The Looking Glass: All the world is made of trust

That, and faith, and pixie dust.

Dear readers,

I used to think the glittering prize of a hard-fought battle, of a well-played game, was winning.

But winning what, exactly?

Was it the glory, the pride, the winner’s identity? Was it the smug satisfaction of rightness? Was it the cha-ching of the bank account, was it the compliments scattered in my face like petals?

Here’s what I want to win now: trust.

This essay is adapted from a letter I sent to my team at Sundial.

Warmly,

~Julie

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A definition of trust

Let me posit something both stupidly simple and outrageous — trust makes the world go round. Our team will be nothing without it.

Because it is so fundamental, so life-giving. I want to excavate and understand it deeply.

Let me offer first a definition for trust:

Trust: the belief that “This person will fulfill my hopes for his/her behavior in this specific context.”

Right away from this definition, we can see that trust is a relational idea. It exists between me and you, and it exists within some particular context.

If I trust you to tackle Problem X, I am saying that I believe you will do what it takes to find a solution to Problem X that fulfills the criteria I have in mind.

If I say “I trust you with my life” and we are in a high-speed car chase, I am saying that I believe you are a capable enough driver and that you care deeply enough about me to ensure I don’t die.

Why does trust matter?

Trust matters because everything would be painfully inefficient without it.

Imagine you and I are complete strangers, plucked from the lottery of life by alien forces that conspires to bring us together for an important task—making an apple pie. How will we go about this?

Since we don’t know anything about each other, I will start with an empty trust bank for you. I have no idea what you are capable of, or what you care about. Many doubts flit through my mind, like:

• Do you even know what an apple pie is?

• Do you know the ingredients in apple pie?

• Do we know where to get these ingredients?

• Do you know the tools we need?

• Do you care at all about this task?

• Do you do what you say you will?

• Are you capable of operating an oven?

• Can you handle slicing apples?

• Do we agree on the right proportion of these ingredients?

• Do we agree on the distribution of tasks between us?

• … and so forth and so on

Getting signal on this entire list of questions will take time. Some of the above I can try to get at through conversation (for example, asking you in a friendly manner about your familiarity with apple pie / ingredients / tools / etc).

But a bunch of these I can’t know without seeing you in action. For example, I can’t know whether you’re a person of your word until you show me you are. Until then, the jury’s still out and I’ll need to observe you carefully.

Contrast this with making apple pie with a sibling. It’s probably going to be way more efficient. Why?

For one thing, we can assume shared knowledge. My sister knows what apple pie is, what the ingredients are, where to get those supplies in the kitchen, etc. We don’t have to spend time talking about that.

For another, I have a deeper understanding of my sister’s skills and experience. I know that she can handle an oven. I know she’s diligent, so she will measure the right proportion of ingredients. I don’t have to monitor the process.

For my sister and I to make apple pie together, we don’t need to say anything more than “You prepare the filling and I’ll do the crust,” especially if we’ve done this task before together. In the rare instances where we need to exchange words, it’s on the salient differences, like “Are you feeling nutmeg today?” Or “How sweet should this pie be?”

Trust is the lubricant against the friction of human collaboration.

Nothing could happen quickly and efficiently in this world without some levels of trust. Everything would quickly spiral into constant surveillance and the discussion of minutiae.

Trust is contextual

Recall my proposed definition of trust — “This person will fulfill my hopes for his/her behavior in this specific context.”

This specific context is incredibly important to call out. I might say to my roommate, “Why don’t you order our dinners for the next week? I trust you,” and what I am specifically saying is “I believe you to be responsible enough to remember to put in a daily dinner order, and I believe that what you choose will be acceptable to me.”

I am NOT saying that I now trust my roommate to: a) drive my car b) complete my coding task c) keep my secrets, d) … a million other things.

Not trusting him to drive my car or complete my coding task doesn’t mean I don’t like my roommate, or that I don’t respect him. Trusting someone in some specific context can be completely orthogonal to my like or admiration for them.

This may seem obvious in my example above, but it’s nuanced in the day-to-day.

For example, I have enormous respect and like for my colleagues on Team X. Given what I know about them, I believe they will make better decisions than me in many contexts. I believe they will make worse decisions than me in some contexts. I suspect they feel the same way about me.

