How to Work with (Almost) Anyone: Five Questions for Building the Best Possible Relationships by Michael Bungay Stanier – A Comprehensive Summary

In “How to Work with (Almost) Anyone,” Michael Bungay Stanier (MBS) presents a groundbreaking approach to transforming our professional interactions from chance encounters into intentionally designed, thriving partnerships. This isn’t just another self-help book; it’s a practical manual for cultivating what MBS calls “Best Possible Relationships” (BPRs) — connections that are safe, vital, and repairable. He argues that the quality of our working relationships directly dictates our success and happiness, yet most of us leave them to fate, hoping for the best but often settling for disappointment. Through a series of five foundational questions and actionable strategies, MBS promises to equip readers with the tools to build resilience, foster genuine connection, and ensure our professional bonds don’t just survive but flourish, even amidst inevitable challenges. This summary will comprehensively break down every important idea, example, and insight from the book, providing a clear and accessible guide to mastering the art of relational maintenance.

The Best Possible Relationship

This foundational chapter introduces the core concept of the Best Possible Relationship (BPR), asserting that the quality of our working relationships is paramount to both our success and happiness. MBS highlights a critical truth: most of us leave these crucial relationships to chance, hoping for the best and getting into the work immediately. This often leads to misunderstandings, unmet expectations, and eventual disappointment, with relationships becoming suboptimal, stale, or even broken. Instead of blaming others or ourselves, MBS proposes an active, intentional approach to designing and managing how we work with people.

Imagine a world where you could keep brilliant relationships humming, contain the dysfunction of messy ones, and quickly reset solid relationships when they wobble. This is the promise of the BPR, which is built on three essential attributes: safe, vital, and repairable.

• Safe focuses on removing fear and establishing psychological safety. Drawing on Amy Edmondson’s work, MBS defines this as a belief that one will not be punished or humiliated for speaking up with ideas, questions, or mistakes. He also references Deloitte’s 2013 study on “covering,” where almost two-thirds of employees downplay their identities, and Google’s Project Oxygen, which emphasizes creating an inclusive team environment. A psychologically safe environment unlocks benefits like diversity, agility, and innovation.
• Vital means amplifying the good in a relationship. MBS chose this word for its dual meaning: essential and enlivening. It goes beyond safety to encapsulate Dan Pink’s trinity of motivation: purpose, autonomy, and mastery. A vital relationship offers the right blend of support and challenge, enabling both individuals to do meaningful work, take responsibility, and grow.
• Repairable addresses the inherent fragility of all relationships. MBS acknowledges that relationships will inevitably face moments of being cracked (damaged from within) and dented (damaged from without). This attribute ensures that when problems arise, there’s a commitment and capacity to fix the damage and carry on, preventing harm from escalating and allowing the relationship to reset and often emerge stronger.

The impacts of safe, vital, and repairable relationships are far-reaching, leading to better work, increased retention, improved mental health, flourishing engagement, and fewer HR interventions.

Central to building BPRs is the Keystone Conversation. MBS uses the architectural metaphor of a keystone, which stabilizes an arch and allows it to bear weight, and Robert Paine’s biological concept of a keystone species, which disproportionately affects and organizes its ecosystem. In either case, the keystone enables the system to bear stress, stay healthy, and grow stronger.

The Keystone Conversation helps build BPRs by establishing three key outcomes:

• Shared Responsibility: It’s an unexpected, often countercultural act that clarifies that caring for the relationship is both individuals’ responsibility. It asks, “How will we, together and individually, work towards this shared objective?”
• Permission to Continue the Conversation: It creates a space to talk about the relationship’s health in good times and hard times, acknowledging that adjustments and repairs will be needed. It normalizes asking, “How are we doing?”
• Deeper Understanding: It provides a profound insight into the other person, moving beyond incomplete and inaccurate assumptions to reveal their complexity and humanity.

MBS describes this work as radical, requiring bravery and energy, as it often disrupts traditional expectations of hierarchy, power, and leadership. While it may feel unusual and awkward at first, it gets easier over time. The author shares his “hard-won wisdom” from thirty years of diverse working relationships, emphasizing that success and failure in these interactions have shaped his understanding.

The chapter concludes by asking readers to identify their “BPR Person” – a specific individual with whom they’d like to build a BPR. This exercise includes characteristics such as relationship type (direct report, boss, peer, client), stage (onboarding, new, middle, ending), health (untested, beautiful, frustrating, stale), and personal motivation (commitment to flourishing, setting up for success, addressing unhappiness, maintaining a good thing, lessening future disappointments, or being braver/clearer).

The Five Questions of the Keystone Conversation

This section sets the stage for the practical application of the Keystone Conversation, likening the preparation process to the rigorous, behind-the-scenes work of a great chef. Just as a chef meticulously prepares ingredients hours before a meal, readers are encouraged to thoroughly prepare their answers to the five essential questions that form the backbone of this transformative conversation. This preparation is crucial for having the “ingredients” on hand for a fantastic relational meal.

The five questions, while straightforward, require thoughtful engagement and vulnerability. They are:

• The Amplify Question: What’s Your Best? This question, rooted in principles like positive psychology and Appreciative Inquiry, focuses on what’s working well. It’s about identifying and amplifying your talents, what you love to do, and when you shine brightest. It encourages a “turn it up to 11” approach to strengths.
• The Steady Question: What Are Your Practices and Preferences? This acknowledges our ingrained habits and predictable behaviors. It asks you to make your preferred ways of working explicit, which helps others support you and can even reveal unconscious patterns for the first time.
• The Good Date Question: What Can You Learn from Successful Past Relationships? This invites reflection on positive past relationships to identify patterns of success. By analyzing what made those connections flourish, you can replicate favorable conditions and actively construct an environment for mutual thriving.
• The Bad Date Question: What Can You Learn from Frustrating Past Relationships? The inverse of the “Good Date” question, this delves into difficult past relationships. It encourages examining both your own and others’ contributions to these struggles, offering valuable data on recurring dynamics to avoid or manage actively.
• The Repair Question: How Will You Fix It When Things Go Wrong? This question confronts the uncomfortable truth that all relationships will experience rough patches. It’s a proactive step to develop strategies for getting back on track after disappointments, acknowledging that “time heals all wounds” isn’t a viable strategy.

