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How to communicate with empathy and collaboration


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We've all been in unproductive conversations, unproductive meetings, unproductive arguments where no one can agree and everyone seems to be talking past each other. When you're mired within these situations it can seem like there is no clear way out, like the only way out is for everyone to acquiesce or fall in line.

Sometimes this is true but most of the time it isn't. Learning How to communicate with empathy and collaboration can help prevent and overcome these conversational roadblocks.

This essay is not about agreement or how to convince someone to your way of thinking. This essay is about working to remove the frustrating obstacles that get in the way of understanding.

What is the point of this type of communication?

to act as the connective sinew between people and ideas

to facilitate forward movement

Why Empathy and Collaboration

For any disagreement to be resolved everyone at the table needs to feel heard. By talking past each other, not listening to each other, or not agreeing on the base reality of the topic discussions are at an impasse and agreement is impossible. The only outcomes are spinning wheels or acquiescence.

It's quite simple to lose sight of this. To solve this a readjustment of priorities is necessary. Empathy is what drives this.

Empathy: understanding what is driving a person, accepting it, and often saying that subtext aloud. “The beauty of empathy is that it doesn’t demand that you agree with the other person’s ideas.”

This isn't necessarily massive insights (though if you have them they can be helpful)

Collaboration is the half of this. All productive conversations are joint endeavors and it's important to hold that ideal as a core belief. It's not me vs you, it's you and me versus the problem.

Collaboration: A sense of connectivity, of mutual purpose.

Where is this information coming from?

I've always been able to do this and understood how important this type of communication is. Only recently have I started to more closely examine the how's, why's and minutia that can course correct a floundering disagreement. I have compiled an incomplete of the various books that I have helped put words to and shape this process. You can see my list of

and further reading below.

It's also important to keep in mind that doing this in real time during an argument or a meeting is high-stakes conversational jujitsu. It takes practice and many many failures for it to be seamless but by breaking apart the practice into component parts each element can practiced individually and combined later.

This is something I used extensively when I was a musician. By taking apart a complex piece of music you can begin to understand each moving part and how it relates to the whole.


Nothing comes from nothing.

This is your starting point. Agreement can only come from common ground and can only move forward once each party accepts the base reality of a conversation.

( By base reality here I don't mean the laws of physics I am talking about a common agreed upon foundation of facts that can be built upon. )

At its essence that's what this type of communication tries to do; explicitly establish a base reality for a conversation. This typically needs to be done at several scales; at a macro-level for the entire conversation and continuously at a micro-level for individual points of a conversation

Remove the self

If we want to act to forge connection the first step is to completely remove the self. Whatever's happening is not about you and has everything to do with the people around you. Don't think. The more you think the more you insert yourself.

Playing both connector and arguer is often times to much

Practically how do you remove the self

removing the self is different from removing yourself. You want to stay a part of the conversation but one without a personal stake. The easiest way to do that is to stop using 'I' or 'me'.

> “the word “I” gets people’s guard up. When you say “I,” it says you’re more interested in yourself than the other person, and it makes you take personal responsibility for the words that follow—and the offense they might cause. But when you phrase a label as a neutral statement of understanding, it encourages your counterpart to be responsive.” .float-right Book/Never Split the Difference

When you stop using those words it becomes easier to stop thinking about your opinion on the matter. Your opinion can come later, first we need to debug this conversation.

Don't know what to say without using 'I' or 'me'? Try these phrases

"What you seem to be saying..."

"It sounds like . . ."

“It seems like . . .:

"It looks like . . .”

Relearn how to listen.

However good you think you are at listening, you're most likely wrong. Listening is a full body skill. Agreement and disagreement is not only in literal vocal agreement. How something is phrased can be a clue into what drove the person to say it.

I really don't know how to teach this digitally. I learned just how in-depth listening can be while learning improv at the Upright Citizens Brigade in NYC. The next best thing to doing improv is watching improv so as an exercise when you have some time give this video a watch.

Pay special attention to the start of each new two person scene. One person initiates the scene with an idea, and the other person listens to understand the new world they have just walked into. The look for all kinds of clues about who the other person is, what kind of personality they have, where they are, what they are doing, what their relationship is, and even who they are themselves.

This is a particularly difficult skill to teach digitally where no ears are involved :P

Quick trick to allow yourself to listen easier: When you have something you want to say it's easy to fixate on that and not actually hear what the other person is saying. Cross your fingers behind your back or out of sight to give you a physical reminder of what you wanted to say. This can free up your brain to focus back on what the other person is saying.

Project backwards to move forwards

Every conversation contains within itself many universes. To work to connect those universes is to constantly wake up into worlds that already exist.

To find common ground you must be able or at least try to intuit where a person is leading and where they are coming from, the reasons behind the words.

Very often disagreements aren't about the actual topic you are discussing. Maybe that person got burned on the deadline for their last project. Maybe they have more in their plate than than can handle. If you can find that unspoken root concern and bring it to light ( or get the other person to bring it to light ) you can work as a group to address them. The best compromises leave everyone equal parts happy and {{or: frustrated. |tense.}}

Take three steps back

How do you do this? Taking your observations ( word choice, body language ) and what you know about a person ( demeanor, disposition ) and ask yourself:

"If this then what?"

If you know what a person has said take your observations and guess what would cause them to say that

This can be overwhelming, especially in the midst of a rapid fire disagreement, but it doesn't have to be done for every single sentence. You only need to take all of what they're saying, maybe one or two of their points.

When you do this for both sides of an argument you can begin to see the {{or: points of disconnect |suppositions}} and how each party is missing the other.

