Today on The Startup Chat, Steli and Hiten talk about how to ask better questions.

Asking questions is the best way to understand or gain deeper insights about anything or anyone at any time. Unfortunately, most founders don’t do it.

In today’s episode of the show, Steli and Hiten talk about the importance of asking questions, how asking questions helps you gain a common understanding, how to improve your questioning skills and much more.

Time Stamped Show Notes:

00:00 About today’s topic

00:35 Why this topic was chosen.

02:29 How people tend to make a lot of assumptions.

03:01 How asking questions helps you gain a common understanding.

05:00 Why you need to ask a lot of questions.

05:50 How you can miss a lot of information if you don’t ask enough questions.

06:31 How active listening is super important.

04:43 How Hiten is able to help people by asking them questions.

10:38 How to improve your questioning skills.

3 Key Points:

  • Most people just don’t ask enough questions. 
  • People tend to assume a lot of things.
  • Asking questions helps you gain a common understanding.


Steli Efti: Hey everybody, this is Steli Efti.


Hiten Shah: And this is Hiten Shah.


Steli Efti: And today on the Startup Chat we’re going to talk about how to learn how to ask better questions. Here’s the deal on this episode Hiten, and why I wanted to talk to you about this. The last two weeks I’ve been a number of different workshops and events and I’ve, for whatever reason, I 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 two weeks, of just interacting with a ton of founders and doing some deal coaching with them. Asking those founders to tell me about a customer deal they’re currently trying to close, they’re in the middle of a negotiation that may or may not be going well or 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, it’s the core problem for a lot of things is that these people and most people just don’t ask enough questions and 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 that sound familiar? I assume that you have witnessed this pattern yourself many, many times before?


Hiten Shah: 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 those assumptions they have. One way to think about this is, 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 and getting stuff done. Simply because if somebody says, “I think we need to grow our business and we need to get more signups.” You can assume a lot of things about that. Even something like even that specific. If someone said, “Oh we need to go our business,” you can assume, oh we need to grow revenue if they didn’t tell you about the signup thing in their head. You could ask them, “Well what do you mean by that?” And I know that’s a really simple question, but it could be as simple as that. 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 means when they say something.


Steli Efti: 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 are constantly adding pieces and bits of information that is missing from the language, those sentences that somebody’s communicating to us. And that can be useful in order to speed things up. But it can be very detrimental when you really want to understand 100% what the other person needs. Even if I say a simple sentence like, “I bought a house last week.” Now that sentence sounds perfectly fine. Most people will not be confused by that, but your brain has to add a lot of information to make sense of this sentence because it’s not complete. I bought with what? Money? What money? What currency? US dollars? Euros? Zlotys? I didn’t specify any of this. Maybe a bought it with something else than money. It could may be equity in my company or something else. But we just, because it would slow us down to explain everything in such detail, you hear me and think you understand me because your brain added a lot of information that’s contextual for you. Bought from whom? The owner? Was it the state? The police department? Is this from a ex-convict? 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 that sentence to make sense of it. Now, when it comes to situations of high importance, where you’re trying to understand 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 interpretation is just going to be wrong. Somebody telling you, “Hey, please send us three proposals,” is not giving you enough context to understand why three? What are you going to do with those proposals? What are you’re trying to accomplish? What do you want to see in those proposals? Others’ proposals going to be compared with competitors’ proposals? There’s so much more to know and this is just one of the examples of people that I was asking. And most founders when they talk to a prospect and eventually the prospect says, “Hey, send me three proposals.” They just go, “Cool, sounds good.” They hang up and they go, “Whoa, all I have to do the three proposals and then hope for the best when I hit send.” But really, you’re really missing so much information. What is really happening? What is really the purpose and the goal here? And what’s fascinating Hiten 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 taking a class in asking questions and active listening. There’s really nobody that’s teaching us how to ask good questions and how to actively listen so we elicit the correct and complete information from the person that’s communicating to us.


Hiten Shah: Yeah, it’s kind of ridiculous because you can get away with a lot if you’re just asking a lot of questions. And get away meaning you can understand almost anything, pretty much anything if you’re just able to figure out what’s the right question to ask. For me it’s I’m not an engineer. I don’t know how to code and I tend to have great conversations with engineers just because I’m able to ask them good questions. And that helps me understand how to help them because usually their 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, then we can go down the wrong path for months or even longer sometimes. For me, it’s this learning that if I don’t figure out how to ask good questions to 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 from a relationship, interpersonal relationship sort of standpoint, which is 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. If for example, someone says, “I can only meet for two hours,” and maybe you want to meet longer. You can ask them or you can tell them, “Hey, I’d like to meet longer,” and tell them, “I’d like to meet for three hours.” This is just an example. It’s actually an example from a few weeks ago for me. And instead I’m saying that I actually just said, “Oh, can you help me understand what your constraints are? Why it’s only two hours. Because usually when we meet it’s not constrained like that. I’m just curious, 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 completely amazing just because I asked instead of trying to say, “Hey I want to meet longer,” or anything like that. I was just like, “Hey, why is it two hours? What’s going on?” And I even gave my context, which is sometimes when we talk it takes a while. And I come in with no expectation of how long or not. And so I’d just love to understand because maybe we might take longer. And then it turned into a great convo about just understanding where that person was coming from. I think that’s just an example, but it really matters even in interpersonal kind of relationships and things that you’re trying to figure out on seemingly obvious things where you could just respond. I could just respond to say, “I’d like to meet longer.” Instead I was like, “Whoa, What’s up? What’s different?”


