468: How to Ask Better Questions
The Startup Chat with Steli and Hiten
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Full episode transcript -

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Hey, everybody, this is still UFT and this is eating choc. And today in the set up, we're gonna talk about how to learn out, ask better questions. You like talking about more than your sales and market. We just want a bullshit and chat about business and life. Hopefully, while we're doing that, provide along value to the business for people trying to get shit way. Don't want to give you feedback. That's bullshit. You want you to do your best. So here's the deal on this episode heating and why I wanted to talk to you about this I am. The last two weeks have been a number of different workshops and events, and for whatever reason,

I had piled on a ton of coaching sessions, and now I'm done for the year. So that's great. But one thing that I noticed in the last weeks of just interacting with a ton off founders and doing some deal coaching with him. So asking those founders to tell me about a customer deal they're currently trying to close there in the middle of negotiation that may not be going well over there might be some questions of how to make this happen. One thing that I noticed doing this with many different founders in many different countries is that the common denominator of the source of everybody's problems when it comes to closing a customer deal. And I'm sure not just that the core problem for a lot of things is that these people and most people just don't ask enough questions that they don't ask the right questions. So they inevitably find themselves in a position where they have to guess what is going on because they never took the time to ask the right questions and get the information and context needed to know what's going on. Does it sound familiar? I assume that you witnessed this pattern yourself many, many times before.

1:56

Yeah, I think in general people tend to assume a lot of things and as a result of making a bunch of assumptions, what ends up happening is they operate without actually checking in on what kind of is really going on or what's happening or checking in on some of the assumptions they have. So, you know, one way to think about this is like we run around the world, kind of assuming things based on our own sort of opinion, And it's not necessarily the right way to think about interacting with people on getting stuff done. Simply because if somebody says, I think we need to grow our business and you know we need to get more sign up, you can assume a lot of things about that, even something like even that specific. So if someone said we need to do our business, you can assume, Oh, we need to grow revenue. If they didn't tell you about a sign up thinking their head,

you could ask him, Well, what do you mean by that? And I know that's like a really simple question, but it could be a simple of that. So to me, asking questions helps you gain a common understanding that you might not have if you're making assumptions about what the other person needs when they say something,

3:9

I love that because that really points to the heart of the issue. I think that most of us are not really aware of how we interpret or parse language, and in many ways, in order for language to be practical, we are at all times in need of adding a ton of information to make sense, quote unquote of what somebody is telling us. And so we're constantly adding pieces and bits of information that is missing from the language, those sentences that somebody's communicated to us and that can be useful in order, just speed things up. But it can be very detrimental when you really want to understand 100% what the other person needs, right? So even if I say a simple sentence like, you know, I bought a house last week. Now that sentence sounds perfectly fine. Most people will not be confused by that, but your brain is to add a lot of information to make sense of this sense because it's not complete.

I bought with what money? What money? What currency? US dollars? Euros slot is like. I didn't specify any of this. Maybe I bought it with something else than money, right? It could maybe equity my company or something else, but we just because it would slows down to explain everything in such detail. You, you know, hear me and think you understand me because your brain added a lot of information that's contextual for you. I bought from whom the owner, like, you know,

Was it? It rose at the State Police Department. This is from a ex convict like there's a lot of things that aren't in the sentence. I bought a house last week, but we add a ton of information that is lacking within the sentence to make sense of it. Now, when it comes to situations of high importance, we tried to understand, you know, people that work with you when you're trying to understand people you're trying to hire. When you're trying to understand your customers, you don't want to just be interpreting everything they say because a lot of your interpretations just gonna be wrong, right? Somebody telling you a police send us three proposals is not giving you enough context to understand why. Three. What are you gonna do with those proposals,

What you're trying to accomplish? What do you want to see in those purples? Others propose is gonna be compared with competitors proposals, you know, like there's so much more to know. And this is just one of the examples of people there was asking and most ponders when they talked to a prospect. Eventually, the prospect says a 73 proposals. They just go cool. Sounds good. They hang up and they go. Well, I'll have to do is to get the three proposals and and then hope for the best when I hit sent. But I really you're really missing so much information. Like what? What is really happening?

