A Guide to Asking Better Questions - From the Archive

0:18Hey, this is interim producer Barshop 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.

0:58So 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 to you 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.

1:29I don't collect watches or cars. I collect questions. And so this podcast is all about some of the great questions from 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.

2:07I'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. Okay. These are slight improvements when you're talking to other people. So one of the worst questions, that's the most common question, is just, oh, hey, how's it going? Hey, how's your day? Right? 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.

2:46It words don't matter. It's just trying 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. You know, what'd you, what'd you have for breakfast? Or, 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 them talking. It was a genuine question and they start to open up a little bit more instead of just getting stuck in the cookie cutter, fine and good trap.

3:20Okay, what else? If you wanna 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 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, 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 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 thinking about vague, generic things that they like, they'll recall something specific that they do as a habit.

4:02And that'll actually tell you a lot about a person. They like to go hiking every Sunday with their friends or, you know, 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 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 going to 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.

4:33I 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? When will that get done? And people hate getting timelines. And there's just a generic problem with this. Some people will always sandbag. So they'll always say a long time and try to 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.

5:05And 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.

5:51Like 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.

6:22But 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 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.

6:58So 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, what's a con what's a conversation you've been avoiding? Ooh, 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, professionally, and we kind of put off dealing with it because we don't have to.

7:35The 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 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?

8:18Another one, I would say, I've asked this question out loud before, what would Suli do? I have a friend, Suli, 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. I 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?

8:51Or 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 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 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?

9:27What do I hate? And 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 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, the little water squirt gun game where you 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.

10:02And 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. I played a stupid game. And if you play a stupid game, you're going to 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 convince somebody to change their mind when it doesn't really matter. Convince people I'm right.

10:36That 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.

11:08Similar one that's a little bit kind of like self-help-y 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 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 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?

11:49This goes back to my phrase, inertia is a bitch. 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 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?

12:20We all have things that we're really cost 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. 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.

12:54And 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 a way to get to know somebody else. It's a 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.

13:25So go to seanpourri.com, just pop your email in there and 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, you know, 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 enjoy this mini episode. Let me know what you think. Tweet at me or email me. I'm Sean at SeanPourri.com. Hey, my first million listeners. This is Steph again from Trends.co.

13:55Now, 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 diverse framework, ideas are worth almost nothing and execution is everything. Great execution can take a brilliant idea from being worth$20 to$20 million. 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.

14:24Trends 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 100 deals in the pocket. So let me share a few highlights. We've got a deal of the month from SendEats, which is actually a trend success story. They raised their Series A at a$17 million valuation and they do e-commerce fulfillment. So they're basically e-com as a service. They're offering Trends members free storage fees for life, which means thousands of dollars a month saved. We also have one of Sean's very own unicorns, Deal, D-E-E-L. They have a deal of the month coming up, but for now, they're letting Trends subscribers manage contractors for three months free and then 20 % off and 20 % off full-time employee hires.

15:01We all know Sam loves a good cold email. One of the best tools I've used is hunter.io, allowing you to source professional email addresses, and they're giving you 30 % off. We also have Toucan, an investment of Sam's and my own. They are giving six months free of premium. We've got up to$50 ,000 in segment credits. And of course, we have a great HubSpot deal on the way. So if you want in on these deals, all you got to do is go to trends.co slash MFM. Trends.co slash MFM. We've got a special deal for you 50 bucks off at trends.co slash MFM. You can try all of this out for a buck. We'll see you on the inside.

15:39All 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. It's incredibly fascinating. I listen to it daily. So check it out. The Hustle Daily Show.

16:17All right. This episode is brought to you by Mercury. They are the finance platform of choice for over 200 ,000 companies. Shouldn't be surprised because I I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of. And then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder.

16:44It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to actually fix it himself. And really, any type of entrepreneur you are, let's say you're an agency, well, one of the things every agency has to do is be able to send invoices, easily create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show.

17:10For more information, check out Mercury.com. Mercury is a financial technology company, not a bank. Check show notes for details.