multiplier. Are there situations when you’re acting like a diminisher? It might be worth asking coworkers you trust to give you an honest assessment. Perhaps you’re unintentionally behaving in a way that is diminishing others.

Is your cultural change effort languishing because it’s more important for your team to showcase its knowledge rather than to build a platform for the ideas of others?

Monty told me once that “the quickest way to gain influence over others is by helping them get promoted.” It’s a bit of a joke with a strong thread of truth woven into it. Bottom line, people are more receptive to your ideas if you’re building on the work they’re doing. They’ll be more willing to share what they’re learning and contribute if they believe you’re investing in their growth.

When working with others, consider spending time reflecting on their superpower. Perhaps it’s something they do that they don’t even realize is valuable. If they don’t see their own value, be sure to point it out to them. These are opportunities to invest in others and help them build on their strengths. You’ll not only get more out of them, but you’ll find they are far more willing to invest in your change effort.

To encourage a change movement, you need to get into the business of multiplying others’ strengths rather than constantly pointing out their weaknesses.

Creating the Space to Learn

If you want others to own the job of learning, you must give them a safe space to experiment and learn from their findings. Mistakes and miscalculations will happen—it’s inevitable in any business. Exploring one’s mistakes is a necessary part of learning, and it starts from being able to admit you were wrong and it ends with being given the opportunity to adjust your approach.

That’s what’s so great about using a language of learning and adopting the hypothesis as the instrument to engage in coexperienced learning. When your culture trades in hypotheses instead of ideas, you find that employees are able to separate their identities from their ideas, which makes them easier to discard when they’ve been proven wrong.

“Ideas are things you can fall in love with,” says John Montgomery.

Hypotheses are disposable, in fact, a great hypothesis is designed to be proven wrong. The more hypotheses we have that we can invalidate, the better off we are, because that’s work that we don’t have to do. In an environment where resources are finite, knowing that you don’t have to do some collection of work, is tremendously powerful.11

It’s painful to see teams lose a valuable contributor because they had the audacity to try something novel and it didn’t produce the desired result. Many times, these people feel that the only way to save face after a mistake is to leave the company or team.

So how do you prevent that from happening?

  • If you’re a leader, the first and most profound way to encourage psychological safety is by demonstrating it. Be willing to admit where you were wrong or where you had to correct your thinking. Give credit to those who’ve helped you learn, even if it’s someone who reports to you. If it’s someone in a junior position or someone who just joined your team, even better. Showing this level of humility will not only make you a great leader, it will show your team that you value learning. Modeling that you’re willing to learn when proven wrong is the best way to encourage the same behavior within your team.

  • If you’re not in a leadership position, be sure to support your colleagues and celebrate how they’ve helped you learn. A fantastic way to build a culture of trust and connection is by pointing out what you’re learning from the people you’re working with. It not only makes them feel helpful, but it also demonstrates that you’re willing and capable of learning new things. If a project fizzles out, instead of covering up what went wrong, spend time reflecting on what you learned and share those lessons with your coworkers. Engage with others by asking for feedback. An undesirable outcome is the best opportunity to make a discovery and learn something new.

Too many times, status meetings drone on as people go through their inventory of accomplishments and project work. It’s a way to signal to everyone how busy and successful they are. Pretty soon, you’re saying to yourself, “Susan sounds like she’s really busy and important. Look at all the projects she’s working on! I’d better update my list so I sound busy, too!”

There are better alternatives to these types of meetings.

At the dinner table, our family plays the game “Rose, Bud, Thorn.” Essentially, you go around the table and have each person describe three things:

  • Rose: Something that went great today.

  • Bud: Something that you’re excited about.

  • Thorn: Something that’s causing you frustration, anxiety, or pain.

It’s a great way for us to unpack one another’s days, celebrate the things that are going well, revel in the excitement of things to come, and support one another through things that are causing worry or pain.

Consider trying this game or some variant of it during your next status meeting. Instead of everyone giving a complete list of everything they’re working on, scope it to three items: something successful, something promising, and something frustrating. It’s a great way to just get to the point and focus the team’s energy on celebrating success and providing support.