MBS emphasizes the importance of taking your time, being brave, vulnerable, and truthful in your preparation. He advises against modesty when identifying strengths and encourages acknowledging messier aspects. While not every insight needs to be shared, robust preparation provides ample material for shaping a successful BPR. For those wanting to delve deeper, the book references a bonus “Know Your Stuff” section.

The Amplify Question: What’s Your Best?

The Amplify Question asks us to identify and articulate what truly makes us shine, drawing a parallel to the meticulous preparation of climbers like Alex Honnold and Edmund Hillary who reached their “peak moments” through natural talent, honed mastery, and finding the right context. This question is about uncovering your talents, what you love to do, and when you tend to shine.

The power of this question lies in its focus on amplifying what’s already working, shifting the bias from problem-fixing to strength-building. MBS clarifies that a “strength” isn’t just something you’re good at; it’s an activity that strengthens you, makes time fly, and leaves you feeling invigorated. He introduces the concept of the “curse of competence,” where individuals can be trapped doing things they are good at but not fulfilled by, leading to exhaustion rather than energy. When both parties share their strengths, it provides valuable information for creating a BPR that leverages and brings out the best in both.

Core Exercise: Good At versus Fulfilled By

This exercise uses a two-by-two matrix to differentiate between tasks you are “Good At” (low to high) and tasks you are “Fulfilled By” (low to high). By assigning your key responsibilities and day-to-day tasks to one of the four quadrants (High/High, Low/High, High/Low, Low/Low), you can visualize where your energy is truly invested and where it’s drained. The most insightful outcome is identifying tasks in the Low Fulfilled By / High Good At quadrant, which represents the “curse of competence.” This allows you to say in the Keystone Conversation, “I’m good at this… and I don’t love doing it,” opening a dialogue for managing these tasks more effectively.

The chapter encourages readers to thoughtfully answer how they would identify their best qualities. For those seeking deeper self-awareness, it points to the “Archetypes” and “The Boasting Friend” exercises in the “Know Your Stuff” bonus section.

The Steady Question: What Are Your Practices and Preferences?

The Steady Question delves into the predictable, consistent aspects of how we work, drawing a metaphor to the Moon’s steadying influence on Earth, which enables consistent seasons and, consequently, civilization. Just as the Earth has a “steady axis,” individuals also have their own ruts and grooves – ways of working that are thoroughly predictable, even if unconsciously so. This question prompts you to make these practices and preferences explicit.

The power of the Steady Question lies in its ability to bring unconscious habits into awareness. While some practices might be common sense to you, they could be quirky or inexplicable to others. By knowing and sharing your preferences, you and the other person can identify areas of similarity and difference that might cause conflict. More importantly, it allows for a collaborative effort to accommodate different working styles within the BPR, making it easier for others to support your best work.

Core Exercise: Deep Read Me

This exercise builds on the popular “Read Me” document concept, which typically involves individuals listing their work preferences for others to review. While “Read Me” documents are a good start, MBS highlights their limitations: they can be “me-me-me” focused and assume that simply informing others is enough. Instead, the “Deep Read Me” is designed to prepare you for a conversational exchange about your preferences.

The exercise suggests listing your preferences across nine key areas, providing structure for your thoughts:

• Name and Identity: How you like to be addressed and any important language around your identity.
• Extrovert/Introvert: What this means for you and how it manifests in your work.
• Peak Work Time: When you are most productive.
• Communication Quirks: Channel preferences (Slack, email), abbreviations, response patterns.
• Meeting Preferences: What makes a good or bad meeting for you.
• Feedback Style: What kind of feedback is most helpful and how you prefer to receive it.
• Deadline Management: Whether you work consistently or in bursts, close to deadlines.
• Work Approach: Do you start with the big picture and move to details, or vice versa?
• Pet Peeves: Seemingly small things that frustrate you.

By articulating these preferences, you gain a clearer understanding of your operating system, which then becomes valuable shared knowledge in the Keystone Conversation. The chapter also suggests two deeper exercises in “Know Your Stuff”: “Where Did You Learn Your Work Habits?” and “Calm or Volatile?” to further explore these ingrained behaviors.

The Good Date Question: What Can You Learn from Successful Past Relationships?

The Good Date Question invites reflection on your most successful past working relationships, drawing an analogy to a lighting maestro who illuminates “the talent” to make them shine. Just as precise lighting enhances appearance, certain relationships have made you glow and bring out your best. This question encourages you to share the story and insights from what has worked before.

The power of this question lies in mining the wisdom from past successes. MBS notes that these relationships often feel “ridiculously easy” and “clicked,” balancing challenge and support, and fostering connection and alignment. While luck and timing play a role, he emphasizes that there’s also intentionality and “hard work” involved. By dissecting these positive experiences, you can identify repeatable patterns and actively construct an environment where you are most likely to flourish. It’s about understanding how you, and the other person, “got the lighting right.”

Core Exercise: How Did You Build It?

This exercise counteracts the self-serving cognitive bias, which leads us to overattribute success to ourselves and blame others for failures. To gain a balanced perspective, the exercise begins by encouraging you to celebrate the other person’s role in the successful relationship:

• What did they say (and not say)? What words made a difference?
• What did they do (and not do)? What actions elevated and nurtured the relationship?
• How did they “be”? What qualities did they exhibit that contributed positively?

Only after giving them due credit, you then shift to claiming your own credit, without false modesty:

• What did you say (and not say)? What were your well-measured words?
• What did you do (and not do)? What big and small actions added to the good?
• How did you “be”? How did you show up in a way that helped both of you succeed?

Finally, the exercise prompts consideration of the setting of success, acknowledging that context also plays a crucial role:

• What about the context gave this relationship the best chance to flourish? Who else played a role?
• Which moment tested the relationship, and how was it successfully managed? What light does this shed?

By answering these questions, you gain a deeper, more nuanced understanding of the elements that contribute to a thriving working relationship. The chapter suggests exploring “How Did They Love You?” and “Hide & Seek” in the “Know Your Stuff” section for further insights.

The Bad Date Question: What Can You Learn from Frustrating Past Relationships?

The Bad Date Question serves as the crucial flipside to the Good Date, inviting you to extract wisdom from frustrating past relationships. MBS uses the analogy of a disastrous Dungeons & Dragons tournament experience – starting badly and quickly deteriorating – to illustrate how some working relationships can become messy, difficult, and frustrating. However, these experiences are not just sources of pain; they are rich sources of wisdom.

