When Working Together Doesn’t Work by Joey Stabile Schewee
Introduction
“When Working Together Doesn’t Work”: We spend a large part of our life working with other people. We work with colleagues, managers, employees, clients, and team members. Sometimes, we find people who understand our ideas, support our decisions and make our work easier. But other times, even simple conversation can become frustrating. A small misunderstanding can turn into a conflict, a direct comment can sound offensive, and a well-intentioned action can be interpreted in a completely different way.
But why do we experience such difficulty while working with others? Is it because people are too different, or because we do not understand how our own personalities influence our behavior.
When Working Together Doesn’t Work by Joey Stabile Schewee explores this important question through the lens of the enneagram. The book connects self-awareness with workplace relationships and helps readers reflect on how their personal tendencies can influence teamwork, communication, and collaboration.
One of the most interesting ideas presented in the book is that, “Our intentions and others’ perceptions are not always the same. We may believe that we are being efficient, thoughtful, supportive or direct, while others may see us slow, distant, needy, or too blunt.”
This makes the book relevant for anyone who wants to improve their professional relationships, understand their behavior better and build healthier working environments.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
What the Book is About
The central idea of When Working Together Doesn’t Work is that better workplace relationships begin with better self-understanding. Instead of focusing only on what other people are doing wrong, we can start by examining our own motivations, habits and responses.
The book uses the enneagram, a personality framework with nine types, two explain different patterns of thinking, feeling and action. It shows how people with different enneagram tendencies may understand their own strengths, while others may experience the same behavior differently.
For example, a person who sees themselves as thoughtful may be viewed by others as slow or unresponsive. Someone who believes they are direct and decisive may come across as dominating or dismissive. Similarly, a person who wants to help everyone may unwittingly make others feel that they are interfering or talking too much.
This difference between intention and impact is a key theme in the material you shared. It reminds us that good intentions do not automatically guarantee good communication.
Another important concept is the three centers of intelligence: the doing center, the thinking center, and the feeling center. The book describes them as different ways of processing experience and responding to the world.
The doing center relates to action, implementation, and accomplishment.
The thinking center relates to analysis, information, and objective reasoning.
The feeling center relates to emotions, people awareness, and interpersonal relationships.
This framework encourages readers to reflect on their default way if approaching situations. Someone may quickly move to action, while someone else may need time to think. Another person may first consider how a decision will affect the team.
None of these approaches is automatically wrong. The problem arises when we assume that our own way is the only reasonable way to work.
The book also explores the nine enneagram types through workplace behavior. For example, type one is presented as improvement-minded and detail-oriented, but others may perceive this person as critical or micromanaging.
Type two wants to help and build connection, but may be perceived as needy or overly involved. Type five values deep thinking and autonomy, but may be misunderstood as distant or unresponsive.
That’s why, the enneagram becomes a tool for reflection rather than just a label. The value lies not in pigeonholing people, but in noticing patterns and understanding how these patterns affect our relationships.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
What I Liked About the Book
One thing that stands out from the shared pages is the practical focus on everyday workplace behavior. The book does not limit the discussion to general ideas about personality. Instead, it connects personality patterns to the way people communicate, handle disagreements, make big decisions and collaborate with colleagues.
This makes the concepts easier to reflect on. It is one thing to read that people have different personalities. It is another thing to realize that a quality you see as a strength may be experienced by someone else as a challenge.
I also like the emphasis on self-reflection. When a workplace conflict happens, it is natural to focus on the other person. We may think that our manager is too controlling, our colleague is too slow, or our teammate is not committed enough. But self-awareness asks us to consider another question: “How might my own behavior be contributing to this situation?”
This does not mean taking blame for every problem. Rather, it means recognizing the part we can control our own responses. We cannot choose other peoples personalities, but we can learn to communicate more consciously.
Another strength is the comparison between how people see themselves and how others may see them. A person may say, “I am direct, blunt, and firm,” while someone else may feel personally attracted. A person may think, “I take time to process,” while a colleague may interpret that behavior as unresponsive.
