My First Million: A Guide to Asking Better Questions - From the Archive

Hey, this is Interim Producer, Bar Shop, and I'm going to be playing y'all an episode

from the archives.

This one is one of my all-time favorites.

It's Sean's guide to asking better questions, just tons of gems in this one, so I'll go

ahead and play it.

But just to note, I've included a worksheet in the show notes with all the questions Sean

lays out, so feel free to grab that below.

All right, enjoy the episode.

All right, I sat down to record this and I asked myself, what would be amazing?

What would be awesome if I was going to share it with you?

And I decided to pull something out of my secret stash.

So if you go to someone's house, imagine, you go to some billionaire's house, you walk

through the front door, the gate's open, the butler takes your coat, you walk through.

Somebody walks by with an hors d'oeuvres platter, you grab it, you like the tuna.

You keep walking forward and he says, oh, would you like to see my collection?

He said, my collection.

You don't know what it's going to be, shoes, watches, cars.

He takes you down into the cellar and he shows you the wine collection and starts talking

about it.

That's what I'm going to do right now.

I'm going to take you to my collection, but I don't collect wine.

I don't collect watches or cars.

I collect questions.

And so this podcast is all about some of the great questions for my question stash.

I have been keeping a notebook or a notepad of great questions because I have this phrase,

which is ask a better question, get a better answer.

And it's really come true for me in my life.

I've been able to connect with people or get to the heart of the issue or find out information

that I needed to find out just by asking a slightly different question.

It's kind of amazing.

Just phrasing things differently will have a totally different result.

So I'm going to go through rapid fire.

I'll try to keep this short.

So we'll go through rapid fire.

If people are interested, we could always talk more about this later.

But I'm going to go through quickly of some great questions.

So let's start with the lighthearted stuff.

These are slight improvements when you're talking to other people.

So one of the worst questions as the most common question is just, oh, hey, how's it

going?

Hey, how's your day?

And that results in fine, good, right?

And that's it.

Kind of a dead end question as far as I'm concerned.

So I like to frame things a little differently.

When I see somebody that I want to talk to for a meeting or whatever it is, I'll say something

just a little bit different.

It doesn't even matter.

The words don't matter.

I'm going to get to something specific that will get beyond the trap of fine or good.

So I might say, oh, you got a little pep in your step today.

What'd you have for breakfast?

Or you look happy.

What were you doing right before this?

So somebody could just pop on a Zoom and I'll hit them with that.

You look happy.

What were you doing before this?

Oh, actually, I was on a call with blah, blah, blah, blah, or I was actually just cooking

food.

It doesn't matter what it is.

I got them talking.

It was a genuine question.

And they just start to open up a little bit more instead of just getting stuck in the

cookie cutter, fine and good trap.

Okay.

What else?

If you want to get to know somebody, instead of saying, oh, what do you like to do?

And then they'll start to think about hobbies and just sort of say, generic, I like to travel.

Oh, I like the movies.

Of course, everybody likes the movies.

Instead, what I'll do is I'll say, I'll say, you know, I only ever see you at the office.

What's an ideal Friday night for you?

What do you like to do?

Right?

Take me through.

You wake up or take me through ideal Sunday morning, right?

And then people will start to tell me what they actually do in their life.

So instead of thinking about vague, generic things that they like, they'll recall something

specific that they do as a habit and that'll actually tell you a lot about a person.

They like to go hiking every Sunday with their friends or, you know, oh, I always, you know,

me and my daughter, we have this toothbrush routine and then we watch the cartoons and

I make her pancakes, whatever it is.

You'll get something real out of it.

Okay.

So those are some quick, lighthearted ones.

Let's go to work related.

Okay.

So here's some, and by the way, each one of these, I have a long list, but I'm just gonna

hop between categories.

Okay.

So work related.

I've said this one before on the pod, but one question many bosses and managers ask

is they're asking about a timeline for something.

I always did this.

I worked with engineers.

I don't know how long stuff takes to make.

Sometimes I thought things would be really complicated and they're like, oh, that's one

line of code.

And other times I thought things would be simple and they're like, that's six months of refactoring

code if you want that.

And so I used to always ask, when will we have this done, right?

When will that get done?