The power of this question lies in recognizing that while difficult past experiences felt deeply personal, they often reveal repeating patterns. By honestly examining your behavior, the other person’s behavior, and the situation, you can uncover recurring dynamics. This allows you to understand what conditions you need to flourish and, more critically, the ways you might behave badly to undermine or sabotage relationships. MBS stresses that it’s a mistake to cover up these experiences or solely blame the other party, as there’s invaluable “wisdom in the wound.” Sharing these struggles in a Keystone Conversation, rather than hiding them, can build trust and provide clarity on what to avoid or actively manage in the current relationship.

Core Exercise: How Did You Break It?

This exercise is designed as the alter-ego to “How Did You Build It?” and explicitly aims to counteract the bias of assigning more blame to others when things go wrong. It starts by prompting you to take your share of the “credit” for the mess:

• What did you say (and not say)? What words and silences caused damage?
• What did you do (and not do)? What small and big actions undermined good intentions?
• How did you “be”? How did you show up in a way that soured dynamics?

After this crucial self-reflection, you then consider how the other party contributed to the mess:

• What did they say (and not say)? What angered, frustrated, or saddened you?
• What did they do (and not do)? What actions set things back?
• How did they “be”? What qualities did they exhibit that were problematic?

Finally, the exercise brings in the contextual elements, acknowledging that the time and place influence outcomes:

• What about the context made this relationship odds-against? What other people played a role?
• Which moment tested the relationship, leading to failure and significant damage? What does this moment reveal?

By working through these prompts, you gain a more balanced and insightful perspective on past failures, identifying specific behaviors and situations to address moving forward. The chapter suggests “What Do People Get Wrong about You?” and “Claim Your Villain” from the “Know Your Stuff” section for deeper exploration of these challenging aspects.

The Repair Question: How Will You Fix It When Things Go Wrong?

The Repair Question tackles the uncomfortable, yet inevitable, reality that every working relationship will have its rough patches. MBS uses the powerful analogy of tsunamis in Japan, referencing the “tsunami stones” that enshrine generational memory and warn against building in vulnerable areas. Just as calamities are predictable, so too is the occurrence of problems in relationships. This question focuses on how you will proactively fix things when they go wrong, rather than assuming “time heals all wounds.”

The power of the Repair Question lies in its role as a rehearsal for speaking up when things are “a little off, or when you’ve been let down, or when you’ve done damage.” While it might feel awkward, the most important aspect is the shared recognition that things will break. By talking about repair before problems arise, you become better equipped to notice when the relationship is failing and to address it collaboratively. It fosters a sense of safety that enables difficult conversations, moving beyond the fear of a “Huh, what are you talking about?” response. John C. Maxwell’s quote, “Anything that’s human is mentionable, and anything that is mentionable can be more manageable,” underscores this point.

Core Exercise: Bridging

This exercise draws on the metaphor of bridges, like those on Euro banknotes, which symbolize unity and connection. When relationships are damaged, they often cause individuals to turn away from each other. Building a “bridge back to connection” requires courage, skill, and a willingness to soften your stance for a bigger game. The exercise prompts you to reflect on past relationships you’ve improved and the strategies you employed, whether in the “heat of the battle” or in the aftermath.

While acknowledging that these strategies may not always feel available, the exercise encourages identifying which ones you tend to draw upon at your best. These include:

• Name what’s happening: Surfacing unspoken issues and articulating your experience.
• Stay curious: Breathing, staying open, examining defensiveness, and remembering the other person’s humanity.
• Remember the goal: Understanding what “winning” means in the context of the BPR, letting go of “being right.”
• Seek understanding: Listening fully to ensure the other person feels heard, separating facts from opinions.
• De-escalate: Introducing lightness, owning your statements (“I make up that…” instead of “You did…”), and reducing tension.
• Rebuild: Making the first move to reconnect, reframing the issue away from “you versus me,” and apologizing.

Identifying and sharing these “bridging” strategies helps both parties understand and recognize when efforts are being made to repair the relationship. The chapter also suggests two deeper exercises in “Know Your Stuff”: “Is That a Cigar?” and “Stressed Out,” to further explore personal stress responses and potential misunderstandings that can damage relationships.

How to Have a Keystone Conversation

This section serves as a practical manual for executing the Keystone Conversation, acknowledging that while the preparation is crucial, the actual conversation itself will likely feel weird, awkward, and vulnerable, especially at first. MBS draws on his personal experience of having his first “Keystone Conversation” on a bus with his future wife, where they discussed fundamental expectations. He emphasizes that this discomfort is normal and not a sign of failure; instead, it indicates that you are co-creating something important, rare, and transformative.

The section is structured as an instruction manual, with “Do This” and “Say This” prompts, encouraging readers to find their own authentic ways to implement the advice. It promises to cover how to invite someone to the conversation, make it less tricky at the start, keep it useful in the middle, and finish strong.

Invitation: Make the First Move

The Invitation chapter stresses the importance of initiating the Keystone Conversation yourself, likening it to asking someone to dance at a school event. Most people won’t initiate this conversation, so being the one to start is crucial. MBS asserts that there’s rarely a “bad time” to have this conversation, given its inherent awkwardness.

Do This:

1. Invite Them to a Keystone Conversation: This can be done before you first meet, when starting a long-term working relationship (e.g., with a new team member or important client). It’s also suitable for existing relationships that are going well, have gone stale, or feel stuck and broken. However, it’s generally not recommended during moments of “high conflict”; instead, use it after immediate repair and de-escalation, to prevent future recurrence.
2. Tell Them What the Conversation Is About: Avoid creating anxiety by explaining the purpose of the Keystone Conversation upfront. Clearly state that it’s about building a successful working relationship and that you’ll both spend time preparing using the five questions. MBS suggests sharing a copy of the book, relevant pages, or a role-modeling video, and inviting them to decide on details like time and place to foster autonomy.

