Transcript

A Guide to Asking Better Questions - From the Archive

I feel like I can rule the world, I know I could be what I want to I put my all in it like my day's off On the roadless travel never looking back Hey. This is Interim Producer.

Par shot. And I'm gonna be playing y'all an episode from the archives. This one is uh one of my all time favorites. It's Sean's Guide to Asking Better Questions. Um 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. Alright, I sat down to record this and I asked myself

What would be Amazing. What would be awesome if I was gonna share it with you? And I decided to pull something out. Of my secret stash. So you know

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 You know, 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?

You don't know what it's gonna be. Shoes, watches, cars. He takes you down into the cellar and he shows you the wine collection and starts talking to you about it. That's what I'm gonna do right now. I'm gonna 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 uh note.

Yeah, 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 gonna 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 about this later, but I'm gonna go through quickly of some great questions. So let's start with the lighthearted stuff, okay? These are slight improvements when you're talking to other people. So one of the worst questions that's the most common question. It's just

Oh hey, how's it going? Hey, how's your day? Right. And that results in Fine.

Good. Right. And that's it. Uh 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, um, that you know, we we for a meeting or whatever it is. I'll say something, you know, just a little bit different. It doesn't even matter, like the words don't matter. It's just trying to get to something specific. that will get beyond the the trap of fine or good. So I might say Uh you got a little pep in your step today. You know, what'd you what'd you have for breakfast?

More. Um You look happy. What were you doing right before this? Right. 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 or oh I was actually just cooking food.

Doesn't matter what it is. I got him talking. It was a genuine question. And uh they to start to open up a little bit more instead of just getting stuck in the uh 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 like hobbies and just sort of say generically, I like to travel, oh I like the movies. Course, everybody likes the movies. Um instead what I'll do is I'll say I'll say um You know, I I only ever see you at the office. Um, what's an ideal Friday night for you? What do you like to do?

Right. Take me through ideal 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 for Th thinking about Vague, generic

Things that they like. They'll recall something specific that they do as a 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 teeth brush 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 of the things that we're going to Quick light hearted ones. Let's go to um work related. Okay, so here's some

And I 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. Uh 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, you know, when 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 uh Dan Clanter. He's this He's the uh ch I don't know, chief product officer at Twitch when I was there. And what he would say is He goes, um

You know, I know we don't know the exact timeline, but When would you uh what w if if I said that this was gonna 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 was just that created kind of like the

First it got people's guard down. They weren't being asked for an estimate. Um in in the traditional way. The second thing is that they would take that and they would start to um 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 gonna be out by then. Um, and then he would, you know, follow up and say Okay, great. And uh 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 gonna be done? So better question, you got a better answer. Uh 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. Uh similarly, if somebody says a big plan, like a long like we're gonna do this and then this and then this. I'll say um Oh okay, like That sounds like a huge plan? Like it what

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.

Uh some other ones I will ask. Um You know, if I'm leading if I'm if I manage somebody and they manage people, I'll say uh Hey, you don't have to tell me this answer. But it's a good question to ask yourself.

Uh what's a c what's a conver what's a conversation you've been avoiding? Mm. 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? Oftentimes there's people in the company that are struggling, either personally or professionally. And we kinda put off dealing with it because we don't have to. The fire's not burning yet. The house is not burning down. But you kinda wanna 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

Um dialogue you know happens in our head. And so you know, here's some of the ones that I ask myself on a daily basis. So the this one's work related. I'll say um 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 or easy to just eat up our time and just say, Okay, if I really could only work for two hours today, what would be what would I work on for those two hours? Um Another one, you know, I would say I I've asked this question out loud before.

What would Sulli do? I have a friend Sully who I think is just amazing at business. He just has a knack for Just finding the the the the fastest path solution for just being like kind of a PhD in common sense. And so I just step back. I said, What would Psuli do? Or similarly, if I'm talking to somebody else, I'll say, um

Sounds like you're stuck and you don't know what to do. Um, 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 if you weren't you Or I'll 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 that really fucks people's uh fucks people's minds. They don't know what to do with that one. But it it is actually pretty useful as a way to again. Shake their pattern, get them to think differently. Um Questions I will ask uh Ask myself, let's go back to this.

