This article is an excerpt from the Shortform book guide to "The Practice of Adaptive Leadership" by Ronald A. Heifetz. Shortform has the world's best summaries and analyses of books you should be reading.
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Adaptive challenges are problems with unknown solutions which, by definition, require a fundamental change in order to be solved. There are two steps to solving such challenges: 1) diagnosis, and 2) treatment.
In The Practice of Adaptive Leadership, Ronald Heifetz, Alexander Grashow, and Marty Linsky recommend that you start by examining your organization to determine what resources you have available and what obstacles you might anticipate. Then, examine the challenge itself. In the article below, we’ll outline their recommendations for both.
Originally Published: September 8, 2021
Last Updated: January 8, 2026
Examine Your Organization
When you assess your organization for adaptive challenges, look for areas where you’ll find openness to change as well as areas you’ll find resistance. This will help you determine what messages to craft, which people or departments you can rely on for assistance, which team members you’ll need to convince, and so on.
Heifetz, Grashow, and Linsky advise that you focus your analysis on three aspects of your organization: culture, structure, and habits.
Culture
An organization’s culture is its typical way of interacting internally. Heifetz, Grashow, and Linsky write that when you examine a group’s culture, you’re looking for signs of potential adaptability—does the group seem open to change? Are there areas where you may encounter resistance? Look for indicators such as:
- Do leaders encourage team members to advance?
- What behaviors are implicitly and explicitly allowed and not allowed? For example, are mistakes tolerated? Is dissent encouraged?
- What are the dynamics between team members and departments? Which employees have the most say in decisions?
The authors note that you can discover a lot about an organization’s culture by focusing on four aspects: lore, customs, norms, and meeting policies.
Lore: The collective memories, jokes, and stories shared by team members hint at the values and priorities of the group. Listen for stories of, for example, why the founders created the organization, games employees played at the last holiday party, or why someone was fired or resigned.
Customs: The practices that people repeat throughout the years—such as parties, charity events, milestone celebrations—can help you plan how to infuse adaptability into the organization. For example, if a company includes a section of team shout-outs in their monthly company email, you might encourage them to shout out people embarking on new projects, not just those who are wrapping them up.
Norms: How people relate to each other on a day-to-day basis reflects the general vibe of the company. How do people address others? How casual or formal is work attire? How accessible are managers? These habits can indicate adaptability: If there’s a lot of cross-fertilization of people in daily interactions, the group as a whole may be more open to change.
Meetings policies: The way an organization’s meetings are structured and held can shed light on how its leadership treats lower-level team members. This can indicate how power is distributed and how open to change leaders might be. Are meeting attendees encouraged to participate and be creative or just to receive orders? Are they allowed to comment on other people’s areas of expertise? What does the most senior attendee do during the meeting? How do they handle conflict?
| Culture From the Top Down and Bottom Up In You Win in the Locker Room First, leadership expert Jon Gordon and former NFL coach Mike Smith argue that the success of any team, be it a sports team or a business, starts with its culture—its shared purpose, attitudes, values, and practices. With a positive culture, employees stay engaged and can both repeat past successes and implement new methods. Gordon and Smith argue that while technical expertise and skills are important, they’re less significant than culture to a company’s long-term success. Their argument underpins that of Heifetz, Grashow, and Linsky, explaining why culture can have an outsized impact on the adaptability of an organization. So how do you create a good organizational culture? Gordon and Smith write that a winning culture is built from both the top down and bottom up: Not only must owners and executives have shared values and expectations, but team members at every level must also have good characters and attitudes. The examinations that Heifetz, Grashow, and Linsky recommend align with this mindset because they look at an organization’s culture from both directions: how leaders set the tone of the group’s dynamics, and how team members themselves interact with each other. For example, many of the questions Heifetz, Grashow, and Linsky suggest are top-down questions, exploring how leadership interacts with lower-level team members—what leadership allows, encourages, or discourages. Their examination of how a group runs its meetings is a specific way to observe these dynamics: Meetings are microcosms of a team’s dynamics and a direct reflection of how a group is run. But the lore, customs, and norms of an organization reflect how its team members at all levels interact, and examining these elements can shed light on employees as human beings, rather than just as colleagues. This can show you, from a bottom-up direction, how an organization’s culture has formed, how it impacts day-to-day behavior, and how the people within the organization might react to any proposed change. |
Structures
In addition to its culture, another characteristic that affects your organization’s adaptability is its formal structure—the rules and hierarchies that govern an organization. These include organizational charts, employment contracts, compensation plans, incentive programs, and so on. These structures encourage certain activities and discourage others, both implicitly and explicitly, and can hint at how open to change an organization is. For example, incentive programs that encourage risk-taking indicate more adaptability than incentive programs that reward individual performance on established, static metrics, such as sales numbers.