Say This (Your Word & Phrase Toolkit):

The toolkit provides various prompts to initiate the conversation:

• “I’d like us to chat about how we work together.”
• “I’d love to spend time figuring out with you what will make this the best possible relationship.”
• “Could we have a Keystone Conversation where we’ll talk about how to work together, rather than focusing on what to work on? It will give us the best chance to figure out what works, to avoid what doesn’t, and to fix the things that get broken.”
• “Let’s chat about how we work together before we talk about what we’re working on.”
• “Before we jump back into what needs to be done/the project/our priorities, let’s talk about how we’re working together.”
• “I want to talk about how we bring out the best in both of us, what things we want to avoid, and how we’ll keep this relationship at its best even when the work is hard.”
• Explicitly list the five questions: “Here are the five main questions I’d like us to talk about… I’ve been thinking about my answers, and I want to make sure we both get a chance to ask and answer these: 1. What’s your best? 2. What are your practices and preferences? 3. What can we learn from successful past relationships? 4. What can we learn from frustrating past relationships? 5. How will you fix it when things go wrong?”

At the Start: Make It Safe

This chapter emphasizes the critical importance of making the Keystone Conversation feel safe, given its unusual and vulnerable nature. Drawing on neuroscience, MBS introduces the TERA Quotient (Tribe, Expectation, Rank, Autonomy), a model that explains how the brain scans the environment five times a second for safety. The “lizard brain” (primitive brain) will perceive this conversation as potentially dangerous, so actively increasing the TERA Quotient is essential to foster engagement and reduce the fight, flight, or fix response.

Do This:

1. Increase the TERA Quotient: Actively manage the four drivers to create a safe environment:
   • Tribe: Ensure the other person feels you are “with them,” not against them.
   • Expectation: Provide clarity about the conversation’s agenda and flow.
   • Rank: Be mindful of power dynamics and show respect for their perspective.
   • Autonomy: Give them agency and choice in the conversation.
     Foundational ways to do this include:
   • Location: Choose a formal or informal, neutral, or mutually agreed-upon space.
   • Curiosity: Ask open-ended questions and use “And what else?” to encourage deeper sharing.
   • Sharing and Vulnerability: Answer every question you ask, sharing both the “messy and hard” alongside the “shiny and good.”
   • Co-creation: Involve them in shaping the conversation, asking what they want to discuss or if anything else needs to be said.
     Setting a shared BPR goal (Tribe), communicating the agenda (Expectation), sharing your own vulnerability (Rank), and offering choices for time/place (Autonomy) are powerful pre-conversation TERA boosters.
2. Be the Strongest Signal in the Room: Leverage the concept of mirror neurons, where our moods are contagious. MBS encourages taking the lead in establishing the emotional tone of the conversation. He suggests actively embodying qualities like generous, curious, vulnerable, and delighted. For him, this involves conscious physical cues: smiling, nodding, laughing, keeping feet on the floor, and hands open, all while breathing deeply and maintaining curiosity. This proactive approach helps manage natural anxiety and sets a positive precedent.

Say This (Your Word & Phrase Toolkit):

The toolkit provides prompts designed to build safety:

• “Thanks for having this conversation with me—it means a lot.” (Tribe)
• “What do you want from this conversation? What would make it most helpful for you? Here’s what I want.” (Tribe, Autonomy)
• “I want to talk about five things: what we are individually best at, our normal patterns of work, what makes for a great working relationship, what happens when things go bad, and how we will fix things when needed.” (Expectation – reinforcing the agenda)
• “Where do you want to start?” (Rank, Autonomy)
• “Here’s the first question I’d like us to answer.” (Tribe, Expectation)
• “Do you want to answer this first, or shall I?” (Rank, Autonomy)
• “What’s been helpful so far?” (Rank, Autonomy)
• “Right, mm-hmm, nice, uh-huh, OK, good, sure, yep, lovely.” (These small, repeated words of encouragement are crucial for infusing the conversation with encouragement, curiosity, and connection, acting as “lubrication.”)

In the Middle: Ask and Answer

This chapter emphasizes that the core of the Keystone Conversation is about sharing information and listening with intent, not about solving problems or making immediate decisions. MBS compares it to his online and in-person “different-from-usual conversations,” where participants are given space to answer a single, provocative question without interruption or the need to “fix” anything. The mantra from “The Coaching Habit” — “stay curious a little bit longer, and rush to action and advice-giving a little bit more slowly” — applies here.

Do This:

1. Don’t Skip the Hard Things: It is crucial to work through all five questions, even the ones about past failures or future breakdowns. MBS argues that avoiding uncomfortable topics will only make them harder to discuss later. He reminds us that even brief answers to these challenging questions contribute significantly to building the BPR. Ignoring difficulties prevents both wisdom and resilience during tough times. The goal is to build a relationship where raising difficult topics feels safe and normalized, not just to gather answers in the moment. Your prior preparation is key to having the courage to address these areas.
2. Ask and Answer: MBS reiterates Peter Block’s concept of “social contracting,” emphasizing that a true contract involves a mutual exchange of value. If you hold more power (as a boss, senior person, or client), it’s tempting to only ask questions. However, the Keystone Conversation requires both parties to answer. This reciprocity, where you share your own vulnerability and insights, ensures the exchange feels equal and builds the shared openness fundamental to a BPR. Asking without answering significantly lessens the chance of creating a truly safe, vital, and repairable relationship.

Say This (Your Word & Phrase Toolkit):

The toolkit provides prompts to facilitate the middle of the conversation:

• “I’m curious to hear your answer to this.”
• “And what else?” (A core coaching question to encourage deeper thinking)
• “Here’s how I’d answer that.” (Modeling vulnerability and reciprocity)
• “Here’s a hard question, but I think it’s helpful for us to answer it.” (Framing difficult topics as valuable)
• “What needs to be said that hasn’t yet been said?” (An invitation for completeness)
• “That’s powerful/useful/illuminating to hear.” (Acknowledging and validating their sharing)
• “Right, mm-hmm, nice, uh-huh, OK, good, sure, yep, lovely.” (Repeatedly emphasizes the importance of these small, encouraging acknowledgments as “lubrication” for the conversation.)

At the End: Appreciate the Good

This chapter highlights the importance of ending the Keystone Conversation on a strong, positive note, leveraging the brain’s “recency effect” (better remembering the last things). MBS draws parallels to musical theater’s rousing closing numbers or a well-designed event where the audience finishes on a high. A strong ending amplifies the conversation’s impact, even if some parts were challenging.

Do This:

1. Share the Learning: Set a precedent for all future conversations by making them learning opportunities. Ask the other person, “What was most useful here for you?” By asking and then answering this question yourself, you achieve three things:
   • Tangible Value: You make the most helpful insights concrete and memorable for yourself.
   • Feedback: You give the other person valuable feedback on what worked well, guiding future interactions.
   • Confirmation: You reinforce that the conversation was useful, normalizing future productive exchanges.
2. Appreciate the Conversation: Recognize that both parties took a risk and showed commitment to building a BPR. This is a significant step. Celebrate and appreciate this shared effort. This acknowledgment reinforces the foundation of a safe, vital, and repairable working relationship.