Um, 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. I learned this from Andrew Wilkinson. He he used to Talk about anti goals, meaning Instead of thinking about what's the perfect life and how do I wanna make my life better, he thinks about what's misery, what do I hate? And let me just avoid misery, right? Invert. And just instead of thinking about what's the dream.

Think about Yeah, what's instead of thinking about heaven, think about hell. And uh and then just make sure you avoid that. And you end up doing pretty well then. Um A question I asked 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.

little water squirt gun game where you gotta squirt the water into a little hole and if if you could do it the best out of everybody, you know, you win the giant stuffed animal and then There you are. Forty minutes later, you've put eighty five dollars into this game. And you win and you win the six dollar stuffed animal that you could had to begin with. And um this 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 gonna win a stupid prize. So I try 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 uh convince somebody to you know change their mind.

Um when it doesn't really matter. You know, convince people I'm right. Um That that sort of thing is a is an example of a stupid game uh that you can play. Um Another question to ask.

Is this the beginning or is this the end? This is great for relationships. You get in a breakup. Breakups are tough. Is this the beginning or the end? Feels like the end. But it's also the beginning and you gotta ask yourself.

If I treat this like the end, then yeah, I'm gonna feel a certain type of way, right? I'm gonna feel the way you feel at the end. But if I view this as the beginning, I'm gonna feel very differently. So I gotta ask myself, is this the beginning or the end? They happen at the same time. Um, similar one that's a little bit kind of like self helpy 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 as if somebody else is acting In some way that you find stupid. Are you making that 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 it control your own experience that way. Um, 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. And so it's worth having an honest question. If 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? Uh right. So so You wanna avoid doing things that you wouldn't do.

If you weren't already doing that. And I'll leave you with a couple more that I think are are fun. Um, I like to ask this for myself and for others, which is like, what's something you're happy to overspend on? Right. We all have things that were really

cost conscious about, really fruitful. We penny pinch. We have other things that we're willing to splurge on. So what am I happy to overspend on, right? I always pick this from for me, this was books. I 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'cause that's sort of a potential knowledge, a potential life change that I could have.

For ten bucks. And um Socks. Socks is another one. I hate fussing with having Mismatch socks or not enough socks. So I will overspend on socks. I will buy

a hundred of my favorite pair of socks. And then when they're those are done, I'll just buy a hundred more. I'm happy to overspend. It just gives me joy. And so similarly, it's a way to get 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? Uh, even though they know it's maybe not the The best, most logical solution. Okay. Uh 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 uh I will publish that on my my newsletter. If you uh if you subscribe, you'll get the written version of that,'cause those are probably Hard to remember. So uh go to go to SeanPuri dot com. Just pop your email in there and I'll put it in uh

I'll put it into the welcome sequence where I Put up just a 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, you know, whatever, twenty, twenty five of these that I really like

Ask a better question, get a better answer. All right. That's all for me. Hope you enjoy this mini episode. Let me know what you think. Tweet at me or email me. I'm Sean at SeanPurry.com. Hey, my first million listeners. This is Steph again from trends.co. Now, most of you probably know trends as the idea newsletter because that's what we do. We send you business ideas weekly and then we show you how to capitalize on them. But anyone that's run a business before knows that ideas only get you so far. In fact, if you've ever heard of Derek Sever's framework, ideas are worth almost nothing and execution is everything. Great execution can take a brilliant idea from being worth twenty dollars to twenty million dollars. But that's exactly why we're investing in making trends a product for not just idea generators, but operators. And we've built a new feature called Trends Deals. Trend subscribers now get exclusive deals that make it easier and cheaper for them to run their businesses. We launched this month and already have around a hundred deals in the pocket. So let me share a few highlights.

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Mm-hmm. I feel like I can root Well I know I can be what I want to I put my law in it like my day's off On the road less travel never looking back All right, everyone, that's the end of my first million. However, I've got good news. You see, if you liked this episode, we actually have another podcast. The Hustle has another podcast. It's called The Hustle Daily Show. It's a daily podcast that has everything you need to know about business and tech in only a few minutes. It's awesome. Our best writers like Zach Crockett are behind it.

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