How to Make Sense of Any Mess: Information Architecture for Everybody

How to Make Sense of Any Mess

Abby Covert’s How to Make Sense of Any Mess is a practical guide to understanding and organizing information in an increasingly complex world. The book introduces information architecture (IA) as a tool to help anyone—entrepreneurs, leaders, and professionals—bring clarity to chaotic situations. Covert breaks down IA into simple steps, making it accessible to anyone, regardless of background or industry.

For entrepreneurs and leaders, the ability to make sense of information is crucial. Whether managing a startup, developing a product, or leading a team, clear communication and structured processes are necessary for success. Covert’s book provides a systematic approach to untangling complexity, ensuring that decision-making is based on clarity and intent.

Relevance to Leadership, Entrepreneurship, and Self-Improvement

Entrepreneurs and leaders constantly face challenges that require clear thinking and structured decision-making. Whether designing a new business model, organizing a company’s workflow, or improving customer experience, the principles of information architecture can help.

For example, consider an entrepreneur launching an online platform for vegetarian food delivery. Without proper structuring, customers may struggle to find relevant options, leading to frustration and lost sales. By applying Covert’s approach—identifying the mess, defining intent, and organizing information effectively—the entrepreneur can create a seamless user experience that drives engagement and satisfaction.

Key Concepts and Arguments from the Book

Covert structures her book around a step-by-step approach to making sense of messes. The process consists of seven core steps:

1. Identify the Mess

Messes are made of information and people. A mess is any situation that is confusing or full of difficulty. Covert encourages readers to recognize the structure of their organizations, processes, and products to better understand their challenges.

2. State Your Intent

Intent defines the desired outcome. Language plays a key role in shaping intent—words influence decisions and actions. Leaders must clearly communicate what success looks like to align stakeholders and teams.

3. Face Reality

Understanding the current state of affairs is essential. Leaders must analyze their businesses objectively, recognizing strengths, weaknesses, opportunities, and threats. Tools like mapping and diagramming help make sense of complex realities.

4. Choose a Direction

Decision-making requires clarity. Leaders must navigate multiple options, balancing business goals with user needs. Defining key terms and creating a shared language within an organization fosters alignment.

5. Measure the Distance

Once intent and direction are clear, measuring progress is necessary. Covert emphasizes setting measurable goals and tracking indicators such as customer satisfaction, conversion rates, and process efficiency.

6. Play with Structure

Experimentation is key to refining information architecture. Entrepreneurs can test different business models, workflows, or digital interfaces to find the most effective structure for their ventures.

7. Prepare to Adjust

No plan is perfect. Leaders must be adaptable, refining their strategies based on feedback and changing circumstances. The ability to pivot effectively determines long-term success.

How to Make Sense of Any Mess is a must-read for entrepreneurs, leaders, and anyone seeking clarity in complexity. By applying Covert’s principles, business professionals can make better decisions, improve processes, and create meaningful experiences for their customers and teams. Whether launching a new product or restructuring an organization, this book provides a valuable framework for turning chaos into order.

1: Identify the Mess

Every entrepreneur, business leader, or innovator faces messes—situations that seem chaotic, disorganized, or overwhelming. Messes arise in businesses when teams struggle with unclear processes, customers find it difficult to navigate services, or leaders make decisions without enough structured information. According to Abby Covert in How to Make Sense of Any Mess, the first step to resolving any mess is recognizing and identifying it. Without a clear understanding of the problem, any attempt at improvement is ineffective.

Messes are made of information and people. They exist in everything from internal workflows to customer experiences, product development, and business models. The challenge is not just the volume of information but how it is structured and interpreted. Identifying the mess allows business leaders to make sense of what they are dealing with and outline a path forward.

Recognizing the Signs of a Mess

The first step in identifying a mess is to recognize when you are in one. Messes can take many forms, but they usually share common characteristics.

Confusion among stakeholders – If different team members have conflicting understandings of a project or goal, this is a sign of an underlying mess. When communication is unclear, execution becomes inconsistent.
Inefficiency and wasted effort – If employees or customers struggle to find information or complete tasks, it suggests that processes are poorly structured. Unnecessary meetings, unclear instructions, and repeated work are signs that an organization is working within a mess.
Overwhelming complexity – Businesses often collect vast amounts of data, but when that data is not organized effectively, it becomes more of a burden than an asset. A mess exists when leaders feel stuck and unable to make informed decisions.
Frustration and resistance to change – Employees and customers may struggle with confusing systems or unclear expectations, leading to frustration. If teams are resistant to new initiatives, it may be because they do not understand the reasoning behind them.
Misalignment between intent and outcome – If a business sets a goal but fails to reach it despite significant effort, there is likely a disconnect between intent and execution. Identifying the mess helps to realign the strategy.

Steps to Identifying a Mess

Identifying a mess is about breaking down complexity and shining a light on the underlying problems. Covert’s approach provides a structured way to assess and analyze the mess before jumping into solutions.