Say This (Your Word & Phrase Toolkit):

The toolkit provides prompts for a strong closing:

• “Thank you, that was really helpful. I’m excited for what’s ahead.”
• “What was most useful or most helpful for you?”
• “Here’s what was most valuable for me.”
• “What do you know now that you didn’t know before?”
• “I’m celebrating [insert what’s true for you].”
• “I appreciate [insert what’s true for you].”

The chapter concludes by re-emphasizing the “brilliant start” achieved by having this conversation, regardless of perceived imperfections. It’s a rare and courageous act that opens the door to a BPR, establishing shared commitment and permission for ongoing dialogue. However, it also cautions that this is “not a ‘one and done’ deal” and underscores the necessity of regular maintenance to keep the BPR alive and thriving.

Keep Your Best Possible Relationship Alive

This section transitions from initiating the Keystone Conversation to the ongoing art and science of maintaining a Best Possible Relationship (BPR). MBS emphasizes that despite a brilliant start, “disintegration is inevitable” without regular upkeep. He uses the metaphor of space debris (Kessler effect) and the daily “minor damage” relationships incur from everyday actions – small dings, hiccups, or flare-ups. Just as gardens need pruning, engines need fine-tuning, and software needs debugging, relationships require constant care.

MBS proposes six principles of maintenance to guide your actions and mindset. The first three principles focus on the state of mind to bring to everyday interactions, calling for openness despite the natural wiring to shut down under stress:

• Stay Curious: Assume you don’t know the full picture. Genuine curiosity dispels ambiguity and frustration, helps you understand the situation and the other person more deeply, and reveals your own contributions to challenges. It calls for open-mindedness.
• Stay Vulnerable: Acknowledge that others also don’t know the full picture, and that you might be holding back useful data, opinions, or feelings. Sharing these, even if half-formed, can be illuminating for both parties, moving from being “closed-fisted” to open-handed.
• Stay Kind: Recognize that this work is difficult and imperfect. Assume positive intent for both yourself and the other person, remembering your shared commitment to the BPR. It calls for open-heartedness.

These three principles form the very foundation of a BPR. The final three principles concern the rhythm of successful maintenance, addressing daily, regular, and occasional interventions:

• Adjust Always: Like sailing, relationships require constant fine-tuning to changing conditions. Small adjustments to the waves and wind are necessary to avoid big disasters and make the most of the moment.
• Repair Often: When relationships get “dinged,” deal with it quickly. Bring the “wound into the light” (sunlight disinfects), understand what’s hurting, and apply a salve to prevent small flare-ups from becoming long-term damage.
• Reset as Needed: Over time, relationships may go flat or face significant changes. Moments of reset are necessary to keep the BPR safe and vital. This can involve actively changing and recharging the experience, preventing fatal breakdowns during stress.

Before acting on these principles, MBS introduces the crucial step of Orient: Know What’s Going On, which is detailed in the subsequent chapter. This foundational understanding is necessary to develop a nuanced perspective of unfolding relational dynamics.

Orient: Know What’s Going On

Before acting, it is essential to orient yourself to the situation and truly know what’s going on. MBS highlights that when a working relationship becomes difficult, we often feel stuck, overwhelmed, and flooded with emotions like fear, shame, and anger. This “flooding” narrows our vision, making it seem like our perspective is the only truth. Drawing on Colonel John Boyd’s OODA loop (Observe, Orient, Decide, Act), MBS emphasizes the importance of observing and orienting before acting, especially in conflict.

He provides two “maintenance questions” to help map the situation and gain a nuanced understanding:

1. What Are the Facts?
   This question draws on Marshall Rosenberg’s Nonviolent Communication framework to break down the swirl of thoughts and emotions into four distinct “buckets”:
   • Data: These are the verifiable facts – what happened, what can be pointed at as objective evidence. MBS notes that we often find fewer facts than we assume.
   • Opinions/Judgments: This is the second bucket, where we interpret the data. These include suggestions, points of view, interpretations, advice, and “good ideas.” We often form opinions about the other person, ourselves, and the situation as a whole, linking them with the word “because” (e.g., “They’re unreliable because the report is two days past due”).
   • Feelings: The third element, which MBS simplifies to five core emotions: mad, sad, glad, ashamed, and afraid. He cautions that sentences starting “I feel that…” are usually judgments, not actual feelings. Our feelings are often intertwined with our judgments, forming a “cocktail of distorted understanding.”
   • Wants: The fourth bucket, focusing on what you desire. This is about building “adult-to-adult” relationships, which practically means developing the skill of asking for what you want, even if the answer is no. MBS cites Brené Brown’s “Clear is kind,” emphasizing that clarifying wants cuts through confusion and unlearns assumptions like “It’s not my place to ask” or “They should already know.”
   This discipline helps distinguish between truth and assumptions, and prevents feelings from hijacking the conversation.
2. What Position Are You In?
   Drawing on Edgar Schein’s “Humble Inquiry” and Terry Real’s work on dysfunctional relationships, this question examines whether you are in a “one up” or “one down” position relative to the other person in this specific relationship and moment.
   • “One up” might manifest as being in control, high status, indifferent, directive, incurious, cold, angry, passive-aggressive, or blaming. It involves explicit power, decision-making, and not trusting the other person.
   • “One down” might manifest as being blamed, low status, “victim-y,” resigned, complaining, desperate, manipulative, or passive. It involves a lack of explicit power and self-trust.
   The power here is stepping back to observe this dynamic. If the relationship is out of balance, one person will be “one up” and the other “one down,” revealing a shared “dance” where both parties contribute.

By adopting these two practices, you are invited to step out of your personal perspective to objectively observe yourself and the situation. This wider, more systemic, and often more compassionate perspective helps you see your role in the dynamics and then decide the best next step: to adjust, repair, or reset.

Adjust Always: Give and Take Receive

This chapter focuses on the ongoing, subtle adjustments necessary for relationship maintenance, emphasizing the dual importance of giving and receiving. MBS references Adam Grant’s “Give and Take,” highlighting that sustainable givers flourish, and Peter Block’s “social contract” requiring mutual exchange. John Gottman’s “bids” – “the fundamental unit of emotional connection” – are introduced as an everyday currency for interaction, building better relationships “bid by bid.”

