How to Work with (Almost) Anyone: Five Questions for Building the Best Possible Relationships - By Michael Bungay Stanier

Date read: 2025-06-22
How strongly I recommend it: 8/10
(See my list of 150+ books, for more.)

Go to the Amazon page for details and reviews.

Focused on change management and how to improve relationships, good advice on how asking the right questions can help improve building relationships. Very short and easy read to digest.

My Notes

Here’s how you use the Keystone Conversation to start building a Best Possible Relationship. First, prepare by asking yourself the five essential questions:

The Amplify Question: What’s your best?
The Steady Question: What are your practices and preferences?
The Good Date Question: What can you learn from successful past relationships?
The Bad Date Question: What can you learn from frustrating past relationships?
The Repair Question: How will you fix it when things go wrong?

THE AMPLIFY QUESTION
What’s your best? It asks you to name what creates your peak moments, your talents, what you love to do and are good at, and when you tend to shine.

A powerful outcome of this exercise is to be able to say in the Keystone Conversation: “I’m good at this... and I don’t love doing it.” To do this exercise, you tease apart “good at” and “fulfilled by.” Work with a two-by-two matrix—a box with a cross separating it into four equal spaces. One axis is I’m Good At (low to high), the other I’m Fulfilled By (also low to high). Consider your key responsibilities and most common day-to-day tasks and assign them to the appropriate box.

THE STEADY QUESTION
A popular approach to building working relationships with others is the “Read Me” document (aka user manual). The idea is that you fill out your Ways of Doing Things and then send it out to people. “If I were an IKEA bookshelf,” the promise is, “then this is how you’d assemble me for minimum wobble and maximum Nordic aesthetic.”

THE GOOD DATE QUESTION
So, start this exercise by celebrating the other person’s role in the success of the relationship:

What did they say (and also not say)? What words made a difference?
What did they do (and also not do)? What actions elevated and nurtured the relationship?
How did they “be”? What qualities did they exhibit that added to the goodness of what was there?

Now that you’ve given them due credit, take the credit that’s yours to claim. Don’t be overly modest here. The relationship was so good in part because of the way you showed up:

What did you say (and also not say)? What were your well-measured words?
What did you do (and also 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 you both put your best foot forward?

What about the context gave this relationship the best chance to flourish? Who else played a role? • Which moment tested the relationship, a test that you successfully managed? What light does that shed?

THE BAD DATE QUESTION
Let’s start with you taking your share of the “credit” for the mess:

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

How did the other party contribute to the mess?:

What did they say (and also not say)? What got you angry or frustrated or sad?
What did they do (and also not do)? What actions set things back?
How did they “be”? What qualities did they exhibit that, frankly, sucked?

What do you notice here about the context?:

What about the context made this odds-against? What other people played a role?
Which moment tested the relationship, a moment you failed to navigate and that was particularly damaging? What light does that shed?

THE REPAIR QUESTION
Name what’s happening: Surface the unspoken; name what’s going on for you:

Stay curious: Breathe rather than react; stay open; examine your defensiveness and your righteousness; remember they’re human too.
Remember the goal: Understand what “winning” means; hold on to the idea of the Best Possible Relationship; let go of “being right.”
Seek understanding: Listen fully so they feel heard; tease apart fact and data from opinion and judgment.
De-escalate: Introduce lightness and grace; own your statements (less “you did...” and more “I make up that...”); turn down the heat.
Rebuild: Make the first move to reconnect; reframe it away from “you versus me”; apologize.

KEYSTONE CONVERSATION
Wherever you are in the arc of a working relationship, consider pausing the current action and inviting that other person to a Keystone Conversation.

Explain what the Keystone Conversation is, either in person or in writing, and that the point is to give you both the best chance of a successful working relationship.

Example of what to say: "Let’s chat about how we work together before we talk about what we’re working on."

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:

What’s your best?
What are your practices and preferences?
What can we learn from successful past relationships?
What can we learn from frustrating past relationships?
How will we fix it when things go wrong?

Creating a Safe Space for the Conversation: The location of the conversation (whether it’s formal or informal; whether it’s in “your” space or theirs or somewhere neutral):

How curious you are (asking questions; asking, “And what else?” after their first answers).
Your own level of sharing and vulnerability (my rule of thumb is that you answer every question you ask of the other person, sharing the messy and hard, not just the shiny and good).
The extent to which you co-create the conversation with the other person (asking them what they’d like to ask about; checking if there’s anything that needs to be said that hasn’t yet been said).

Example of what to say: "What do you want from this conversation? What would make it most helpful for you? Here’s what I want."

The Keystone Conversation belongs to the same family as those two formats. Nothing needs to be solved. You’re sharing information that’s useful, true, and heartfelt. You’re listening with intent and seeking to understand.

Examples of things to say:

I’m curious to hear your answer to this.
And what else?
Here’s how I’d answer that.
Here’s a hard question, but I think it’s helpful for us to answer it.
What needs to be said that hasn’t yet been said?

Wrapping up or closing a Keystone Conversation: Set a precedent of making every conversation with you a learning one. Ask, “What was most useful here for you?”

SIX PRINCIPLES OF MAINTENANCE

Stay Curious
Stay Vulnerable - Share what’s useful for the Best Possible Relationship. Be open-handed.

Assume positive intent. Be generous. Remember that you’re both committed to the Best Possible Relationship, and you can be kind to them and kind to yourself as you navigate that. Be open-hearted.

Adjust Always - Conditions shift in relationships, and you need to adjust to what the moment requires.

Reset as Needed - A BPR with any longevity will need some moments of reset to keep it safe and vital.
But before You Act, Orient - When you notice the swirl going on in your mind and heart, you can gain a calmer and more nuanced understanding of what’s true by teasing apart the dynamics and sorting them into four buckets:
1. The data. These are the facts you can point at and say: this is true, this is a thing, this happened.
2. Judgments, also known as suggestions, points of view, interpretations, readings of the situation, advice, and “good ideas.”
  
  In a single situation you’ll have opinions about three different factors: the other person (“They are...”), you and your role in this (“I am...”), and the situation as a whole (“This is...”).
3. Your feelings - Mad, sad, glad, ashamed, and afraid. Ironically, any sentence you utter that begins “I feel that...” is most likely a judgment.
4. What you want - At a practical level, it can mean asking for what you want, knowing that the answer might be no.

When you feel overwhelmed by a situation, pause, and break it into these four buckets. This discipline helps you understand what’s true and what’s being made up about what’s true.

You don’t need to know what’s wrong. You need to name that something might be wrong. “I’m noticing something feels off. What’s up?” “What needs to be said that hasn’t yet been said?”

Ask yourself which role you are most comfortable playing, the role you most often default to. Is there one you aspire to? What role might the other person most usefully play?

In this exercise, notice a few of your key work habits, and use them as a springboard to backfill the story of what you’ve learned, where you learned it, and why you decided that it was important.

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?

Your answers can make you more curious about the gap between intentions and the perception of actions, both yours and others.

Contents:

My Notes