Ask Powerful Questions

An event becomes really powerful when you know how to ask the right questions. Do you want to know how that works? Keep watching. Chad Littlefield is our expert today

Kevin Van der Straeten
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An event becomes really powerful when you know how to ask the right questions. Do you want to know how that works? Keep watching. Chad Littlefield is our expert today.


Hi Chad, welcome to our studio. 


Hey, thanks for having me on.


We are going to talk about powerful questions, but that’s still a little bit abstract for me. So help me out. What is a powerful question? 


Sure. So, part of the intention, or the purpose of even asking powerful questions to begin with is, comes from this idea that it’s, when I am at a conference or a meeting, my aim, my main aim is to gently eradicate small talk. There is difference by culture for sure, but there’s a certain natural and comfortable way, that we begin to connect or interact when strangers get together.


How is the weather?


What’s up?


How is the weather? Something like that.


How is the weather? How are you? What do you do? And, it’s not that those are bad questions necessarily, but when somebody asks you, “What do you do?”, it doesn’t call for any new thinking, any creative thinking. What it does is allows people to just plug in a disc into their head, and just repeat out what they’ve said a hundred times before. And so, asking powerful questions are questions that make you think that you might not have considered before, that actually create new neural pathwaysin your brain.


I think a good example was we had a little chat before we started shooting. And a question you asked me is, “you had five interviews today”, and then you asked, “What is the thing you remember most of today?” So that is a powerful question?


Yeah, well I don’t know if I should be judging my own questions. . It’s not about saying ‘this is a powerful question’, ‘this isn’t a powerful question’. One way that I like to think about it is, if you set up a continuum and on this end you have small talk. So one of the ways when I’m about to speak at a conference, the first time I ask these two questions to an audience of 500 people. I was so surprised by their response that I almost swore on stage. And that was I asked them, “How many of you really enjoy small talk, however you define it?” And out of 500 people, two hands in the room went up, and so my response was, “Okay, great you two find each other, you can chat. For the other 498 of you I asked, how many of you have had in the last 48 hours more than five conversations, at this conference that you would categorize as small talk?” And every single hand in the room went up. And so there’s a huge gap between the conversations that we want to have and that we’re having. So your example of me asking a question of, you know,“What’s something that stuck out to you about the last five interviews that you’ve done?” I think one of the reasons, one of the characteristics that makesthat a powerful question or creates a conversation that matters, is the fact that I was genuinely, naturally curious about your response to that. If I asked you, “How are you?” Or, “What’s the weather?” Or anything like that, there would be a very low degree of curiosity in the conversation.


How could you use that idea even before, during and after your event?


Before, one of the things that event planners... I work with lots of event planners. And event planners are generally really, tend to be creative,they’re excited about their event. I have never heard an event planner say, you know “This year I want our conference to really just kind of, fade into peoples’ distant memories, I don’t want it to stick out people”. You know, they want it to be unique, they want it to be interactive, they want it to be impactful. And then when I ask them “This is great, I love this, what’s your plan?” “How are you planning on making this impactful?” They say “Oh well we got together, the Board or the Committee, and we decided this is the theme, and this is what we are going to focus on”. And, very rarely is there a concept of, “Did you listen to the people that you are inviting?” And so if you are going to have a 1,000 people, 10 people, 10,000 people in a room, my question to you as an event planner is “How did you listen to that group of people before they showed up. In terms of what they need, in terms of what compelled them to say yes to paying to show up, to voluntarily paying to show up to an event?” Or if it’s an event that people are showing up to get credit for something, or something like that, if they’re mandatory. You know, if they have to be there, what do they care about? And if you can really tap into what they care about in terms of the theme and the content that shows up for people, there’s amazing potential to allow people to feel heard, seen and create a place where they belong. And as an event planner, if you can create spaces where people can belong, you create a trendy recidivism, I call it. You want people coming back to your events right,you don’t want people coming and then telling people, Don’t go to this next year, it wasn’t good”. You want people to be really present and interested in what’s about to happen next or next year.


Yeah, sure. You just mentioned that one of the ingredients is, of course, your genuine curiosity to the answer. But I can imagine there are other ingredients? – Yeah.


Well, let me ask you, let’s flip this rather than… you are asking lots of powerful questions I’m answering. For you, Kevin, in conversations that you feel like, “Ah, like this was just a really good conversation”, what were some of the ingredients that made that conversation worth having?


It’s a difficult one. But I think the genuine interest, of course, is something you notice immediately. But also a feeling of trust I think. If I don’t trust a person then I won’t answer. Even if it’s a good powerful question, I won’t answer it honestly I think. But also the content. If you are at a conference and you start asking questions about something totally different, I don’t think that’s appropriate then.


Yeah, sure. If you are at a conference to talk about how to grow your small business, and you are asking somebody what the typeof tires they have on their car, that’s going to create a disconnect, sure. So, what I would say, the trust element is certainly present but trust is a very big word, right?


It is.


So, breaking that down a little bit, I think that one way that trust can be created really easily from it an event planner standpoint, and in a attendee standpoint in terms of connecting is, Very often in conversations we have an intention. Very rarely do we actually share that intention with either our attendees or the person that we are talking to. And so, in conversation I think that I could actually ask somebody about what type of tires they have on their car. If I said, hey, my intention in asking this question which feels a little off-topic is, “My tire just blew out on the way to the conference and I need a new one”. Something like that, right.