Here are two maintenance questions, one for the other person and one for yourself, to help create and receive bids in service of your BPR:

1. What’s Working Well?
   This question is presented as a deliberate counter-bias to our tendency to focus on what’s not working. Inspired by the “Learning Question” from “The Coaching Habit,” it’s not “Is anything working well?” but “Things are working well. What should we highlight?” Regularly asking this question serves several purposes:
   • Calms Nerves: It shifts focus away from immediate problems.
   • Strengthens Foundation: It reinforces the positive aspects of the BPR.
   • Builds Resilience: Drawing on John Gottman’s research, which suggests a 5:1 ratio of positive to negative interactions for relationship resilience, actively noticing, celebrating, and telling stories about what’s working well contributes to this positive ledger.
2. What’s the Quiet Gesture?
   This question addresses “bid busters” – the ways we inadvertently turn down or ignore the other person’s attempts at connection. MBS explains that bids are often subtle (small gestures, inconsequential remarks), making them easy to miss due to distraction or mood. When a bid is ignored, it can lead to feelings of being downcast, or even resignation (“They hate me. I give up.”).
   The exercise encourages constant vigilance for the “quiet gestures” the other person offers. These small acts of giving and adjustment are ongoing contributions to the vitality of the working relationship. It emphasizes that if you’re giving, keep giving, and try not to be disheartened if not always heard, while remaining alert to what the other person is offering.

Even with consistent attention to what’s working and the give-and-take of bids, relationships will still get “dented.” This leads into the next principle: Repair Often.

Repair Often: Manage the Damage

This chapter addresses the proactive management of damage in working relationships, comparing it to Australia’s bushfire seasons where pre-emptive burning of undergrowth (using Indigenous wisdom) minimizes larger conflagrations. Just as fires are inevitable, so too are moments when your BPR is threatened by small flare-ups or larger conflicts. Active commitment to repair maintains the BPR by preventing minor burns from turning into long-term damage.

MBS presents two maintenance questions to help minimize hurt:

1. What’s As Yet Unsaid and Unsurfaced?
   This question focuses on detecting hidden threats, akin to painful “subterranean pimples” that are hard to pinpoint. These are moments when something feels “off” – either within yourself (acting weirdly, a vague sense of unease) or in the other person (a shift in tone, unusual behavior).
   The key is to name that something might be wrong, even if you don’t know precisely what it is. Prompts include, “I’m noticing something feels off. What’s up?” or “What needs to be said that hasn’t yet been said?” This opens the door to address minor transgressions, acknowledge hurts, or deal with brewing conflict before it escalates.
2. How Will You Fight?
   This question prepares for explicit conflict, acknowledging that sometimes what’s small becomes loud. While “good conflict is healthy,” the challenge is fighting with generosity and grace. Drawing on various conflict resolution experts (Amanda Ripley, Cinnie Noble, Stone, Patton, Heen), MBS offers a range of tactics:Fundamentals (not easy):
   • Breathe: To manage immediate physiological stress.
   • Remember what success is: Often not winning the immediate fight, but preserving the relationship.
   • Listen to understand what they want: Essential for them to feel heard.
   • Be clear about what you want: State your request.
   • Distinguish data from judgments: Separate facts from interpretations.
   • Concede points: Acknowledge when they are right or might be right.
   • Own your statements: Use “I am…” or “I feel…” instead of “You did…” or “You are…”.
   • Open physical stance: Body language that signals receptiveness (e.g., feet flat, unclenched hands).
   Advanced skills (harder still):
   • Keep breathing: Continued self-regulation.
   • Abandon proving “The Truth”: Acknowledge there are always multiple truths; ask “Who cares?” about being right.
   • Be curious about what is defended: Underlying fundamental issues often relate to power, trust, respect, and recognition.
   • Say “I don’t know”: Can de-escalate quickly.
   • Check for understanding: “What do you think I was saying then?” to catch misinterpretations.
   • Ask for a break: A “time out” can benefit everyone.

MBS concludes by noting that while fire can cause devastation, it also initiates a cycle of regeneration in eucalyptus species, cracking open seeds and allowing new growth. Similarly, moments of conflict can be an opportunity for reset and new beginnings in working relationships.

Reset as Needed: Ending (and Beginning)

This chapter focuses on the necessity of resetting relationships, not just repairing them, and also how to navigate the ending of a working relationship with grace. MBS shares a personal anecdote about facilitating a “Keystone Conversation” between his dying father and mother, highlighting the deep discomfort and eventual profound benefit of addressing unspoken tensions in a critical transition.

He outlines various reasons for resetting a relationship:

• Post-crisis: After a significant conflict, to rebuild from the ground up.
• Significant Change: Shifts in roles, status, or context that necessitate a new BPR.
• “Stable Ambiguity”: When a relationship settles into mediocrity because it’s easier to maintain than to disrupt.
• Relationship Ending: To conclude with dignity, appreciation, and grace.

Here are two maintenance questions to navigate ends and new beginnings:

1. Should We Begin Again?
   This question leverages the precedent set by the initial Keystone Conversation, making the health of the relationship a discussable topic. After conflict or a period of stasis, another “Keystone Conversation” can “reforge a BPR.” It acknowledges that initial plans meet reality and that new behaviors and patterns emerge. The goal is to answer: “What do we need to know about each other so that we can reforge a BPR together?”
   Avoiding this reset will likely lead to further deterioration. Taking the opportunity to plant seeds of repair and recovery will strengthen the relationship. MBS suggests layering in these questions:
   • Stay compassionate (towards them and you): “How are you doing? Here’s how I’m doing.” “I found that hard/difficult/upsetting/confusing. How did you find it?”
   • Stay curious (about how you ended up in this place): “What’s the data, and what did we both make up about what that meant?” “What spark set this off?” “What do you wish you’d done differently? Here’s what I wish I’d done differently.” “How would we do a better job with something like this in the future?”
   • Stay committed (to the BPR and to repair): “What would you like to hear from me? Here’s what I’d like to hear from you.” “What needs to be said that hasn’t yet been said?” “What else is needed, so we can begin this again?”
2. How Do We Finish This?
   When the decision is to end a relationship, MBS outlines different approaches, contrasting them with unfortunate endings like Antigonus’s demise in “The Winter’s Tale”:
   • The Ghost: Disappearing without a trace, clean for you, confusing/frustrating for them.
   • The Cortés: Burning bridges, showing disdain, with no intention of return.
   • The Wake: (The preferred option) A deliberate gathering to celebrate a “death” with sorrow and celebration, reminiscent of an Irish tradition. It’s generous, safe, and dignified. You can shape it using questions like:
     • “What’s the best story you can tell about this BPR?”
     • “What needs to be celebrated? What do you need to say thank you for?”
     • “What have you learned? How have you changed and grown?”
     • “What doesn’t need to be said? What can you keep quiet?”
     • “What does dignity look and sound like? How can both of you “save face”?”