And people hate getting timelines and there's just a generic like problem with this.

Some people will always sandbag.

So they'll always say a long time and try to like deliver faster than that.

Some people want to make you happy so they tell you an optimistic timeline, but it always

ends up taking longer.

And so these things were so inaccurate.

So I heard a better question from Dan Clancy.

He's the chief product officer at Twitch when I was there.

And what he would say is, he goes, you know, I know we don't know the exact timeline, but

if I said that this was going to launch in August or September, what month would you

be surprised?

Oh man, we didn't launch it by then.

So he said, when would you be surprised if we didn't have this done?

And that created kind of like the first it got people's guard down.

They weren't being asked for an estimate in a traditional way.

The second thing is that they would take that and they would start to kind of like, like

when you would be surprised by it not being out means that's sort of like the bottom bar.

Like it's definitely going to be out by then.

And then he would, you know, follow up and say, okay, great.

And, you know, so best case scenario, what are you thinking?

Right.

And he would get a more accurate time range using that rather than just saying, when is

this going to be done?

So better question.

You got a better answer.

Some other questions I like to ask in the work context.

Sometimes I'll listen to people explain something and it's a really big, heavy plan and I'll

just say, man, all that sounds really hard.

What would be easy?

And this question annoys people because they're like, oh, if it was easy, I would have told

you.

But in reality, when you ask them and you ask them what would be easy, they actually do

come up with an answer that's pretty good.

Similarly, if somebody says a big plan like a long, like we're going to do this and then

this and then this, I'll say, oh, okay, like that sounds like a huge plan.

Like, you know, my brain, I'm not as smart as you.

So like, imagine we were all like that.

Imagine we all had half the IQ we have today.

What would be the dumb, simple plan we would do to make some progress?

And I'm trying to get them to think outside the box, think differently because people

get stuck in one track thinking and they have blinders on to all the other possibilities.

So I'm trying to just break that pattern and get them to see some other possibilities.

Some other ones, I will ask, you know, if I'm leading, if I manage somebody and they

manage people, I'll say, hey, you don't have to tell me this answer, but it's a good question

to ask yourself, what's a conversation you've been avoiding?

Oh, we're all avoiding some conversations, whether it's personal or professional.

Another one will be, I'll wake up in the morning and I'll think about work and I'll say, who

needs my help today?

Sometimes there's people in the company that are struggling, either personally or professionally,

and we kind of put off dealing with it because we don't have to.

The fire is not burning yet, the house is not burning down, but you kind of want to

address it when it's a little spark before the house burns down.

So who needs my help today?

Okay, let's go to self-talk, right?

The most important dialogue happens in our head.

And so, you know, here's some of the ones that I ask myself on a daily basis.

So this one's work-related, I'll say, if I could only work two hours today, but I still

wanted today to be a huge success, what would I do in those two hours?

This is a way of cutting through all the BS, all the busy work, the small things that are

easy to just eat up our time and just say, okay, if I really could only work for two

hours today, what would I work on for those two hours?

Another one, you know, I would say, I've asked this question out loud before, what would

Sully do?

I have a friend, Sully, who I think is just amazing at business.

He just has a knack for just finding the fastest path solution for just being like kind of

a PhD in common sense.

And so I just step back and say, what would Sully do?

Or similarly, if I'm talking to somebody else, I'll say, sounds like you're stuck and you

don't know what to do, but you've always given me great advice.

So what would you advise yourself in this situation?

If you were giving advice to yourself, what would you say?

If you weren't you, or I'll ask them, yeah, I know you don't know the answer, but if you

did know, if you did know the answer, what would you say?

People that really fucks people's minds, they don't know what to do with that one, but it

is actually pretty useful as a way to, again, shake their pattern, get them to think differently.

Questions I will ask myself, let's go back to this.

What are my anti-goals?

I can often think about what I want, but sometimes it's very useful to think about what I don't

want.

He used to talk about anti-goals, meaning instead of thinking about what's the perfect

life and how do I want to make my life better, he thinks about what's misery, what do I hate?

Let me just avoid misery, right?

Invert.

And just instead of thinking about what's the dream, think about, you know, what's, instead

of thinking about heaven, think about hell.

And then just make sure you avoid that.

You end up doing pretty well then.