Yes, that’s something totally different.


Yeah, so, when you share your intention with somebody and with an audience, or with an individual, it allows you to say “Hey, this is the game that I am playing, do you want to play too?”. And when you create that level of transparency in a conversation, then people are kind of like at ease, you feel a little bit more psychologically safe, which is really... Psychological safety is, you know the PhD term for ‘trust’, ‘inner personal trust’. Do I trust that you have my best interest in mind? That you want me to succeed? That you are not going to talk about me behind my back?




The other really big one that I think... So that trust and sharing an intention is one low hanging fruit. It is very easy to do as an event planner. When you stand up often times an event will start, or it’s a bigger conference it’ll start off with thanking sponsors, or something like that. And that’s great, we need to thank sponsors. And the events that I have seen or facilitated or spoken at where the intention is shared right in the beginning, of, hey, for the next 48 hours or for the next three days, we are here to, I just got back from a conference, speaking at a conscious capitalism conference. And their mission and intention is to elevate humanity through business. And so in the very beginning, for the next 48 hours, we are here to elevate humanity through business. So everybody is now able to play that game and is on board and it actually creates this container of community. And then the second low hanging fruit is these things. When we ask a question... I would say there’s two dominant ways that our brains are able to listen. And one comes from the part of our brain that develops first, so this kind of lizard brain. And that’s the part that when you ask somebody’s name, you forget it three seconds later. And I would say actually even for people that say“Oh I’m really bad with names” at events, I would say actually, you are not bad at names because you never got them to begin with. Because when we ask somebody’s name, often times, we ask them, you know, “What do you do?” “What’s your name?”“Who are you?” Etc. And when we ask that question, we are actually more focused on this person than that person. So I’m focused on ‘how am I coming across’, ‘am I standing far enough away’. We have all these things going through our mind of self-conscious, and if we are able to shift that ‘me’ focused perspective, through like a ‘we’ focused perspective to say “Actually, in this moment I just care about you”. And I’m excited to hear some of your story, that is a way that really changes the conversation. And so there are two dominant ways that our brains listen. One is this place of listening to win, right. So I ask you where you are from, and I say “Ah, Belgium, this is so... I had a second cousin who went to Belgium once”. And all of a sudden we are talking about me, and I think we do it with a great intention of wanting to connect with somebody else, but the deeper and more deliberate way to listen that requires our prefrontal cortex in this part of our brain is listening to understand. If I am able, when I ask you that question before we started filming, when I asked, you know, “What’s something that stuck out to you about the last five interviews?” I was really curious to know your response to that question. And so I was really listening to just understand what is was that you took away, and meet and connect with you a bit. Rather than thinking ;’oh, we’re on camera’, ‘we’re about to on’, I need to focus on myself in some way’.


I do have a question about something you said in the beginning of the interview. We were talking about asking powerful questions upfront, and I think it’s a great idea if you organize a conference that you ask your audience “What do you want to see?”, instead of deciding yourself based on nothing, but how do you do that then? Is it just okay to send out a survey?


Yeah, there’s a tool that I really love to use, event planners watching this might really love, it’s called ‘Type form. It’s a company based in Barcelona and it’s like a survey tool, but they specifically create conversational survey tools. And so, when you see the interface it feels more like you’re connecting with a person or like in a conversation. Whereas surveys usually feel like just somebody’s trying to mine data from you.


That’s exactly why I am asking this question. Because a lot of surveys don’t feel like the person is genuinely interested in what I have to tell.


Yeah, oh yeah. The general curiosity is completely absent. So I’ll give you an example of an event I facilitated recently. One of the things that I will do personally is, I will create a type-form and you can imbed videos in the top. And so I’ll create a video definitely no longer than 60 seconds to say, Hey, I’m Chad Littlefield, I’ll be one of your speakers or facilitators, or an MC for this event. The intention of me even reaching out right now, is that we are going to spend a bunch of time together, and your time is really important, and so I want to make the absolute most use of it. And so I’d love to know that, I put two questions below, would love to know your responses. So that I can help design, facilitate and experience that really meets what you need and what you want to get out of this time. And so via video we’ll share that intention and express that genuine curiosity. And for the most part response rates go way, way up. Because it’s this personal relationship and creates this connection before content.


Yeah, and even people get to know you, even before you will go on stage, that also gives a bond or something like that.


Yeah, sure. Yes, I’ll walk on up and by the time I show up, or before I even show up, I walk into the room, and somebody will kind of out of the corner of their eye, look at me, like, do a double take, like, ‘do I know you’. And then you’ll see the light ball go off of like, ‘oh right, you sent us this video’.


You can exactly do the same after your events get feedback and things like that. 


Yeah, after events we’ll do, Often speaking on the topic of gently, eradicating small talk from your events and asking powerful questions. And so we’ll do a 7 day or a 30 day connection challenge after an event where people will be put into a sequence, and they’ll get a very very brief email each day that just has an invitation... just a question in the subject line and nothing else. Something is just sparking and continue that connection and impact after the fact. Yeah, we have the technology to do it and it’s really not terribly difficult to set up. It just takes an event planner to take some time and put some intention into it.


Okay. I think that’s a great one to conclude with, Chad. Thank you very much for your time.


Yeah, thank you. It was great to spend some time together today.


And you at home, thank you for watching our show. I hope to see you next week.