MBS concludes the section by referencing Kathryn Mannix’s “With the End in Mind,” a book about facing death with less fear. He applies two key lessons: the unknown is often scarier than reality, and actively managing the experience for all involved leads to more generosity, presence, and grace in the ending.

Bonus: Know Your Stuff

This bonus section is designed to help readers “better understand your hand and which cards are your best,” offering exercises to deepen self-awareness regarding who you are, how you show up, and how you give and receive in relationships. Likening it to a game of cribbage, MBS suggests that these exercises are a chance to quickly sort your hand and identify your strengths.

He provides two additional exercises for each of the five Keystone Conversation questions, aiming to stretch thinking and self-awareness. Some exercises are direct, while others are more oblique, inviting deeper insights. MBS encourages “curious skepticism,” reminding readers that their answers are often a first step towards deeper understanding rather than definitive truths. He also mentions four ways to “triangulate” answers and reality-check them, available online.

A Deeper Dive on the Amplify Question

This section offers two exercises to deepen the understanding and articulation of your “best” qualities, inspired by the recent quest for the “most” of any color (Vantablack, Black 3.0, Pinkest Pink, Whitest White) which highlights the intensity of bringing one’s best into the world. When you show up as your best, you shine more brightly.

Exercise: Archetypes

This exercise draws on the concept of the Hero’s Journey and the roles within it, as well as the four energies (warrior, healer/lover, teacher/magician, ruler/visionary) from First Nations communities.

• Hero’s Journey Roles: Reflect on which roles you are most comfortable playing, most often default to, or aspire to:
  • Hero: Carries the quest’s weight, makes decisive moves.
  • Mentor: Teacher, guide, shares hard-earned wisdom.
  • Ally: Has the hero’s back, supports, cheers, provides resources.
  • Shapeshifter: Adapts as needed, fits in or stands out, elusive.
    Consider what role the other person in your BPR might most usefully play.
• Four Energies: Identify which energy you most naturally embody or easily summon, and which ones feel more elusive, requiring you to rely on others:
  • Warrior: Boundaries, engaging conflict, fierce protection.
  • Healer/Lover: Comfort, care, recovery, gentle protection.
  • Teacher/Magician: Knowledge, learning, wisdom, exploration.
  • Ruler/Visionary: Ambition, big picture, strategy, clarity.

Exercise: The Boasting Friend

This exercise helps overcome modesty and articulate your strengths by adopting an external perspective. Imagine your best friend is asked to describe what they truly appreciate about you, setting aside sarcastic or jokey comments. What five (or more) things would they say about your technical, emotional, and relational strengths? This third-person perspective makes it easier to objectively identify and claim your great qualities, offering insights you might not have noticed when self-reflecting.

A Deeper Dive on the Steady Question

This section further explores your “steady axis” of work habits and preferences, building on the idea that while labels simplify, they are also limited and sticky, much like René Magritte’s “Ceci n’est pas une pipe.” The exercises aim to add nuance and complexity to the self-identified labels from the core Steady Question exercise.

Exercise: Where Did You Learn Your Work Habits?

Inspired by a question from Salesforce’s leadership coaching, this exercise invites you to explore the origins of your unconscious work habits.

• Choose a few of your key work habits (e.g., work preferences, how you manage stress/conflict, how you show up in relationships).
• For each habit, “backfill the story” of what you learned, where you learned it, and why you decided it was important.
• A helpful formula: “I [work like this] because I’ve learned [story of when you learned this preference].”
  This exercise helps uncover the underlying narratives and experiences that shaped your “This is just how I do it” ways of working.

Exercise: Calm or Volatile?

This exercise moves beyond binary choices to explore deeper, more fundamental currents of behavior using spectrums. It acknowledges that human complexity cannot be reduced to simple “on or off” switches.

• Consider various polarities (e.g., spotlight vs. wings, calm vs. volatile).
• Instead of choosing one or the other, identify where you would place yourself on the spectrum between the two endpoints.
• Reflect on the “prizes and punishments” associated with each end of the spectrum for you.
• You are encouraged to build your own spectrums that best describe your unique qualities and complexities. This helps bring more nuance to self-description beyond simple labels.

A Deeper Dive on the Good Date Question

This section offers two exercises to further deepen your understanding of why past relationships were strong and nourishing, echoing Jan van Eyck’s “The Arnolfini Portrait” as a reminder of the interdependence in life and the need to test self-knowledge in relationship. These exercises go beyond what you and they did and said, delving into the underlying dynamics of appreciation and self-expression.

Exercise: How Did They Love You?

This exercise draws on Gary Chapman’s “The 5 Love Languages” (words of affirmation, acts of service, receiving gifts, quality time, physical touch), which describes how individuals prefer to receive appreciation.

• Identify the love language that most lights you up.
• Reflect on past successful relationships and notice which forms of appreciation particularly resonated with you.
• Consider what you can learn about how you give and how you receive appreciation.
  MBS notes that people often “give” in the language they prefer to receive, which can be helpful (if mutual) or a blind spot (assuming others want what you want).

Exercise: Hide & Seek

Inspired by the “hides” used by bird watchers and the Deloitte study on “covering” (downplaying identity), this exercise is about naming your gifts and understanding when you hide them and when you bring them forth.

• Identify your gifts: What are your best contributions? What are you known for? What should you be known for? (This builds on “The Boasting Friend” exercise). Your gifts typically combine technical expertise, experience, natural inclinations, and collaborative style.
• Explore hiding and seeking:
  • In what moments do you doubt yourself and retreat from the spotlight? What’s happening when you choose to stay silent?
  • What enabled you to share your gifts, achieve early wins, and bring your best self to work in your best relationships?
    This exercise highlights the delicate and precious act of sharing your authentic self and gifts in a working relationship.

