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What are your thoughts?

Walk me through^ that v (upward-downward inflection)

If you knew you were going to have to lose and have to relearn all the knowledge you've accumulated, but were granted a few things to keep, what would you keep?

If you had to go back to day 1 with only 1 piece of knowledge you have now that you didn't have before, what would it be?

What did you do early on, that if you didn't do, things could have turned out way different?

What was your biggest time waster day 1?

Is this the beginning or the end?

Beliefs

What evidence from the past can I point to to prove this as demonstrably false?

What actions can I take to prove the validity of this belief?

What assumptions are being made in this belief?

Can you absolutely know that this is true?

Who would you be without this belief?

What are you really committed to?

Am I allowing another person to have control of me and my actions?

Why do you think that?

If your life depended on overcoming this obstacle, what would you do?

How important to you is _______, have your actions reflected that?

What have you missed out on in life because of your belief?

What will you miss out on in life because of your belief?

What is the unfortunate future that is approaching if you continue to hold on to this belief?

What actions do you take regularly that contributes to this belief?

What would you have to give up if you overcame this belief?

What would you gain if you overcame this belief?

Rules
What unspoken rule/s of yours would you be breaking if you did __________
where do you think that rule might have come from?
What do you think was the original purpose behind the rule?
How does that rule apply now?

What are your thoughts

Why this way?

Why is that?

Why ________  {repeat what they just said}

Business Problem Identification
What’s the biggest existential threat to this business? 
What are the things that keep you up at night?
What is the metaphorical crater coming to ruin your business?
What are the most recent examples of things the company has tried and failed at?
What were the single best and worst days/weeks in Instacart's journey?
What are some of the key financial metrics that the company optimizes for?
What are the things that absolutely delight your customers?
What are the things that are hard for you but table stakes for your customer?
How do you enable your customers to win?
What are the top three customers that you’ve won, and the top three customers that you’ve lost?
Which companies does the leadership admire and hope to emulate? Why?
What’s most important in your next role?
What area of the business would you say this company is behind on, given its stage?
If you had a magic wand, what would you change about the company?
What’s something that would only happen here but wouldn’t at other organizations?
How have you changed during your time here?
When you’ve done your best work here, what about the culture has enabled you to do that?
Has the company ever made a decision that prioritized its values over revenue?
What common attributes have you found among people who join and are successful, versus those who aren't?
What are the top reasons that people have left the company of their own volition?
Can you tell me about your founding team’s background and why you’re tackling this particular problem?
 If I asked your investors what they're worried about, what would they say?
What's the hardest piece of feedback you've received, and what's the hardest feedback you've given?
How would your team describe you?
If after 12 months I’ve failed, where did we go wrong?
What will separate someone who is good at this job from someone who is really stellar?
Think back on a really great experience that you had with the last person who previously held this role. Why was it so great?

5 Conversation Questions
Who/What/Why are you seeking
What do expect
How have things gone in the past
How would others describe your situation
What do you ultimately want

Use this before making an important decision

What am I doing or planning to do that I feel is right to do in the moment but I know from learning or past experience that it's actually the wrong thing to do.

What's the easiest thing I can do right now to lower the chance I can get distracted?

What do you make of...?

“Do these problems surprise you at all?”

How can {value prop} be impactful for your organization

A good question response to any question: 
Who wants to know / who would find that important / from who's perspective?

When you bring up that objection, is it because you’re trying to kill the idea, or trying to strengthen it?

10 Sales Questions to Build, Quantify, and Grow Business Pain
What are the challenges you're facing that you'd regret not solving in six months?
Why would you regret not solving that in six months?
What challenge is going on in your business that's driving that to be a priority?
What metric is suffering most as a result of that challenge?
What's driving you to solve this now rather than later?
Is this the challenge that ranks most highly on your priority list?
Can you walk me through the ripple effects this challenge is having on the rest of the business?
Who else does this challenge impact? How does it impact them?
How much would you estimate this challenge costs the business?
What impact does this challenge have on other parts of the business

Life Changing Probing Prompts

Starred

Dunk (exclude from study)

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Review Questions

Todos

Sensemaker