1/ Here’s a list of conversational frameworks I’ve picked up that have been helpful.

Please add your own.

2/ The Magic Question: "What would need to be true for you to...X?"

3/ On evaluating where someone’s head is at regarding a topic they are being wishy-washy about or delaying.

“Gun to the head—what would you decide now?”

“Fast forward 6 months after your sabbatical--how would you decide: what criteria is most important to you?”
4/ Other Q’s re: decisions:

“Putting aside a list of pros/cons, what’s the *one* reason you’re doing this?” “Why is that the most important reason?”

“What’s end-game here?”

“What does success look like in a world where you pick that path?”
5/ When listening, after empathizing, and wanting to help them make their own decisions without imposing your world view:

“What would the best version of yourself do”?
6/ When someone asks you a personal or vulnerable question and you don’t yet have an answer, although you want to answer soon:

“The Quakers have this idea where you don’t speak unless the spirit moves you. I'm waiting for the spirit to move me.”

h/t a friend
7/ When someone confronts you w/ a problem they have with you

A/ Thanks for sharing because I value this relationship + want both of us to get needs met
B/ What I heard was X (summary)-- was that accurate?
C/ How can I contribute to meeting your needs?
8/ When really angry:

“….” Don't’ say anything!

Take a lap. Or cold shower. Workout. Change your mind state before re-entering the conversation
9/ When really angry during the heat of the moment:

“....” Still don’t say anything!

Ask for a pause: “Do you mind if we take a quick break and return tonight? I want to make sure I can fully listen to your story + appreciate where you are coming from.”

That last part is key.
10/ When giving unsolicited feedback

“…” Probably best not to.

Unless you ask the caveat: "Are you interested in hearing feedback?"
11/ When confronting somebody:

Instead of “Why did you do that?”

Maybe: “What was going on for you?”
12/ Discovering ambition:

“If you had a billion dollars what would you do with

a) the money
b) your time”?

This shows where they want to change society and what they truly want to be doing.
13/ "What was your past manager (or friend) like?"

This determines how they'll talk about you in the future--whether they'll view you in a charitable light or not.
14/ When rambling with nowhere to go:

“I’m going to pause right there for reactions”

15/ in group meetings when two people are talking about something unrelated:

“Let’s take this offline”.
16/ When assessing VC/founder alignment in an VC pitch:

“Why not bootstrap it so you can control your own destiny and have more optionality over selling for 50m, 100m?”

Also just a good question for every founder to ask themselves.
17/ Note: conversational frameworks are effective when coming from a genuine place of wanting mutual benefit--seeking win-win.

18/ When someone asks a somewhat vague Q:

"What's the question behind the question?"

Most Liked Replies

Jen Choi:
When you’re not sure of the direction / approach you want to go in...

“What’s the problem I am trying to solve for?”

The right approach will tie directly to answering the problem statement.
'last day on earth. The person you are meets the person you could have become. Are you proud?'
Eric Friedman:
Working backwards, what do you want to have accomplished by the end

“What are the takeaways you want from your talk”

“What do you want to look back on at the end of next year and have done”

Another fav
“What does the press release for this product look like after launch”
Ben Longstaff:
assume we are a fit, what are the steps to get into production and who has to be involved to sign off on each step?

what similar deals have you done in the last 12 months and how long did they take?
jonathan poma:
Additionally and alternatively, after someone communicates something to you, responding with “Alright, what I heard you say was ___xx___. Sometimes I miss the mark, so please let me know if you feel my interpretation was accurate or not?”
Eric Friedman:
“If we had 5 mins left, what would you want to have had covered” gets to the meat earlier
jonathan poma:
After thinking you’ve expressed your point clearly, asking the recipient: “Alright, now what did you hear me say.” As a way to pursue actual (not feigned) alignment + commitment.
Steve Simitzis Ⓥ:
“What would you do if you were me?” has been a good one when asking for advice. Sometimes people will reflect back a balanced pros and cons list for each option, mostly to be polite. This gives people permission to open up and express their honest preferences.
"When's the latest I can get this to you that it would still be valuable?"

Unveiling the real deadline, not the idealistic/selfish one.
Natalie Cernecka:
When faced with a 'No', ask a solution-based question :
What about this does not work for you?
What would you need to make it work?
It seems there is something here that bothers you...
(courtesy of @VossNegotiation )

More from Erik Torenberg

1/“What would need to be true for you to….X”

Why is this the most powerful question you can ask when attempting to reach an agreement with another human being or organization?

A thread, co-written by @deanmbrody:

2/ First, “X” could be lots of things. Examples: What would need to be true for you to

- “Feel it's in our best interest for me to be CMO"
- “Feel that we’re in a good place as a company”
- “Feel that we’re on the same page”
- “Feel that we both got what we wanted from this deal

3/ Normally, we aren’t that direct. Example from startup/VC land:

Founders leave VC meetings thinking that every VC will invest, but they rarely do.

Worse over, the founders don’t know what they need to do in order to be fundable.

4/ So why should you ask the magic Q?

To get clarity.

You want to know where you stand, and what it takes to get what you want in a way that also gets them what they want.

It also holds them (mentally) accountable once the thing they need becomes true.

5/ Staying in the context of soliciting investors, the question is “what would need to be true for you to want to invest (or partner with us on this journey, etc)?”

Multiple responses to this question are likely to deliver a positive result.


1/ Some initial thoughts on personal moats:

Like company moats, your personal moat should be a competitive advantage that is not only durable—it should also compound over time.

Characteristics of a personal moat below:

2/ Like a company moat, you want to build career capital while you sleep.

As Andrew Chen noted:

3/ You don’t want to build a competitive advantage that is fleeting or that will get commoditized

Things that might get commoditized over time (some longer than

4/ Before the arrival of recorded music, what used to be scarce was the actual music itself — required an in-person artist.

After recorded music, the music itself became abundant and what became scarce was curation, distribution, and self space.

5/ Similarly, in careers, what used to be (more) scarce were things like ideas, money, and exclusive relationships.

In the internet economy, what has become scarce are things like specific knowledge, rare & valuable skills, and great reputations.

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