MFM Mini - A Guide to Asking Better Questions

**Shaan** (0:16)
All right, 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? He said, 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, he 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 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. 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. 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, you know, for a meeting or whatever it is, I'll say something, you know, just a little bit different. It doesn't even matter. The 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, you got a little pep in your step today. You know, what'd you have for breakfast?
Or, you look happy. What were you doing right before this?

**Steph** (2:32)
Right?

**Shaan** (2:32)
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, 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. 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 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. 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 about vague, generic things that they like, they will recall something specific that they do as a habit, and that will 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. 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 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. 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 the 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 follow up and say, okay, great. And 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?