It’s also a way to create a psychologically safe environment for team members to talk honestly about where they need help or suggestions. It’s an opportunity to say, “You know what? I’m frustrated by something and I could use some help.”

It might feel awkward or forced at first; that’s OK. As people begin to become more comfortable sharing their status in this way, you’ll find that resistance will begin to soften.

Collaboration isn’t always sunshine and rainbows. As we discussed in Chapter 1, there are times when you’ll need to “fight and unite.” It’s important to remove threatening language when collaborating. Avoid using extreme language (e.g., “You never…,” “You always…”) and ask questions that foster more understanding (e.g., “Tell me more about…”). However, it must be stated that this technique can be manipulated. If you’re asking questions just to poke holes into someone else’s idea, that can be easily spotted. If I have a question after someone has presented a new idea, I like to say things like, “I’m not asking this to challenge your idea, I want to better understand what you’re proposing.” A simple comment like this can diffuse questioning and help the presenter understand that I’m here to help make their idea better. Presenting new ideas takes courage, and diffusing my language when asking questions helps the conversation stay collaborative. If I demonstrate humility during collaboration, I’m much more likely to see that behavior reciprocated by the person with whom I’m trying to collaborate.

Break the Script

Sometimes, you’ll find yourself in a situation in which the team is burnt out or morale is low. Perhaps they’re struggling after a disappointing launch or they’re lacking the inspiration to generate new ideas. They’re just stuck in a rut. In these moments, consider trying something radically different in terms of triggering another wave of learning. It can be something that “shocks the system” or simply breaks the monotonous day-to-day routines.

In 2011, Microsoft Corporate Vice President of Cloud and AI, Scott Guthrie, did just that. At that time, he was leading the group responsible for Microsoft Azure, the company’s ambitious cloud-computing platform. The competition was stiff as Amazon had garnered significant market share with its Amazon Web Services (AWS) platform. Both companies were throwing their weight behind their respective platforms because the cloud business space represented the future of applications and services.

Although Azure presented a unique value proposition that helped customers move to the cloud more gradually by taking advantage of their previous Microsoft investments, its users were frequently complaining that Azure was difficult to use.

Guthrie decided to hold an offsite meeting and asked all of his senior leaders to attend. When they arrived, he had a simple request.

“Basically, the deal was all the senior managers and architects had to bring their laptops, and we were going to build an app from scratch together for two days,” Guthrie says. The goal was simple: he wanted his key executives to go through exactly what Azure customers go through when trying to get started with the service.

“It was a complete disaster,” Guthrie said.12 For two days, the organization’s highest-ranking people struggled with basic tasks like getting their account set up and deploying their first app. It was a shocking revelation.

In their book The Power of Moments: Why Certain Experiences Have Extraordinary Impact, authors Dan and Chip Heath refer to this moment as “tripping over the truth.”

Essentially, Guthrie needed to break the script. He had to create a moment when his leadership team and creative leaders were faced with the cold, hard truth: their customers were struggling with Azure. These issues were no longer up for debate; if the top people at the company couldn’t use the product successfully, how could they expect their customers to be successful?

For the team, the shame they felt in that moment had a lasting impression. By the second day, they had compiled more than 100 items that needed to be fixed. They came up with a plan to correct the issues and spent the following year building upon what they had learned.

Guthrie had helped his team empathize with its customers’ frustrations because he took team members out of their day-to-day environments and had them experience what it was like to struggle with getting started with Azure. Because they had felt the pain for themselves, their mission was lasting and tangible. As soon as they felt the customer’s pain, they couldn’t forget it. They were now compelled to fix the issues.

“We spent the next year completely rebuilding Azure,” Guthrie remembers. “It was fun because people could see the progress. People could feel the energy.”

Consider how you might build similar moments for your team to have a learning that surprises them. Many times, our teams are so convinced that they have all the answers, their egos can benefit from a small dose of humility.