What is really the purpose in the gold here? And you know what's fascinating heating is that we've all at least had to learn at some point in school how to read, write and speak. But I've never heard of anybody ever taken a class in asking questions and active listening. This really know nothing. Nobody that's teaching us and ask the questions and how to actively listen. So we elicit the correct and complete information from the person is communicating to us.

6:27

Yeah, it's kind of ridiculous since because you can get away with a lot if you're just asking a lot of you know, a lot of questions and get away meaning like you can understand almost anything pretty much anything. If you're just able to figure out what's the right question to ask me for me, it's like I'm not an engineer. I don't not a code and attend to, like, have great conversations of engineers just because I'm able to ask them good questions. And that helps me understand how to help them, because usually they're efforts lead to different choices and options that lead to different things that cause our product to be a certain way. And if I don't understand what they're dealing with, especially when they're coming to me and needing to make a trade off, I don't know how to ask questions, and we can go down the wrong path for months are even longer something So for me, like it's this learning that if I don't figure out how to ask good questions, said whoever about whatever they're coming to me with or whatever I'm going to them with, then basically what happens is I don't get the best outcome,

and that means we in a company as a team don't get the best outcome. There's one other part of this that I find really fascinating. That is more like from a relationship interpersonal relationship sort of standpoint, which is like even someone who you've known for a long time, you might not really understand where they're coming from when they say something and you could make assumptions about what they're saying. So if, for example, someone says I could only meet for two hours, right? And and maybe you want to be longer, you know, you can ask them or you can tell them Hey, I'd like to meet longer and tell them I'd like to me for three hours, right? This is just one example is actually an example from a few weeks ago on, Instead of saying that I actually just said like,

Oh, can you help me understand what you're constraints are? No. Why? Why? It's only two hours Because usually when we meet, it's not constraint like that. So I'm just curious, like you know what's different or what's going through your head. And that opened up the conversation, and I actually got a much deeper level of understanding about the person and how they think about their time and their time with me. That was, like completely amazing just because I asked, instead of trying to say, Hey, I want to be longer,

anything like that, just like a Why is it to out what's going up right? And I even gave my context, which is like Sometimes we talk. It takes a while, right? So I come in with no expectation of how long are not. And so I just love to understand because because maybe we might take longer right? And then it turned into a great combo about just understanding where that person was coming from. So I think that's just a example. But it really matters, even in interpersonal kind of relationships and things that you're trying to figure out on seemingly like obvious things where you could just respond right? I just responded. I would like to be longer right? Instead, I was like, Well, what's up like? Looks different.

9:33

I love that. So there's an episode I want to recommend to people if you have not heard it yet, Even if you heard it, it's been a while. So you might want Toe Goto Episode 225 off the sort of chat to 25 listening skills for solid founders. We talk a little bit about this subject there. Here's one thing that I want to highlight here. There's gonna be a bunch of people listen, just this one hidden good. Think this sounds good. I probably could improve. In what questions? I asked how many questions I asked, but how do I improve this? Like, how did you guys get good at this? Why do you do this a lot?

When did you learn this? Who did you learn it from? You know the first. Yeah, first at this point. And I'll say, you know, I never I don't think I've ever read a book about this. I never went to a seminar workshop. There's not a one person. Probably that I can point to is like this person really influenced me on this. But I do think that, you know, for me, I've learned asking a ton of questions first, as I was kind of entering the world of selling and entrepreneurship,

and it was trying to convince people off purchasing my product or my services. I think I In the beginning, my framework was always that selling is probably just talking. So let's just talk a lot and hopefully one of the many things you say who will convince people and then, you know, I realized that you know, the person it's talking is not really in control of the conversation and really the core. The core way of really guiding a conversation and having no control of it is to ask questions. And I think studying and we had we have episodes about this as well. Studying hypnosis really helped me a lot with this because it was when I started studying hypnosis. We did an episode, I think, Episode 93. What's hypnosis? One on one? And a lot of people have told me that they really didn't want to listen to that one.