Acknowledge that a mess exists – The hardest part of making sense of anything is admitting that it is messy. Leaders must be willing to step back and assess the situation objectively. Recognizing a mess is not a sign of failure but the first step toward solving it.
Define the scope of the mess – Messes exist at different levels—some are company-wide, while others affect only a single department or process. Business leaders should determine whether the mess impacts employees, customers, or both. Mapping out the affected areas helps narrow down the scope.
Gather perspectives from those affected – Messes involve people, so it is essential to listen to employees, customers, and other stakeholders. Conducting interviews, surveys, or informal discussions can provide valuable insights into how people experience the mess. Often, those closest to the issue have the clearest understanding of the pain points.
Look for patterns in the chaos – While every mess may seem unique, common patterns often emerge. Are communication breakdowns happening in the same way across teams? Are customers struggling with the same steps in a process? Recognizing recurring issues helps pinpoint the root causes.
Document the mess visually – A powerful way to clarify complexity is to diagram or map out the problem. Whether through flowcharts, mind maps, or simple sketches, visualizing the mess can make it easier to understand and communicate to others. Leaders can use diagrams to show relationships between issues, bottlenecks in processes, or inefficiencies in workflows.
Identify missing or excessive information – Messes often result from too much information, too little information, or the wrong kind of information. Leaders should evaluate whether employees and customers have access to the knowledge they need when they need it. If people are overwhelmed with unnecessary details or struggling to find relevant data, adjustments need to be made.
Clarify the impact of the mess – Every mess has consequences, whether it is lost revenue, decreased productivity, poor customer experiences, or employee burnout. Understanding these impacts helps prioritize which messes need immediate attention and which can be addressed over time.

The Role of Information Architecture in Identifying Messes

Information architecture is the practice of organizing and structuring information to make it usable. Businesses rely on information architecture in everything from website navigation to team structures, internal communication, and customer interactions. Identifying a mess is the first step toward building a better architecture.

For example, an e-commerce company struggling with declining sales might initially assume the issue is poor marketing. However, after identifying the mess, they might discover that customers abandon their carts because the checkout process is too complicated. By restructuring the information flow on their website—clarifying shipping costs, reducing the number of form fields, and simplifying navigation—they can improve conversion rates.

The process of making sense of a mess starts with identifying it. Leaders and entrepreneurs who recognize and analyze their messes gain a significant advantage. Instead of reacting to symptoms, they can address root causes, leading to smarter decisions and more effective solutions.

By acknowledging confusion, defining the scope, gathering input, looking for patterns, documenting issues, evaluating information flow, and clarifying impact, business professionals can begin the journey toward clarity. Information architecture is not just about organizing data—it is about organizing the way businesses operate, communicate, and grow. Identifying the mess is the foundation for success.

2: State Your Intent

Intent is the foundation of every decision, action, and strategy in business. Without a clear understanding of intent, leaders risk making arbitrary choices, wasting resources, and creating confusion among teams and stakeholders. In How to Make Sense of Any Mess, Abby Covert emphasizes that intent is not just about having goals—it is about defining the effect you want to have and ensuring that your language and actions align with that purpose.

In leadership and entrepreneurship, intent shapes everything from product development to company culture and customer experience. A business that aims to provide “affordable, high-quality vegetarian food” must ensure that every part of its operations—pricing, ingredient sourcing, and branding—supports that intent. Without this clarity, mixed messages can create frustration among customers and employees.

Why Intent Matters

Intent is more than just an abstract idea; it directly influences how a business operates and how people perceive it. A lack of defined intent leads to miscommunication, misaligned efforts, and a scattered approach to problem-solving. Leaders must clearly articulate their intent to ensure that teams, customers, and stakeholders understand and support their direction.

Intent guides decision-making – Every business decision, from hiring employees to choosing marketing strategies, should align with the company’s core intent. Without a defined intent, leaders may struggle to make consistent choices.
Intent sets expectations – Employees, customers, and partners look to leadership for clarity. If a company claims to value sustainability but partners with suppliers who engage in unethical practices, stakeholders will quickly notice the contradiction.
Intent influences perception – The words and phrases a business uses shape how people interpret its mission and values. If a brand markets itself as “luxurious and exclusive” but offers constant discounts, it creates confusion. The way intent is communicated affects how a company is perceived.
Intent aligns teams – A clearly stated intent ensures that employees work toward the same goal. When every team member understands the company’s purpose, collaboration becomes smoother, and motivation increases.
Intent reduces wasted effort – Businesses without clear intent often invest time and resources into projects that do not contribute to their long-term goals. By defining intent, leaders can prioritize initiatives that truly matter.

Steps to Stating Your Intent Clearly

Articulating intent requires careful thought and precision. It is not enough to have a vague idea; intent must be structured in a way that guides decisions and actions effectively. Abby Covert outlines a process for defining and refining intent so that it becomes a practical tool rather than an abstract concept.

Define the effect you want to have – Before setting goals or making decisions, leaders must ask themselves what they truly want to achieve. This goes beyond just financial targets; it includes the impact they want to have on customers, employees, and the industry. A company that wants to “make healthy eating accessible to everyone” must design its products, pricing, and distribution to reflect that mission.
Choose your words carefully – The language used to define intent has a powerful impact. Words carry meaning, and choosing the right ones ensures that stakeholders interpret intent correctly. If a business describes its service as “efficient and reliable,” those words set customer expectations. If employees interpret “efficient” as fast and customers interpret it as high-quality, misalignment occurs. Leaders should test their language with different audiences to ensure clarity.
Understand what you are not – Stating intent is not just about what you want to be; it is also about defining what you are not. This helps eliminate confusion and ensures focus. A business that aims to be “affordable and family-friendly” should acknowledge that it is not “luxury-focused” or “exclusive.” By defining what the company does not prioritize, leaders make it easier to set boundaries and make strategic choices.
Consider the perspective of your audience – Intent must be communicated in a way that resonates with the people it affects. Employees, customers, and investors all have different concerns and motivations. Leaders should think about how each group will interpret their stated intent. If employees see the intent as unrealistic, they may disengage. If customers see it as inconsistent, they may lose trust. Tailoring the message ensures that it is meaningful to the right audience.
Test and refine your intent over time – Business environments change, and so do customer needs and industry trends. Leaders should regularly revisit their intent to ensure that it remains relevant. What made sense five years ago may no longer be applicable. Testing intent through customer feedback, employee input, and market analysis helps refine it to stay aligned with current realities.
Ensure alignment across all actions – Stating intent is only valuable if it is reflected in business operations. Leaders must evaluate whether marketing, product development, hiring practices, and customer service align with the stated intent. If a company claims to be “customer-centric” but has long wait times and poor support, its actions contradict its message. Aligning intent with execution ensures credibility and trust.
Use intent as a decision-making tool – Every major business decision should be evaluated through the lens of intent. Leaders should ask themselves: “Does this align with what we stand for?” If a proposed initiative does not support the company’s stated purpose, it may not be worth pursuing. Using intent as a guiding principle helps filter out distractions and focus on what truly matters.