This is a useful reminder that our self-image is not the complete picture. Listening to construct feedback can help us discover blind spots that we might otherwise miss.
I find the three centers of intelligence another interesting aspect. The doing, thinking, and feeling centers offers a simple way to reflect on how we approach work. Do we rush to solve the problem? Do you need more information before deciding? Or do we first consider the emotional and relational impact?
Understanding these differences can help teams award unnecessary misunderstandings. Instead of seeing a slower decision-making process as incompetence, we can recognize that some people need time to analyze risks. Instead of seeing emotional consideration as a distraction, we can understand it’s role in building trust.
Most of all, the book’s approach encourages us to see personality differences as something to understand, not something to judge immediately. That perspective can make a meaningful difference in professional relationships.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
Best Lesson that Stayed With Me
The most important lesson I take from When Working Together Doesn’t Work is that “Working better with others starts with understanding ourselves better.”
When something goes wrong at work, we almost automatically look for the reason outside ourselves. We may blame a colleague’s communication style, a manager’s decision, or teammate’s lack of effort. Sometimes, our concerns are justified. But even then, self-awareness can help us respond more effectively.
Consider a situation where a team member does not respond to a message immediately. One person might assume that the team member is unresponsive or uninterested. But that person might be taking time to process information, finishing a priority task, or thinking carefully about the right response.
Without clarification, a small delay can become a personal judgement. With better communication, the same situation can be handled with more clarity and less frustration.
The same principle applies to directness, perfectionism, empathy, and the need for autonomy. Qualities that helps us succeed in one situation can create difficulty in another. The goal is not to remove our personality or pretend to be someone else. The goal is to become aware of our impact and adapt when necessary.
Another valuable lesson is that people do not always need to think or work the way we do. Some people prefer quick action, others prefer deep analysis, and others priorities relationships and emotional awareness. A strong team can benefit from all three approaches.
When we respect these differences, we become more willing to ask questions, clarify expectations and find common ground.
This is why self-awareness is not just a personal growth exercise. It can become a practical skill for better teamwork, healthier conflict resolution and more effective collaboration.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
Who Should Read this Book
When Working Together Doesn’t Work maybe useful for readers who want to understand why workplace relationships sometimes become difficult, even when everyone is trying to do their best.
Managers and team leaders can find the perspective helpful when working with people who have different communication styles, decision-making habits and expectations. Understanding these differences can support better feedback, clearer expectations and more productive team conversations.
Employees and professionals who feel misunderstood at work may find it valuable to reflect on how their intentions are interpreted. This can help them identify opportunities to improve communication without giving up their authenticity.
People who experience regular workplace conflicts can use the book’s ideas as a starting point for self-reflection. Instead of focusing only on others’ faults, they can explore their own responses and look for more constructive ways to handle disagreements.
Readers interested in personality and enneagram may also enjoy the book’s workplace focus. It connects personality concepts with common professional experiences, making them relevant to everyday interaction.
Finally, anyone who wants to become a more thoughtful colleague, better listener or more aware communicator may find valuable questions to reflect on.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
Conclusion
When Working Together Doesn’t Work by Joey Stabile Schewee offers a useful perspective on the challenges of working with people who think, feel and behave differently. The book highlights the role of self-awareness the enneagram and the three centers of intelligence in understanding workplace behavior.
It reminds us that our strengths can sometimes become sources of misunderstanding. Being efficient may be seen as being impatient. Being caring may be seen as being overly involved. Being thoughtful may be seen as being slow. The challenge is to understand this gap and learn how to bridge it.
The most practical take away is simple:
“We cannot control every persons behavior, but we can take responsibility for our own. We can listen more carefully, explain our intentions more clearly, ask for feedback and stay open to the perspectives of others.”
Better collaboration does not require everyone to become the same. It requires people to understand their differences and work with them more consciously.
If we want our working relationships to improve, the first step may not be changing everyone around us. It may be looking inward, recognizing our patterns and learning how to meet others with more awareness and understanding.
Because, when we understand ourselves better, we create a better chance of working better together.
Get your copy here: When Working Together Doesn’t Work by Joey Stabile Schewee
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