(Shortform note: Business consultants note that there’s no one “right” way to structure an organization for adaptability. Loose, informal frameworks can work well for small companies, but as a company grows, it usually needs more defined departmentalization and chains of command. But either structure can promote flexibility—the key is to find the right balance between centralization and decentralization of decision-making. A single company can have both; some franchises, for example, have rigid centralized power structures within individual stores, stemming from the store manager, but a looser, decentralized structure companywide, allowing stores to make purchasing and pricing decisions based on regional demands.)
Habits
Heifetz, Grashow, and Linsky also write that you should examine your organization’s habits—the typical policies and procedures employees use to do their work, interact with others, and solve problems. These are patterns of behavior that have effectively solved problems in the past, so people are comfortable with them and default to them without much reflection. If too ingrained, they can indicate areas where you may encounter resistance to change.
The problem with people defaulting heavily to their habits is that while new challenges require new solutions, habits encourage people to view problems, even novel ones, through a familiar lens. Because of this, they often fail to see that solutions they’ve used before won’t work this time. This can lead to two consequences: First, they’ll end up using an ineffective solution. Second, their competitors will be able to anticipate their next move.
| Randomness as a Way to Counter Habits In The Art of Strategy, game theorists Avinash Dixit and Barry Nalebuff also argue that you should try to break out of your predictable habits—not only because habits hold you to outdated solutions, but also because randomness can give you a competitive edge. They write that any game—including business—is a match-up of opposing predictions: Each player is trying to guess the others’ next moves. If you can keep your opponent from detecting patterns in your behavior, you can make their job harder. Dixit and Nalebuff caution that you shouldn’t push randomness too far, however. While being unpredictable can give you an edge in things like marketing strategy and product launches, many business relationships thrive on predictable reliability—negotiators, for example, don’t usually appreciate surprises. This suggests a limit to Heifetz, Grashow, and Linsky’s argument: Though shaking up habits can spark ideas and innovation, it also has the potential to make people uncomfortable. When examining the habits of an organization, you may not want to view all established procedures as negative, and don’t insist that people abandon habits that help them work more efficiently and effectively. |
Identity the Problem
The authors write it’s imperative that you properly identify what kind of a problem you face. The most common reason change initiatives fail is because people confuse technical problems with adaptive problems, and they then attempt to apply the wrong kind of solution.
It can sometimes be difficult to recognize when you’re facing an adaptive challenge rather than a technical one, as complex problems often have elements of both. The authors cite corporate acquisitions as an example: Merging departments from two companies poses technical challenges, but the overall success of the merger depends on larger, adaptive challenges, such as merging differing corporate cultures—challenges involving human elements that require people to adjust their worldviews and mindsets.
Once you’ve identified the adaptive challenge you’re facing, examine the details of the issue:
- Is the challenge caused by external changes (for example, changing market conditions) or internal changes (for example, changing company values)?
- Who is affected by or invested in the challenge and what do they think about it?
- Where are people running into conflict? Do they disagree about the mission or values of the group, or about the strategy and goals, or about tasks?
| Searching for the Less Obvious Answer In Think Like a Freak, psychologists Stephen Levitt and Steven Dubner write that a key reason people fail to implement workable solutions is that they identify the wrong problem, then set out to solve that instead of addressing the true, core issue. This can happen because we’ve evolved to quickly identify the most obvious problem, a strategy that historically helped us survive. If there’s a tiger hiding in a bush, for example, our lives depend on us quickly identifying that danger, not carefully considering alternative explanations. However, more complex questions have more complex, less obvious answers. And because we’re hard-wired to look for the obvious problem, we often mistakenly address what seems like the problem rather than the actual problem. A more modern example of this evolutionary trait playing out might be seen in a clothing store examining their declining sales. To tempt customers to buy more, company leaders might jump to identify the problem as the most simple, obvious one: Their prices are too high. They might then try to address that by running sales and advertising price cuts. However, the true problem might be more systemic, complex, and harder to spot—for example, changing fashion trends the company isn’t keeping up with. If they spend their time and energy trying to “fix” the pricing problem, they may miss the window to address the style problem that’s the actual key to increasing their sales. In this example, the company might have had more success identifying the true problem by running through the questions Heifetz, Grashow, and Linsky propose. In this case, the core issue might be external changes—shifting market conditions due to fluctuating customer tastes. Levitt and Dubner write that people typically miss the true cause of a problem when it’s a new development but they’re still asking the same questions and blaming the usual causes. In the terminology of Heifetz, Grashow, and Linsky, this means you’re looking to solve technical problems that require existing expertise, rather than realizing you’re faced with an adaptive challenge that requires new insights. Levitt and Dubner advise that to avoid this path, you should try to view your problem from different perspectives and look for alternative causes. The questions recommended by Heifetz, Grashow, and Linsky provide a framework to get you there, prompting you to search for the broad causes underlying the superficial symptoms. Levitt and Dubner also suggest you try to think like a kid. Children inherently see the world from a new angle, which allows them to spot things adults overlook. To do this, question beliefs and processes you’ve come to rely on but haven’t thought about for a while. This can help you see beyond the common knowledge that often leads to an obvious answer, so that you can instead figure out a less-obvious solution. |
Interpret the Problem
When you’ve identified the problem, you may be tempted to dive in with solutions, but the authors advise that you first pause to fully analyze the issue. This will prevent you from interpreting the problem wrongly and then trying to implement ineffective solutions.