The Role of Intent in Information Architecture

In the world of information architecture, intent determines how information is structured and communicated. Whether designing a website, organizing a company’s internal documentation, or developing a product, intent helps ensure that the right information reaches the right people in the right way.

For example, a Montessori preschool that states its intent as “fostering independent learning and creativity in children” must ensure that everything—from its website content to its classroom layout—reflects that purpose. If its website is difficult to navigate or its admissions process is unclear, it contradicts the message of independence and accessibility. By structuring information in a way that supports its intent, the preschool enhances trust and engagement with parents.

Stating intent is not just a formality; it is the foundation of effective leadership and business strategy. Without a clear and well-communicated intent, companies risk sending mixed signals, creating inefficiencies, and losing trust.

By defining the desired effect, choosing words carefully, setting boundaries, considering different perspectives, refining intent over time, ensuring alignment, and using intent as a decision-making tool, leaders can create clarity and direction. Businesses that articulate their intent effectively are better positioned to make informed decisions, build strong teams, and create meaningful customer experiences.

Understanding and stating intent is not just about what a business does—it is about the impact it wants to have on the world. When intent is clear, everything else falls into place.

3: Face Reality

One of the biggest barriers to solving problems is avoiding reality. Many leaders and entrepreneurs get stuck because they either refuse to acknowledge the true nature of a situation or they rely on outdated assumptions. In How to Make Sense of Any Mess, Abby Covert emphasizes that progress begins with an honest assessment of the current state.

Ignoring reality leads to poor decision-making, wasted resources, and frustration. Whether running a startup, managing a team, or improving a business process, leaders must face the facts before they can create meaningful solutions. The reality of a situation is often more complex than it appears, and addressing it requires both courage and strategic thinking.

Why Facing Reality Matters

Reality is unavoidable. No matter how much a business wants to present an idealized version of itself, the truth always surfaces. Facing reality provides a clear picture of the problems at hand and allows for informed decision-making.

Reality reveals the root cause of problems – Many businesses attempt to fix symptoms rather than addressing underlying issues. For example, if customer complaints are rising, the instinct might be to improve customer service. However, the real problem may be a confusing product design. Facing reality helps uncover the true source of challenges.
Reality prevents wasted effort – Without an honest understanding of the situation, businesses often invest time and money into the wrong solutions. If a restaurant experiences declining sales, it might focus on advertising when the real issue is poor service or an outdated menu. Facing reality helps direct efforts where they are needed most.
Reality aligns stakeholders – Teams, investors, and customers all have their own perceptions of a business. If leadership avoids reality, these perceptions become fragmented, leading to misalignment and conflict. Acknowledging the truth helps create a shared understanding and fosters collaboration.
Reality enables adaptability – The business landscape is constantly changing. Companies that refuse to accept market shifts, technological advancements, or customer behavior changes risk becoming obsolete. Leaders who embrace reality can adjust their strategies and stay ahead of challenges.
Reality builds trust and credibility – Employees and customers respect leaders who acknowledge challenges rather than hiding behind optimism. Transparent leadership fosters trust and encourages collective problem-solving.

Steps to Facing Reality in Business

Facing reality is a structured process. It involves stepping back, gathering information, analyzing challenges, and making decisions based on truth rather than assumptions. Abby Covert outlines a practical approach to confronting reality and using it as a foundation for progress.

Acknowledge that perception is not always reality – Every individual sees the world through their own lens, shaped by experiences, biases, and expectations. Leaders must recognize that their view of the business may not match what employees, customers, or stakeholders experience. The first step in facing reality is admitting that multiple perspectives exist and that assumptions should be challenged.
Gather input from those involved – Reality is best understood through direct feedback. Leaders should seek insights from employees, customers, and other stakeholders. This can be done through surveys, interviews, data analysis, or simple conversations. When employees express frustrations about internal processes or customers complain about usability issues, these are signals of deeper problems. Listening to different voices provides a comprehensive view of the current situation.
Analyze data to uncover patterns – Numbers do not lie. Sales reports, website analytics, employee turnover rates, and customer feedback trends all provide valuable insights into reality. If engagement is declining, if revenue is dropping, or if productivity is suffering, these numbers tell a story. Leaders must analyze data objectively, identifying patterns and trends rather than focusing on isolated incidents.
Identify contradictions and inconsistencies – A major sign that reality is being ignored is when different sources provide conflicting information. If leadership believes a company has strong employee morale, but internal surveys show dissatisfaction, there is a disconnect. If a business assumes customers love its product, but reviews indicate frustration, there is a gap between perception and truth. Leaders should actively look for contradictions and investigate them further.
Map out the complexity of the situation – Reality is rarely simple. Businesses must deal with overlapping challenges, dependencies, and external factors. Using diagrams, mind maps, or process charts can help visualize the complexity of a problem. If a manufacturing company struggles with delays, mapping out the supply chain can reveal bottlenecks. If a startup is experiencing slow growth, diagramming customer interactions may highlight friction points.
Evaluate the constraints and limitations – Every business operates within certain constraints—budget, time, talent, market demand, and technological capabilities. Leaders must assess what they can and cannot change. While some problems require structural changes, others may need incremental adjustments. Understanding limitations helps prioritize realistic solutions rather than pursuing unattainable goals.
Accept that facing reality is an ongoing process – Reality is not static. Market conditions, customer expectations, and internal dynamics constantly evolve. Leaders must regularly reassess their understanding of reality and adjust their strategies accordingly. Businesses that succeed are those that embrace continuous learning and remain flexible in their approach.