🚧 Don't assume you know what they are saying

🚧 This section is very incomplete but and cribs pretty heavily from Book/Never Split the Difference 🚧

If clarification is needed be a mirror, repeat the 3 critical words or phrase of their position as a question and then wait

This isn't a battle of opinions it's a process of discovery

Pay attention to your body language and subtly mirror the body language of who you are talking to

Book/Never Split the Difference calls this 'Tactical Empathy' which feels a bit cynical to me. This type of empathy doesn't have to be artificial or some kind of rehearsed conversation tic. It can act as a natural extension of an inquisitive and questioning attitude.

Don't understand their position, label it

So you've done all this excellent mental work removing yourself, listening, projecting backwards and forwards but you still haven't actually said anything. Congratulations the mental stuff is the hard part so now it's time to check your work.

Approach each conversation like an explorer. Start to label what you've observed phrased as a question and remember to keep "I" and "me" out of it

" You seem to be hesitant to commit to a new phase of the project"

"It looks like you don't see this strategy as a viable way forward"

"It sounds like you want C to come before A because you believe..."

Asking these questions is extremely important. It gets the other person to start thinking critically about what they're actually saying and starts to foster explanation. Honestly sometimes just asking the question can be enough to get people {{or: reoriented towards agreement | back to the same side}}

🚧 Look for moments of understanding

🚧This section is very incomplete🚧

probe for clarification and compare to what the other is saying

use 'processing silence' to postulate more potential middle ground

don't be afraid to tell them to wait if someone jumps to a conclusion

A quick observation on productivity:

Understanding people is hard. Understanding communication isn't.

I only intervene when I know two people are 'speaking past each other'. The chaos streams of ideation should be messy and they need to be separated from actual decision making. Everyone can't have equal input at every stage. I've found that conversational bridges are most helpful when they are built in the first-most stages of a project/conversation.

At some point a decision needs to be made. You're not facilitating complete agreement you're working to make sure everyone understands what the other is actually saying so that a more informed decision can be made.

🚧 Remote Decision Making and ___

🚧This section is very incomplete🚧

Breakout groups, breakout groups, breakout groups

make mini decision {{or: cabals |groups}} with autonomy

Remote decision making relies more heavily on

trust from the top

everyone speaking up and voicing concerns

Lay out an argument

be confident in your choice and have reasons for why the other option has disadvantages

the most difficult situations are stylistic differences. Differences of opinion where both options are objectively equally valid

"Listening is the willingness to change."

Questions yet to answer

in a Zoom call with a team, how do we know decisions are made already, or if they are just ideas thrown in the air?

I think this is, in part, a respect thing. You have to trust that your teammate has made a good decision and respect their autonomy even if you disagree.

I think that's on the presenter to signal

It's fine to entertain alternate options or to present alternate ways of approaching a problem but the 'best' way is often subjective so it will ultimately fall on the decision maker. When working with a group I often think about who 'owns' a decision. I can't do everything. Even if I believe that I would do the task better than the other group members I have to trust in my teammates.

I can present an alternate way of looking at something or inquire if they have considered a specific option but I can't micromanage their decisions.

On the flip side if the decision is significant enough then we will all have buy in

Where in the decision hierarchy does this fall?

What is absolute and what is not?

Stop talking about it and make a decision.

I'm a decisive person

if the group is talking in circles

Once a decision is made it doesn't need to be remade unless new information has been presented

Be careful not to nickle-and-dime

How strong do you feel your objection is?

How can I prime others to signal if they are giving a decision or a suggestion?

hmm that's an interesting one also kind of weird

are they a decision maker

how we can move past 'middle ground' into something that will be good for one party and 'manageable/commit-able' for the other?

I have no clue here...

Drawings that would be useful

Conversational illustrations

Professional Communication

In my experience this needs to run on your backburner all throughout a meeting. You can be seen as dead weight if you're not engaged and contributing to a meeting beyond this.

It's also not always needed!

The first step is identifying a miscommunication

you're talking about x in relation to y and they're talking about x in relation to z

listen for pauses in speech and hesitation

push back on something small typical is related to something else

Casual Communication

I have put considerably less thought into using these techniques in casual conversation between friends and acquaintances. I think this is because contention and disagreement are far more common in the professional world.

Do I have less experience with this or have I invested less thought?

Perhaps it's more intuitive?


What's the difference between

Professional Communication

is goal oriented and a whole lot easier. A commonality of intent makes communication more straightforward

is far more murky. A lot more work needs to be done on your part to bridge the gap of commonality. Most people don't want to debate or come to common ground. Not for selfish reasons but because wanting to discuss is a very specific mindset

This is all gathered from many in-person meetings, zoom meetings like all zoom activities are more difficult. Body language is harder to determine when all you can see is a person's head

Group dynamics are delicate things and they've always felt like physical actions to me. Lobbing a rock or keeping a volleyball up in the air. That's what good conversation is like. This isn't about how to have good conversation though, this is about about to connect a conversation, which in my experience leads to much more boring but productive conversations.

New Questions to consider

va8GzJ27L where one says 'move this a tiny bit there', 'change the wording to this' → 'ok how about this?' - the final product is completely different from both people's expectations and potentially end up 20% worst than it was before

This is something I've dealt with a lot at work, I think anyone in a creative field has to deal with this.

First it depends on who is asking for the changes

Client Requests small changes

CoWorker Requests small changes

You want to avoid being creatively "nickel and dime'd" while allow for iterative work.

Being "nickel and dime'd" is hyper focused on a single aspect of a project without a cohesive view of everything that is going on

For someone's mind to be changed requires persistence (bringing up the issues while dancing the line of disrespect)

Let your ideas be nimble and easily to pivot. Holding on to a specific idea usually isn't productive in a group design situation