An accurate interpretation is one that pinpoints the key issues underpinning the problem and helps people see how they’ll need to change. This step is important because a person’s brain typically interprets events unconsciously, automatically, and often wrongly. For example, people frequently focus on details that paint themselves in a good light and leave out details that don’t. As a result, people may misinterpret adaptive problems and their own roles in them—for instance, one person may blame the mistakes of the legal department but ignore the procedures that their own marketing department established that led to those mistakes.
You’ll also need to guide your team to correctly interpret the issue so you can all be aligned.Your team members may resist accurate interpretations of a problem because they reflect poorly on them or will require them to think and act differently. As an adaptive leader, your job is to guide people’s interpretations toward what’s most accurate, not what’s easiest to accept.
To help make this process effective, encourage people to see that challenges are usually systemic, not personal—adaptive problems rarely involve just one person, and even when they are caused by certain people’s behavior, those behaviors are likely influenced by operational structures and frameworks. When people see things through this lens, they can distance themselves from the problem emotionally, which increases the likelihood they’ll accept the changes that need to happen.
| Cognitive Biases Distort Decision-Making Heifetz, Grashow, and Linsky’s advice echoes that of other psychologists who caution that quick reactions can lead to poor decisions due to automatic and unconscious thought processes. In Thinking, Fast and Slow, Daniel Kahneman defines these thought processes as heuristics—mental shortcuts your brain uses to quickly interpret a situation. We’ve evolved mental shortcuts to help us survive; they allow us to react to stimuli we’ve encountered before (such as, to return to an earlier example, a rustling in the bushes at night) without having to slowly consider it. The problem is that shortcuts can lead us to overlook new details of a situation, so that we don’t properly assess the cause behind the stimuli (in this example, the rustling might be a friend looking for a lost object, not a tiger). This type of shortcut creates cognitive biases—errors in thinking. There are many types of cognitive biases, each springing from a different survival-related instinct. The issue Heifetz, Grashow, and Linsky refer to is known as a confirmation bias, when people selectively pay attention only to information that confirms what they want to believe. An adaptive leader trying to get people to overcome their cognitive biases will have a hard task—Kahneman notes that even when we’re aware of our biases, we still struggle to see past them. Like Heifetz, Grashow, and Linsky, Kahneman recommends slowing down and thinking things through carefully as well as distancing yourself emotionally from a situation by viewing it in broad, not specific or personal, terms. |
Judge the Problem Against Your Purpose
The authors caution that adaptive leadership will upset people and could potentially jeopardize your job. Thus, you should be careful not to take on every adaptive challenge possible—focus on the ones that will help you fulfill your organization’s purpose.
To determine what your organization’s purpose is, ask what you’re ultimately trying to do. This may be an abstract goal, such as “helping the environment.” Identify, then, more concrete purposes by asking “how” you can achieve that abstract purpose. In this example, you might say a more concrete purpose is designing toys that leave a very small environmental footprint. An even more concrete purpose might then be that you’ll design toys from recycled materials.
(Shortform note: In Grit, Angela Duckworth proposes a different approach for coming up with purpose statements; instead of starting with an abstract goal and then repeatedly asking “how” to craft more specific goals to support it, she advises starting with a specific goal and repeatedly asking “why” until you’ve arrived at your most abstract, high-level vision. For example, say you have a specific goal to arrive at the office on time every day. Ask why—is it so you can be respected at work? Why? To be given more responsibilities? Why? To obtain more decision-making power? Why? So you can make a difference in the world? Why? Once you’ve arrived at an answer of “Just because,” you’ve found your ultimate “why”—your purpose.)
The authors write that you should move up and down these levels of abstraction to continually determine if all your strategies are pulling in the same direction. Then, use these stated purposes to determine if the adaptive challenge you’ve identified is worth resolving—will it make a meaningful difference to one of these purposes?
(Shortform note: Duckworth likewise advises examining all levels of your goals to make sure they’re aligned. If a low-level goal isn’t moving you closer to a high-level goal, stop pursuing it, and instead switch it out for a different low-level goal. In this framework, adaptive challenges can be viewed as low-level goals that must support your ultimate high-level purpose—and if they don’t directly move you toward that high-level purpose, they’re not worth your time.)
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- How to deal with unknown solutions that require innovation, experimentation, and adaptation
- How to determine if a problem is technical or adaptive
- Five tips for launching initiatives to address adaptive challenges