The Role of Reality in Information Architecture

Information architecture is about structuring and organizing information effectively. Facing reality plays a crucial role in this process. Whether designing a website, developing a product, or improving an internal workflow, reality dictates how information should be structured.

For example, a company launching an employee training platform might assume that workers prefer long-form video tutorials. However, after gathering feedback and analyzing data, they may realize that employees engage more with short, interactive lessons. By facing this reality, the company can redesign its platform to better serve user needs.

Similarly, an e-commerce business might believe its website is easy to navigate. If analytics reveal that users frequently abandon their shopping carts due to a confusing checkout process, reality suggests that changes are needed. Addressing these issues requires accepting feedback and making data-driven adjustments.

Facing reality is not about focusing on problems—it is about creating opportunities for meaningful change. Leaders and entrepreneurs who confront the truth head-on are better equipped to solve challenges, make informed decisions, and drive progress.

By acknowledging that perception is not always reality, gathering diverse input, analyzing data, identifying inconsistencies, mapping complexity, evaluating constraints, and embracing continuous reassessment, businesses can develop a clear and actionable understanding of their challenges.

In a world where information is abundant but often disorganized, those who can make sense of reality have a significant advantage. Whether improving a product, refining a business model, or aligning a team, clarity begins with the courage to face reality.

4: Choose a Direction

Every business, project, or initiative requires a defined direction. Without it, teams become unfocused, efforts are wasted, and decision-making becomes chaotic. In How to Make Sense of Any Mess, Abby Covert explains that choosing a direction is not just about picking a goal; it is about selecting a path that aligns with reality, intent, and available resources.

Leaders and entrepreneurs often hesitate to commit to a direction because of uncertainty. The fear of making the wrong choice can lead to indecision, which is often worse than choosing imperfectly. Progress is made when leaders analyze their options, assess their limitations, and move forward with confidence. By understanding how to evaluate different paths, they can avoid costly mistakes and set a clear course for success.

Why Choosing a Direction Matters

Direction provides clarity, focus, and momentum. Without a defined path, organizations and individuals face several risks that can hinder growth and effectiveness.

Direction aligns teams and stakeholders – When everyone understands the chosen path, collaboration becomes smoother. Employees work toward the same goals, and stakeholders have a clear expectation of outcomes.
Direction prevents wasted time and effort – Without a clear direction, businesses may experiment with different strategies without a structured approach, leading to inefficiency. Having a defined course allows for targeted action.
Direction enables better decision-making – When leaders have a guiding framework, they can evaluate opportunities and challenges more effectively. They can ask, “Does this fit within our chosen path?” rather than making reactive choices.
Direction builds confidence and accountability – A well-communicated direction gives employees and stakeholders a sense of purpose. It also creates accountability, ensuring that progress is measured against a defined path rather than vague aspirations.
Direction allows for adaptability – While committing to a path is important, businesses must remain flexible. A chosen direction provides a foundation for pivoting effectively when needed, rather than making sudden, unstructured changes.

Steps to Choosing a Direction

Selecting the right direction is a structured process that requires assessing reality, considering available options, and making a commitment to a path forward. Abby Covert provides a systematic approach that leaders and entrepreneurs can use to confidently define their course of action.

Clarify the scope of your decision – Before selecting a direction, it is essential to define what decision is being made. Is it about a product launch, a company strategy, an internal process, or a customer experience improvement? The more specific the scope, the easier it is to evaluate options. Leaders should avoid vague decision-making, as it leads to unclear action steps and confusion.
Review existing constraints and realities – Choosing a direction requires an honest assessment of what is possible. Leaders must evaluate budget limitations, available resources, technological constraints, and market conditions. If a company is considering expanding into a new market but lacks the necessary funding, its direction must account for this reality. Understanding constraints ensures that choices are practical and achievable.
Generate multiple options before selecting one – A common mistake in decision-making is locking into one idea too quickly. Instead, leaders should explore multiple potential directions before committing. They can brainstorm different paths, seek input from stakeholders, and compare approaches. For example, a restaurant wanting to increase revenue might consider expanding delivery services, launching a loyalty program, or redesigning its menu. Evaluating different possibilities allows for better decision-making.
Evaluate options based on impact and feasibility – Once several options are identified, they must be assessed based on their potential impact and feasibility. Leaders should ask key questions: Does this align with our goals? Can we execute this effectively with our current resources? What risks are involved? A direction that has high impact but is impossible to implement is not a viable choice. The best options balance ambition with practical execution.
Seek input but avoid decision paralysis – While gathering feedback from employees, customers, and stakeholders is valuable, leaders must avoid over-analysis. Too much input can lead to indecision. Instead of waiting for a perfect choice, they should make the best-informed decision based on available data. A startup launching a new feature, for example, should listen to user feedback but avoid delaying the release indefinitely in pursuit of perfection.
Define success metrics for the chosen direction – A decision is only meaningful if there is a way to measure its success. Leaders must establish clear metrics that indicate progress. If a retail business decides to shift toward online sales, key success indicators could include website traffic, conversion rates, and customer satisfaction. Defining these metrics ensures that progress is tracked and adjustments can be made when necessary.
Communicate the decision clearly and align stakeholders – Once a direction is chosen, it must be communicated effectively. Employees, investors, and customers need to understand the rationale behind the decision and what it means for them. Clear communication prevents misunderstandings and ensures that everyone is working toward the same goal. Leaders should articulate the reasoning behind the choice, the expected outcomes, and how the transition will be managed.
Commit to the decision while remaining adaptable – Choosing a direction does not mean being rigid. The business environment is dynamic, and unexpected challenges may arise. Leaders must balance commitment with adaptability. If new data suggests that a strategy is not working, adjustments should be made rather than blindly following a failing path. However, frequent shifts in direction without clear reasoning can create confusion and instability. The key is to stay committed while remaining open to course corrections.

