This is based on an internal quip doc I wrote up about careful communication in the context of rebuilding trust. I got a couple requests to turn it into a blog post for sharing purposes; here you go.🌈✨🥂

In this doc I mention Christine, my wonderful, brilliant cofounder and CEO, and the time (years ago) when our relationship had broken down completely, forcing us to rebuild our trust from the ground up.

(Cofounder relationships can be hard. They are a lot like marriages; in their difficulty and intensity, yes, but also in that when you’re doing it with the right person, it’s all worth it. 💜)

Tips for Careful Communication

When a relationship has very little trust, you tend to interpret everything someone says in the worst possible light, or you may hear hostility, contempt, or dismissiveness where none exists. On the other side of the exchange, the conversation becomes a minefield, where it feels like everything you say gets misinterpreted or turned against you no matter how careful you are trying to be. This can turn into a death spiral of trust where every interaction ends up with each of you hardening against each other a little more and filing away ever more wounds and slights. 💔

Yet you HAVE to communicate in order to work together! You have to be able to ask for things and give feedback.

The way trust gets rebuilt is by ✨small, positive interactions✨. If you’re in a trust hole, you can’t hear them clearly, and they can’t hear you (or your intent) clearly. So you have to bend over backwards to overcommunicate and overcompensate.

There are lots of books out there on how to talk about hard topics. (We actually include a copy of “Crucial Conversations” in every new employee packet.) They are all pretty darn cheesy, but it’s worth reading at least one of them.

I’m not going to try and cover all of that territory. What follows is a very subjective list of tactics that worked for Christine and me when we were digging our way out of a massive trust deficit. Power dynamics can admittedly make things more difficult, but the mechanics are the same.

Acknowledge it is hard beforehand:

“I want to say something, but I am having a hard time with it.”

“I have something to say, but I don’t know how you’ll take it.”

“I need to tell you something and I am anxious about your reaction.”

What this does: forces you to slow down and be intentional about the words you’re going to use. It gives the other person a heads up that this was hard for you to say. Most of all, it shows that you do care about their feelings, and are trying to do your best for them (even if you whiff the landing).

… or check in afterwards.

“I’m not sure how that came across. Is there a better way I could have phrased it?”

“In my head that sounded like a compliment…how did you hear it?”

“Did that sound overly critical? I’m not trying to dwell on the past, but I could use your help in figuring out a better way.”

It’s okay if it’s minutes or hours or days later; if it’s still eating at you, ✨clear the fucking air.✨

Speak tentatively.

“Speak tentatively” is the exact opposite of the advice that people (especially women) tend to get in business. But it’s actually super helpful when the relationship is frayed because you are explicitly allowing that they may have a different perception, and making it safer to share it.

“From my perspective, it looks like these results might be missing some data… do you see the same thing?” opens the door for a friendly conversation based on concrete outcomes, whereas “You’re missing data” might sound accusatory and trigger fear and defensiveness.

Try to sound friendly.

Say “please” and “thank you” a lot. Add buffer words like “Hey there”, or “Good morning!” or “lol”. Even just using 🌱emojis🍃 will soften your response to an almost unsettling degree. This may seem almost insultingly simple, but it works. When trust is low, the lack of frills can easily be read as brusque or rude.

Take a breath.

If you are experiencing a physical panic response (sweating, heart racing, etc), announce that you need a few minutes before responding. Compose yourself. Firing off a reply while you are in fight-or-flight mode reliably leads to unintentional escalations.

If you need to take a few beats to read and process, take the time. But empty silence can also generate anxiety 🙂 so maybe say something to indicate “I’m listening, but I need a minute to absorb what you said”, or “I’m still processing”. (We often use “whoa…” as shorthand for this.)

(Alternately, if you find yourself really pissed, “whoa” becomes a great placeholder for yourself to get yourself under control 😬 before saying something you’ll regret having to deal with later.)

“The story in my head”.

When you are in a state where you are assuming the worst of someone and reading hostile intent into their words or actions, try to check yourself on those assumptions.

Repeat the words or behaviors back to them along with your interpretation, like: “The story in my head is that you asked me to send that status email because you don’t trust me to have done the work, or maybe even gathering evidence that I am not performing for a PIP.” This gives them the opportunity to reply and clarify what they actually meant.

Engineer positive interactions, even if you have to invent them.

Relationship experts say that there’s a magic ratio for happy, healthy relationships, which is at least five positive interactions for every one negative interaction. If you only interact with the people you have difficult relationships when you have something difficult to say, you are always going to dread it. Forever.

It might seem artificial at first, but look for chances to have any sort of positive interactions, and seize them.

Communicate positive intent.

In a low trust environment, you can assume everything you say will be read with a voice that is menacing, dismissive or sneering. It behooves you to pay extra attention to tone and voice, and to add extra words that overcommunicate your intended meaning. A neutral statement like “That number seems low”, or “Why is that number low?” will come out sounding brusque and accusatory, e.g. why isn’t that number growing? it’s your fault, you should know this, I blame you, you’re bad at your job. Not might: it will. Try to immunize your communication from distortion by saying things like,

“Hey, I know this just got dropped in your lap, but do you have any idea why this number is so low?”

“This number seems lower than usual. I’m wondering if it’s due to this other thing we tried. Do you have any better ideas?”

“I know it isn’t exactly in your wheel house, but can you help me understand this?”

“I’m new to this system and still trying to figure out how it works. Should this number be going down like this?”

It may seem excessive and time consuming, but it will save you time and effort overall because you will have fewer miscommunications to debug. ☺️

Give people the opening to do better.

We tend to make up our minds about people very quickly, and see them through that lens from then on. It takes work to open our selves up again.

“Assume positive intent” is a laudable goal, but in practice falls short. If every word someone says sounds accusatory or patronizing to you, what are you supposed to do with that advice? Just pretend you don’t hear it, or tell yourself they mean well? That’s not sustainable; your anger will only build up.

But if you can hold just enough space for the idea that they might mean well, then you can give them the opportunity to clarify (and hopefully use different words next time). Like,

Person A: “Why is that number low?”

Person B: “I’m not sure.”


Person B: “…. Hey, sorry to interrupt, but the story in my head is that you think owning that number is part of my job, and now you’re upset with me, or you think I’m incompetent at my job.”

Person A: “OMG no, not at all. I’m just trying to figure out who understands this part of the system, since it seems like none of us do! 😃 Sorry for stressing you out!”

and maybe next time it will start off like…

Person A: “Hey, do you have any idea why this number is low? It’s a mystery … nobody I’ve talked to yet seems to know.” 🙂

Remember the handicaps, value the effort.

Ever meet someone you didn’t like online, and realize they’re terrific in person? Online communication loses sooooo much in transit. Christine and I know each other extremely well, and still sometimes we realize we’re reading way too much into each other’s written words. That’s when we try to remember to move it to “mouth words”, aka zoom or phone. Not as good as in person, but eons better than text.

Once you’ve met someone in person, it’s usually easier to read their written words in their voice, too.

Some people just aren’t great at written communication. Some people have neurodiversities that make it difficult for them to hear tone. Some people have English as a second language. And so on. Do give points for effort; if they’re trying, obviously, they care about your experience.

To the best of your ability, try to resist reading layers of meaning into textual communication; keep it simple, overcommunicate intent, and ask for clarity. And if someone is asking you for clarity, help them do a better job for you.

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