Having them complete common scenarios using the product you’re building or spend time with a customer who’s never used the product before can be great ways to quickly build empathy. Look for those moments to inspire others into action.

Yes, and…

Collaboration and ideation are critical tools that should be encouraged in your culture of learning.

A classic game that’s played in improv groups all around the world is Yes, and. Essentially, the object of the game is to continually add to the scene being built from the various players.

For example, one player—let’s call her Alisha—might sit on the ground and pretend to cast a fishing line out on an imaginary lake. She says, “Hey James! You think we’re going to catch the big one today?”

The next player—James, in this case—must creatively add to the scene he’s been given. He needs to work with her idea of fishing at the lake and add an element to keep the story going. James sits down next to Alisha, pretends to open his tackle box, and says, “Yes, and I think we’re gonna have a good shot ‘cuz I brought this here special bait I made!”

When performed in front of an audience, the crowd delights in how each player quickly adds to the scene, building the story together, right there on stage.

What’s powerful about this technique of ideation is that it forces each person to build on the idea of the other. In meetings, it’s too easy to jump in and squash a creative session by critiquing an idea before it has time to flourish. The proverbial “that will never work” gets uttered and the brainstorming session comes to a grinding halt.

In a culture that encourages learning, you need to build the patience that’s required to let others explore their ideas.

Many times, we’re quick to want to add value to a discussion, but often, the best way to provide value is to listen and only ask questions to help others clarify their ideas.

During your next collaboration meeting, play a little game with yourself. Try only adding to everyone else’s idea and not submitting one of your own. Notice how it will require you to listen intently and be fully present in the room. You’ll get out of your own head because you won’t be constantly comparing your ideas to those of your peers. Your entire focus will be on enriching the ideas of others, shedding what you know, and preparing yourself to learn something new.

Applying the Hack

Here are some ideas you can use to encourage learning over knowing in your teams and throughout your organization:

  • Genuinely celebrate invalidated hypotheses. When a hypothesis has been invalidated, it’s a discovery—not a situation for which a team has failed to predict the outcome.

  • Create a library. Create an atmosphere in which team members are sharing books and online articles.

  • Consider using physical books in your library. You can tag pages or highlight important findings. The books become a physical manifestation of where the team has collected its learning. It’s also a powerful belonging cue to anyone joining your team. A bookcase full of highlighted books and reports screams, “We love learning new things here!” These books are tangible and visible. They’re not tucked away in some folder on your PC, but available to anyone who happens to be walking by.

  • Openly question overstated confidence and encourage continued experimentation.

  • Publicly thank those who offer a different opinion than yours. Even if you don’t agree, you should acknowledge the courage it takes to present an alternative point of view.

  • Don’t make points through questioning. It’s passive aggressive and easily spotted. Use questioning as a genuine way to seek understanding and clarification. If you have a point to make, just make it openly and respectfully.

  • During status meetings, consider playing a game like “Rose, Bud, Thorn.” Each team member goes through their status by picking one thing that is going well (Rose), one thing that’s promising (Bud), and one thing that’s causing them frustration or anxiety (Thorn).

  • In your next collaborative discussion with your team, consider only building off the ideas of others and resist adding a new idea of your own. You can play a game of “Yes, and,” essentially limiting yourself and others to responses that start with “yes.” Brainstorming in this way forces your brain to look for a way to add to someone else’s idea rather than state a problem with it.

  • Check your ego. When you’ve made a misstep or mistake, own it. In moments of failure, we have an opportunity to show our best selves and demonstrate the culture we want to have. Don’t shy away from mistakes—embrace them as an opportunity to model learning from one’s mistakes.

1 [Nadella] p. 100

2 [Nap] pp. 38–39

3 [SafetyRules]

4 [Edmondson]

5 [Friedman] p. 19

6 [Values]

7 [Friedman] p. 23

8 [Drucker] p. 353

9 [Montgomery]

10 [Wiseman] p. 12

11 [Montgomery]

12 [Nusca]

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