The Role of Information Architecture in Choosing a Direction

Information architecture plays a critical role in making informed decisions. The way information is structured and analyzed determines the clarity of available options. Without proper organization, leaders may struggle to see patterns, understand data, or communicate decisions effectively.

For example, a company planning a rebranding effort must first assess how customers currently perceive its brand. If its website, marketing materials, and customer surveys present inconsistent messaging, making an informed decision becomes difficult. Organizing this information effectively allows leaders to identify the best rebranding strategy.

Similarly, an entrepreneur launching a new service must structure market research, competitor analysis, and customer feedback in a way that reveals the best opportunities. Poorly organized information leads to unclear choices, while a well-structured approach ensures that decisions are based on reliable insights.

The ability to choose a clear direction is essential for business success. Without it, organizations become disorganized, teams lose focus, and opportunities are missed. Leaders and entrepreneurs must develop the skill of assessing options, evaluating constraints, and committing to a strategic path.

By clarifying the scope of the decision, reviewing constraints, generating multiple options, evaluating feasibility, seeking input without overanalyzing, defining success metrics, communicating clearly, and balancing commitment with adaptability, leaders can confidently navigate uncertainty.

A well-chosen direction does not guarantee success, but it provides the structure necessary for progress. Businesses that embrace this process are better positioned to respond to challenges, seize opportunities, and achieve meaningful results. Whether launching a new product, restructuring an organization, or improving customer experience, selecting the right path is the first step toward success.

5: Measure the Distance

Once a direction has been chosen, the next step is to measure the distance between where you are and where you want to be. Without measurement, leaders and entrepreneurs risk losing focus, misallocating resources, and failing to recognize when adjustments are needed. In How to Make Sense of Any Mess, Abby Covert emphasizes that tracking progress is essential to making informed decisions and ensuring that a chosen direction is leading to the desired outcome.

Measurement is not just about tracking numbers—it is about understanding whether efforts are producing meaningful results. By establishing clear benchmarks, evaluating key indicators, and using data effectively, businesses can stay on course and avoid wasting time on strategies that are not working.

Why Measuring the Distance Matters

Tracking progress allows businesses to refine their approach, stay motivated, and make better decisions. Without clear measurements, businesses and teams can fall into the trap of assuming they are making progress when they are actually stagnating or moving in the wrong direction.

Measurement keeps teams focused – When progress is tracked, employees and stakeholders stay engaged and motivated. A clear understanding of success ensures that everyone is working toward the same goal.
Measurement reveals what is working and what is not – Without data, businesses may continue investing in failing strategies. By regularly assessing performance, leaders can identify what needs improvement and where to allocate more resources.
Measurement prevents wasted effort – If a business does not track key indicators, it may spend months or years pursuing a strategy that does not produce results. Early measurement allows for course correction before too much time is lost.
Measurement enables informed decision-making – Leaders need accurate information to make good decisions. Tracking progress provides insights that help businesses adjust strategies, improve operations, and achieve long-term success.
Measurement builds credibility and accountability – Investors, employees, and customers want to see progress. When businesses can demonstrate measurable improvements, they build trust and strengthen relationships with stakeholders.

Steps to Measuring the Distance

Effective measurement requires a structured approach. It is not enough to simply collect data; businesses must determine what to measure, how to interpret results, and how to adjust based on insights. Abby Covert outlines a clear process for ensuring that measurement drives meaningful progress.