A Deeper Dive on the Bad Date Question

This section offers two exercises to deepen the understanding of frustrating, broken, and failed relationships, encouraging you to take ownership of your “villainous” traits. Using the metaphor of “black hats” (hackers, Western outlaws, pantomime villains like Darth Vader), MBS emphasizes that acknowledging and sharing these vulnerabilities is a powerful act that strengthens trust and resilience in current working relationships.

Exercise: What Do People Get Wrong about You?

Inspired by leadership coach Randall Stutman’s insightful question, this exercise asks:

• “When you meet people for the first time, what do they get wrong about you? What do they misperceive about you? What do they overestimate about you, underestimate about you? What do they just get wrong?”
  This question serves three purposes:

1. External View: It helps you see yourself from an external perspective and notice how you present to the world, disrupting self-certainty.
2. Information for Others: It provides insights to share in a Keystone Conversation about common misperceptions.
3. Intentions vs. Actions Bias: Most deeply, it reveals the gap between how you judge yourself (by your good intentions) and how you judge others (by their perceived actions). When things go wrong, you know your intentions were good, but you don’t have access to others’ intentions, leading to quicker judgments. This exercise helps you become more curious about this gap, both for yourself and others.
   The prompt encourages exploring the “kernel of truth” behind these misperceptions.

Exercise: Claim Your Villain

This exercise is a direct invitation to “grab your black hat” and loudly and proudly claim your villainous moves. It lists seven archetypal villainous behaviors, with fictional role models:

• Betrayal: Breaking promises (e.g., Macbeth)
• Neglect: Ignoring, deeming unworthy (e.g., Miss Havisham)
• Smothering: Keeping in a cage, controlling (e.g., Hansel and Gretel’s witch)
• Temptation: Leading others astray (e.g., Darth Vader)
• Obsession: Nothing gets in the way of a goal (e.g., Captain Ahab)
• Bullying: Putting others in their place (e.g., Dolores Umbridge)
• Destruction: Destroying what others build (e.g., President Snow)
  You are asked to name the top two or three moves you’ve pulled off over the years, emphasizing that “none of the below” is not an option. For deeper insight, consider the motivation behind these behaviors when you were under stress (e.g., insecurity, threatened status/ambition, victim mode, neediness). The goal is to recognize and take ownership of these patterns, making them less likely to resurface unconsciously.

A Deeper Dive on the Repair Question

This section offers two exercises that focus on the “dangers facing the pigeon” (referring to Cher Ami, the heroic WWI pigeon that delivered a vital message despite being wounded), deepening the understanding of how relationships can be inadvertently damaged and how personal stress responses can exacerbate problems.

Exercise: Is That a Cigar?

Inspired by Sigmund Freud’s famous quote about a cigar sometimes just being a cigar (meaning not everything is symbolic), this exercise prompts reflection on recurring misunderstandings in past relationships.

• Review times when people have seemingly misinterpreted something you’ve done.
• Identify the misunderstandings that tend to reoccur, as they are likely to happen again.
• For each misunderstanding, make explicit what happens, what you think it means, and how your actions are taken the wrong way.
• Consider how your common, unconscious responses (e.g., silence, asking questions, furrowing brows, tangents) might be loaded and triggering for others.
• Often, these misinterpretations center on Howard Markman’s “trilogy of conflict foci”: power and control, trust and closeness, and respect and recognition. Do people think you’re trying to control, push away, or lessen them?
  The exercise suggests using the structure: “When I do/say [x], it means [this] and rarely [this]” to articulate these nuances, both for self-reflection and for sharing in the Keystone Conversation.

Exercise: Stressed Out

This exercise encourages mapping your typical response under stress, recognizing that the primitive brain and body react before the rational mind is fully aware. These reactions often fall into three main categories: fight, flight, or fix (Terry Real’s addition).

• Fight: Attacking, which can be loud/messy or cold/mean.
• Flight: Withdrawal, physical or walled-off/checked out (includes “freeze”).
• Fix: “Rescuer mode,” taking all responsibility, often with self-immolation.
• Go beyond the labels to describe specifically how you act when stressed: Do you ghost, behave passively aggressively, get paralyzed, lash out, blame, become “stupid” or quiet, or try to escape the spotlight?
  Mutually sharing this information in a Keystone Conversation can be incredibly valuable. It allows both parties to notice the other’s stress response (“Huh, they’re in ‘fix-it’ mode”), name it (“I’m noticing…”), and inquire about it (“Is there anything stressing you out right now?”). This awareness helps prevent misinterpretation and exacerbation of issues when relationships are already dented.

Key Takeaways

“How to Work with (Almost) Anyone” fundamentally argues that our success and happiness are intrinsically tied to the quality of our working relationships, and that leaving these to chance is a missed opportunity. The book’s core lesson is that we can and should intentionally design and manage these relationships to make them safe, vital, and repairable. The Keystone Conversation, guided by five powerful questions, is the essential tool for initiating this transformation. It’s a courageous act of vulnerability and curiosity that establishes shared responsibility, grants permission for ongoing dialogue about relational health, and fosters a deeper, more nuanced understanding of each other. Furthermore, MBS stresses that this is not a one-time event; consistent maintenance, grounded in principles of curiosity, vulnerability, and kindness, alongside timely adjustments, repairs, and resets, is critical for keeping Best Possible Relationships alive and thriving amidst inevitable challenges.

Next Actions:

• Identify Your BPR Person: Immediately choose one key working relationship you want to improve, using the “build your own” menu provided in the book.
• Prepare Your Answers: Dedicate time to thoroughly answer the five Keystone Conversation questions for your chosen BPR person. Use the core exercises and consider the deeper “Know Your Stuff” prompts to gain profound self-awareness.
• Make the Invitation: Be brave and take the first step to invite your BPR person to this conversation. Be clear about its purpose and what you hope to achieve, emphasizing mutual benefit.

Reflection Prompts:

• Which of your current working relationships would most benefit from a Keystone Conversation, and what specific challenge are you hoping to address by initiating it?
• Considering your own “Amplify” and “Bad Date” insights, what is one “strength” you tend to hide, and one “villainous move” you sometimes resort to under stress? How might acknowledging these, both to yourself and (carefully) to others, change your relational dynamics?