But it was not to be one of their favorite episodes, but, uh, like many things in life, the easier really turned off by might have a big value somewhere hidden below the surface, waiting for you. But hypnosis? What's interesting to me? Because I really started studying language and understanding, kind of how language works. And even the little comment that I made at the beginning of this episode off understanding how much information is missing from a typical sentence. And hypnotic language patterns are all about using very, you know, making language even less clear and concrete in ways that influences the brain in the subconscious mind in a certain way so playing with that topic and reading and experiencing and learning more about it. Talk me Ah, lot about how much information is missing from a typical conversation.

And it made me a lot more where, when I want to zero in and elicit more information through asking more questions versus when it's fine to leave, things kind of a bit blurry because if you try to really understand every sentence and every person perfectly, it would just slow things down to almost a whole. But I think that those things really help me. I don't know if this is practical for people that out that they want to learn how to ask better questions. But maybe the one heck a lot and with my side on this is a piece of advice I've given and we have given in many different other situations with which is just surround yourself with people that are great at this. Just ask yourself who is the best listener I know who is the person that I know that asks the best questions and just spend more time with that person. When you interact with that person, try to understand how that person is interacting and communicating with you versus just communicating with them. And if you have more people in your life that asked Mawr and really, really great questions, it is going to influence you. It's gonna rub off on you. It's gonna teach you how to do that yourself as well.

13:22

Yeah, I started asking good questions because people were asking me bad questions. E think a really a really good example is when you were raising money for kiss metrics for the first round. What did you do? How'd it go? I'm like, Are you trying to raise money? How much, Uh, you know, what do you have like? So I started asking questions because I was like, Wait, that's not really a good question to ask me, because whatever I did is likely not going to be what you need to do. And that's a pretty simple example, cause,

like, I'd meet with people and they were like, really interesting raising money. I think another thing that is a little bit of a side note but really fascinating is that if you've done something, people normally try to bucket you. So the amount of introductions I get to anything that's analytics related or marketing related is really interesting because people think, Are you built a bunch of analytics companies or you you've been in marketing or whatever, and when they when they come to me, most people get intro like that. They're being very specific about what I did instead of asking me about what they should do and so that just help me get better asking questions because I wanted to be as hopeful as I could be to them. And I didn't need to sit here and repeat my story because it wasn't what they wanted. It's not actually what they needed, even though they asked it like that. So I would say that's an example of what I would call a bad question. Don't. If you're looking for advice or helping something,

don't ask people what they did gave them your situation and ask them for, uh, kind of what they would do in your situation and you'll things will turn out better in terms of the value you get from them. Uh, for me, my co founder, Marie, is really good at asking really good question and a lot of them, too. And so when something comes up. Her first reaction tends to be asking a lot of questions. So that has helped me a lot about asking questions were also one giving advice. Ah, bunch topping it and then working with their has taught me, and especially when it comes, like different business type of things that we're doing.

One thing it's also done as a side effect is it's made me actually go more thorough before I present something to her. Because I can anticipate the question she's gonna ask. I'm not thinking like, Oh, she's gonna ask these 10 questions. I'm just like, you know what? I'm just gonna go toe a little bit of extra level that I might normally, because if I do that, then she could ask even better questions, and that enables us to get to the same place faster. Uh, same place mean getting aligned or making a really great decision about something. And I only do that with, like, things that I think are really important.

The other thing I learned and this is more on someone who I would say on my end, I wasn't actually as good at answering questions that she would bring up in the beginning is I would just tell her like I don't know the answer to that yet. And here's when I think that answer might be important. Or, you know, that's a really good question. I don't know, let me go find out. So it was even being able to respond to questions like that has been really helpful to. So I think there's a back and forth of being able to answer questions and also being able to ask them. That has been really helpful, like you said, by being around someone who's actually really get it. Both of those things

16:36

beautiful all right. There is really true power behind asking one, asking better questions. I think we all have probably a life in front of us of the, you know, continues improvement on this. I don't think that anybody is like grated it, but people are, like less added it than others. So there's definitely a lot more to learn, even for for us and I. Hopefully this inspired a bunch of you the guys that are listening to spend more time and more attention in practice this and and invest morning because so many problems so many challenges could have been solved if you only ask the right questions earlier. So that's it from us for this episode with you very soon later.

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