Define what success looks like – Before tracking progress, it is essential to establish clear goals. Leaders must ask themselves, “What does success mean for this project, initiative, or business?” Success can take many forms, including increased revenue, improved customer satisfaction, higher efficiency, or stronger brand recognition. Without a well-defined vision of success, measurement lacks direction and purpose.
Identify key performance indicators (KPIs) – Not all data is useful. Leaders must determine which metrics truly indicate progress toward their goals. If a company aims to improve its online presence, KPIs might include website traffic, engagement rates, and conversion rates. If the goal is to improve customer service, response time and satisfaction scores might be the most relevant indicators. Selecting the right metrics ensures that measurement efforts are focused on what matters most.
Establish a baseline measurement – Progress can only be assessed if there is a starting point for comparison. A baseline measurement captures the current state before any changes are implemented. If a business wants to increase sales by 20%, it must first determine what its current sales numbers are. Without a baseline, it is impossible to evaluate whether efforts are making a difference.
Determine how often to measure progress – Some metrics need to be tracked daily, while others are best evaluated weekly, monthly, or quarterly. The frequency of measurement depends on the type of goal. If a business is testing a new marketing strategy, weekly performance reviews may be necessary. If a company is tracking long-term employee retention, annual assessments might be more appropriate. Choosing the right measurement timeline prevents overreacting to short-term fluctuations while ensuring that long-term trends are properly analyzed.
Analyze patterns and trends – Isolated data points can be misleading. To truly understand progress, businesses must look for patterns over time. If a company sees a spike in website traffic but no increase in sales, it may indicate that visitors are not finding what they need. If employee engagement scores drop after a policy change, it may signal a problem with internal communication. Recognizing trends allows businesses to make adjustments based on meaningful insights rather than reacting to random fluctuations.
Use measurement to drive action – Data without action is meaningless. Once trends and patterns are identified, leaders must decide how to respond. If an online store’s conversion rate is lower than expected, the business might test different checkout processes. If a restaurant sees declining customer satisfaction, it might retrain staff or adjust menu offerings. Measurement should lead to specific, actionable decisions that improve performance.
Set up alerts and checkpoints for early detection – Waiting until a problem becomes obvious can be costly. Businesses should establish warning signs that indicate when something is going off track. If a company’s goal is to maintain customer retention at 80% or higher, an alert should be triggered when retention drops below 75%. By setting checkpoints, businesses can address issues before they become major obstacles.
Regularly reassess goals and measurement strategies – Business environments change, and measurement strategies must evolve accordingly. A metric that was once important may become irrelevant as priorities shift. Leaders should periodically review their goals and KPIs to ensure they are still aligned with the company’s objectives. Regular reassessment ensures that measurement remains relevant and useful.

The Role of Measurement in Information Architecture

Information architecture is about organizing information effectively so that it serves its intended purpose. Measuring progress plays a crucial role in structuring and optimizing information flows. Whether designing a website, streamlining a business process, or improving customer communication, data-driven insights ensure that changes lead to better outcomes.

For example, a company revamping its website might assume that simplifying navigation will improve user engagement. By measuring time spent on pages, bounce rates, and click-through rates, the business can determine whether the new design is truly more effective. If engagement does not improve, further adjustments may be needed.

Similarly, an entrepreneur introducing a new workflow management system for employees must track adoption rates, efficiency improvements, and user feedback. If employees are not using the system as expected, measurement will highlight the obstacles, allowing leaders to refine the implementation strategy.

Measuring the distance between where a business is and where it wants to be is a critical part of achieving success. Without structured measurement, businesses operate in the dark, relying on guesswork rather than informed decision-making.

By defining success, identifying key metrics, establishing baselines, tracking progress consistently, analyzing trends, using data to drive action, setting alerts for early detection, and regularly reassessing strategies, businesses can ensure that they stay on the right path.

The most successful companies are not those that never face challenges, but those that recognize problems early, adjust strategies effectively, and continuously measure their progress. Whether improving a product, growing a customer base, or optimizing internal operations, structured measurement is the key to sustainable success.

6: Play with Structure

Every system, process, and piece of information has a structure, whether intentional or not. In How to Make Sense of Any Mess, Abby Covert emphasizes that structure is the foundation for making sense of complex situations. Without structure, businesses and teams operate in confusion, leading to inefficiency, miscommunication, and lost opportunities.

Structure determines how information is arranged, accessed, and understood. A well-organized structure makes it easier to solve problems, improve workflows, and enhance user experiences. Whether designing a website, developing a product, or managing a team, leaders must be intentional about structure to ensure clarity and efficiency.

Why Playing with Structure Matters

Experimenting with structure allows businesses to find the best way to organize information, tasks, and resources. A rigid or ineffective structure can cause bottlenecks, misunderstandings, and inefficiency.

Structure enhances usability and efficiency – When information is structured well, users can find what they need quickly and perform tasks more efficiently. A poorly structured website, for example, frustrates users and leads to lost business.
Structure reduces cognitive overload – Too much information, presented chaotically, overwhelms people. A clear structure breaks information into manageable sections, making it easier to process and use.
Structure improves communication and collaboration – Teams work better when they have a shared understanding of processes, roles, and expectations. A structured approach to communication prevents misalignment and confusion.
Structure enables scalability and growth – Businesses evolve, and so must their structures. A flexible and well-organized system allows for expansion without unnecessary complications.
Structure supports better decision-making – Organizing information in a structured way helps leaders analyze data, identify trends, and make informed choices. Without structure, critical insights can be overlooked.

Steps to Playing with Structure Effectively

Creating an effective structure is an ongoing process of testing, refining, and adapting. Abby Covert outlines a practical approach to experimenting with structure to find the best way to organize information and workflows.