Steli Efti: I love that. There’s an episode I want to recommend to people if you’ve not heard it yet, even if you heard it, it’s been a while. You might want to go to episode 225 of the Startup Chat. 225, listening skills for startup founders. We talk a little bit about this subject there. Here’s one thing that I want to highlight here. There’s going to be a bunch of people listening to us at this point Hiten, that think this sounds good. I probably could improve in what questions I ask and how many questions I ask, but how do I improve this? 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? I’ll go first. I’ll go first at this point and I’ll say, 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 as this person really influenced me on this. But I do think that for me, I’ve learned asking a ton of questions first as I was kind of entering the world of selling and entrepreneurship and I was trying to convince people of purchasing my product or my services. I think in the beginning my framework was always that selling is probably just talking. Let’s just talk a lot and hopefully one of the many things you say will convince people. And then, I realized that, the person that’s talking is not really in control of the conversation. And really the core way of really guiding a conversation and having more control over it is to ask questions. And then I think studying, and we have episodes about this as well. Studying hypnosis really helped me a lot with this because it was when I started studying hypnosis and we did an episode, I think episode 93 was hypnosis 101 and a lot of people had told me that they really didn’t want to listen to that one, but it turned out to be one of their favorite episodes. But like many things in life, the things you are really turned off by might have a big value somewhere hidden below the surface waiting for you. But hypnosis was so 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 of understanding how much information is missing from a typical sentence and hypnotic language patterns are all about using very, making language even less clear and concrete in ways that influences the brain and the subconscious mind in a certain way. Playing with that topic and reading and experiencing and learning more about it taught me a lot about how much information is missing from a typical conversation. And it made me a lot more aware of 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 halt. But I think that those things really helped me. I don’t know if this is practical for people that are out there that want to learn how to ask better questions, but maybe the one hack with my side on this is a piece of advice I’ve given and we have given in many different other situations 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 ask more and really, really great questions, it is going to influence you. It’s going to rub off on you and it’s going to teach you how to do that yourself as well.


Hiten Shah: Yeah. I started asking good questions because people were asking me bad questions. I think a really good example is when you were raising money for Kissmetrics for the first round, what did you do? How’d it go? I’m like, are you trying to raise money? How much? What do you have? 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 so that’s a pretty simple example because I’d meet with people and they were like really interested in 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. The amount of introductions I get to anything that’s analytics related or marketing related is really interesting because people think, oh you built a bunch of analytics companies or you’ve been in marketing or whatever. And they get, and when they come to me, most of the people I get introed like that, they’re being very specific about what I did instead of asking me about what they should do. And so that just helped me get better at 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. I would say that’s an example of what I would call bad questions. If you’re looking for advice or help with something, don’t ask people what they did, give them your situation and ask them for kind of what they would do in your situation and I think it’ll turn out better in terms of the value you get from them. 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. That it has taught me a lot about asking questions as well. While I’m giving advice, a bunch of taught me it and then working with her has taught me and especially when it comes to different business type of things that we’re doing. One thing that’s also done as a side effect is it made me actually go more thorough before I present something to her because I can anticipate the questions she’s going to ask. I’m not thinking like, oh, she’s going to ask these 10 questions. I’m just like, you know what? I’m just going to go to a little bit of extra level than 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. Same place, meaning getting aligned or making a really great decision about something. And I only do that with 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, wasn’t necessarily as good at answering questions that she would bring up in the beginning is I would just tell her, “I don’t know the answer to that yet. And here’s when I think that answer might be important.” Or, “That’s a really good question. I don’t know. Let me go find out.” It was even being able to respond to questions like that has been really helpful too. 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 good at both of those things.


Steli Efti: Beautiful. All right. There is really true power behind asking more and asking better questions. And I think we all have probably a life in front of us of continuous improvement on this. I don’t think that anybody’s great at it, but people are less bad at it than others. There’s definitely a lot more to learn even for us. And hopefully this inspired a bunch of you, the guys that are listening to spend more time and more attention and practice this and invest more in it because so many problems, so many challenges could have been solved if you only asked the right questions earlier. That’s it from us for this episode. We’ll hear you very soon.


Hiten Shah: Later.