A question I ask myself, another one I like here, I like this one.

Am I playing a stupid game?

Naval has this phrase, play stupid games, win stupid prizes, right?

If you're at a carnival and you go up to, you know, the little water squirt gun game

where you've got to squirt the water in the little hole and if you could do it the best

out of everybody, you know, you win the giant stuffed animal and then there you are, 40

minutes later, you've put $85 into this game and you win and you win the $6 stuffed animal

that you could have had to begin with.

And it's just a reminder, there are many examples of this.

I've done this many, many times.

I've worked on dumb startups, worked on dumb ideas, right?

I played a stupid game and if you play a stupid game, you're going to win a stupid prize.

So I tried to stop and ask myself, am I playing a stupid game?

An example of a stupid game is trying to win an argument on Twitter or convince somebody

to, you know, change their mind when it doesn't really matter.

You know, convince people I'm right.

That sort of thing is an example of a stupid game that you can play.

Another question to ask, is this the beginning or is this the end?

This is great for relationships.

You get into breakup, breakups are tough.

Is this the beginning or the end?

Feels like the end, but it's also the beginning and you got to ask yourself, if I treat this

like the end, then yeah, I'm going to feel a certain type of way, right?

I'm going to feel the way you feel at the end.

But if I view this as the beginning, I'm going to feel very differently.

So I got to ask myself, is this the beginning or the end?

They happen at the same time.

Another one that's a little bit kind of like self-help in that vein is, is that the thing

or am I the thing?

That's just a reminder of where is the power?

When a situation is overwhelming you, you're saying, oh, man, I'm making that the thing.

No, no, no, I'm the thing.

So you make it about yourself.

So if somebody else is acting in some way that you find stupid, are you making them

the thing or are you the thing?

It's about taking back control and being able to own parts that you control and control

your own experience that way.

Another one for work that I like is, if I wasn't already doing this, would I do this?

This goes back to my phrase, inertia is a bitch.

When you're, a lot of times the things that we are doing, we're only doing because we

were already doing them.

So it's worth having an honest question.

I wasn't already doing this, would I be doing this?

If I wasn't already in this job, would I be in the, would I apply for this job?

If I wasn't dating this person, would I ask them out on a date?

So you want to avoid doing things that you wouldn't do if you weren't already doing them.

And I'll leave you with a couple more that I think are fun.

I like to ask this for myself and for others, which is like, what's something you're happy

to overspend on?

We all have things that we're really conscious about, we're really frugal, we penny pinch.

We have other things that we're willing to splurge on.

So what am I happy to overspend on?

I always pick this, for me, this was books.

I will always buy a book instantaneously, whether I plan to read it or not.

Whether I have money or not, I will always buy a book because that's sort of a potential

knowledge, a potential life change that I could have for 10 bucks.

And socks, socks is another one.

I hate fussing with having mismatched socks or not enough socks.

So I will overspend on socks.

I will buy 100 of my favorite pair of socks.

And then when those are done, I'll just buy 100 more.

I'm happy to overspend.

It just gives me joy.

And so similarly, it's way too good to know somebody else.

It's a good way to get to know yourself and to get to know somebody else.

What are they willing to stupidly overspend on?

Even though they know it's maybe not the best, most logical solution.

Okay. Those were some rapid fire questions from my question stash.

I don't know if this is entertaining to you.

I don't know if that was helpful to you, but I will publish that on my newsletter.

If you subscribe, you'll get the written version of that because those are probably

hard to remember.

So go to SeanPurri.com.

Just pop your email in there and I'll put it in.

I'll put it into the welcome sequence where I put just a list,

a little question bank of some of my favorite questions.

I don't give you all of them.

These are precious.

I've been hunting these for a long time, but I will give you whatever,

20, 25 of these that I really like.

Ask a better question, get a better answer.

All right. That's all for me.

Hope you enjoyed this mini episode.

Let me know what you think.

Tweet at me or email me.

I'm Sean at SeanPurri.com.

Hey, my first million listeners.

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But anyone that's run a business before knows that ideas only get you so far.

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Alright everyone, that's the end of my first million.

However, I've got good news.

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we actually have another podcast.

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Machine-generated transcript that may contain inaccuracies.