Identify the elements that need structuring – Before experimenting with structure, leaders must determine what needs organization. This could be a company’s internal documentation, a website’s navigation, a team’s workflow, or a product’s user interface. Breaking down the components of the mess allows for a targeted approach to structuring. If a business is struggling with inefficient team collaboration, structuring communication channels and task management may be the priority.
Consider different organizational methods – There are many ways to structure information, and the best approach depends on the context. Common methods include chronological order, hierarchical categorization, alphabetical listing, or grouping by topic. A content-heavy website may benefit from a hierarchical structure, while a customer service department may need an issue-based categorization system. Exploring different models helps determine the most effective way to organize information.
Test multiple structures before committing – Rather than assuming a single structure will work best, leaders should experiment with different approaches. This can be done through prototypes, mockups, or trial runs. A restaurant designing a new menu layout might test different category groupings—by meal type, dietary restrictions, or popularity—before finalizing the structure. Testing allows for feedback and refinement.
Analyze how users or stakeholders interact with the structure – The best structure is the one that makes sense to the people using it. Leaders should observe how employees, customers, or stakeholders engage with different structures. Are they able to find what they need quickly? Do they struggle with navigation? For example, an online retailer may discover that customers prefer filtering products by use case rather than brand. Adapting to user behavior ensures that the structure serves its intended purpose.
Simplify where possible – Overcomplicating structure can be just as harmful as having no structure at all. Leaders should aim for simplicity, removing unnecessary complexity and redundant steps. If a company’s approval process involves too many layers of management, streamlining the workflow improves efficiency. Simplicity makes systems more user-friendly and reduces the chances of errors.
Document the structure to ensure consistency – Once a structure is finalized, it must be documented clearly. This ensures that everyone understands how information is organized and how to use it effectively. A business that restructures its internal knowledge base should create guidelines explaining how documents should be categorized and accessed. Without documentation, inconsistencies arise, and the structure may gradually fall apart.
Allow for flexibility and future adjustments – No structure is perfect from the start, and needs change over time. Leaders must regularly reassess and refine structures based on feedback and new requirements. A company expanding its product line may need to reorganize its website navigation to accommodate new categories. A flexible structure allows for growth and adaptation without disrupting existing systems.
Measure the effectiveness of the structure – Just as progress needs to be measured, the success of a structure should be evaluated over time. Leaders should establish metrics to determine whether the new structure improves efficiency, user experience, or overall business performance. If a business restructures its employee onboarding process, measuring new hire retention and satisfaction scores can indicate whether the changes were effective. Regular assessment ensures that structures continue to serve their purpose.

The Role of Information Architecture in Structuring Information

Information architecture plays a central role in structuring content, processes, and systems. Whether organizing a digital platform, an internal knowledge base, or a customer support system, thoughtful information architecture ensures that users can access and understand information easily.

For example, an educational platform that offers hundreds of online courses must structure its content in a way that allows users to find relevant courses quickly. If courses are categorized only by instructor name rather than subject, users may struggle to locate what they need. By structuring content based on topics, skill levels, and learning objectives, the platform improves usability and engagement.

Similarly, a business that implements a new project management system must structure tasks, timelines, and responsibilities in a way that enhances collaboration. If tasks are randomly assigned without categorization, team members may miss important deadlines. A structured system, with clearly defined task categories and priority levels, improves efficiency and accountability.

Playing with structure is essential for making sense of complexity and improving efficiency. Whether organizing information, refining workflows, or enhancing user experiences, structure determines how effectively people interact with systems.

By identifying elements that need structuring, exploring different organizational methods, testing multiple approaches, analyzing user interactions, simplifying where possible, documenting the structure, allowing for flexibility, and measuring effectiveness, businesses can develop structures that support clarity and success.

An intentional approach to structure reduces confusion, increases efficiency, and makes information more accessible. Leaders who embrace structured thinking create environments where teams collaborate effectively, customers navigate systems easily, and decision-making becomes more informed. In a world where information overload is common, structure provides the clarity needed to move forward with confidence.

7: Prepare to Adjust

No plan, system, or structure remains perfect forever. Change is inevitable, and businesses that fail to adjust risk falling behind. In How to Make Sense of Any Mess, Abby Covert emphasizes that preparation for change is just as important as the initial design of a structure or strategy. A well-structured system should not only work in the present but also allow for future adaptations as circumstances evolve.

For leaders and entrepreneurs, adaptability is a crucial skill. Markets shift, customer preferences change, technology advances, and internal processes require continuous refinement. The ability to recognize when adjustments are needed and implement changes effectively determines long-term success.

Why Preparing to Adjust Matters

The best systems, organizations, and workflows remain effective because they are designed with change in mind. Businesses that resist adjustment often struggle with inefficiencies, customer dissatisfaction, and lost opportunities.

Adjustment allows businesses to stay relevant – Consumer behavior, industry trends, and economic conditions change constantly. Businesses that fail to evolve become outdated, while those that adjust remain competitive.
Adjustment prevents small problems from becoming major crises – Minor inefficiencies and inconsistencies, if ignored, can grow into larger problems. Regular assessment and small adjustments prevent major disruptions.
Adjustment ensures that structures remain functional – A well-organized system can deteriorate over time if not maintained. Regular adjustments ensure that processes, workflows, and information systems continue to serve their intended purpose.
Adjustment improves efficiency and effectiveness – Businesses that embrace change can optimize processes, improve customer experiences, and increase productivity. Small refinements over time lead to significant improvements.
Adjustment fosters a culture of learning and innovation – Organizations that encourage continuous improvement and adaptability create an environment where employees feel empowered to contribute new ideas and solutions.

Steps to Preparing for Adjustment

Adapting effectively requires a structured approach. Businesses should not only react to problems but proactively plan for change. Abby Covert provides a clear process for ensuring that adjustments are made thoughtfully and strategically.