In fact, everyone should feel the same about me. For example if I popped into a production support channel and said “Data pipeline issue can be solved with this PR, please review,” you should be skeptical and monitor my work very, very closely. You should not think to yourself, “Because I trust Julie to write a blog post, I’ll automatically trust her to fix our data pipeline issues.”

Same goes for you. If you earn my trust in being an expert on brand and color, it does not mean you’ve earned my trust in front-end implementation, or even in a different design domain like onboarding usability. Even if you trust in your own skills, I might not — we all have blind spots after all.

For example, I thought I was a pretty capable and experienced manager when I started Sundial, and I’m sure many folks trusted me in that capacity, but it turns out I was only decent in the context of being an exec at a particular, in-person, large tech company. I was actually terrible within this new context of a start-up that is remote and cross-cultural!

Luckily, realizing I was terrible was the first step to getting better.

That is why it’s our job to hold up mirrors for one another — feedback helps us see ourselves more clearly.

The 3 ingredients for trust

For me to trust you to make a decision or take an action, I will have to check 3 boxes in my head:

1. You have the intent — we should be aligned on the outcome we want. In our cooking example, I have to believe that you care about making a delicious apple pie.

2. You have the skill to do the task — the thing I am asking you to do is something you are capable of doing well. With apple pie, these skills include: measuring ingredients, peeling and coring apples, operating an open. Another way to think of skill, especially in high-ambiguity areas like product sense or systems thinking, is “How high-quality is your decision model?”

3. You have the necessary context — you have all the crucial information to do the job well. In our apple pie example, knowing what apple pie is, where we should get the ingredients, how much to make, how sweet it should be, to whom or what occasion it should be served for, etc.

If I want the best pie of my life, I won’t ask my husband — while he’s perfectly capable and knowledgable about apple pies, he doesn’t particularly care for baking; I won’t ask my 5-year-old — while he loves apple pies and is eager to help in the kitchen, he can’t operate an oven; and I won’t ask my mother, because while she’s happy to help and skilled at baking Chinese goodies, she’s not familiar with western desserts.

I find this breakdown useful because “I don’t trust you to do X” should not automatically translate to: “I think you are immoral or unintelligent” (although that is what many of us on the receiving end might instinctively feel.)

I may not trust you to do X because I suspect how you see success and how I see success differ. This is so typical in a workplace setting because we are different people, perhaps working on different teams with different goals.

My primary goal as a designer might be “ship an excellent user experience”; your primary goal as an engineer might be to “ship quickly and with high performance and very few bugs.” This does not mean either of us are bad people! In fact, we can probably agree that both of these aspirations are noble and good; the nuance comes from exactly how we trade things off.

I may also not trust you to do X because you don’t have the context. Let’s say you are an excellent sales person, way more charismatic and persuasive than me, and we need to try and close a sale. However, I am the person who knows the most about this particular customer — their problem space, the way they think, our past conversations with them. Who should handle the sales conversation? You have the upper hand in skill, but I have more context. Again, this is not a judgement on your talents or worth as an individual!

Breaking down trust into its 3 components — intent, skill, and context — allows us to have a deeper conversation about exactly why we do or don’t trust each other on some specific task.

Shared intent matters tremendously

Of the 3 ingredients for building trust — shared intent, the right skills, and the necessary context — shared intent is the most important to explicitly align on.

When I trust your intent, I can come up with many generous interpretations to the inevitable bumps or mistakes that will pop up. When I am wary of your intent, I will feel the need to scrutinize your every decision, even if they seem good on the surface.

Usually when people say “I trust you” this is a shorthand for saying “I trust you care about me and have my best interests at heart.” It’s enormously connective to know that we matter to others!

In a company setting, shared intent should be a given. After all, we both want our company to succeed.

Alas, the challenge lies in how narrowly we define out intent. For example, because we both work at Company X, I of course care deeply about X succeeding, same as you. But as a front-end engineer, I might also care deeply about producing high-quality sustainable front-end code. Meanwhile, you, as customer success manager, may care deeply about responding to a client ask quickly. We may clash over these misaligned intents — speed to new feature, or sustainable code?

We may start feeling suspicious that the other party does not care as much as we do about our precious intent! Imagine that arguments of the variety of “new feature vs. sustainable code” flares up every two weeks or so. After a few months, worn out by the constant clashing, we may start to develop an “us vs. them” mentality. We may feel a growing urgency that we are Right in our intent, and that that they are WRONG!