Recognize that no system is perfect – The first step in preparing to adjust is accepting that every system, structure, or decision will need refinement over time. Businesses must move away from the mindset that once a process is established, it should remain unchanged. Leaders who acknowledge that adjustments are necessary can approach change with confidence rather than resistance.
Establish a feedback loop – Continuous improvement is only possible when businesses actively gather input from employees, customers, and stakeholders. Feedback can be collected through surveys, performance metrics, direct conversations, or regular review meetings. A company that redesigns its website should monitor user behavior and listen to customer feedback to determine if further improvements are needed. Without a structured way to collect input, businesses risk making changes based on assumptions rather than actual needs.
Regularly review performance and effectiveness – Businesses should set scheduled times to assess whether their current strategies, processes, and systems are still working as intended. This could be quarterly performance reviews, annual audits, or ongoing monitoring of key metrics. If an online store implements a new checkout process, it should analyze whether cart abandonment rates have decreased. Regular reviews prevent businesses from realizing too late that something is not working.
Identify early warning signs of necessary adjustments – Some problems become obvious only when they escalate into major issues. Businesses should develop systems for detecting early warning signs that indicate a need for change. Declining employee morale, increasing customer complaints, or dropping sales numbers are all indicators that adjustments may be needed. By catching these signs early, businesses can make small refinements before issues grow into major setbacks.
Test potential adjustments before fully committing – Change should be strategic, not impulsive. Before implementing major adjustments, businesses should test small variations to see what works best. This can be done through A/B testing, pilot programs, or phased rollouts. If a company wants to update its customer service model, it might start by testing new response times or communication methods with a small group before applying changes company-wide. Testing minimizes risks and ensures that changes lead to meaningful improvements.
Communicate changes clearly to all stakeholders – Adjustments can create confusion if not communicated properly. Employees, customers, and partners should be informed about what is changing, why it is happening, and how it will affect them. Internal changes to a company’s workflow should be clearly explained to employees, ensuring that they understand new expectations. External changes, such as pricing adjustments or product updates, should be communicated transparently to customers. Clear communication reduces resistance and increases adoption of new processes.
Provide support and training when necessary – Some adjustments require employees or customers to learn new systems, tools, or workflows. If a business introduces a new project management system, providing training ensures that employees can use it effectively. Without proper guidance, changes may be met with frustration and resistance. Support resources, training sessions, and documentation help ease transitions and ensure that adjustments lead to improvements rather than confusion.
Monitor the impact of changes and refine further – Change does not end after implementation. Businesses should track how adjustments are affecting performance and be ready to make further refinements if necessary. If a restaurant changes its menu and notices a drop in customer satisfaction, it should analyze feedback and make additional modifications. Continuous monitoring ensures that adjustments produce the desired outcomes and allows businesses to fine-tune their approach over time.

The Role of Information Architecture in Making Adjustments

Information architecture plays a critical role in structuring changes effectively. Whether updating a company’s knowledge management system, redesigning a website, or reorganizing internal workflows, businesses must ensure that adjustments do not create new confusion.

For example, an e-commerce company that restructures its product categories must ensure that users can still find items easily. If the new structure is not intuitive, customers may abandon purchases. By using data analytics and customer behavior tracking, businesses can refine the structure over time to improve navigation.

Similarly, a business that introduces a new employee training system must structure information in a way that makes learning easy and accessible. If employees struggle to find resources or navigate the system, the intended benefits of the change may not be realized. Thoughtful information architecture ensures that adjustments enhance usability rather than introduce new challenges.

Conclusion: Embracing Change as a Continuous Process

Preparing to adjust is not about reacting to problems—it is about proactively creating a system that allows for continuous improvement. Businesses that embrace change as an ongoing process remain agile, competitive, and efficient.

By recognizing that no system is perfect, establishing feedback loops, reviewing performance regularly, identifying early warning signs, testing changes before full implementation, communicating effectively, providing training, and monitoring impact, businesses can ensure that adjustments lead to positive outcomes.

Change is not something to fear; it is a necessary part of growth. Organizations that build adaptability into their culture, processes, and decision-making are better positioned for long-term success. Whether refining customer experiences, optimizing internal workflows, or responding to market shifts, the ability to adjust effectively separates thriving businesses from those that struggle to keep up.

8. Additional Reading

If you found How to Make Sense of Any Mess by Abby Covert insightful, here are other books on information organization, decision-making, and problem-solving that might interest you:

Books on Information Architecture and Organization

Information Architecture: For the Web and Beyond – Louis Rosenfeld, Peter Morville, & Jorge Arango
A foundational book on structuring websites, apps, and digital experiences to improve usability and findability.
How to Make Sense of Any Mess (Expanded Edition) – Abby Covert
If you enjoyed the original, check out an updated or expanded version (if available) for new insights and case studies.
Pervasive Information Architecture – Andrea Resmini & Luca Rosati
Explores how information architecture goes beyond websites and into our everyday environments.

Books on Decision-Making and Problem-Solving

Thinking, Fast and Slow – Daniel Kahneman
A deep dive into how humans make decisions, exploring cognitive biases and ways to improve rational thinking.
The Art of Thinking Clearly – Rolf Dobelli
A practical guide to identifying common thinking errors that affect business and personal decisions.
Decisive: How to Make Better Choices in Life and Work – Chip Heath & Dan Heath
A framework for making smarter decisions and avoiding common traps like confirmation bias.

Books on Organizing Complexity and Systems Thinking

The Signal and the Noise: Why So Many Predictions Fail – but Some Don’t – Nate Silver
Explores how to make sense of complex data and distinguish valuable insights from noise.
Thinking in Systems: A Primer – Donella Meadows
A must-read for understanding how complex systems work and how to intervene effectively.
The Fifth Discipline: The Art & Practice of the Learning Organization – Peter Senge
A classic on how organizations can build learning and adaptability into their structures.

Books on Communication and Structuring Information

Made to Stick: Why Some Ideas Survive and Others Die – Chip Heath & Dan Heath
Explains why some messages resonate and how to structure communication for maximum impact.
The Elements of User Experience: User-Centered Design for the Web and Beyond – Jesse James Garrett
A guide to structuring digital experiences with a user-first approach.
Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content – Ann Handley
Focuses on how to structure written content effectively for clarity and impact.

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